Norethisterone
Identification
- Summary
Norethisterone is a synthetic second-generation progestin used for contraception, prevention of endometrial hyperplasia in hormone replacement therapy, and in the treatment of other hormone-mediated illnesses such as endometriosis.
- Brand Names
- Activella 1/0.5 28 Day, Activelle, Alyacen 1/35, Alyacen 7/7/7, Amabelz 0.5/0.1 28 Day, Aranelle 28, Aurovela, Aurovela Fe, Aygestin, Balziva 28 Day, Blisovi 21 Fe 1.5/30 28 Day Pack, Blisovi 21 Fe 1/20 28 Day Pack, Blisovi 24 Fe 1/20 28 Day, Brevicon, Briellyn 28 Day, Camila 28 Day, Charlotte 24 Fe Chewable 28 Day, Combipatch, Cyclafem 1/35 28 Day, Cyclafem 7/7/7 28 Day, Cyonanz 28 Day, Dasetta 1/35 28 Day, Dasetta 7/7/7 28 Day, Deblitane 28 Day, Emzahh 28 Day, Errin 28 Day, Estalis, Etyqa 0.5/0.1 28 Day, Femcon Fe 28 Day, Femhrt 0.5/2.5 28 Day, Finzala 24 Fe Chewable 28 Day, Fyavolv, Gemmily 28 Day, Hailey 1.5/30 21 Day, Hailey 24 Fe 28 Day, Hailey Fe 1.5/30 28 Day, Hailey Fe 1/20 28 Day, Heather 28 Day, Incassia, Jencycla 28 Day, Jinteli, Junel 1.5/30 21 Day, Junel 1/20 21 Day, Junel Fe 1.5/30 28 Day, Junel Fe 1/20 28 Day, Junel Fe 24 1/20 28 Day, Kaitlib Fe 28 Day, Larin 1.5/30, Larin 1/20, Larin 24 Fe 1/20, Larin Fe 1.5/30, Larin Fe 1/20, Layolis Fe 28, Leena 28 Day, Lo Loestrin Fe 28 Day, Loestrin 1.5/30 21 Day, Loestrin 24 Fe 28 Day, Loestrin Fe 1/20 28 Day, Lolo, Lomedia 24 Fe, Lopreeza 1/0.5 28 Day, Lupaneta Pack 1-month, Lyleq 28 Day, Lyza, Melodetta 24 Fe Chewable 28 Day, Merzee 28 Day, Mibelas 24 Fe Chewable 28 Day, Microgestin 1.5/30 21 Day, Microgestin 1/20 21 Day, Microgestin 24 Fe 28 Day, Microgestin Fe 1.5/30 28 Day, Microgestin Fe 1/20 28 Day, Mimvey, Minastrin 24 Fe Chewable 28 Day, Myfembree, Necon 0.5/35 28 Day, Necon 1/35 28 Day, Necon 7/7/7 28 Day, Nexesta Fe 28 Day, Nora-BE 28 Day, Norlutate, Norlyda 28 Day, Norlyroc 28 Day, Nortrel 1/35 21 Day, Nortrel 1/35 28 Day, Nortrel 7/7/7 28 Day, Nylia 1/35 28 Day, Nylia 7/7/7 28 Day, Oriahnn 28 Day Kit, Ortho Micronor, Ortho Micronor 28 Day, Ortho-novum 7/7/7 28 Day, Philith 28 Day, Pirmella 1/35 28 Day, Pirmella 7/7/7 28 Day, Rhuzdah 28 Day, Select, Sharobel 28 Day, Synphasic, Tarina 24 Fe 1/20 28 Day, Tarina Fe 1/20 28 Day, Taysofy 28 Day, Taytulla 28 Day, Tilia Fe, Tri-legest 28 Day, Tulana 28 Day, Vyfemla 28 Day, Wera 28 Day, Wymzya Fe 28 Day, Zenchent
- Generic Name
- Norethisterone
- DrugBank Accession Number
- DB00717
- Background
Norethisterone, also known as norethindrone, is a synthetic progestational hormone belonging to the 19-nortestosterone-derived class of progestins.8 It is further classified as a second-generation progestin, along with levonorgestrel and its derivatives, and is the active form of several other progestins including norethynodrel and lynestrenol.8 Norethisterone mimics the actions of endogenous progesterone, albeit with a greater potency,5 and is used on its own or in combination with estrogen derivatives in a variety of applications including contraception and hormone replacement therapy.14,15,16,19 First derived in 1951 in Mexico City, norethisterone was originally intended for use as a remedy for irregular menstruation and endometriosis, and was not marketed for use as an oral contraceptive until 1962.21
- Type
- Small Molecule
- Groups
- Approved
- Structure
- Weight
- Average: 298.4192
Monoisotopic: 298.193280076 - Chemical Formula
- C20H26O2
- Synonyms
- (17alpha)-17-ethynyl-17-hydroxyestra-4,8(14),9-trien-3-one
- 17-hydroxy-19-nor-17-α-pregn-4-en-20-yn-3-one
- 17-hydroxy-19-nor-17α-pregn-4-en-20-yn-3-one
- 17-α-ethynyl-17-hydroxy-4-estren-3-one
- 17-α-ethynyl-19-norandrost-4-en-17-β-ol-3-one
- 17-α-ethynyl-19-nortestosterone
- 17-α-ethynyl-4-estren-17-ol-3-one
- 17-β-hydroxy-19-norpregn-4-en-20-yn-3-one
- 17α-ethinyl-19-nortestosterone
- 17α-ethinylestra-4-en-17β-ol-3-one
- 17α-ethynyl-17-hydroxy-4-estren-3-one
- 17α-ethynyl-17β-hydroxy-19-norandrost-4-en-3-one
- 17α-ethynyl-19-nor-4-androsten-17β-ol-3-one
- 17α-ethynyl-19-norandrost-4-en-17β-ol-3-one
- 17α-ethynyl-19-nortestosterone
- 17α-ethynyl-4-estren-17-ol-3-one
- 17β-hydroxy-19-norpregn-4-en-20-yn-3-one
- 19-nor-17-α-ethynyl-17-β-hydroxy-4-androsten-3-one
- 19-nor-17-α-ethynylandrosten-17-β-ol-3-one
- 19-nor-17-α-ethynyltestosterone
- 19-Nor-17alpha-ethynyl-17beta-hydroxy-4-androsten-3-one
- 19-nor-17α-ethynyl-17β-hydroxy-4-androsten-3-one
- 19-nor-17α-ethynylandrosten-17β-ol-3-one
- 19-nor-17α-ethynyltestosterone
- 19-nor-ethindrone
- 19-norethisterone
- 4-estren-17α-ethynyl-17β-ol-3-one
- Norethindrone
- Norethisteron
- Noréthistérone
- Norethisterone
- Norethisteronum
- Noretisterona
- External IDs
- NSC-9564
- SC-4640
Pharmacology
- Indication
Norethisterone is indicated as an oral contraceptive when given as monotherapy14 or in combination with an estrogen component, such as ethinylestradiol or estradiol.18,19 In combination with an estrogen component, oral norethisterone is also indicated as a hormone replacement therapy in the treatment of postmenopausal osteoporosis and moderate-to-severe vasomotor symptoms arising from menopause.16 When applied via transdermal patch, the combination of norethisterone and estradiol is indicated for the treatment of hypoestrogenism, vulvovaginal atrophy, and moderate-severe vasomotor symptoms.15
Norethisterone, taken in combination with intramuscular leuprolide, is also indicated for the symptomatic treatment of endometriosis-related pain.17
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 Used in combination for symptomatic treatment of Endometriosis related pain Combination Product in combination with: Ethanol (DB00898), Leuprolide (DB00007) •••••••••••• •••••••••• ••••••••••• •••••••• •••••••• •••••• Used in combination to manage Heavy menstrual bleeding Combination Product in combination with: Estradiol (DB00783), Relugolix (DB11853) •••••••••••• ••••••••••••• •••••• Used in combination to treat Moderate to severe vasomotor symptoms Combination Product in combination with: Estradiol (DB00783) •••••••••••• ••••• Used in combination to prevent Osteoporosis Combination Product in combination with: Estradiol valerate (DB13956) •••••••••••• •••••• •••••••••••••• •••••••••• •• •• •••••••••• •• ••••• •••••••••• •••• •••• •• •••••••• •••••• Used in combination to prevent Postmenopausal osteoporosis (pmo) Combination Product in combination with: Ethinylestradiol (DB00977) •••••••••••• •••••• - 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
Norethisterone is a synthetic oral progestin used for contraception or to treat other hormone-related conditions such as menopausal symptoms and endometriosis. As a synthetic progestin, norethisterone acts similarly to endogenous progesterone but with a much higher potency - it acts at the pelvic level to alter cervical and endometrial function, as well as via the inhibition of pituitary hormones that play a role in follicular maturation and ovulation.14 A small increase in the risk of developing breast cancer has been observed in patients using combined oral contraceptives, with some evidence also implicating progestin-only pills - patients starting hormonal contraception should be advised of this risk and should employ routine breast self-examinations to check for evidence of any developing masses.14
- Mechanism of action
On a molecular level, progestins like norethisterone exert their effects on target cells via binding to progesterone receptors that result in downstream changes to target genes.16 Target cells are found in the reproductive tract, breast, pituitary, hypothalamus, skeletal tissue, and central nervous system.16 Contraceptive efficacy is derived mainly from changes to the cervical mucus, wherein norethisterone increases the cell content and viscosity of the mucous to impede sperm transport and migration.14 Norethisterone also induces a variety of changes to the endometrium - including atrophy, irregular secretion, and suppressed proliferation - that make it inhospitable for implantation.14,12 Working via a negative feedback loop, norethisterone also acts on both the hypothalamus and anterior pituitary to suppress the release of follicle-stimulating hormone (FSH) and luteinizing hormone (LH) from the anterior pituitary. Suppression of these hormones prevents follicular development, ovulation, and corpus luteum development.12
When used as a component of hormone replacement therapy in menopausal women, norethisterone’s value is mainly in suppressing the growth of the endometrium.13 As estrogen stimulates endometrial growth, the unopposed use of estrogen in postmenopausal women with an intact uterus can lead to endometrial hyperplasia which can increase the risk of endometrial cancer. The addition of a progestin to a hormone replacement therapy in this population protects against this endometrial hyperplasia and, therefore, lowers the risk associated with the use of hormone replacement therapies.
Norethisterone, along with other progestins and endogenous progesterone, has a low affinity for other steroid receptors, such as the androgen receptor and glucocorticoid receptor.8,5 While affinity and agonistic activity at these receptors is minimal, it is thought that androgen receptor agonism is responsible for some of the adverse effects observed with progestin use (e.g. acne, serum lipid changes).8
Target Actions Organism AProgesterone receptor agonistHumans UAndrogen receptor agonistHumans UGlucocorticoid receptor agonistHumans - Absorption
The Cmax of norethisterone following oral administration of a single dose ranges from 5.39 to 7.36 ng/mL with a Tmax of 1-2 hours.14,16,19 AUC0-24 values following single oral doses range from approximately 30 to 37 ng*hr/mL.14,16,19 The oral bioavailability of norethisterone is approximately 64%.19 When applied transdermally, norethisterone is well-absorbed through the skin, reaches steady-state concentrations within 24 hours, and has a Cmax ranging from 617 to 1060 pg/mL at steady state.15
Norethisterone is often formulated as norethisterone acetate, which is completely and rapidly deacetylated to norethisterone following oral administration - the disposition of norethisterone acetate is indistinguishable from that of orally administered norethisterone.19
- Volume of distribution
The volume of distribution of norethisterone is approximately 4 L/kg.4,19 Sulfated metabolites of norethisterone, as well as small quantities of parent drug, have been shown to distribute into breast milk.11
- Protein binding
Norethisterone is 38% bound to sex hormone-binding globulin and 61% bound to albumin.4,19
- Metabolism
Norethisterone is extensively metabolized, primarily in the liver, to a number of metabolites via partial and total reduction of its A-ring.6 The enzymes predominantly involved are 3α- and 3β-hydroxysteroid dehydrogenase (HSD) as well as 5α- and 5β-reductase.6,5 The 5α-reduced metabolites, including 5α-dihydronorethisterone and its derivatives, appear to carry biological activity while the 5β-reduced metabolites appear inactive.5 Norethisterone and its metabolites are also extensively conjugated - most of the plasmatic metabolites are sulfate conjugates, while most of the urinary metabolites are glucuronide conjugates.4,19 The major metabolites in plasma are a disulfate conjugate of 3α,5α-tetrahydronorethisterone and a monosulfate conjugate of 3α,5β-tetrahydronorethisterone, while the major metabolite(s) in the urine are comprised of glucuronide and/or sulfate conjugates of 3α,5β-tetrahydronorethisterone.10
Norethisterone has also been observed to undergo some degree of metabolism via the cytochrome P450 enzyme system, predominantly by CYP3A4 and, to a much lesser extent, by CYP2C19, CYP1A2, and CYP2A6.7 The metabolites generated by these reactions have not been fully characterized.
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- Route of elimination
Following administration of radio-labeled norethisterone, slightly more than 50% of the administered dose was eliminated in the urine and 20-40% was eliminated in the feces.1
- Half-life
The half-life of norethisterone has been variably estimated as 8-10 hours.4,3,8,14,18
- Clearance
The plasma clearance of norethisterone has been estimated as 0.4 L/hr/kg,4,19 and the intrinsic clearance is approximately 73-81 L/h.9
- Adverse Effects
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- Toxicity
The oral LD50 in mice 6 g/kg and the TDLo in human women is 42 mg/kg.20 There have been no reports of serious ill effects following overdose of oral contraceptives, including following ingestion by children.19,18 Symptoms of overdosage are likely to be consistent with the adverse effect profile of the contraceptive and may, therefore, include significant nausea and/or vomiting.
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">
- Not Available
Interactions
- Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">
- 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 Norethisterone can be increased when it is combined with Abametapir. Abatacept The metabolism of Norethisterone can be increased when combined with Abatacept. Abciximab The risk or severity of adverse effects can be increased when Norethisterone is combined with Abciximab. Abemaciclib The metabolism of Abemaciclib can be decreased when combined with Norethisterone. Acalabrutinib The metabolism of Acalabrutinib can be decreased when combined with Norethisterone. - Food Interactions
- Take with or without food. Co-administration with food slightly alters pharmacokinetics, but not to a clinically significant extent.
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 Ingredients
Ingredient UNII CAS InChI Key Norethisterone acetate 9S44LIC7OJ 51-98-9 IMONTRJLAWHYGT-ZCPXKWAGSA-N - Product Images
- International/Other Brands
- Conludag / Micronovum / Mini-PE / Mini-pill / Norcolut / Noriday / Norluten / Norlutin / Primolut-N / Utovlan
- Brand Name Prescription Products
- Generic Prescription Products
- Mixture Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image Activella Norethisterone acetate (0.1 mg/1) + Estradiol (0.5 mg/1) Tablet, film coated Oral Novo Nordisk 2007-04-09 2017-04-30 US Activella Norethisterone acetate (0.1 mg/1) + Estradiol (0.5 mg/1) Tablet, film coated Oral Gemini Laboratories, LLC 2016-05-12 2019-08-31 US Activella Norethisterone acetate (0.5 mg/1) + Estradiol (1 mg/1) Tablet, film coated Oral Novo Nordisk 2003-07-22 2018-10-31 US Activella Norethisterone acetate (0.1 mg/1) + Estradiol (0.5 mg/1) Tablet, film coated Oral Amneal Pharmaceuticals LLC 2019-05-01 Not applicable US Activella Norethisterone acetate (0.5 mg/1) + Estradiol (1 mg/1) Tablet, film coated Oral Amneal Pharmaceuticals LLC 2019-05-01 Not applicable US
Categories
- ATC Codes
- H01CC53 — Elagolix, estradiol and norethisterone
- H01CC — Anti-gonadotropin-releasing hormones
- H01C — HYPOTHALAMIC HORMONES
- H01 — PITUITARY AND HYPOTHALAMIC HORMONES AND ANALOGUES
- H — SYSTEMIC HORMONAL PREPARATIONS, EXCL. SEX HORMONES AND INSULINS
- H01CC — Anti-gonadotropin-releasing hormones
- H01C — HYPOTHALAMIC HORMONES
- H01 — PITUITARY AND HYPOTHALAMIC HORMONES AND ANALOGUES
- H — SYSTEMIC HORMONAL PREPARATIONS, EXCL. SEX HORMONES AND INSULINS
- G03AA — Progestogens and estrogens, fixed combinations
- G03A — HORMONAL CONTRACEPTIVES FOR SYSTEMIC USE
- G03 — SEX HORMONES AND MODULATORS OF THE GENITAL SYSTEM
- G — GENITO URINARY SYSTEM AND SEX HORMONES
- G03DC — Estren derivatives
- G03D — PROGESTOGENS
- G03 — SEX HORMONES AND MODULATORS OF THE GENITAL SYSTEM
- G — GENITO URINARY SYSTEM AND SEX HORMONES
- G03AB — Progestogens and estrogens, sequential preparations
- G03A — HORMONAL CONTRACEPTIVES FOR SYSTEMIC USE
- G03 — SEX HORMONES AND MODULATORS OF THE GENITAL SYSTEM
- G — GENITO URINARY SYSTEM AND SEX HORMONES
- G03AC — Progestogens
- G03A — HORMONAL CONTRACEPTIVES FOR SYSTEMIC USE
- G03 — SEX HORMONES AND MODULATORS OF THE GENITAL SYSTEM
- G — GENITO URINARY SYSTEM AND SEX HORMONES
- 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
- Anti-Gonadotropin-Releasing Hormones
- Combination Contraceptives (with Estrogen and derivatives)
- Contraceptive Agents, Female
- Contraceptive Agents, Hormonal
- Contraceptives, Oral
- Contraceptives, Oral, Hormonal
- Contraceptives, Oral, Synthetic
- Cytochrome P-450 CYP1A2 Substrates
- Cytochrome P-450 CYP2A6 Substrates
- Cytochrome P-450 CYP2C19 Inducers
- Cytochrome P-450 CYP2C19 Inducers (strength unknown)
- Cytochrome P-450 CYP2C19 Substrates
- Cytochrome P-450 CYP3A Substrates
- Cytochrome P-450 CYP3A4 Substrates
- Cytochrome P-450 CYP3A4 Substrates (strength unknown)
- Cytochrome P-450 CYP3A5 Substrates
- Cytochrome P-450 CYP3A7 Substrates
- Cytochrome P-450 Enzyme Inducers
- Cytochrome P-450 Substrates
- Estren Derivatives
- Fused-Ring Compounds
- Genito Urinary System and Sex Hormones
- Hormonal Contraceptives for Systemic Use
- Hyperglycemia-Associated Agents
- Hypothalamic Hormones
- Norpregnenes
- Norsteroids
- P-glycoprotein inhibitors
- Pituitary and Hypothalamic Hormones and Analogues
- Progestin Contraceptives
- Progestins
- Progestogens and Estrogens, Sequential Preparations
- Reproductive Control Agents
- Sex Hormones and Modulators of the Genital System
- Steroids
- Systemic Hormonal Preparations, Excl. Sex Hormones and Insulins
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as estrogens and derivatives. These are steroids with a structure containing a 3-hydroxylated estrane.
- Kingdom
- Organic compounds
- Super Class
- Lipids and lipid-like molecules
- Class
- Steroids and steroid derivatives
- Sub Class
- Estrane steroids
- Direct Parent
- Estrogens and derivatives
- Alternative Parents
- 3-oxo delta-4-steroids / 17-hydroxysteroids / Delta-4-steroids / Cyclohexenones / Ynones / Tertiary alcohols / Cyclic alcohols and derivatives / Acetylides / Organic oxides / Hydrocarbon derivatives
- Substituents
- 17-hydroxysteroid / 3-oxo-delta-4-steroid / 3-oxosteroid / Acetylide / Alcohol / Aliphatic homopolycyclic compound / Carbonyl group / Cyclic alcohol / Cyclic ketone / Cyclohexenone
- Molecular Framework
- Aliphatic homopolycyclic compounds
- External Descriptors
- terminal acetylenic compound, tertiary alcohol, 3-oxo Delta(4)-steroid, 17beta-hydroxy steroid (CHEBI:7627) / Pregnane and derivatives [Fig], C21 steroids (gluco/mineralocorticoids, progestogens) and derivatives (C05028) / C21 steroids (gluco/mineralocorticoids, progestogins) and derivatives (LMST02030097)
- Affected organisms
- Humans and other mammals
Chemical Identifiers
- UNII
- T18F433X4S
- CAS number
- 68-22-4
- InChI Key
- VIKNJXKGJWUCNN-XGXHKTLJSA-N
- InChI
- InChI=1S/C20H26O2/c1-3-20(22)11-9-18-17-6-4-13-12-14(21)5-7-15(13)16(17)8-10-19(18,20)2/h1,12,15-18,22H,4-11H2,2H3/t15-,16+,17+,18-,19-,20-/m0/s1
- IUPAC Name
- (1R,3aS,3bR,9aR,9bS,11aS)-1-ethynyl-1-hydroxy-11a-methyl-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@@](O)(C#C)[C@@]1(C)CC[C@]1([H])[C@@]3([H])CCC(=O)C=C3CC[C@@]21[H]
References
- Synthesis Reference
Djerassi C, Miramontes L, Rosenkranz G, Sondheimer F: Steroids LIV. Synthesis of 19-nor-17α-ethynyltestosterone and 19-nor-17α-methyltestosterone. Am J Obstet Gynecol. 2006. 194(1):289.
- General References
- Stanczyk FZ, Roy S: Metabolism of levonorgestrel, norethindrone, and structurally related contraceptive steroids. Contraception. 1990 Jul;42(1):67-96. [Article]
- Frohlich M, Albermann N, Sauer A, Walter-Sack I, Haefeli WE, Weiss J: In vitro and ex vivo evidence for modulation of P-glycoprotein activity by progestins. Biochem Pharmacol. 2004 Dec 15;68(12):2409-16. doi: 10.1016/j.bcp.2004.08.026. [Article]
- Stanczyk FZ, Mroszczak EJ, Ling T, Runkel R, Henzl M, Miyakawa I, Goebelsmann U: Plasma levels and pharmacokinetics of norethindrone and ethinylestradiol administered in solution and as tablets to women. Contraception. 1983 Sep;28(3):241-51. doi: 10.1016/0010-7824(83)90065-3. [Article]
- Barra F, Scala C, Ferrero S: Current understanding on pharmacokinetics, clinical efficacy and safety of progestins for treating pain associated to endometriosis. Expert Opin Drug Metab Toxicol. 2018 Apr;14(4):399-415. doi: 10.1080/17425255.2018.1461840. Epub 2018 Apr 10. [Article]
- Schoonen WG, Deckers GH, de Gooijer ME, de Ries R, Kloosterboer HJ: Hormonal properties of norethisterone, 7alpha-methyl-norethisterone and their derivatives. J Steroid Biochem Mol Biol. 2000 Nov 15;74(4):213-22. doi: 10.1016/s0960-0760(00)00125-4. [Article]
- Walker CJ, Cowan DA, James VH, Lau JC, Kicman AT: Doping in sport: 3. Metabolic conversion of oral norethisterone to urinary 19-norandrosterone. Steroids. 2009 Mar;74(3):341-9. doi: 10.1016/j.steroids.2008.11.008. Epub 2008 Nov 19. [Article]
- Korhonen T, Turpeinen M, Tolonen A, Laine K, Pelkonen O: Identification of the human cytochrome P450 enzymes involved in the in vitro biotransformation of lynestrenol and norethindrone. J Steroid Biochem Mol Biol. 2008 May;110(1-2):56-66. doi: 10.1016/j.jsbmb.2007.09.025. Epub 2008 Feb 15. [Article]
- Sitruk-Ware R: Pharmacological profile of progestins. Maturitas. 2004 Apr 15;47(4):277-83. [Article]
- Kuhnz W, Gieschen H: Predicting the oral bioavailability of 19-nortestosterone progestins in vivo from their metabolic stability in human liver microsomal preparations in vitro. Drug Metab Dispos. 1998 Nov;26(11):1120-7. [Article]
- Sahlberg BL, Landgren BM, Axelson M: Metabolic profiles of endogenous and ethynyl steroids in plasma and urine from women during administration of oral contraceptives. J Steroid Biochem. 1987 May;26(5):609-17. doi: 10.1016/0022-4731(87)90014-8. [Article]
- Sahlberg BL: The characterization of sulphated metabolites of norethindrone in human milk after oral administration of contraceptive steroids. J Steroid Biochem. 1987 Apr;26(4):481-5. doi: 10.1016/0022-4731(87)90060-4. [Article]
- Rivera R, Yacobson I, Grimes D: The mechanism of action of hormonal contraceptives and intrauterine contraceptive devices. Am J Obstet Gynecol. 1999 Nov;181(5 Pt 1):1263-9. [Article]
- Gompel A: Progesterone, progestins and the endometrium in perimenopause and in menopausal hormone therapy. Climacteric. 2018 Aug;21(4):321-325. doi: 10.1080/13697137.2018.1446932. Epub 2018 Mar 27. [Article]
- DPD Approved Drugs: Jencycla oral tablets [Link]
- FDA Approved Drug Products: CombiPatch® transdermal system [Link]
- FDA Approved Drug Products: Femhrt® tablets [Link]
- FDA Approved Drug Products: Lupaneta Pack for intramuscular and oral use [Link]
- FDA Approved Drug Products: Generess Fe chewable tablets [Link]
- FDA Approved Drug Products: Lo Loestrin Fe oral tablets [Link]
- CaymanChem: Norethisterone MSDS [Link]
- The Embryo Project Encyclopedia: Progestin [Link]
- External Links
- Human Metabolome Database
- HMDB0014855
- KEGG Drug
- D00182
- KEGG Compound
- C05028
- PubChem Compound
- 6230
- PubChem Substance
- 46504816
- ChemSpider
- 5994
- BindingDB
- 50148732
- 7514
- ChEBI
- 7627
- ChEMBL
- CHEMBL1162
- ZINC
- ZINC000085205451
- Therapeutic Targets Database
- DAP001212
- PharmGKB
- PA450651
- PDBe Ligand
- NDR
- RxList
- RxList Drug Page
- Drugs.com
- Drugs.com Drug Page
- PDRhealth
- PDRhealth Drug Page
- Wikipedia
- Norethisterone
- PDB Entries
- 1sqn / 2w8y
Clinical Trials
- Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
Phase Status Purpose Conditions Count 4 Completed Basic Science Contraception / Fertility 1 4 Completed Other Contraception 1 4 Completed Prevention Bacterial Vaginosis (BV) / Human Immunodeficiency Virus (HIV) Infections 1 4 Completed Prevention Breastfeeding / Contraception 1 4 Completed Prevention Changes in menstrual flow 1
Pharmacoeconomics
- Manufacturers
- Parke davis div warner lambert co
- Barr laboratories inc
- Glenmark generics ltd
- Ortho mcneil janssen pharmaceuticals inc
- Watson laboratories inc
- Duramed research inc
- Glenmark generics ltd india
- Warner Chilcott
- Packagers
- A-S Medication Solutions LLC
- Barr Pharmaceuticals
- Breckenridge Pharmaceuticals
- Bristol-Myers Squibb Co.
- Dept Health Central Pharmacy
- Dispensing Solutions
- Diversified Healthcare Services Inc.
- Duramed
- Glenmark Generics Ltd.
- Innovative Manufacturing and Distribution Services Inc.
- Kaiser Foundation Hospital
- Lake Erie Medical and Surgical Supply
- Murfreesboro Pharmaceutical Nursing Supply
- Novartis AG
- Noven Pharmaceuticals Inc.
- Novo Nordisk Inc.
- Ortho Mcneil Janssen Pharmaceutical Inc.
- Ortho-McNeil-Janssen Pharmaceuticals Inc.
- Patheon Inc.
- Pfizer Inc.
- Pharmaceutical Utilization Management Program VA Inc.
- Pharmaceutics International Inc.
- Pharmacia Inc.
- Physician Partners Ltd.
- Physicians Total Care Inc.
- Qualitest
- Quality Care
- Redpharm Drug
- Southwood Pharmaceuticals
- Teva Pharmaceutical Industries Ltd.
- Warner Chilcott Co. Inc.
- Watson Pharmaceuticals
- WC Pharmaceuticals
- Dosage Forms
Form Route Strength Tablet, coated Oral Kit; tablet Oral Tablet Oral 0.35 mg/1 Patch, extended release Transdermal Kit; tablet, film coated Oral Plaster Transdermal Patch Transdermal Tablet, film coated Oral Tablet Oral Tablet, chewable Oral Kit; tablet, chewable Oral Kit; tablet; tablet, chewable Oral Kit Oral Injection, powder, lyophilized, for suspension; kit; tablet Intramuscular; Oral; Topical Tablet Oral Tablet Oral 0.35 mg Tablet Oral 5 mg/1 Tablet Oral 350 mcg Kit Oral 0.35 mg/1 Kit; tablet, film coated Oral 0.35 mg/1 Tablet, film coated Oral 0.35 mg/1 Capsule; kit Oral Tablet Oral 10 MG Kit; tablet Oral 0.35 mg/1 Capsule, liquid filled; kit Oral Tablet Oral 5 mg Tablet Tablet, film coated Oil 200 mg/1ml Tablet, sugar coated Oral - Prices
Unit description Cost Unit Ovcon-35 (28) 28 0.4-35 mg-mcg tablet Disp Pack 89.09USD disp Ovcon-50 28 50-1 mcg-mg tablet Disp Pack 89.09USD disp Loestrin 1.5/30 (21) 21 1.5-30 mg-mcg tablet Disp Pack 79.32USD disp Loestrin 1/20 (21) 21 1-20 mg-mcg tablet Disp Pack 79.32USD disp Loestrin Fe 1/20 28 1-20 mg-mcg tablet Disp Pack 79.32USD disp Loestrin Fe 1.5/30 28 1.5-30 mg-mcg tablet Disp Pack 77.1USD disp Loestrin 24 Fe 28 1-20 mg-mcg tablet Disp Pack 75.15USD disp Nor-QD 28 0.35 mg tablet Disp Pack 65.87USD disp Tri-Norinyl (28) 28 0.5/1/0.5-35 mg-mcg tablet Disp Pack 62.63USD disp Ortho-Novum 10/11 (28) 28 35 mcg tablet Disp Pack 60.25USD disp Modicon (28) 28 0.5-35 mg-mcg tablet Disp Pack 59.99USD disp Norinyl 1+35 (28) 28 1-35 mg-mcg tablet Disp Pack 55.99USD disp Ortho-Novum 1/35 (28) 28 1-35 mg-mcg tablet Disp Pack 55.99USD disp Brevicon (28) 28 0.5-35 mg-mcg tablet Disp Pack 53.0USD disp Norinyl 1+50 (28) 28 1-50 mg-mcg tablet 1 Disp Pack = 28 Pills 52.99USD disp Necon 10/11 (28) 28 35 mcg tablet Disp Pack 35.99USD disp Ortho-Novum 7/7/7 (28) 28 0.5/0.75/1-35 mg-mcg tablet Disp Pack 33.99USD disp Necon 0.5/35 (28) 28 0.5-35 mg-mcg tablet Disp Pack 32.99USD disp Necon 1/35 (28) 28 1-35 mg-mcg tablet Disp Pack 31.99USD disp Loestrin fe 1-20 tablet 5.23USD tablet Loestrin 21 1.5-30 tablet 3.66USD tablet Loestrin 21 1-20 tablet 3.66USD tablet Aygestin 5 mg tablet 3.27USD tablet Ovcon-35 28 tablet 3.06USD tablet Loestrin fe 1.5-30 tablet 2.75USD tablet Norethindrone Acetate 5 mg tablet 2.75USD tablet Norethindrone 5 mg tablet 2.65USD tablet Ovcon-50 28 tablet 2.62USD tablet Micronor tablet 2.44USD tablet Nor-q-d tablet 2.24USD tablet Necon 1-35-28 tablet 2.11USD tablet Modicon 28 tablet 2.07USD tablet Tri-norinyl 28 tablet 2.01USD tablet Ortho-novum 1-35-28 tablet 1.9USD tablet Brevicon 28 tablet 1.8USD tablet Norinyl 1+35-28 tablet 1.73USD tablet Norinyl 1+50-28 tablet 1.73USD tablet Demulen 1-50-21 tablet 1.67USD tablet Ortho-novum 7-7-7-21 tablet 1.4USD tablet Errin 0.35 mg tablet 1.34USD tablet Ortho-novum 7/7/7-28 tablet 1.33USD tablet Camila tablet 1.32USD tablet Jolivette tablet 1.32USD tablet Nora-be tablet 1.32USD tablet Norethindrone 0.35 mg tablet 1.32USD tablet Demulen 1-50-28 tablet 1.29USD tablet Ortho micronor tablet 1.23USD tablet Necon 0.5-35-28 tablet 1.15USD tablet Necon 7-7-7-28 tablet 1.15USD tablet Necon 1-50-28 tablet 1.05USD tablet Ortho-novum 7-7-7-28 tablet 1.02USD tablet Micronor (28 Day) 0.35 mg Tablet 0.66USD tablet DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.- Patents
Patent Number Pediatric Extension Approved Expires (estimated) Region US6036976 No 2000-03-14 2016-12-13 US US6667050 No 2003-12-23 2019-04-06 US US7704984 No 2010-04-27 2029-02-02 US US6652880 No 2003-11-25 2020-03-29 US US7419983 No 2008-09-02 2024-07-06 US US7462625 No 2008-12-09 2021-01-25 US US7179815 No 2007-02-20 2021-03-07 US US7056927 No 2006-06-06 2024-09-10 US US6872728 No 2005-03-29 2021-01-25 US US10881659 No 2021-01-05 2034-03-14 US US8058280 No 2011-11-15 2024-01-28 US US7300935 No 2007-11-27 2024-01-28 US US9346822 No 2016-05-24 2024-02-17 US US11033551 No 2021-06-15 2037-09-29 US US11045470 No 2021-06-29 2034-03-14 US US11459305 No 2008-11-07 2028-11-07 US US11542239 No 2019-07-23 2039-07-23 US US11690845 No 2020-08-27 2040-08-27 US US11793812 No 2018-05-03 2038-05-03 US US11795178 No 2013-09-27 2033-09-27 US
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 202-208C Canadian Jencycla label - Predicted Properties
Property Value Source Water Solubility 0.00668 mg/mL ALOGPS logP 2.72 ALOGPS logP 3.22 Chemaxon logS -4.6 ALOGPS pKa (Strongest Acidic) 17.59 Chemaxon pKa (Strongest Basic) -1.7 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 2 Chemaxon Hydrogen Donor Count 1 Chemaxon Polar Surface Area 37.3 Å2 Chemaxon Rotatable Bond Count 0 Chemaxon Refractivity 87.42 m3·mol-1 Chemaxon Polarizability 34.59 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 + 0.9413 Caco-2 permeable + 0.8572 P-glycoprotein substrate Substrate 0.6346 P-glycoprotein inhibitor I Inhibitor 0.5079 P-glycoprotein inhibitor II Non-inhibitor 0.9087 Renal organic cation transporter Non-inhibitor 0.7603 CYP450 2C9 substrate Non-substrate 0.7759 CYP450 2D6 substrate Non-substrate 0.9237 CYP450 3A4 substrate Substrate 0.7415 CYP450 1A2 substrate Non-inhibitor 0.844 CYP450 2C9 inhibitor Non-inhibitor 0.8688 CYP450 2D6 inhibitor Non-inhibitor 0.9386 CYP450 2C19 inhibitor Inhibitor 0.8994 CYP450 3A4 inhibitor Non-inhibitor 0.8333 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.7876 Ames test Non AMES toxic 0.9319 Carcinogenicity Non-carcinogens 0.9417 Biodegradation Not ready biodegradable 0.9512 Rat acute toxicity 1.8788 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.8777 hERG inhibition (predictor II) Non-inhibitor 0.7744
Spectra
- Mass Spec (NIST)
- Download (11.3 KB)
- Spectra
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 183.9978433 predictedDarkChem Lite v0.1.0 [M-H]- 182.9018433 predictedDarkChem Lite v0.1.0 [M-H]- 182.9171433 predictedDarkChem Lite v0.1.0 [M-H]- 173.74422 predictedDeepCCS 1.0 (2019) [M+H]+ 184.5141433 predictedDarkChem Lite v0.1.0 [M+H]+ 183.6266433 predictedDarkChem Lite v0.1.0 [M+H]+ 183.4477433 predictedDarkChem Lite v0.1.0 [M+H]+ 175.70131 predictedDeepCCS 1.0 (2019) [M+Na]+ 183.9629433 predictedDarkChem Lite v0.1.0 [M+Na]+ 182.8139433 predictedDarkChem Lite v0.1.0 [M+Na]+ 181.79655 predictedDeepCCS 1.0 (2019)
Targets
![](https://go.drugbank.com/assets/locked/DrugTargets2-682eb846d210ae4bf33ca03febccfb57bb1c61318e699b729e5df4dfab2c5b67.png)
- 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
- Garcia-Becerra R, Cooney AJ, Borja-Cacho E, Lemus AE, Perez-Palacios G, Larrea F: Comparative evaluation of androgen and progesterone receptor transcription selectivity indices of 19-nortestosterone-derived progestins. J Steroid Biochem Mol Biol. 2004 Jun;91(1-2):21-7. [Article]
- Sitruk-Ware R: Pharmacological profile of progestins. Maturitas. 2004 Apr 15;47(4):277-83. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Agonist
- 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
- Sitruk-Ware R: Pharmacological profile of progestins. Maturitas. 2004 Apr 15;47(4):277-83. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- 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
- Sitruk-Ware R: Pharmacological profile of progestins. Maturitas. 2004 Apr 15;47(4):277-83. [Article]
Enzymes
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- 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
- Korhonen T, Turpeinen M, Tolonen A, Laine K, Pelkonen O: Identification of the human cytochrome P450 enzymes involved in the in vitro biotransformation of lynestrenol and norethindrone. J Steroid Biochem Mol Biol. 2008 May;110(1-2):56-66. doi: 10.1016/j.jsbmb.2007.09.025. Epub 2008 Feb 15. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- Retinal dehydrogenase activity
- Specific Function
- Catalyzes the transformation of the potent androgen dihydrotestosterone (DHT) into the less active form, 5-alpha-androstan-3-alpha,17-beta-diol (3-alpha-diol). Also has some 20-alpha-hydroxysteroid...
- Gene Name
- AKR1C4
- Uniprot ID
- P17516
- Uniprot Name
- Aldo-keto reductase family 1 member C4
- Molecular Weight
- 37066.52 Da
References
- Schoonen WG, Deckers GH, de Gooijer ME, de Ries R, Kloosterboer HJ: Hormonal properties of norethisterone, 7alpha-methyl-norethisterone and their derivatives. J Steroid Biochem Mol Biol. 2000 Nov 15;74(4):213-22. doi: 10.1016/s0960-0760(00)00125-4. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- Steroid delta-isomerase activity
- Specific Function
- 3-beta-HSD is a bifunctional enzyme, that catalyzes the oxidative conversion of Delta(5)-ene-3-beta-hydroxy steroid, and the oxidative conversion of ketosteroids. The 3-beta-HSD enzymatic system pl...
- Gene Name
- HSD3B2
- Uniprot ID
- P26439
- Uniprot Name
- 3 beta-hydroxysteroid dehydrogenase/Delta 5-->4-isomerase type 2
- Molecular Weight
- 42051.845 Da
References
- Schoonen WG, Deckers GH, de Gooijer ME, de Ries R, Kloosterboer HJ: Hormonal properties of norethisterone, 7alpha-methyl-norethisterone and their derivatives. J Steroid Biochem Mol Biol. 2000 Nov 15;74(4):213-22. doi: 10.1016/s0960-0760(00)00125-4. [Article]
- Kind
- Protein group
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- Electron carrier activity
- Specific Function
- Converts testosterone into 5-alpha-dihydrotestosterone and progesterone or corticosterone into their corresponding 5-alpha-3-oxosteroids. It plays a central role in sexual differentiation and andro...
Components:
Name | UniProt ID |
---|---|
3-oxo-5-alpha-steroid 4-dehydrogenase 1 | P18405 |
3-oxo-5-alpha-steroid 4-dehydrogenase 2 | P31213 |
Polyprenol reductase | Q9H8P0 |
References
- Schoonen WG, Deckers GH, de Gooijer ME, de Ries R, Kloosterboer HJ: Hormonal properties of norethisterone, 7alpha-methyl-norethisterone and their derivatives. J Steroid Biochem Mol Biol. 2000 Nov 15;74(4):213-22. doi: 10.1016/s0960-0760(00)00125-4. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- Steroid binding
- Specific Function
- Efficiently catalyzes the reduction of progesterone, androstenedione, 17-alpha-hydroxyprogesterone and testosterone to 5-beta-reduced metabolites. The bile acid intermediates 7-alpha,12-alpha-dihyd...
- Gene Name
- AKR1D1
- Uniprot ID
- P51857
- Uniprot Name
- 3-oxo-5-beta-steroid 4-dehydrogenase
- Molecular Weight
- 37376.615 Da
References
- Schoonen WG, Deckers GH, de Gooijer ME, de Ries R, Kloosterboer HJ: Hormonal properties of norethisterone, 7alpha-methyl-norethisterone and their derivatives. J Steroid Biochem Mol Biol. 2000 Nov 15;74(4):213-22. doi: 10.1016/s0960-0760(00)00125-4. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- SubstrateInducer
- 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
- Flockhart Table of Drug Interactions [Link]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- Oxidoreductase activity, acting on paired donors, with incorporation or reduction of molecular oxygen, reduced flavin or flavoprotein as one donor, and incorporation of one atom of oxygen
- 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
- CYP1A2
- Uniprot ID
- P05177
- Uniprot Name
- Cytochrome P450 1A2
- Molecular Weight
- 58293.76 Da
References
- Korhonen T, Turpeinen M, Tolonen A, Laine K, Pelkonen O: Identification of the human cytochrome P450 enzymes involved in the in vitro biotransformation of lynestrenol and norethindrone. J Steroid Biochem Mol Biol. 2008 May;110(1-2):56-66. doi: 10.1016/j.jsbmb.2007.09.025. Epub 2008 Feb 15. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- 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
- Korhonen T, Turpeinen M, Tolonen A, Laine K, Pelkonen O: Identification of the human cytochrome P450 enzymes involved in the in vitro biotransformation of lynestrenol and norethindrone. J Steroid Biochem Mol Biol. 2008 May;110(1-2):56-66. doi: 10.1016/j.jsbmb.2007.09.025. Epub 2008 Feb 15. [Article]
Carriers
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- Toxic substance binding
- Specific Function
- Serum albumin, the main protein of plasma, has a good binding capacity for water, Ca(2+), Na(+), K(+), fatty acids, hormones, bilirubin and drugs. Its main function is the regulation of the colloid...
- Gene Name
- ALB
- Uniprot ID
- P02768
- Uniprot Name
- Serum albumin
- Molecular Weight
- 69365.94 Da
References
- FDA Approved Drug Products: Lo Loestrin Fe oral tablets [Link]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- 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
Transporters
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- 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
- Frohlich M, Albermann N, Sauer A, Walter-Sack I, Haefeli WE, Weiss J: In vitro and ex vivo evidence for modulation of P-glycoprotein activity by progestins. Biochem Pharmacol. 2004 Dec 15;68(12):2409-16. doi: 10.1016/j.bcp.2004.08.026. [Article]
Drug created at June 13, 2005 13:24 / Updated at February 20, 2024 23:55