Identification
- Summary
Progesterone is a hormone used for a variety of functions, including contraception, control of abnormal uterine bleeding, maintenance of pregnancy, and prevention of endometrial hyperplasia.
- Brand Names
- Bijuva, Crinone, Endometrin, Prochieve, Prometrium
- Generic Name
- Progesterone
- DrugBank Accession Number
- DB00396
- Background
Progesterone is a hormone that occurs naturally in females, and is essential for endometrial receptivity, embryo implantation, and the successful establishment of pregnancy. A low progesterone concentration or an insufficient response to progesterone can cause infertility and pregnancy loss 7. Progesterone is used in various contraceptive preparations to prevent ovulation and fertilization 15, 8 as well as in other formulations to promote and support pregnancy. Please see Medroxyprogesterone acetate, Megestrol acetate, Dydrogesterone and Hydroxyprogesterone entries for information on various other forms of progesterone.
Pharmaceutical progesterone is made from a plant source as a starting material and is chemically identical to progesterone of human ovarian origin Label. Progesterone is available in gelatinized capsule form, vaginal gel form, tablet form, vaginal insert form, and injection form, all used for various purposes Label,20,22,21,23.
- Type
- Small Molecule
- Groups
- Approved, Vet approved
- Structure
Structure for Progesterone (DB00396)
- Weight
- Average: 314.4617
Monoisotopic: 314.224580204 - Chemical Formula
- C21H30O2
- Synonyms
- (S)-4-Pregnene-3,20-dione
- (S)-Pregn-4-en-3,20-dione
- (S)-Progesterone
- 17alpha-Progesterone
- 17α-progesterone
- 4-Pregnene-3,20-dione
- Agolutin
- Akrolutin
- Corpus Luteum Hormone
- delta(4)-Pregnene-3,20-dione
- Gelbkörperhormon
- Luteohormone
- Lutogynon
- Pregn-4-ene-3,20-dione
- Progesteron
- Progesterona
- Progestérone
- Progesterone
- Progesteronum
- External IDs
- BP 14
- NSC-64377
- NSC-9704
- U 3672
Pharmacology
- Indication
Gelatinized capsules
The gelatinized capsules are indicated for use in the prevention of endometrial hyperplasia in non-hysterectomized postmenopausal women who are receiving conjugated estrogens tablets. They are also indicated for use in secondary amenorrhea Label.
Vaginal gel
Progesterone gel (8%) is indicated as progesterone supplementation or replacement as part of an Assisted Reproductive Technology (“ART”) treatment for infertile women with progesterone deficiency. The lower concentration progesterone gel (4%) is used in the treatment of secondary amenorrhea, with the use of the 8% concentration if there is no therapeutic response to the 4% gel 20.
Vaginal insert
This form is indicated to support embryo implantation and early pregnancy by supplementation of corpus luteal function as part of an Assisted Reproductive Technology (ART) treatment program for infertile women 21.
Injection (intramuscular)
This drug is indicated in amenorrhea and abnormal uterine bleeding due to hormonal imbalance in the absence of organic pathology, such as submucous fibroids or uterine cancer 23.
Tablets, contraceptive
The tablet form of progesterone in contraceptive formulations is indicated for the prevention of pregnancy 22.
Reduce drug development failure ratesBuild, train, & validate machine-learning modelswith evidence-based and structured datasets.Build, train, & validate predictive machine-learning models with structured datasets.- Associated Conditions
Indication Type Indication Combined Product Details Approval Level Age Group Patient Characteristics Dose Form Treatment of Abnormal uterine bleeding •••••••••••• ••••••••• Treatment of Amenorrhea •••••••••••• •••• ••••••••• Prevention of Endometrial hyperplasia caused by conjugated estrogen •••••••••••• •••••••••••••• Used in combination to treat Moderate to severe vasomotor symptoms Combination Product in combination with: Estradiol (DB00783) •••••••••••• •••••••••• ••••••• Prevention of Pregnancy •••••••••••• - Associated Therapies
- Contraindications & Blackbox Warnings
Prevent Adverse Drug Events TodayTap into our Clinical API for life-saving information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events with our Clinical API- Pharmacodynamics
Progesterone, depending on concentration and dosage form, and timing of exposure may have several pharmacodynamic effects. These actions, according, to various preparations, are listed below:
General effects
Progesterone is the main hormone of the corpus luteum and the placenta. It acts on the uterus by changing the proliferative phase to the secretory phase of the endometrium (inner mucous lining of the uterus). This hormone, stimulated by a hormone called luteinizing hormone (LH) is the main hormone during the secretory phase to prepare the corpus luteum and the endometrium for implantation of a fertilized ovum. As the luteal phase concludes, the progesterone hormone sends negative feedback to the anterior pituitary gland in the brain to decrease FSH (follicle stimulating hormone) and LH (luteinizing hormone) levels. This prevents ovulation and maturation of oocytes (immature egg cells). The endometrium then prepares for pregnancy by increasing its vascularity (blood vessels) and stimulating mucous secretion. This process occurs by progesterone stimulating the endometrium to decrease endometrial proliferation, leading to a decreased uterine lining thickness, developing more complex uterine glands, collecting energy in the form of glycogen, and providing more uterine blood vessel surface area suitable for supporting a growing embryo. As opposed to cervical mucous changes observed during the proliferative phase and ovulation, progesterone decreases and thickens the cervical mucus, rendering it less elastic. This change occurs because the fertilization time period has passed, and a specific consistency of mucous amenable to sperm entry is no longer required 16.
Gelatinized capsules
Progesterone capsules are an oral dosage form of micronized progesterone which, chemically identical to progesterone of ovarian origin. Progesterone capsules have all the properties of endogenous progesterone with induction of a secretory phase endometrium with gestagenic, antiestrogenic, slightly antiandrogenic and anti-aldosterone effects 24. Progesterone opposes the effects of estrogen on the uterus, and is beneficial in women with unopposed estrogen exposure, which carries an increased risk of malignancy 24.
Vaginal gel and vaginal insert
The gel preparation mimics the effects of naturally occurring progesterone. In the presence of adequate levels of estrogen, progesterone converts a proliferative endometrium into secretory endometrium. This means that the endometrium changes from a growing and thickening stage into a subsequent preparation stage for pregnancy, which involves further preparatory changes. Progesterone is necessary for the development of decidual tissue (specialized tissue amenable to supporting a possible pregnancy). Progesterone is required to increase endometrial receptivity for the implantation of a fertilized embryo. Once an embryo is implanted, progesterone helps to maintain the pregnancy 20.
Injection (intramuscular)
Intramuscularly injected progesterone increases serum progesterone and aids in the prevention of endometrial tissue overgrowth due to unopposed estrogen (which leads to abnormal uterine bleeding and sometimes uterine cancer) 18, 25. In the absence or deficiency of progesterone, the endometrium continually proliferates, eventually outgrowing its limited blood supply, shedding incompletely, and leading to abnormal and/or profuse bleeding as well as malignancy 18.
Tablets, contraceptive
Progesterone-only contraceptive tablets prevent conception by suppressing ovulation in about half of users, causing a thickening of cervical mucus to inhibit sperm movement, lowering the midcycle LH and FSH hormone peaks, slowing the movement of the ovum through the fallopian tubes, and causing secretory changes in the endometrium as described above 22.
- Mechanism of action
Progesterone binds and activates its nuclear receptor, PR, which plays an important part in the signaling of stimuli that maintain the endometrium during its preparation for pregnancy.
Progesterone receptor (PR) is a member of the nuclear/steroid hormone receptor (SHR) family of ligand-dependent transcription factors that is expressed primarily in female reproductive tissue as well as the central nervous system. As a result of its binding its associated steroid hormone, progesterone, the progesterone receptor (PR) modulates the expression of genes that regulate the development, differentiation, and proliferation of target tissues 14. In humans, PR is found to be highly expressed in the stromal (connective tissue) cells during the secretory phase and during pregnancy 10.
Progesterone may prevent pregnancy by changing the consistency of cervical mucus to be unfavorable for sperm penetration, and by inhibiting follicle-stimulating hormone (FSH), which normally causes ovulation. With perfect use, the first-year failure rate for progestin-only oral contraceptives is approximately 0.5%. The typical failure rate, however, is estimated to be approximately 5%, due to late or missed pills 22.
Target Actions Organism AProgesterone receptor agonistHumans AMineralocorticoid receptor antagonistagonistHumans UEstrogen receptor alpha agonistinhibitordownregulatorHumans USteroid 17-alpha-hydroxylase/17,20 lyase substrateinhibitorHumans UKappa-type opioid receptor activatorpotentiatorHumans UAlpha-1-acid glycoprotein 1 binderHumans UGlucocorticoid receptor partial agonistHumans UAndrogen receptor agonistpotentiatorHumans USex hormone-binding globulin binderpotentiatorHumans UEstrogen receptor beta agonistdownregulatorHumans - Absorption
Oral micronized capsules
Following oral administration of progesterone in the micronized soft-gelatin capsule formulation, peak serum concentration was achieved in the first 3 hours. The absolute bioavailability of micronized progesterone is unknown at this time. In postmenopausal women, serum progesterone concentration increased in a dose-proportional and linear fashion after multiple doses of progesterone capsules, ranging from 100 mg/day to 300 mg/day Label.
IM administration
After intramuscular (IM) administration of 10 mg of progesterone in oil, the maximum plasma concentrations were achieved in about 8 hours post-injection and plasma concentrations stayed above baseline for approximately 24 hours post-injection. Injections of 10, 25, and 50 mg lead to geometric mean values for maximum plasma concentration (CMAX) of 7, 28, and 50 ng/mL, respectively 25. Progesterone administered by the intramuscular (IM) route avoids significant first-pass hepatic metabolism. As a result, endometrial tissue concentrations of progesterone achieved with IM administration are higher when compared with oral administration. Despite this, the highest concentrations of progesterone in endometrial tissue are reached with vaginal administration 11.
Note on oral contraceptive tablet absorption
Serum progestin levels peak about 2 hours after oral administration of progesterone-only contraceptive tablets, followed by rapid distribution and elimination. By 24 hours after drug administration, serum levels remain near the baseline, making efficacy dependent upon strict adherence to the dosing schedule. Large variations in serum progesterone levels occur among individuals. Progestin-only administration leads to lower steady-state serum progestin levels and a shorter elimination half-life than concurrent administration with estrogens 22.
- Volume of distribution
When administered vaginally, progesterone is well absorbed by uterine endometrial tissue, and a small percentage is distributed into the systemic circulation. The amount of progesterone in the systemic circulation appears to be of minimal importance, especially when implantation, pregnancy, and live birth outcomes appear similar for intramuscular and vaginal administration of progesterone 11.
- Protein binding
96%-99% bound to serum proteins, primarily to serum albumin (50%-54%) and transcortin (43%-48%) Label.
- Metabolism
Progesterone is mainly metabolized by the liver. After oral administration, the major plasma metabolites found are 20 a hydroxy-Δ4 a-prenolone and 5 a-dihydroprogesterone. Some progesterone metabolites are found excreted in the bile and these metabolites may be deconjugated and subsequently metabolized in the gut by reduction, dehydroxylation, and epimerization Label. The major plasma and urinary metabolites are comparable to those found during the physiological progesterone secretion of the corpus luteum 24.
Hover over products below to view reaction partners
- Route of elimination
Progesterone metabolites are excreted mainly by the kidneys. Urinary elimination is observed for 95% of patients in the form of glycuroconjugated metabolites, primarily 3 a, 5 ß–pregnanediol (pregnandiol) 24. The glucuronide and sulfate conjugates of pregnanediol and pregnanolone are excreted in the urine and bile. Progesterone metabolites, excreted in the bile, may undergo enterohepatic recycling or may be found excreted in the feces.
- Half-life
Absorption half-life is approximately 25-50 hours and an elimination half-life of 5-20 minutes (progesterone gel) 20.
Progesterone, administered orally, has a short serum half-life (approximately 5 minutes). It is rapidly metabolized to 17-hydroxyprogesterone during its first pass through the liver 11.
- Clearance
Apparent clearance
1367 ± 348 (50mg of progesterone administered by vaginal insert once daily) 11.
106 ± 15 L/h (50mg/mL IM injection once daily) 11.
- Adverse Effects
Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.- Toxicity
Intraperitoneal LD50 (rat): 327 mg/kg MSDS.
Use in pregnancy
Only forms of progesterone that are indicated on product labeling for pregnancy should be used. Some forms of progesterone should not be used in pregnancy Label, 22. Refer to individual product monographs for information regarding use in pregnancy. Many studies have found no effects on fetal development associated with long-term use of contraceptive doses of oral progestins. Studies of infant growth and development that have been conducted have not demonstrated significant adverse effects, however, these studies are few in number. It is therefore advisable to rule out suspected pregnancy before starting any hormonal contraceptive 22.
Effects on fertility
Progesterone at high doses is an antifertility drug and high doses would be expected to impair fertility until cessation 25. The progesterone contraceptive should not be used during pregnancy.
Carcinogenicity
Progesterone has been shown to induce or promote the formation of ovarian, uterine, mammary, and genital tract tumors in animals. The clinical relevance of these findings is unknown 24. Certain epidemiological studies of patients using oral contraceptives have reported an increased relative risk of developing breast cancer, especially at a younger age and associated with a longer duration of use. These studies have mainly involved combined oral contraceptives, and therefore, it is unknown whether this risk is attributable to progestins, estrogens, or a combination of both. At this time, there is insufficient data to determine whether the use of progestin-only contraceptives increases the risk in a similar way to combined contraceptives. A meta-analysis of 54 studies showed a small increase in the frequency of breast cancer diagnosis for women who were currently using combined oral contraceptives, or had used them within the past 10 years. There was no increase in the frequency of having breast cancer diagnosed ten or more years after cessation of hormone use. Women with breast cancer should not use oral contraceptives, as there is no sufficient data to fully establish or negate the risk of cancer with hormonal contraceptive use 22.
Use in breastfeeding
Progesterone has been detected in the milk of nursing mothers 21, 22. No adverse effects, in general, have been found on breastfeeding ability or on the health, growth, or development of the growing infant. Despite this, isolated post-marketing cases of decreased milk production have been reported 22.
- Pathways
- Pharmacogenomic Effects/ADRs
- Not Available
Interactions
- Drug Interactions
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Drug Interaction Integrate drug-drug
interactions in your softwareAbametapir The serum concentration of Progesterone can be increased when it is combined with Abametapir. Abatacept The metabolism of Progesterone can be increased when combined with Abatacept. Abciximab The therapeutic efficacy of Abciximab can be decreased when used in combination with Progesterone. Abemaciclib Progesterone may decrease the excretion rate of Abemaciclib which could result in a higher serum level. Abiraterone The metabolism of Progesterone can be decreased when combined with Abiraterone. - Food Interactions
- Administer vitamin supplements.
- Avoid alcohol.
- Limit caffeine intake.
- Take at the same time every day.
- Take with food.
Products
Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.- Product Images
- International/Other Brands
- Agolutin (Biotika) / Cyclogest (Actavis) / Gesterol / Gestone (Nordic Pharma) / Progestasert / Progestogel (Besins) / Qi Ning (Aisheng Pharmaceutical) / Relantan (Aversi) / Susten (Sun Pharma) / Utrogestran (Faran Laboratories) / Utrovin (Bestochem) / Vasclor (Verisfield)
- Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Act Progesterone Injection Solution 50 mg / mL Intramuscular TEVA Canada Limited 2016-04-13 Not applicable Canada 
Crinone Gel 90 mg/1.125g Vaginal Actavis Pharma, Inc. 1997-05-13 2015-03-31 US 
Crinone Gel 90 mg/1.125g Vaginal Allergan, Inc. 1997-05-13 Not applicable US Crinone Gel 45 mg/1.125g Vaginal Actavis Pharma, Inc. 1997-05-13 2020-02-29 US Crinone Gel 45 mg/1.125g Vaginal Columbia Laboratories 1997-05-13 Not applicable US - Generic Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Auro-progesterone Capsule 100 mg Oral Auro Pharma Inc 2020-03-16 Not applicable Canada PMS-progesterone Capsule 100 mg Oral Pharmascience Inc 2018-08-08 Not applicable Canada PMS-progesterone Capsule 200 mg Oral Pharmascience Inc 2019-02-07 Not applicable Canada PMS-progesterone Inj 50mg/ml USP Liquid 50 mg / mL Intramuscular Pharmascience Inc 1989-12-31 2004-01-21 Canada Progesterone Capsule 100 mg/1 Oral Asclemed Usa, Inc. 2017-09-11 Not applicable US - Over the Counter Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Advanced Formula Progesto-Life Cream 16.9 mg/1mL Topical Smoky Mountain Naturals, LLC - DBA SMNutrition 2022-04-01 Not applicable US P25 Progesterone Cream Cream 25 mg/85g Transdermal SHYNE BRANDS 2021-06-10 Not applicable US P50 Progesterone Cream Cream 1 mg/1mg Transdermal SHYNE BRANDS 2021-06-14 Not applicable US P75 Lav Progesterone Cream Cream 1 mg/1mg Transdermal SHYNE BRANDS 2021-06-10 Not applicable US P75 Maxx with Retinol All Natural Progesterone 75 Cream Cream 1 mg/1mg Transdermal SHYNE BRANDS 2021-06-10 Not applicable US - Mixture Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image Bijuva Progesterone (100 mg) + Estradiol hemihydrate (1 mg) Capsule Oral Knight Therapeutics Inc. Not applicable Not applicable Canada Bijuva Progesterone (100 mg/1) + Estradiol (0.5 mg/1) Capsule Oral Mayne Pharma 2023-12-01 Not applicable US Bijuva Progesterone (100 mg/1) + Estradiol (1 mg/1) Capsule Oral Mayne Pharma Llc 2019-04-03 Not applicable US Bijuva Progesterone (100 mg) + Estradiol hemihydrate (0.5 mg) Capsule Oral Knight Therapeutics Inc. Not applicable Not applicable Canada Bijuva Progesterone (100 mg/1) + Estradiol (0.5 mg/1) Capsule Oral Mayne Pharma Llc 2023-03-31 Not applicable US - Unapproved/Other Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image Advanced Formula Progesto-Life Progesterone (16.9 mg/1mL) Cream Topical Smoky Mountain Naturals, LLC - DBA SMNutrition 2022-04-01 Not applicable US Fluocinolone Acetonide 0.01% / Minoxidil 7% / Progesterone 0.1% Progesterone (0.1 g/100g) + Fluocinolone acetonide (0.01 g/100g) + Minoxidil (7 g/100g) Solution Topical Sincerus Florida, LLC 2019-05-09 Not applicable US Minoxidil 5% / Progesterone 0.1% / Tretinoin 0.025% Progesterone (0.1 g/100g) + Minoxidil (5 g/100g) + Tretinoin (0.025 g/100g) Solution Topical Sincerus Florida, LLC 2019-05-07 Not applicable US Minoxidil 7% / Progesterone 0.1% Progesterone (0.1 g/100g) + Minoxidil (7 g/100g) Solution Topical Sincerus Florida, LLC 2019-05-01 Not applicable US Minoxidil 7% / Progesterone 0.1% / Tretinoin 0.025% Progesterone (0.1 g/100g) + Minoxidil (7 g/100g) + Tretinoin (0.025 g/100g) Solution Topical Sincerus Florida, LLC 2019-05-07 Not applicable US
Categories
- ATC Codes
- G03FA04 — Progesterone and estrogen
- G03FA — Progestogens and estrogens, fixed combinations
- G03F — PROGESTOGENS AND ESTROGENS IN COMBINATION
- G03 — SEX HORMONES AND MODULATORS OF THE GENITAL SYSTEM
- G — GENITO URINARY SYSTEM AND SEX HORMONES
- Drug Categories
- Adrenal Cortex Hormones
- BCRP/ABCG2 Inducers
- BCRP/ABCG2 Inhibitors
- BSEP/ABCB11 Inhibitors
- Corpus Luteum Hormones
- Cytochrome P-450 CYP2A6 Inducers
- Cytochrome P-450 CYP2C19 Inhibitors
- Cytochrome P-450 CYP2C19 inhibitors (strength unknown)
- Cytochrome P-450 CYP2C19 Substrates
- Cytochrome P-450 CYP2C9 Inhibitors
- Cytochrome P-450 CYP2C9 Inhibitors (strength unknown)
- Cytochrome P-450 CYP2C9 Substrates
- Cytochrome P-450 CYP2D6 Substrates
- Cytochrome P-450 CYP3A Inducers
- Cytochrome P-450 CYP3A Inhibitors
- Cytochrome P-450 CYP3A Substrates
- Cytochrome P-450 CYP3A4 Inducers
- Cytochrome P-450 CYP3A4 Inducers (strength unknown)
- Cytochrome P-450 CYP3A4 Substrates
- Cytochrome P-450 CYP3A5 Substrates
- Cytochrome P-450 CYP3A7 Inhibitors
- Cytochrome P-450 CYP3A7 Inhibitors (strength unknown)
- Cytochrome P-450 CYP3A7 Substrates
- Cytochrome P-450 Enzyme Inducers
- Cytochrome P-450 Enzyme Inhibitors
- Cytochrome P-450 Substrates
- Fused-Ring Compounds
- Genito Urinary System and Sex Hormones
- Gonadal Hormones
- Gonadal Steroid Hormones
- Hormonal Contraceptives for Systemic Use
- Hormones
- Hormones, Hormone Substitutes, and Hormone Antagonists
- Hyperglycemia-Associated Agents
- OATP1B1/SLCO1B1 Inhibitors
- OATP1B3 inducers
- OCT1 inhibitors
- OCT2 Inhibitors
- P-glycoprotein inducers
- P-glycoprotein inhibitors
- P-glycoprotein substrates
- Pregnanes
- Pregnenediones
- Pregnenes
- Progesterone and Derivatives
- Progesterone, antagonists & inhibitors
- Progestin-containing Intrauterine Device
- Progestins
- Sex Hormones and Modulators of the Genital System
- Steroids
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as gluco/mineralocorticoids, progestogins and derivatives. These are steroids with a structure based on a hydroxylated prostane moiety.
- Kingdom
- Organic compounds
- Super Class
- Lipids and lipid-like molecules
- Class
- Steroids and steroid derivatives
- Sub Class
- Pregnane steroids
- Direct Parent
- Gluco/mineralocorticoids, progestogins and derivatives
- Alternative Parents
- 20-oxosteroids / 3-oxo delta-4-steroids / Delta-4-steroids / Cyclohexenones / Organic oxides / Hydrocarbon derivatives
- Substituents
- 20-oxosteroid / 3-oxo-delta-4-steroid / 3-oxosteroid / Aliphatic homopolycyclic compound / Carbonyl group / Cyclic ketone / Cyclohexenone / Delta-4-steroid / Hydrocarbon derivative / Ketone
- Molecular Framework
- Aliphatic homopolycyclic compounds
- External Descriptors
- 3-oxo Delta(4)-steroid, 20-oxo steroid, C21-steroid hormone (CHEBI:17026) / Pregnane and derivatives [Fig], Progestagens (C00410) / C21 steroids (gluco/mineralocorticoids, progestogins) and derivatives (LMST02030159)
- Affected organisms
- Humans and other mammals
Chemical Identifiers
- UNII
- 4G7DS2Q64Y
- CAS number
- 57-83-0
- InChI Key
- RJKFOVLPORLFTN-LEKSSAKUSA-N
- InChI
- InChI=1S/C21H30O2/c1-13(22)17-6-7-18-16-5-4-14-12-15(23)8-10-20(14,2)19(16)9-11-21(17,18)3/h12,16-19H,4-11H2,1-3H3/t16-,17+,18-,19-,20-,21+/m0/s1
- IUPAC Name
- (1S,3aS,3bS,9aR,9bS,11aS)-1-acetyl-9a,11a-dimethyl-1H,2H,3H,3aH,3bH,4H,5H,7H,8H,9H,9aH,9bH,10H,11H,11aH-cyclopenta[a]phenanthren-7-one
- SMILES
- [H][C@@]12CC[C@H](C(C)=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CCC2=CC(=O)CC[C@]12C
References
- Synthesis Reference
Nejib M. Nasraoui, Alain Piasco, "Derivatives of 19-nor progesterone; process for producing them and the pharmaceutical compositions incorporating them." U.S. Patent US5223492, issued May, 1971.
US5223492- General References
- Allen WM: THE ISOLATION OF CRYSTALLINE PROGESTIN. Science. 1935 Aug 2;82(2118):89-93. [Article]
- Allen WM: Progesterone: how did the name originate? South Med J. 1970 Oct;63(10):1151-5. [Article]
- Schumacher M, Guennoun R, Robert F, Carelli C, Gago N, Ghoumari A, Gonzalez Deniselle MC, Gonzalez SL, Ibanez C, Labombarda F, Coirini H, Baulieu EE, De Nicola AF: Local synthesis and dual actions of progesterone in the nervous system: neuroprotection and myelination. Growth Horm IGF Res. 2004 Jun;14 Suppl A:S18-33. [Article]
- Hould FS, Fried GM, Fazekas AG, Tremblay S, Mersereau WA: Progesterone receptors regulate gallbladder motility. J Surg Res. 1988 Dec;45(6):505-12. [Article]
- Payne VA, Chang YT, Loew GH: Homology modeling and substrate binding study of human CYP2C18 and CYP2C19 enzymes. Proteins. 1999 Nov 1;37(2):204-17. [Article]
- Yamazaki H, Shimada T: Progesterone and testosterone hydroxylation by cytochromes P450 2C19, 2C9, and 3A4 in human liver microsomes. Arch Biochem Biophys. 1997 Oct 1;346(1):161-9. doi: 10.1006/abbi.1997.0302. [Article]
- Young SL, Lessey BA: Progesterone function in human endometrium: clinical perspectives. Semin Reprod Med. 2010 Jan;28(1):5-16. doi: 10.1055/s-0029-1242988. Epub 2010 Jan 26. [Article]
- Lopez LM, Ramesh S, Chen M, Edelman A, Otterness C, Trussell J, Helmerhorst FM: Progestin-only contraceptives: effects on weight. Cochrane Database Syst Rev. 2016 Aug 28;(8):CD008815. doi: 10.1002/14651858.CD008815.pub4. [Article]
- Khandelwal M: Vaginal progesterone in risk reduction of preterm birth in women with short cervix in the midtrimester of pregnancy. Int J Womens Health. 2012;4:481-90. doi: 10.2147/IJWH.S28944. Epub 2012 Sep 14. [Article]
- Okada H, Tsuzuki T, Murata H: Decidualization of the human endometrium. Reprod Med Biol. 2018 Feb 1;17(3):220-227. doi: 10.1002/rmb2.12088. eCollection 2018 Jul. [Article]
- Paulson RJ, Collins MG, Yankov VI: Progesterone pharmacokinetics and pharmacodynamics with 3 dosages and 2 regimens of an effervescent micronized progesterone vaginal insert. J Clin Endocrinol Metab. 2014 Nov;99(11):4241-9. doi: 10.1210/jc.2013-3937. Epub 2014 Feb 25. [Article]
- Child T, Leonard SA, Evans JS, Lass A: Systematic review of the clinical efficacy of vaginal progesterone for luteal phase support in assisted reproductive technology cycles. Reprod Biomed Online. 2018 Jun;36(6):630-645. doi: 10.1016/j.rbmo.2018.02.001. Epub 2018 Feb 22. [Article]
- Check JH: Luteal Phase Support in assisted reproductive technology treatment: focus on Endometrin(R) (progesterone) vaginal insert. Ther Clin Risk Manag. 2009 Aug;5(4):403-7. Epub 2009 Jun 4. [Article]
- Grimm SL, Hartig SM, Edwards DP: Progesterone Receptor Signaling Mechanisms. J Mol Biol. 2016 Sep 25;428(19):3831-49. doi: 10.1016/j.jmb.2016.06.020. Epub 2016 Jul 2. [Article]
- Danielle B. Cooper; Rotimi Adigun (2018). Oral contraceptives. StatPearls Publishing.
- Dhanalakshmi K. Thiyagarajan; Rebecca Jeanmonod (2019). Physiology, Menstrual Cycle. StatPearls publishing.
- Drug approval package FDA [Link]
- Merck Manuals: Abnormal Uterine Bleeding Due to Ovulatory Dysfunction (AUB-O) [Link]
- AAFP: Abnormal uterine bleeding [Link]
- Progesterone gel: Crinone® 4% and Crinone® 8% [File]
- Endometrin FDA label, vaginal insert [File]
- Norethindrone FDA label [File]
- Progesterone injection, FDA label [File]
- Utrogestan capsules, medsafe NZ label [File]
- PROGESTERONE INJECTION USP IN SESAME OIL FOR INTRAMUSCULAR USE ONLY [File]
- External Links
- Human Metabolome Database
- HMDB0001830
- KEGG Drug
- D00066
- KEGG Compound
- C00410
- PubChem Compound
- 5994
- PubChem Substance
- 46508968
- ChemSpider
- 5773
- BindingDB
- 8903
- 8727
- ChEBI
- 17026
- ChEMBL
- CHEMBL103
- ZINC
- ZINC000004428529
- Therapeutic Targets Database
- DAP000549
- PharmGKB
- PA451123
- PDBe Ligand
- STR
- RxList
- RxList Drug Page
- Drugs.com
- Drugs.com Drug Page
- PDRhealth
- PDRhealth Drug Page
- Wikipedia
- Progesterone
- PDB Entries
- 1a28 / 1dbb / 1h60 / 1mrq / 1w0f / 1ya3 / 2aa5 / 2aa6 / 2aba / 2hzq … show 21 more
- FDA label
- Download (266 KB)
- MSDS
- Download (24 KB)
Clinical Trials
- Clinical Trials
Phase Status Purpose Conditions Count 4 Active Not Recruiting Treatment Dydrogesterone / Female Infertility / Frozen Embryo Transfer / Hormone Replacement Therapy 1 4 Completed Not Available Female Infertility 1 4 Completed Basic Science Contraception / Fertility 1 4 Completed Basic Science Hormone Replacement 1 4 Completed Basic Science Perimenopausal Depression 1
Pharmacoeconomics
- Manufacturers
- Bristol myers squibb
- Amarin pharmaceuticals inc
- Solvay pharmaceuticals
- Esi pharmacal
- Unimed pharmaceuticals llc
- Watson laboratories inc
- App pharmaceuticals llc
- Eli lilly and co
- Pharmaforce inc
- Alza corp
- Ferring pharmaceuticals inc
- Packagers
- Abraxis BioScience Inc.
- APP Pharmaceuticals
- Ascend Therapeutics
- Carlisle Laboratories Inc.
- Catalent Pharma Solutions
- Columbia Labs
- Consolidated Midland Corp.
- Cutis Pharma Inc.
- Darby Dental Supply Co. Inc.
- Fleet Laboratories Ltd.
- Lyne Laboratories Inc.
- Marlex Pharmaceuticals
- Martica Enterprises Inc.
- Martin Surgical Supply
- Merit Pharmaceuticals
- My Healthcare Packaging Ltd. Contract Packaging
- Paddock Labs
- Pharmaceutics International Inc.
- Pharmaforce Inc.
- Physicians Total Care Inc.
- Primedics Laboratories
- Redpharm Drug
- Solvay Pharmaceuticals
- Spectrum Chemicals and Laboratory Products
- V Sab Medical Labs Inc.
- Watson Pharmaceuticals
- Dosage Forms
Form Route Strength Solution Intramuscular 50 mg / mL Cream Topical 16.9 mg/1mL Gel Vaginal 8.000 g Capsule Oral Gel Cutaneous 1.000 g Cream; gel Vaginal Gel Vaginal 4 % Gel Vaginal 45 mg/1.125g Gel Vaginal 8 % Gel Vaginal 80 MG/G Gel Vaginal 90 mg/1.125g Gel Vaginal 90 MG Gel Vaginal 90.000 mg Gel Vaginal 8 g Gel Vaginal 8 % w/w Solution Intramuscular 50.000 mg Suppository Vaginal 200 mg Tablet Vaginal 400 mg Suppository Vaginal 400 mg Suppository Rectal; Vaginal 400 mg Gel Topical 1.00 g Injection Intramuscular Insert Vaginal 100 mg Insert Vaginal 100 mg/1 Tablet Vaginal 100.000 mg Tablet Vaginal Tablet, effervescent Vaginal 100 mg Cream Vaginal 2.5 G Insert Vaginal 200 MG Capsule; spray, metered Oral; Transdermal Ring Vaginal 11 mg/1d Intrauterine device Intrauterine; Vaginal 1 g Capsule Vaginal Capsule Oral; Vaginal 400.000 mg Solution Intramuscular 100 mg Capsule Oral; Vaginal 100.000 mg Capsule, liquid filled Oral; Vaginal 200 mg Capsule, liquid filled Oral; Vaginal 100 mg Liquid Intramuscular 50 mg / mL Solution Subcutaneous 25 mg / 1.112 mL Suspension Intramuscular Capsule Oral; Vaginal 200.000 mg Solution Topical Solution Intramuscular 25 mg Capsule 200.000 mg Cream Transdermal 25 mg/85g Cream Transdermal 1 mg/1mg Injection, powder, for solution Injection, solution Capsule Oral 200 mg Gel Cutaneous 1.00 g Injection, solution Parenteral 25 mg Capsule, liquid filled Oral 400 mg Drug delivery system Vaginal 2.074 g Injection Intramuscular Injection Intramuscular 25 mg/ml Injection Intramuscular 50 mg/ml Injection, solution Intramuscular; Subcutaneous Capsule Not applicable 200 mg/1 Capsule, liquid filled Oral 100 mg Capsule, liquid filled Oral 200 mg Capsule, liquid filled Vaginal 200 mg Solution Parenteral 100 mg Capsule Not applicable 100 mg/1 Capsule, gelatin coated Not applicable 200 mg/1 Capsule, liquid filled Oral 100 mg/1 Capsule, liquid filled Oral 200 mg/1 Injection Intramuscular 50 mg/1 Injection, solution Intramuscular 50 mg/1mL Injection, solution Intramuscular Gel Topical 1 g Gel Solution Intramuscular 25 mg/ml Solution Intramuscular 50 mg/ml Capsule Oral 100 mg/1 Capsule Oral 100 mg Capsule Oral 200 mg/1 Capsule Oral; Vaginal 200 MG Injection, solution Intramuscular 10 MG Injection, solution Intramuscular 25 MG Injection, solution Intramuscular 5 MG Injection, solution Intramuscular 50 mg/ml Injection, solution Parenteral 100 MG/ML Injection, solution Parenteral 50 MG/ML Suspension Parenteral 200 mg Capsule Capsule Vaginal Capsule Vaginal 200 mg Capsule Oral Gel 90 mg Solution Intramuscular Capsule 100 mg Capsule 200 mg Tablet Vaginal 100 mg Gel 1 %w/w - Prices
Unit description Cost Unit Prochieve 4% Gel (18 Applicators Per Box) 160.18USD tube Crinone 8% Gel (1 Box = 6 Applications) 84.26USD box Prochieve 8% Gel 1.45 gm Tube 14.83USD tube Crinone 8% gel 13.61USD g Prochieve 8% gel 12.0USD g Prochieve 4% gel 8.56USD g Progesterone 50 mg/ml 6.6USD ml Progesterone oil 50 mg/ml vial 3.88USD ml Prometrium 200 mg capsule 3.84USD capsule First-progesterone vgs 400 susuppositoryp 3.33USD each First-progesterone vgs 200 suppository 3.15USD each First-progesterone vgs 100 suppository 3.0USD each First-progesterone vgs 50 suppository 2.93USD each First-progesterone vgs 25 suppository 2.88USD each Prometrium 100 mg capsule 1.69USD capsule Progesterone powder micronized 0.74USD g Progesterone powder milled 0.73USD g DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.- Patents
Patent Number Pediatric Extension Approved Expires (estimated) Region US5543150 No 1996-08-06 2013-09-15 US US7300664 No 2007-11-27 2019-11-17 US US7320800 No 2008-01-22 2019-11-17 US US7393543 No 2008-07-01 2019-11-17 US US9006222 No 2015-04-14 2032-11-21 US US9114145 No 2015-08-25 2032-11-21 US US8846649 No 2014-09-30 2032-11-21 US US9301920 No 2016-04-05 2032-11-21 US US8846648 No 2014-09-30 2032-11-21 US US9114146 No 2015-08-25 2032-11-21 US US8633178 No 2014-01-21 2032-11-21 US US10052386 No 2018-08-21 2032-11-21 US US8993548 No 2015-03-31 2032-11-21 US US8987237 No 2015-03-24 2032-11-21 US US8993549 No 2015-03-31 2032-11-21 US US10206932 No 2019-02-19 2032-11-21 US US10639375 No 2020-05-05 2032-11-21 US US10548904 No 2020-02-04 2029-02-03 US US8580293 No 2013-11-12 2030-01-21 US US10537584 No 2020-01-21 2029-02-03 US US10675288 No 2020-06-09 2032-11-21 US US10806740 No 2020-10-20 2032-11-21 US US11033626 No 2021-06-15 2032-11-21 US US11103513 No 2021-08-31 2032-11-21 US US11110099 No 2021-09-07 2032-11-21 US US11103516 No 2021-08-31 2032-11-21 US US8933059 No 2015-01-13 2032-11-21 US US11166963 No 2021-11-09 2032-11-21 US US11529360 No 2012-11-21 2032-11-21 US US11793819 No 2012-11-21 2032-11-21 US
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 128-132 https://www.chemicalbook.com/ChemicalProductProperty_US_CB4224484.aspx boiling point (°C) 394.13°C (rough estimate) https://www.chemicalbook.com/ChemicalProductProperty_US_CB4224484.aspx water solubility <0.1 g/100 mL at 19 ºC https://www.chemicalbook.com/ChemicalProductProperty_US_CB4224484.aspx logP 3.87 http://www.hmdb.ca/metabolites/HMDB0001830 logS -4.43 http://www.hmdb.ca/metabolites/HMDB0001830 pKa Strongest acidic: , Strongest basic: 18.92, -4.8 http://www.hmdb.ca/metabolites/HMDB0001830 - Predicted Properties
Property Value Source Water Solubility 0.00546 mg/mL ALOGPS logP 3.58 ALOGPS logP 4.15 Chemaxon logS -4.8 ALOGPS pKa (Strongest Acidic) 18.47 Chemaxon pKa (Strongest Basic) -4.8 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 2 Chemaxon Hydrogen Donor Count 0 Chemaxon Polar Surface Area 34.14 Å2 Chemaxon Rotatable Bond Count 1 Chemaxon Refractivity 92.71 m3·mol-1 Chemaxon Polarizability 37.26 Å3 Chemaxon Number of Rings 4 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule Yes Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 1.0 Blood Brain Barrier + 0.982 Caco-2 permeable + 0.7724 P-glycoprotein substrate Substrate 0.5449 P-glycoprotein inhibitor I Inhibitor 0.8841 P-glycoprotein inhibitor II Inhibitor 0.6043 Renal organic cation transporter Non-inhibitor 0.6931 CYP450 2C9 substrate Non-substrate 0.847 CYP450 2D6 substrate Non-substrate 0.8795 CYP450 3A4 substrate Substrate 0.7408 CYP450 1A2 substrate Non-inhibitor 0.9045 CYP450 2C9 inhibitor Non-inhibitor 0.9071 CYP450 2D6 inhibitor Non-inhibitor 0.9533 CYP450 2C19 inhibitor Non-inhibitor 0.6514 CYP450 3A4 inhibitor Non-inhibitor 0.8309 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.8203 Ames test Non AMES toxic 0.9626 Carcinogenicity Non-carcinogens 0.9151 Biodegradation Not ready biodegradable 0.9575 Rat acute toxicity 1.8041 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.7451 hERG inhibition (predictor II) Non-inhibitor 0.7454
Spectra
- Mass Spec (NIST)
- Download (11.5 KB)
- Spectra
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 187.3581755 predictedDarkChem Lite v0.1.0 [M-H]- 187.8123755 predictedDarkChem Lite v0.1.0 [M-H]- 187.8051755 predictedDarkChem Lite v0.1.0 [M-H]- 186.7997755 predictedDarkChem Lite v0.1.0 [M-H]- 187.0225755 predictedDarkChem Lite v0.1.0 [M-H]- 180.22621 predictedDeepCCS 1.0 (2019) [M+H]+ 188.3041755 predictedDarkChem Lite v0.1.0 [M+H]+ 175.99825 predictedDarkChem Standard v0.1.0 [M+H]+ 189.1595755 predictedDarkChem Lite v0.1.0 [M+H]+ 187.3317755 predictedDarkChem Lite v0.1.0 [M+H]+ 187.5244755 predictedDarkChem Lite v0.1.0 [M+H]+ 182.30602 predictedDeepCCS 1.0 (2019) [M+Na]+ 188.2207755 predictedDarkChem Lite v0.1.0 [M+Na]+ 187.9469755 predictedDarkChem Lite v0.1.0 [M+Na]+ 188.6825755 predictedDarkChem Lite v0.1.0 [M+Na]+ 187.4057755 predictedDarkChem Lite v0.1.0 [M+Na]+ 187.1997755 predictedDarkChem Lite v0.1.0 [M+Na]+ 188.95586 predictedDeepCCS 1.0 (2019)
Targets
Build, predict & validate machine-learning models
Use our structured and evidence-based datasets to unlock newinsights and accelerate drug research.
Use our structured and evidence-based datasets to unlock new insights and accelerate drug research.
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Agonist
- General Function
- Zinc ion binding
- Specific Function
- The steroid hormones and their receptors are involved in the regulation of eukaryotic gene expression and affect cellular proliferation and differentiation in target tissues. Progesterone receptor ...
- Gene Name
- PGR
- Uniprot ID
- P06401
- Uniprot Name
- Progesterone receptor
- Molecular Weight
- 98979.96 Da
References
- Madauss KP, Stewart EL, Williams SP: The evolution of progesterone receptor ligands. Med Res Rev. 2007 May;27(3):374-400. [Article]
- Gizard F, Robillard R, Gross B, Barbier O, Revillion F, Peyrat JP, Torpier G, Hum DW, Staels B: TReP-132 is a novel progesterone receptor coactivator required for the inhibition of breast cancer cell growth and enhancement of differentiation by progesterone. Mol Cell Biol. 2006 Oct;26(20):7632-44. [Article]
- Boonyaratanakornkit V, McGowan E, Sherman L, Mancini MA, Cheskis BJ, Edwards DP: The role of extranuclear signaling actions of progesterone receptor in mediating progesterone regulation of gene expression and the cell cycle. Mol Endocrinol. 2007 Feb;21(2):359-75. Epub 2006 Nov 30. [Article]
- Tranguch S, Smith DF, Dey SK: Progesterone receptor requires a co-chaperone for signalling in uterine biology and implantation. Reprod Biomed Online. 2006 Nov;13(5):651-60. [Article]
- Luconi M, Bonaccorsi L, Maggi M, Pecchioli P, Krausz C, Forti G, Baldi E: Identification and characterization of functional nongenomic progesterone receptors on human sperm membrane. J Clin Endocrinol Metab. 1998 Mar;83(3):877-85. [Article]
- Okada H, Tsuzuki T, Murata H: Decidualization of the human endometrium. Reprod Med Biol. 2018 Feb 1;17(3):220-227. doi: 10.1002/rmb2.12088. eCollection 2018 Jul. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- AntagonistAgonist
- General Function
- Zinc ion binding
- Specific Function
- Receptor for both mineralocorticoids (MC) such as aldosterone and glucocorticoids (GC) such as corticosterone or cortisol. Binds to mineralocorticoid response elements (MRE) and transactivates targ...
- Gene Name
- NR3C2
- Uniprot ID
- P08235
- Uniprot Name
- Mineralocorticoid receptor
- Molecular Weight
- 107066.575 Da
References
- Rupprecht R, Reul JM, van Steensel B, Spengler D, Soder M, Berning B, Holsboer F, Damm K: Pharmacological and functional characterization of human mineralocorticoid and glucocorticoid receptor ligands. Eur J Pharmacol. 1993 Oct 15;247(2):145-54. [Article]
- Quinkler M, Meyer B, Bumke-Vogt C, Grossmann C, Gruber U, Oelkers W, Diederich S, Bahr V: Agonistic and antagonistic properties of progesterone metabolites at the human mineralocorticoid receptor. Eur J Endocrinol. 2002 Jun;146(6):789-99. [Article]
- Myles K, Funder JW: Progesterone binding to mineralocorticoid receptors: in vitro and in vivo studies. Am J Physiol. 1996 Apr;270(4 Pt 1):E601-7. doi: 10.1152/ajpendo.1996.270.4.E601. [Article]
- Souque A, Fagart J, Couette B, Davioud E, Sobrio F, Marquet A, Rafestin-Oblin ME: The mineralocorticoid activity of progesterone derivatives depends on the nature of the C18 substituent. Endocrinology. 1995 Dec;136(12):5651-8. doi: 10.1210/endo.136.12.7588320. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- AgonistInhibitorDownregulator
- General Function
- Zinc ion binding
- Specific Function
- Nuclear hormone receptor. The steroid hormones and their receptors are involved in the regulation of eukaryotic gene expression and affect cellular proliferation and differentiation in target tissu...
- Gene Name
- ESR1
- Uniprot ID
- P03372
- Uniprot Name
- Estrogen receptor
- Molecular Weight
- 66215.45 Da
References
- Lessey BA, Palomino WA, Apparao KB, Young SL, Lininger RA: Estrogen receptor-alpha (ER-alpha) and defects in uterine receptivity in women. Reprod Biol Endocrinol. 2006;4 Suppl 1:S9. [Article]
- Montero Girard G, Vanzulli SI, Cerliani JP, Bottino MC, Bolado J, Vela J, Becu-Villalobos D, Benavides F, Gutkind S, Patel V, Molinolo A, Lanari C: Association of estrogen receptor-alpha and progesterone receptor A expression with hormonal mammary carcinogenesis: role of the host microenvironment. Breast Cancer Res. 2007;9(2):R22. [Article]
- Mohammed H, Russell IA, Stark R, Rueda OM, Hickey TE, Tarulli GA, Serandour AA, Birrell SN, Bruna A, Saadi A, Menon S, Hadfield J, Pugh M, Raj GV, Brown GD, D'Santos C, Robinson JL, Silva G, Launchbury R, Perou CM, Stingl J, Caldas C, Tilley WD, Carroll JS: Progesterone receptor modulates ERalpha action in breast cancer. Nature. 2015 Jul 16;523(7560):313-7. doi: 10.1038/nature14583. Epub 2015 Jul 8. [Article]
- Jayaraman A, Pike CJ: Progesterone attenuates oestrogen neuroprotection via downregulation of oestrogen receptor expression in cultured neurones. J Neuroendocrinol. 2009 Jan;21(1):77-81. doi: 10.1111/j.1365-2826.2008.01801.x. [Article]
- Tessier C, Deb S, Prigent-Tessier A, Ferguson-Gottschall S, Gibori GB, Shiu RP, Gibori G: Estrogen receptors alpha and beta in rat decidua cells: cell-specific expression and differential regulation by steroid hormones and prolactin. Endocrinology. 2000 Oct;141(10):3842-51. doi: 10.1210/endo.141.10.7734. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- SubstrateInhibitor
- General Function
- Steroid 17-alpha-monooxygenase activity
- Specific Function
- Conversion of pregnenolone and progesterone to their 17-alpha-hydroxylated products and subsequently to dehydroepiandrosterone (DHEA) and androstenedione. Catalyzes both the 17-alpha-hydroxylation ...
- Gene Name
- CYP17A1
- Uniprot ID
- P05093
- Uniprot Name
- Steroid 17-alpha-hydroxylase/17,20 lyase
- Molecular Weight
- 57369.995 Da
References
- Haidar S, Hartmann RW: C16 and C17 substituted derivatives of pregnenolone and progesterone as inhibitors of 17alpha-hydroxylase-C17, 20-lyase: synthesis and biological evaluation. Arch Pharm (Weinheim). 2002;335(11-12):526-34. [Article]
- Vasaitis TS, Bruno RD, Njar VC: CYP17 inhibitors for prostate cancer therapy. J Steroid Biochem Mol Biol. 2011 May;125(1-2):23-31. doi: 10.1016/j.jsbmb.2010.11.005. Epub 2010 Nov 17. [Article]
- Auchus RJ, Sampath Kumar A, Andrew Boswell C, Gupta MK, Bruce K, Rath NP, Covey DF: The enantiomer of progesterone (ent-progesterone) is a competitive inhibitor of human cytochromes P450c17 and P450c21. Arch Biochem Biophys. 2003 Jan 1;409(1):134-44. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- ActivatorPotentiator
- General Function
- Opioid receptor activity
- Specific Function
- G-protein coupled opioid receptor that functions as receptor for endogenous alpha-neoendorphins and dynorphins, but has low affinity for beta-endorphins. Also functions as receptor for various synt...
- Gene Name
- OPRK1
- Uniprot ID
- P41145
- Uniprot Name
- Kappa-type opioid receptor
- Molecular Weight
- 42644.665 Da
References
- Dawson-Basoa ME, Gintzler AR: Estrogen and progesterone activate spinal kappa-opiate receptor analgesic mechanisms. Pain. 1996 Jan;64(1):169-77. [Article]
- Gordon FT, Soliman MR: The effects of estradiol and progesterone on pain sensitivity and brain opioid receptors in ovariectomized rats. Horm Behav. 1996 Sep;30(3):244-50. doi: 10.1006/hbeh.1996.0029. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Binder
- General Function
- Not Available
- Specific Function
- Functions as transport protein in the blood stream. Binds various ligands in the interior of its beta-barrel domain. Also binds synthetic drugs and influences their distribution and availability in...
- Gene Name
- ORM1
- Uniprot ID
- P02763
- Uniprot Name
- Alpha-1-acid glycoprotein 1
- Molecular Weight
- 23511.38 Da
References
- Albani JR: Progesterone binding to the tryptophan residues of human alpha1-acid glycoprotein. Carbohydr Res. 2006 Nov 6;341(15):2557-64. Epub 2006 Aug 8. [Article]
- De Ceukeleire M, Albani JR: Interaction between carbohydrate residues of alpha(1)-acid glycoprotein (orosomucoid) and progesterone. A fluorescence study. Carbohydr Res. 2002 Sep 3;337(15):1405-10. [Article]
- Albani JR: Binding effect of progesterone on the dynamics of alpha1-acid glycoprotein. Biochim Biophys Acta. 1997 Aug 29;1336(2):349-59. [Article]
- Nishi K, Sakai N, Komine Y, Maruyama T, Halsall HB, Otagiri M: Structural and drug-binding properties of alpha(1)-acid glycoprotein in reverse micelles. Biochim Biophys Acta. 2002 Dec 16;1601(2):185-91. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Partial agonist
- General Function
- Zinc ion binding
- Specific Function
- Receptor for glucocorticoids (GC). Has a dual mode of action: as a transcription factor that binds to glucocorticoid response elements (GRE), both for nuclear and mitochondrial DNA, and as a modula...
- Gene Name
- NR3C1
- Uniprot ID
- P04150
- Uniprot Name
- Glucocorticoid receptor
- Molecular Weight
- 85658.57 Da
References
- Attardi BJ, Zeleznik A, Simhan H, Chiao JP, Mattison DR, Caritis SN: Comparison of progesterone and glucocorticoid receptor binding and stimulation of gene expression by progesterone, 17-alpha hydroxyprogesterone caproate, and related progestins. Am J Obstet Gynecol. 2007 Dec;197(6):599.e1-7. [Article]
- Xu XF, Hoebeke J, Bjorntorp P: Progestin binds to the glucocorticoid receptor and mediates antiglucocorticoid effect in rat adipose precursor cells. J Steroid Biochem. 1990 Aug 14;36(5):465-71. [Article]
- Leo JC, Guo C, Woon CT, Aw SE, Lin VC: Glucocorticoid and mineralocorticoid cross-talk with progesterone receptor to induce focal adhesion and growth inhibition in breast cancer cells. Endocrinology. 2004 Mar;145(3):1314-21. doi: 10.1210/en.2003-0732. Epub 2003 Nov 14. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- AgonistPotentiator
- General Function
- Zinc ion binding
- Specific Function
- Steroid hormone receptors are ligand-activated transcription factors that regulate eukaryotic gene expression and affect cellular proliferation and differentiation in target tissues. Transcription ...
- Gene Name
- AR
- Uniprot ID
- P10275
- Uniprot Name
- Androgen receptor
- Molecular Weight
- 98987.9 Da
References
- Miedema BW, Kelly KA, Camilleri M, Hanson RB, Zinsmeister AR, O'Connor MK, Brown ML: Human gastric and jejunal transit and motility after Roux gastrojejunostomy. Gastroenterology. 1992 Oct;103(4):1133-43. [Article]
- Bentel JM, Birrell SN, Pickering MA, Holds DJ, Horsfall DJ, Tilley WD: Androgen receptor agonist activity of the synthetic progestin, medroxyprogesterone acetate, in human breast cancer cells. Mol Cell Endocrinol. 1999 Aug 20;154(1-2):11-20. [Article]
- Yuan X, Balk SP: Mechanisms mediating androgen receptor reactivation after castration. Urol Oncol. 2009 Jan-Feb;27(1):36-41. doi: 10.1016/j.urolonc.2008.03.021. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- BinderPotentiator
- General Function
- Androgen binding
- Specific Function
- Functions as an androgen transport protein, but may also be involved in receptor mediated processes. Each dimer binds one molecule of steroid. Specific for 5-alpha-dihydrotestosterone, testosterone...
- Gene Name
- SHBG
- Uniprot ID
- P04278
- Uniprot Name
- Sex hormone-binding globulin
- Molecular Weight
- 43778.755 Da
References
- Hong H, Branham WS, Ng HW, Moland CL, Dial SL, Fang H, Perkins R, Sheehan D, Tong W: Human sex hormone-binding globulin binding affinities of 125 structurally diverse chemicals and comparison with their binding to androgen receptor, estrogen receptor, and alpha-fetoprotein. Toxicol Sci. 2015 Feb;143(2):333-48. doi: 10.1093/toxsci/kfu231. Epub 2014 Oct 27. [Article]
- Dalton ME: The effect of progesterone administration on sex hormone binding globulin binding capacity in women with severe premenstrual syndrome. J Steroid Biochem. 1984 Jan;20(1):437-9. [Article]
- Misao R, Nakanishi Y, Fujimoto J, Tamaya T: Effects of danazol and progesterone on sex hormone-binding globulin mRNA expression in human endometrial cancer cell line Ishikawa. J Steroid Biochem Mol Biol. 1997 Jul;62(4):321-5. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- AgonistDownregulator
- General Function
- Zinc ion binding
- Specific Function
- Nuclear hormone receptor. Binds estrogens with an affinity similar to that of ESR1, and activates expression of reporter genes containing estrogen response elements (ERE) in an estrogen-dependent m...
- Gene Name
- ESR2
- Uniprot ID
- Q92731
- Uniprot Name
- Estrogen receptor beta
- Molecular Weight
- 59215.765 Da
References
- Aguirre C, Jayaraman A, Pike C, Baudry M: Progesterone inhibits estrogen-mediated neuroprotection against excitotoxicity by down-regulating estrogen receptor-beta. J Neurochem. 2010 Dec;115(5):1277-87. doi: 10.1111/j.1471-4159.2010.07038.x. Epub 2010 Oct 26. [Article]
- Jayaraman A, Pike CJ: Progesterone attenuates oestrogen neuroprotection via downregulation of oestrogen receptor expression in cultured neurones. J Neuroendocrinol. 2009 Jan;21(1):77-81. doi: 10.1111/j.1365-2826.2008.01801.x. [Article]
- Tessier C, Deb S, Prigent-Tessier A, Ferguson-Gottschall S, Gibori GB, Shiu RP, Gibori G: Estrogen receptors alpha and beta in rat decidua cells: cell-specific expression and differential regulation by steroid hormones and prolactin. Endocrinology. 2000 Oct;141(10):3842-51. doi: 10.1210/endo.141.10.7734. [Article]
- Montero Girard G, Vanzulli SI, Cerliani JP, Bottino MC, Bolado J, Vela J, Becu-Villalobos D, Benavides F, Gutkind S, Patel V, Molinolo A, Lanari C: Association of estrogen receptor-alpha and progesterone receptor A expression with hormonal mammary carcinogenesis: role of the host microenvironment. Breast Cancer Res. 2007;9(2):R22. [Article]
Enzymes
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Steroid 17-alpha-monooxygenase activity
- Specific Function
- Conversion of pregnenolone and progesterone to their 17-alpha-hydroxylated products and subsequently to dehydroepiandrosterone (DHEA) and androstenedione. Catalyzes both the 17-alpha-hydroxylation ...
- Gene Name
- CYP17A1
- Uniprot ID
- P05093
- Uniprot Name
- Steroid 17-alpha-hydroxylase/17,20 lyase
- Molecular Weight
- 57369.995 Da
References
- Kossor DC, Kominami S, Takemori S, Colby HD: Role of the steroid 17 alpha-hydroxylase in spironolactone-mediated destruction of adrenal cytochrome P-450. Mol Pharmacol. 1991 Aug;40(2):321-5. [Article]
- Kater CE, Biglieri EG: Disorders of steroid 17 alpha-hydroxylase deficiency. Endocrinol Metab Clin North Am. 1994 Jun;23(2):341-57. [Article]
- Petrunak EM, DeVore NM, Porubsky PR, Scott EE: Structures of human steroidogenic cytochrome P450 17A1 with substrates. J Biol Chem. 2014 Nov 21;289(47):32952-64. doi: 10.1074/jbc.M114.610998. Epub 2014 Oct 9. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- Vitamin d 24-hydroxylase activity
- Specific Function
- Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
- Gene Name
- CYP1A1
- Uniprot ID
- P04798
- Uniprot Name
- Cytochrome P450 1A1
- Molecular Weight
- 58164.815 Da
References
- Schwarz D, Kisselev P, Schunck WH, Chernogolov A, Boidol W, Cascorbi I, Roots I: Allelic variants of human cytochrome P450 1A1 (CYP1A1): effect of T461N and I462V substitutions on steroid hydroxylase specificity. Pharmacogenetics. 2000 Aug;10(6):519-30. [Article]
- Niwa T, Yabusaki Y, Honma K, Matsuo N, Tatsuta K, Ishibashi F, Katagiri M: Contribution of human hepatic cytochrome P450 isoforms to regioselective hydroxylation of steroid hormones. Xenobiotica. 1998 Jun;28(6):539-47. doi: 10.1080/004982598239290 . [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- Oxygen binding
- Specific Function
- Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
- Gene Name
- CYP1B1
- Uniprot ID
- Q16678
- Uniprot Name
- Cytochrome P450 1B1
- Molecular Weight
- 60845.33 Da
References
- Shimada T, Watanabe J, Kawajiri K, Sutter TR, Guengerich FP, Gillam EM, Inoue K: Catalytic properties of polymorphic human cytochrome P450 1B1 variants. Carcinogenesis. 1999 Aug;20(8):1607-13. doi: 10.1093/carcin/20.8.1607. [Article]
- Li F, Zhu W, Gonzalez FJ: Potential role of CYP1B1 in the development and treatment of metabolic diseases. Pharmacol Ther. 2017 Oct;178:18-30. doi: 10.1016/j.pharmthera.2017.03.007. Epub 2017 Mar 16. [Article]
- Jansson I, Stoilov I, Sarfarazi M, Schenkman JB: Effect of two mutations of human CYP1B1, G61E and R469W, on stability and endogenous steroid substrate metabolism. Pharmacogenetics. 2001 Dec;11(9):793-801. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inducer
- General Function
- Steroid hydroxylase activity
- Specific Function
- Exhibits a high coumarin 7-hydroxylase activity. Can act in the hydroxylation of the anti-cancer drugs cyclophosphamide and ifosphamide. Competent in the metabolic activation of aflatoxin B1. Const...
- Gene Name
- CYP2A6
- Uniprot ID
- P11509
- Uniprot Name
- Cytochrome P450 2A6
- Molecular Weight
- 56501.005 Da
References
- Choi SY, Koh KH, Jeong H: Isoform-specific regulation of cytochromes P450 expression by estradiol and progesterone. Drug Metab Dispos. 2013 Feb;41(2):263-9. doi: 10.1124/dmd.112.046276. Epub 2012 Jul 26. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- Steroid hydroxylase activity
- Specific Function
- Responsible for the metabolism of many drugs and environmental chemicals that it oxidizes. It is involved in the metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic...
- Gene Name
- CYP2D6
- Uniprot ID
- P10635
- Uniprot Name
- Cytochrome P450 2D6
- Molecular Weight
- 55768.94 Da
References
- Niwa T, Hiroi T, Tsuzuki D, Yamamoto S, Narimatsu S, Fukuda T, Azuma J, Funae Y: Effect of genetic polymorphism on the metabolism of endogenous neuroactive substances, progesterone and p-tyramine, catalyzed by CYP2D6. Brain Res Mol Brain Res. 2004 Oct 22;129(1-2):117-23. doi: 10.1016/j.molbrainres.2004.06.030. [Article]
- Niwa T, Okada K, Hiroi T, Imaoka S, Narimatsu S, Funae Y: Effect of psychotropic drugs on the 21-hydroxylation of neurosteroids, progesterone and allopregnanolone, catalyzed by rat CYP2D4 and human CYP2D6 in the brain. Biol Pharm Bull. 2008 Mar;31(3):348-51. [Article]
- Miller RT, Miksys S, Hoffmann E, Tyndale RF: Ethanol self-administration and nicotine treatment increase brain levels of CYP2D in African green monkeys. Br J Pharmacol. 2014 Jun;171(12):3077-88. doi: 10.1111/bph.12652. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- SubstrateInhibitor
- General Function
- Steroid hydroxylase activity
- Specific Function
- Responsible for the metabolism of a number of therapeutic agents such as the anticonvulsant drug S-mephenytoin, omeprazole, proguanil, certain barbiturates, diazepam, propranolol, citalopram and im...
- Gene Name
- CYP2C19
- Uniprot ID
- P33261
- Uniprot Name
- Cytochrome P450 2C19
- Molecular Weight
- 55930.545 Da
References
- Lin Y, Lu P, Tang C, Mei Q, Sandig G, Rodrigues AD, Rushmore TH, Shou M: Substrate inhibition kinetics for cytochrome P450-catalyzed reactions. Drug Metab Dispos. 2001 Apr;29(4 Pt 1):368-74. [Article]
- Yamazaki H, Shimada T: Progesterone and testosterone hydroxylation by cytochromes P450 2C19, 2C9, and 3A4 in human liver microsomes. Arch Biochem Biophys. 1997 Oct 1;346(1):161-9. doi: 10.1006/abbi.1997.0302. [Article]
- Gomes LG, Huang N, Agrawal V, Mendonca BB, Bachega TA, Miller WL: Extraadrenal 21-hydroxylation by CYP2C19 and CYP3A4: effect on 21-hydroxylase deficiency. J Clin Endocrinol Metab. 2009 Jan;94(1):89-95. doi: 10.1210/jc.2008-1174. Epub 2008 Oct 28. [Article]
- Mitsuda M, Iwasaki M, Asahi S: Cynomolgus monkey cytochrome P450 2C43: cDNA cloning, heterologous expression, purification and characterization. J Biochem. 2006 May;139(5):865-72. doi: 10.1093/jb/mvj093. [Article]
- Richardson TH, Jung F, Griffin KJ, Wester M, Raucy JL, Kemper B, Bornheim LM, Hassett C, Omiecinski CJ, Johnson EF: A universal approach to the expression of human and rabbit cytochrome P450s of the 2C subfamily in Escherichia coli. Arch Biochem Biophys. 1995 Oct 20;323(1):87-96. doi: 10.1006/abbi.1995.0013. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- SubstrateInhibitor
- General Function
- Steroid hydroxylase activity
- Specific Function
- Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
- Gene Name
- CYP2C9
- Uniprot ID
- P11712
- Uniprot Name
- Cytochrome P450 2C9
- Molecular Weight
- 55627.365 Da
References
- Yamazaki H, Shimada T: Progesterone and testosterone hydroxylation by cytochromes P450 2C19, 2C9, and 3A4 in human liver microsomes. Arch Biochem Biophys. 1997 Oct 1;346(1):161-9. doi: 10.1006/abbi.1997.0302. [Article]
- Du H, Wei Z, Yan Y, Xiong Y, Zhang X, Shen L, Ruan Y, Wu X, Xu Q, He L, Qin S: Functional Characterization of Human CYP2C9 Allelic Variants in COS-7 Cells. Front Pharmacol. 2016 Apr 25;7:98. doi: 10.3389/fphar.2016.00098. eCollection 2016. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- Oxygen binding
- Specific Function
- Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
- Gene Name
- CYP3A5
- Uniprot ID
- P20815
- Uniprot Name
- Cytochrome P450 3A5
- Molecular Weight
- 57108.065 Da
References
- Quinney SK, Benjamin T, Zheng X, Patil AS: Characterization of Maternal and Fetal CYP3A-Mediated Progesterone Metabolism. Fetal Pediatr Pathol. 2017 Oct;36(5):400-411. doi: 10.1080/15513815.2017.1354411. Epub 2017 Sep 26. [Article]
- Bustos ML, Caritis SN, Jablonski KA, Reddy UM, Sorokin Y, Manuck T, Varner MW, Wapner RJ, Iams JD, Carpenter MW, Peaceman AM, Mercer BM, Sciscione A, Rouse DJ, Ramin SM: The association among cytochrome P450 3A, progesterone receptor polymorphisms, plasma 17-alpha hydroxyprogesterone caproate concentrations, and spontaneous preterm birth. Am J Obstet Gynecol. 2017 Sep;217(3):369.e1-369.e9. doi: 10.1016/j.ajog.2017.05.019. Epub 2017 May 15. [Article]
- CYP3A5 cytochrome P450 family 3 subfamily A member 5 [ Homo sapiens (human) ] [Link]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- SubstrateInducer
- General Function
- Vitamin d3 25-hydroxylase activity
- Specific Function
- Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation react...
- Gene Name
- CYP3A4
- Uniprot ID
- P08684
- Uniprot Name
- Cytochrome P450 3A4
- Molecular Weight
- 57342.67 Da
References
- Jang GR, Wrighton SA, Benet LZ: Identification of CYP3A4 as the principal enzyme catalyzing mifepristone (RU 486) oxidation in human liver microsomes. Biochem Pharmacol. 1996 Sep 13;52(5):753-61. [Article]
- Sevrioukova IF, Poulos TL: Understanding the mechanism of cytochrome P450 3A4: recent advances and remaining problems. Dalton Trans. 2013 Mar 7;42(9):3116-26. doi: 10.1039/c2dt31833d. Epub 2012 Sep 27. [Article]
- Polic V, Auclair K: Allosteric Activation of Cytochrome P450 3A4 via Progesterone Bioconjugation. Bioconjug Chem. 2017 Apr 19;28(4):885-889. doi: 10.1021/acs.bioconjchem.6b00604. Epub 2017 Mar 29. [Article]
- Williams PA, Cosme J, Vinkovic DM, Ward A, Angove HC, Day PJ, Vonrhein C, Tickle IJ, Jhoti H: Crystal structures of human cytochrome P450 3A4 bound to metyrapone and progesterone. Science. 2004 Jul 30;305(5684):683-6. Epub 2004 Jul 15. [Article]
- Tsunoda SM, Harris RZ, Mroczkowski PJ, Benet LZ: Preliminary evaluation of progestins as inducers of cytochrome P450 3A4 activity in postmenopausal women. J Clin Pharmacol. 1998 Dec;38(12):1137-43. [Article]
- Choi SY, Koh KH, Jeong H: Isoform-specific regulation of cytochromes P450 expression by estradiol and progesterone. Drug Metab Dispos. 2013 Feb;41(2):263-9. doi: 10.1124/dmd.112.046276. Epub 2012 Jul 26. [Article]
- Prometrium FDA label [File]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- SubstrateInhibitor
- Curator comments
- Data are limited to the results of in vitro studies.
- General Function
- Oxygen binding
- Specific Function
- Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
- Gene Name
- CYP3A7
- Uniprot ID
- P24462
- Uniprot Name
- Cytochrome P450 3A7
- Molecular Weight
- 57525.03 Da
References
- Quinney SK, Benjamin T, Zheng X, Patil AS: Characterization of Maternal and Fetal CYP3A-Mediated Progesterone Metabolism. Fetal Pediatr Pathol. 2017 Oct;36(5):400-411. doi: 10.1080/15513815.2017.1354411. Epub 2017 Sep 26. [Article]
- Sharma S, Ellis EC, Dorko K, Zhang S, Mattison DR, Caritis SN, Venkataramanan R, Strom SC: Metabolism of 17alpha-hydroxyprogesterone caproate, an agent for preventing preterm birth, by fetal hepatocytes. Drug Metab Dispos. 2010 May;38(5):723-7. doi: 10.1124/dmd.109.029918. Epub 2010 Jan 22. [Article]
Transporters
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- SubstrateInhibitorInducer
- General Function
- Xenobiotic-transporting atpase activity
- Specific Function
- Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells.
- Gene Name
- ABCB1
- Uniprot ID
- P08183
- Uniprot Name
- Multidrug resistance protein 1
- Molecular Weight
- 141477.255 Da
References
- Romiti N, Tramonti G, Chieli E: Influence of different chemicals on MDR-1 P-glycoprotein expression and activity in the HK-2 proximal tubular cell line. Toxicol Appl Pharmacol. 2002 Sep 1;183(2):83-91. [Article]
- Wang EJ, Casciano CN, Clement RP, Johnson WW: Active transport of fluorescent P-glycoprotein substrates: evaluation as markers and interaction with inhibitors. Biochem Biophys Res Commun. 2001 Nov 30;289(2):580-5. [Article]
- Leonessa F, Kim JH, Ghiorghis A, Kulawiec RJ, Hammer C, Talebian A, Clarke R: C-7 analogues of progesterone as potent inhibitors of the P-glycoprotein efflux pump. J Med Chem. 2002 Jan 17;45(2):390-8. [Article]
- Ueda K, Okamura N, Hirai M, Tanigawara Y, Saeki T, Kioka N, Komano T, Hori R: Human P-glycoprotein transports cortisol, aldosterone, and dexamethasone, but not progesterone. J Biol Chem. 1992 Dec 5;267(34):24248-52. [Article]
- Nagy H, Goda K, Fenyvesi F, Bacso Z, Szilasi M, Kappelmayer J, Lustyik G, Cianfriglia M, Szabo G Jr: Distinct groups of multidrug resistance modulating agents are distinguished by competition of P-glycoprotein-specific antibodies. Biochem Biophys Res Commun. 2004 Mar 19;315(4):942-9. [Article]
- Yamazaki M, Neway WE, Ohe T, Chen I, Rowe JF, Hochman JH, Chiba M, Lin JH: In vitro substrate identification studies for p-glycoprotein-mediated transport: species difference and predictability of in vivo results. J Pharmacol Exp Ther. 2001 Mar;296(3):723-35. [Article]
- Adachi Y, Suzuki H, Sugiyama Y: Comparative studies on in vitro methods for evaluating in vivo function of MDR1 P-glycoprotein. Pharm Res. 2001 Dec;18(12):1660-8. [Article]
- Borgnia MJ, Eytan GD, Assaraf YG: Competition of hydrophobic peptides, cytotoxic drugs, and chemosensitizers on a common P-glycoprotein pharmacophore as revealed by its ATPase activity. J Biol Chem. 1996 Feb 9;271(6):3163-71. [Article]
- Kim WY, Benet LZ: P-glycoprotein (P-gp/MDR1)-mediated efflux of sex-steroid hormones and modulation of P-gp expression in vitro. Pharm Res. 2004 Jul;21(7):1284-93. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Quaternary ammonium group transmembrane transporter activity
- Specific Function
- Mediates tubular uptake of organic compounds from circulation. Mediates the influx of agmatine, dopamine, noradrenaline (norepinephrine), serotonin, choline, famotidine, ranitidine, histamin, creat...
- Gene Name
- SLC22A2
- Uniprot ID
- O15244
- Uniprot Name
- Solute carrier family 22 member 2
- Molecular Weight
- 62579.99 Da
References
- Hayer-Zillgen M, Bruss M, Bonisch H: Expression and pharmacological profile of the human organic cation transporters hOCT1, hOCT2 and hOCT3. Br J Pharmacol. 2002 Jul;136(6):829-36. [Article]
- Wu X, Kekuda R, Huang W, Fei YJ, Leibach FH, Chen J, Conway SJ, Ganapathy V: Identity of the organic cation transporter OCT3 as the extraneuronal monoamine transporter (uptake2) and evidence for the expression of the transporter in the brain. J Biol Chem. 1998 Dec 4;273(49):32776-86. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Secondary active organic cation transmembrane transporter activity
- Specific Function
- Translocates a broad array of organic cations with various structures and molecular weights including the model compounds 1-methyl-4-phenylpyridinium (MPP), tetraethylammonium (TEA), N-1-methylnico...
- Gene Name
- SLC22A1
- Uniprot ID
- O15245
- Uniprot Name
- Solute carrier family 22 member 1
- Molecular Weight
- 61153.345 Da
References
- Hayer-Zillgen M, Bruss M, Bonisch H: Expression and pharmacological profile of the human organic cation transporters hOCT1, hOCT2 and hOCT3. Br J Pharmacol. 2002 Jul;136(6):829-36. [Article]
- Wu X, Kekuda R, Huang W, Fei YJ, Leibach FH, Chen J, Conway SJ, Ganapathy V: Identity of the organic cation transporter OCT3 as the extraneuronal monoamine transporter (uptake2) and evidence for the expression of the transporter in the brain. J Biol Chem. 1998 Dec 4;273(49):32776-86. [Article]
- Lozano E, Herraez E, Briz O, Robledo VS, Hernandez-Iglesias J, Gonzalez-Hernandez A, Marin JJ: Role of the plasma membrane transporter of organic cations OCT1 and its genetic variants in modern liver pharmacology. Biomed Res Int. 2013;2013:692071. doi: 10.1155/2013/692071. Epub 2013 Jul 31. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Toxin transporter activity
- Specific Function
- Mediates potential-dependent transport of a variety of organic cations. May play a significant role in the disposition of cationic neurotoxins and neurotransmitters in the brain.
- Gene Name
- SLC22A3
- Uniprot ID
- O75751
- Uniprot Name
- Solute carrier family 22 member 3
- Molecular Weight
- 61279.485 Da
References
- Hayer-Zillgen M, Bruss M, Bonisch H: Expression and pharmacological profile of the human organic cation transporters hOCT1, hOCT2 and hOCT3. Br J Pharmacol. 2002 Jul;136(6):829-36. [Article]
- Wu X, Kekuda R, Huang W, Fei YJ, Leibach FH, Chen J, Conway SJ, Ganapathy V: Identity of the organic cation transporter OCT3 as the extraneuronal monoamine transporter (uptake2) and evidence for the expression of the transporter in the brain. J Biol Chem. 1998 Dec 4;273(49):32776-86. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Transporter activity
- Specific Function
- Involved in the ATP-dependent secretion of bile salts into the canaliculus of hepatocytes.
- Gene Name
- ABCB11
- Uniprot ID
- O95342
- Uniprot Name
- Bile salt export pump
- Molecular Weight
- 146405.83 Da
References
- Wang EJ, Casciano CN, Clement RP, Johnson WW: Fluorescent substrates of sister-P-glycoprotein (BSEP) evaluated as markers of active transport and inhibition: evidence for contingent unequal binding sites. Pharm Res. 2003 Apr;20(4):537-44. [Article]
- Abu-Hayyeh S, Williamson C: Progesterone metabolites as farnesoid X receptor inhibitors. Dig Dis. 2015;33(3):300-6. doi: 10.1159/000371565. Epub 2015 May 27. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Transporter activity
- Specific Function
- Mediates export of organic anions and drugs from the cytoplasm. Mediates ATP-dependent transport of glutathione and glutathione conjugates, leukotriene C4, estradiol-17-beta-o-glucuronide, methotre...
- Gene Name
- ABCC1
- Uniprot ID
- P33527
- Uniprot Name
- Multidrug resistance-associated protein 1
- Molecular Weight
- 171589.5 Da
References
- Payen L, Delugin L, Courtois A, Trinquart Y, Guillouzo A, Fardel O: Reversal of MRP-mediated multidrug resistance in human lung cancer cells by the antiprogestatin drug RU486. Biochem Biophys Res Commun. 1999 May 19;258(3):513-8. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Virus receptor activity
- Specific Function
- The hepatic sodium/bile acid uptake system exhibits broad substrate specificity and transports various non-bile acid organic compounds as well. It is strictly dependent on the extracellular presenc...
- Gene Name
- SLC10A1
- Uniprot ID
- Q14973
- Uniprot Name
- Sodium/bile acid cotransporter
- Molecular Weight
- 38118.64 Da
References
- Schroeder A, Eckhardt U, Stieger B, Tynes R, Schteingart CD, Hofmann AF, Meier PJ, Hagenbuch B: Substrate specificity of the rat liver Na(+)-bile salt cotransporter in Xenopus laevis oocytes and in CHO cells. Am J Physiol. 1998 Feb;274(2 Pt 1):G370-5. [Article]
- Abu-Hayyeh S, Williamson C: Progesterone metabolites as farnesoid X receptor inhibitors. Dig Dis. 2015;33(3):300-6. doi: 10.1159/000371565. Epub 2015 May 27. [Article]
- Abu-Hayyeh S, Martinez-Becerra P, Sheikh Abdul Kadir SH, Selden C, Romero MR, Rees M, Marschall HU, Marin JJ, Williamson C: Inhibition of Na+-taurocholate Co-transporting polypeptide-mediated bile acid transport by cholestatic sulfated progesterone metabolites. J Biol Chem. 2010 May 28;285(22):16504-12. doi: 10.1074/jbc.M109.072140. Epub 2010 Feb 20. [Article]
- Kim RB, Leake B, Cvetkovic M, Roden MM, Nadeau J, Walubo A, Wilkinson GR: Modulation by drugs of human hepatic sodium-dependent bile acid transporter (sodium taurocholate cotransporting polypeptide) activity. J Pharmacol Exp Ther. 1999 Dec;291(3):1204-9. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- Curator comments
- Data regarding this transporter activity are limited to in vitro studies.
- General Function
- Sodium-independent organic anion transmembrane transporter activity
- Specific Function
- Mediates the Na(+)-independent uptake of organic anions such as pravastatin, taurocholate, methotrexate, dehydroepiandrosterone sulfate, 17-beta-glucuronosyl estradiol, estrone sulfate, prostagland...
- Gene Name
- SLCO1B1
- Uniprot ID
- Q9Y6L6
- Uniprot Name
- Solute carrier organic anion transporter family member 1B1
- Molecular Weight
- 76447.99 Da
References
- Gui C, Obaidat A, Chaguturu R, Hagenbuch B: Development of a cell-based high-throughput assay to screen for inhibitors of organic anion transporting polypeptides 1B1 and 1B3. Curr Chem Genomics. 2010 Mar 1;4:1-8. doi: 10.2174/1875397301004010001. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- InhibitorInducer
- General Function
- Xenobiotic-transporting atpase activity
- Specific Function
- High-capacity urate exporter functioning in both renal and extrarenal urate excretion. Plays a role in porphyrin homeostasis as it is able to mediates the export of protoporhyrin IX (PPIX) both fro...
- Gene Name
- ABCG2
- Uniprot ID
- Q9UNQ0
- Uniprot Name
- ATP-binding cassette sub-family G member 2
- Molecular Weight
- 72313.47 Da
References
- Mao Q, Unadkat JD: Role of the breast cancer resistance protein (BCRP/ABCG2) in drug transport--an update. AAPS J. 2015 Jan;17(1):65-82. doi: 10.1208/s12248-014-9668-6. Epub 2014 Sep 19. [Article]
- Mao Q: BCRP/ABCG2 in the placenta: expression, function and regulation. Pharm Res. 2008 Jun;25(6):1244-55. doi: 10.1007/s11095-008-9537-z. [Article]
- Wu X, Zhang X, Sun L, Zhang H, Li L, Wang X, Li W, Su P, Hu J, Gao P, Zhou G: Progesterone negatively regulates BCRP in progesterone receptor-positive human breast cancer cells. Cell Physiol Biochem. 2013;32(2):344-54. doi: 10.1159/000354442. Epub 2013 Aug 14. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inducer
- General Function
- Sodium-independent organic anion transmembrane transporter activity
- Specific Function
- Mediates the Na(+)-independent uptake of organic anions such as 17-beta-glucuronosyl estradiol, taurocholate, triiodothyronine (T3), leukotriene C4, dehydroepiandrosterone sulfate (DHEAS), methotre...
- Gene Name
- SLCO1B3
- Uniprot ID
- Q9NPD5
- Uniprot Name
- Solute carrier organic anion transporter family member 1B3
- Molecular Weight
- 77402.175 Da
References
- Patik I, Szekely V, Nemet O, Szepesi A, Kucsma N, Varady G, Szakacs G, Bakos E, Ozvegy-Laczka C: Identification of novel cell-impermeant fluorescent substrates for testing the function and drug interaction of Organic Anion-Transporting Polypeptides, OATP1B1/1B3 and 2B1. Sci Rep. 2018 Feb 8;8(1):2630. doi: 10.1038/s41598-018-20815-1. [Article]
- Gui C, Obaidat A, Chaguturu R, Hagenbuch B: Development of a cell-based high-throughput assay to screen for inhibitors of organic anion transporting polypeptides 1B1 and 1B3. Curr Chem Genomics. 2010 Mar 1;4:1-8. doi: 10.2174/1875397301004010001. [Article]
Drug created at June 13, 2005 13:24 / Updated at February 20, 2024 23:55