Identification
- Summary
Estrone is an estrogen used to treat perimenopausal and postmenopausal symptoms.
- Brand Names
- Estragyn
- Generic Name
- Estrone
- DrugBank Accession Number
- DB00655
- Background
Estrone, one of the major mammalian estrogens, is an aromatized C18 steroid with a 3-hydroxyl group and a 17-ketone. It is produced in vivo from androstenedione or from testosterone via estradiol. It is produced primarily in the ovaries, placenta, and in peripheral tissues (especially adipose tissue) through conversion of adrostenedione. Estrone may be further metabolized to 16-alpha-hydroxyestrone, which may be reduced to estriol by estradiol dehydrogenase.
- Type
- Small Molecule
- Groups
- Approved
- Structure
Structure for Estrone (DB00655)
- Weight
- Average: 270.3661
Monoisotopic: 270.161979948 - Chemical Formula
- C18H22O2
- Synonyms
- 3-Hydroxy-1,3,5(10)-estratrien-17-one
- Estrona
- Estrone
- Estronum
- Follicular hormone
- Folliculin
- Oestrone
- External IDs
- WAY 164397
Pharmacology
- Indication
For management of perimenopausal and postmenopausal symptoms.
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Indication Type Indication Combined Product Details Approval Level Age Group Patient Characteristics Dose Form Symptomatic treatment of Vulvovaginal atrophy •••••••••••• ••••• - 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
Estrone, a synthetically prepared or naturally occurring steroidal estrogen obtained from pregnant equine urine, is the primary circulating estrogen after menopause. Estrone is naturally derived from the peripheral conversion of androstenedione by an aromatase enzyme found in adipose tissues and is converted to estradiol in peripheral tissues. The estrogenic potency of estrone is one third that of estradiol. Estropipate is piperazine-stabilized estrone sulfate. Estrone, and estropipate are used to treat abnormalities related to gonadotropin hormone dysfunction, vasomotor symptoms, atrophic vaginitis, and vulvar atrophy associated with menopause, and for the prevention of osteoporosis due to estrogen deficiency.
- Mechanism of action
Estrogens enter the cells of responsive tissues (e.g. female organs, breasts, hypothalamus, pituitary) where they interact with estrogen receptors. Hormone-bound estrogen receptors dimerize, translocate to the nucleus of cells and bind to estrogen response elements (ERE) of genes. Binding to ERE alters the transcription rate of affected genes. Estrogens increase the hepatic synthesis of sex hormone binding globulin (SHBG), thyroid-binding globulin (TBG), and other serum proteins and suppress follicle-stimulating hormone (FSH) release from the anterior pituitary.
Target Actions Organism AEstrogen receptor alpha agonistHumans UEstrogen receptor beta Not Available Humans UAndrogen receptor Not Available Humans UCytochrome P450 19A1 Not Available Humans USex hormone-binding globulin Not Available Humans - Absorption
43%
- Volume of distribution
Not Available
- Protein binding
> 95%
- Metabolism
Hepatic.
Hover over products below to view reaction partners
- Route of elimination
Not Available
- Half-life
19 hours
- Clearance
Not Available
- 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
Symptoms of overdose include nausea and vomiting. Estrogen related side effects include nausea, breast tenderness, fluid retention and edema, headaches and/or migraines, chloasma and poor contact lens fit. Estrogen hormone deficiency is associated with breakthrough bleeding, hypomenorrhea, irritability, depression and menopausal symptoms. Withdrawal bleeds may occur in females.
- Pathways
Pathway Category Sulfite Oxidase Deficiency Disease Estrone Metabolism Metabolic Androgen and Estrogen Metabolism Metabolic Aromatase Deficiency Disease Sulfate/Sulfite Metabolism Metabolic 17-beta Hydroxysteroid Dehydrogenase III Deficiency Disease Androstenedione Metabolism Metabolic - 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 Estrone can be increased when it is combined with Abametapir. Abciximab Estrone may increase the thrombogenic activities of Abciximab. Acetohexamide The therapeutic efficacy of Acetohexamide can be decreased when used in combination with Estrone. Adalimumab Estrone may increase the thrombogenic activities of Adalimumab. Aducanumab Estrone may increase the thrombogenic activities of Aducanumab. - Food Interactions
- Avoid alcohol. Ingesting alcohol may increase serum concentrations of estradiol.
- Avoid grapefruit products. Grapefruit inhibits CYP3A4 and therefore, may increase estrone concentrations, potentially increasing its adverse effects.
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.- International/Other Brands
- Estrone (Watson)
- Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Estragyn Vaginal Cream Cream 0.1 % w/w Vaginal Searchlight Pharma Inc 1987-12-31 Not applicable Canada 
Oestrilin Cones Vaginaux Suppository .25 mg / sup Vaginal Desbergers LtÉe, Division Of Technilab Inc. 1951-12-31 2004-08-09 Canada Oestrilin Creme Vaginale 1mg Cream 1 mg / g Vaginal Desbergers LtÉe, Division Of Technilab Inc. 1968-12-31 2004-08-23 Canada
Categories
- ATC Codes
- G03CC04 — Estrone
- G03CC — Estrogens, combinations with other drugs
- G03C — ESTROGENS
- G03 — SEX HORMONES AND MODULATORS OF THE GENITAL SYSTEM
- G — GENITO URINARY SYSTEM AND SEX HORMONES
- Drug Categories
- 17-Ketosteroids
- Adrenal Cortex Hormones
- BCRP/ABCG2 Inhibitors
- Cytochrome P-450 CYP1A2 Substrates
- Cytochrome P-450 CYP2B6 Substrates
- Cytochrome P-450 CYP2C9 Substrates
- Cytochrome P-450 CYP2E1 Substrates
- Cytochrome P-450 CYP3A Substrates
- Cytochrome P-450 CYP3A4 Substrates
- Cytochrome P-450 CYP3A5 Substrates
- Cytochrome P-450 Substrates
- Estradiol Congeners
- Estranes
- Estrenes
- Estrogens
- Fused-Ring Compounds
- Genito Urinary System and Sex Hormones
- Gonadal Hormones
- Gonadal Steroid Hormones
- Hormones
- Hormones, Hormone Substitutes, and Hormone Antagonists
- Ketosteroids
- Natural and Semisynthetic Estrogens, Plain
- OAT3/SLC22A8 Substrates
- OATP1B1/SLCO1B1 Inhibitors
- Organic Anion Transporting Polypeptide 2B1 Inhibitors
- P-glycoprotein inducers
- P-glycoprotein substrates
- Sex Hormones and Modulators of the Genital System
- Steroids
- Thyroxine-binding globulin inducers
- 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-hydroxysteroids / 17-oxosteroids / Phenanthrenes and derivatives / Tetralins / 1-hydroxy-2-unsubstituted benzenoids / Ketones / Organic oxides / Hydrocarbon derivatives
- Substituents
- 1-hydroxy-2-unsubstituted benzenoid / 17-oxosteroid / 3-hydroxysteroid / Aromatic homopolycyclic compound / Benzenoid / Carbonyl group / Estrogen-skeleton / Hydrocarbon derivative / Hydroxysteroid / Ketone
- Molecular Framework
- Aromatic homopolycyclic compounds
- External Descriptors
- 17-oxo steroid, 3-hydroxy steroid (CHEBI:17263) / estrane, C18 steroids (estrogens) and derivatives, Estrane and derivatives, Estrogens (C00468) / C18 steroids (estrogens) and derivatives (LMST02010004)
- Affected organisms
- Humans and other mammals
Chemical Identifiers
- UNII
- 2DI9HA706A
- CAS number
- 53-16-7
- InChI Key
- DNXHEGUUPJUMQT-CBZIJGRNSA-N
- InChI
- InChI=1S/C18H22O2/c1-18-9-8-14-13-5-3-12(19)10-11(13)2-4-15(14)16(18)6-7-17(18)20/h3,5,10,14-16,19H,2,4,6-9H2,1H3/t14-,15-,16+,18+/m1/s1
- IUPAC Name
- (3aS,3bR,9bS,11aS)-7-hydroxy-11a-methyl-1H,2H,3H,3aH,3bH,4H,5H,9bH,10H,11H,11aH-cyclopenta[a]phenanthren-1-one
- SMILES
- [H][C@@]12CCC(=O)[C@@]1(C)CC[C@]1([H])C3=C(CC[C@@]21[H])C=C(O)C=C3
References
- Synthesis Reference
Seiichi Takano, Kunio Ogasawara, "Method for producing (+)-estrone derivatives." U.S. Patent US5424462, issued January, 1965.
US5424462- General References
- Miyoshi Y, Tanji Y, Taguchi T, Tamaki Y, Noguchi S: Association of serum estrone levels with estrogen receptor-positive breast cancer risk in postmenopausal Japanese women. Clin Cancer Res. 2003 Jun;9(6):2229-33. [Article]
- Kajta M, Lason W, Bien E, Marszal M: Neuroprotective effects of estrone on NMDA-induced toxicity in primary cultures of rat cortical neurons are independent of estrogen receptors. Pol J Pharmacol. 2002 Nov-Dec;54(6):727-9. [Article]
- External Links
- Human Metabolome Database
- HMDB0000145
- KEGG Drug
- D00067
- KEGG Compound
- C00468
- PubChem Compound
- 5870
- PubChem Substance
- 46505916
- ChemSpider
- 5660
- BindingDB
- 17289
- 4103
- ChEBI
- 17263
- ChEMBL
- CHEMBL1405
- ZINC
- ZINC000013509425
- Therapeutic Targets Database
- DAP001020
- PharmGKB
- PA449512
- Guide to Pharmacology
- GtP Drug Page
- PDBe Ligand
- J3Z
- Wikipedia
- Estrone
- PDB Entries
- 5hs6 / 6mnc / 6mne / 7ry4 / 7x3z
- MSDS
- Download (99.6 KB)
Clinical Trials
- Clinical Trials
Phase Status Purpose Conditions Count 2 Unknown Status Diagnostic Premenstrual Syndrome (PMS) 1 2 Unknown Status Treatment Premenstrual Syndrome (PMS) 1
Pharmacoeconomics
- Manufacturers
- Wyeth ayerst laboratories
- Watson laboratories inc
- Parkedale pharmaceuticals inc
- Packagers
- Carlisle Laboratories Inc.
- Clint Pharmaceutical Inc.
- Consolidated Midland Corp.
- Gallipot
- Martin Surgical Supply
- Medisca Inc.
- Merit Pharmaceuticals
- National Pharmaceuticals
- North America Genescience LLC
- Primedics Laboratories
- Dosage Forms
Form Route Strength Cream Vaginal 0.1 % w/w Suppository Vaginal .25 mg / sup Cream Vaginal 1 mg / g - Prices
Unit description Cost Unit Estrone powder 21.42USD g Estrone crystal 11.76USD g DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 258-261 °C 'MSDS' boiling point (°C) 445.2 °C 'MSDS' water solubility 0.76 g/L at 20 ºC 'MSDS' logP 2.6 'MSDS' logS -3.96 ADME Research, USCD - Predicted Properties
Property Value Source Water Solubility 0.00394 mg/mL ALOGPS logP 4.03 ALOGPS logP 4.31 Chemaxon logS -4.8 ALOGPS pKa (Strongest Acidic) 10.33 Chemaxon pKa (Strongest Basic) -5.4 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 79.08 m3·mol-1 Chemaxon Polarizability 31.24 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 + 0.9529 Caco-2 permeable + 0.8934 P-glycoprotein substrate Substrate 0.6001 P-glycoprotein inhibitor I Non-inhibitor 0.9066 P-glycoprotein inhibitor II Non-inhibitor 0.8882 Renal organic cation transporter Non-inhibitor 0.73 CYP450 2C9 substrate Non-substrate 0.6624 CYP450 2D6 substrate Non-substrate 0.9116 CYP450 3A4 substrate Substrate 0.729 CYP450 1A2 substrate Inhibitor 0.9017 CYP450 2C9 inhibitor Non-inhibitor 0.9353 CYP450 2D6 inhibitor Non-inhibitor 0.9599 CYP450 2C19 inhibitor Non-inhibitor 0.8954 CYP450 3A4 inhibitor Non-inhibitor 0.8309 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.8681 Ames test Non AMES toxic 0.9268 Carcinogenicity Non-carcinogens 0.8917 Biodegradation Not ready biodegradable 0.9717 Rat acute toxicity 1.9267 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.8711 hERG inhibition (predictor II) Inhibitor 0.5459
Spectra
- Mass Spec (NIST)
- Download (9.95 KB)
- Spectra
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 173.1393473 predictedDarkChem Lite v0.1.0 [M-H]- 162.8952464 predictedDarkChem Lite v0.1.0 [M-H]- 173.0936473 predictedDarkChem Lite v0.1.0 [M-H]- 172.9716473 predictedDarkChem Lite v0.1.0 [M-H]- 177.81871 predictedDeepCCS 1.0 (2019) [M-H]- 173.1393473 predictedDarkChem Lite v0.1.0 [M-H]- 162.8952464 predictedDarkChem Lite v0.1.0 [M-H]- 173.0936473 predictedDarkChem Lite v0.1.0 [M-H]- 172.9716473 predictedDarkChem Lite v0.1.0 [M-H]- 177.81871 predictedDeepCCS 1.0 (2019) [M+H]+ 174.6389473 predictedDarkChem Lite v0.1.0 [M+H]+ 174.6442997 predictedDarkChem Lite v0.1.0 [M+H]+ 173.5386473 predictedDarkChem Lite v0.1.0 [M+H]+ 174.1581473 predictedDarkChem Lite v0.1.0 [M+H]+ 180.21426 predictedDeepCCS 1.0 (2019) [M+H]+ 174.6389473 predictedDarkChem Lite v0.1.0 [M+H]+ 174.6442997 predictedDarkChem Lite v0.1.0 [M+H]+ 173.5386473 predictedDarkChem Lite v0.1.0 [M+H]+ 174.1581473 predictedDarkChem Lite v0.1.0 [M+H]+ 180.21426 predictedDeepCCS 1.0 (2019) [M+Na]+ 173.0156473 predictedDarkChem Lite v0.1.0 [M+Na]+ 173.2148473 predictedDarkChem Lite v0.1.0 [M+Na]+ 173.1836473 predictedDarkChem Lite v0.1.0 [M+Na]+ 173.6687473 predictedDarkChem Lite v0.1.0 [M+Na]+ 186.12682 predictedDeepCCS 1.0 (2019) [M+Na]+ 173.0156473 predictedDarkChem Lite v0.1.0 [M+Na]+ 173.2148473 predictedDarkChem Lite v0.1.0 [M+Na]+ 173.1836473 predictedDarkChem Lite v0.1.0 [M+Na]+ 173.6687473 predictedDarkChem Lite v0.1.0 [M+Na]+ 186.12682 predictedDeepCCS 1.0 (2019)
Targets
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Use our structured and evidence-based datasets to unlock newinsights and accelerate drug research.
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- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Agonist
- 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
- Margeat E, Bourdoncle A, Margueron R, Poujol N, Cavailles V, Royer C: Ligands differentially modulate the protein interactions of the human estrogen receptors alpha and beta. J Mol Biol. 2003 Feb 7;326(1):77-92. [Article]
- Sasson S: Equilibrium binding analysis of estrogen agonists and antagonists: relation to the activation of the estrogen receptor. Pathol Biol (Paris). 1991 Jan;39(1):59-69. [Article]
- Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- 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
- Gutendorf B, Westendorf J: Comparison of an array of in vitro assays for the assessment of the estrogenic potential of natural and synthetic estrogens, phytoestrogens and xenoestrogens. Toxicology. 2001 Sep 14;166(1-2):79-89. [Article]
- Dang Z: Comparison of relative binding affinities to fish and mammalian estrogen receptors: the regulatory implications. Toxicol Lett. 2010 Feb 15;192(3):298-315. doi: 10.1016/j.toxlet.2009.11.004. Epub 2009 Nov 12. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- 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
- Kojima H, Iida M, Katsura E, Kanetoshi A, Hori Y, Kobayashi K: Effects of a diphenyl ether-type herbicide, chlornitrofen, and its amino derivative on androgen and estrogen receptor activities. Environ Health Perspect. 2003 Apr;111(4):497-502. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Oxygen binding
- Specific Function
- Catalyzes the formation of aromatic C18 estrogens from C19 androgens.
- Gene Name
- CYP19A1
- Uniprot ID
- P11511
- Uniprot Name
- Aromatase
- Molecular Weight
- 57882.48 Da
References
- Numazawa M, Ando M, Watari Y, Tominaga T, Hayata Y, Yoshimura A: Structure-activity relationships of 2-, 4-, or 6-substituted estrogens as aromatase inhibitors. J Steroid Biochem Mol Biol. 2005 Jun;96(1):51-8. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- 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]
Enzymes
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- No
- 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
- Lee AJ, Cai MX, Thomas PE, Conney AH, Zhu BT: Characterization of the oxidative metabolites of 17beta-estradiol and estrone formed by 15 selectively expressed human cytochrome p450 isoforms. Endocrinology. 2003 Aug;144(8):3382-98. [Article]
- Niwa T, Murayama N, Imagawa Y, Yamazaki H: Regioselective hydroxylation of steroid hormones by human cytochromes P450. Drug Metab Rev. 2015 May;47(2):89-110. doi: 10.3109/03602532.2015.1011658. Epub 2015 Feb 13. [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
- Thomas MP, Potter BV: The structural biology of oestrogen metabolism. J Steroid Biochem Mol Biol. 2013 Sep;137:27-49. doi: 10.1016/j.jsbmb.2012.12.014. Epub 2013 Jan 4. [Article]
- van Duursen MB, Sanderson JT, van der Bruggen M, van der Linden J, van den Berg M: Effects of several dioxin-like compounds on estrogen metabolism in the malignant MCF-7 and nontumorigenic MCF-10A human mammary epithelial cell lines. Toxicol Appl Pharmacol. 2003 Aug 1;190(3):241-50. doi: 10.1016/s0041-008x(03)00166-2. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- 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
- CYP2B6
- Uniprot ID
- P20813
- Uniprot Name
- Cytochrome P450 2B6
- Molecular Weight
- 56277.81 Da
References
- Rendic S: Summary of information on human CYP enzymes: human P450 metabolism data. Drug Metab Rev. 2002 Feb-May;34(1-2):83-448. [Article]
- Zanger UM, Klein K: Pharmacogenetics of cytochrome P450 2B6 (CYP2B6): advances on polymorphisms, mechanisms, and clinical relevance. Front Genet. 2013 Mar 5;4:24. doi: 10.3389/fgene.2013.00024. eCollection 2013. [Article]
- Mo SL, Liu YH, Duan W, Wei MQ, Kanwar JR, Zhou SF: Substrate specificity, regulation, and polymorphism of human cytochrome P450 2B6. Curr Drug Metab. 2009 Sep;10(7):730-53. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- 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
- Rendic S: Summary of information on human CYP enzymes: human P450 metabolism data. Drug Metab Rev. 2002 Feb-May;34(1-2):83-448. [Article]
- Modugno F, Knoll C, Kanbour-Shakir A, Romkes M: A potential role for the estrogen-metabolizing cytochrome P450 enzymes in human breast carcinogenesis. Breast Cancer Res Treat. 2003 Dec;82(3):191-7. doi: 10.1023/B:BREA.0000004376.21491.44. [Article]
- Uno T, Nakano R, Kitagawa R, Okada M, Kanamaru K, Takenaka S, Uno Y, Imaishi H: Metabolism of steroids by cytochrome P450 2C9 variants. Biopharm Drug Dispos. 2018 Sep;39(8):371-377. doi: 10.1002/bdd.2153. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- Steroid hydroxylase activity
- Specific Function
- Metabolizes several precarcinogens, drugs, and solvents to reactive metabolites. Inactivates a number of drugs and xenobiotics and also bioactivates many xenobiotic substrates to their hepatotoxic ...
- Gene Name
- CYP2E1
- Uniprot ID
- P05181
- Uniprot Name
- Cytochrome P450 2E1
- Molecular Weight
- 56848.42 Da
References
- Ohe T, Hirobe M, Mashino T: Novel metabolic pathway of estrone and 17beta-estradiol catalyzed by cytochrome P-450. Drug Metab Dispos. 2000 Feb;28(2):110-2. [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
- Huang Z, Guengerich FP, Kaminsky LS: 16Alpha-hydroxylation of estrone by human cytochrome P4503A4/5. Carcinogenesis. 1998 May;19(5):867-72. [Article]
- Lee AJ, Cai MX, Thomas PE, Conney AH, Zhu BT: Characterization of the oxidative metabolites of 17beta-estradiol and estrone formed by 15 selectively expressed human cytochrome p450 isoforms. Endocrinology. 2003 Aug;144(8):3382-98. [Article]
- Cribb AE, Knight MJ, Dryer D, Guernsey J, Hender K, Tesch M, Saleh TM: Role of polymorphic human cytochrome P450 enzymes in estrone oxidation. Cancer Epidemiol Biomarkers Prev. 2006 Mar;15(3):551-8. doi: 10.1158/1055-9965.EPI-05-0801. [Article]
- 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
- 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]
- Ueno T, Tamura S, Frels WI, Shou M, Gonzalez FJ, Kimura S: A transgenic mouse expressing human CYP1A2 in the pancreas. Biochem Pharmacol. 2000 Sep 15;60(6):857-63. [Article]
- Yamazaki H, Shaw PM, Guengerich FP, Shimada T: Roles of cytochromes P450 1A2 and 3A4 in the oxidation of estradiol and estrone in human liver microsomes. Chem Res Toxicol. 1998 Jun;11(6):659-65. doi: 10.1021/tx970217f. [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
- Ohe T, Hirobe M, Mashino T: Novel metabolic pathway of estrone and 17beta-estradiol catalyzed by cytochrome P-450. Drug Metab Dispos. 2000 Feb;28(2):110-2. [Article]
- van Duursen MB, Sanderson JT, van der Bruggen M, van der Linden J, van den Berg M: Effects of several dioxin-like compounds on estrogen metabolism in the malignant MCF-7 and nontumorigenic MCF-10A human mammary epithelial cell lines. Toxicol Appl Pharmacol. 2003 Aug 1;190(3):241-50. doi: 10.1016/s0041-008x(03)00166-2. [Article]
Carriers
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- No
- 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
- Tan E, Lu T, Pang KS: Futile cycling of estrone sulfate and estrone in the recirculating perfused rat liver preparation. J Pharmacol Exp Ther. 2001 Apr;297(1):423-36. [Article]
Transporters
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Sodium-independent organic anion transmembrane transporter activity
- Specific Function
- Mediates the Na(+)-independent transport of organic anions such as taurocholate, the prostaglandins PGD2, PGE1, PGE2, leukotriene C4, thromboxane B2 and iloprost.
- Gene Name
- SLCO2B1
- Uniprot ID
- O94956
- Uniprot Name
- Solute carrier organic anion transporter family member 2B1
- Molecular Weight
- 76709.98 Da
References
- Tamai I, Nozawa T, Koshida M, Nezu J, Sai Y, Tsuji A: Functional characterization of human organic anion transporting polypeptide B (OATP-B) in comparison with liver-specific OATP-C. Pharm Res. 2001 Sep;18(9):1262-9. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- SubstrateInducer
- 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
- Noguchi K, Kawahara H, Kaji A, Katayama K, Mitsuhashi J, Sugimoto Y: Substrate-dependent bidirectional modulation of P-glycoprotein-mediated drug resistance by erlotinib. Cancer Sci. 2009 Sep;100(9):1701-7. doi: 10.1111/j.1349-7006.2009.01213.x. Epub 2009 May 12. [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
- Sodium-independent organic anion transmembrane transporter activity
- Specific Function
- Mediates the Na(+)-independent transport of organic anions such as sulfobromophthalein (BSP) and conjugated (taurocholate) and unconjugated (cholate) bile acids (By similarity). Selectively inhibit...
- Gene Name
- SLCO1A2
- Uniprot ID
- P46721
- Uniprot Name
- Solute carrier organic anion transporter family member 1A2
- Molecular Weight
- 74144.105 Da
References
- Kanai N, Lu R, Bao Y, Wolkoff AW, Vore M, Schuster VL: Estradiol 17 beta-D-glucuronide is a high-affinity substrate for oatp organic anion transporter. Am J Physiol. 1996 Feb;270(2 Pt 2):F326-31. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- 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
- Imai Y, Tsukahara S, Asada S, Sugimoto Y: Phytoestrogens/flavonoids reverse breast cancer resistance protein/ABCG2-mediated multidrug resistance. Cancer Res. 2004 Jun 15;64(12):4346-52. [Article]
- Sugimoto Y, Tsukahara S, Imai Y, Sugimoto Y, Ueda K, Tsuruo T: Reversal of breast cancer resistance protein-mediated drug resistance by estrogen antagonists and agonists. Mol Cancer Ther. 2003 Jan;2(1):105-12. [Article]
- Suzuki M, Suzuki H, Sugimoto Y, Sugiyama Y: ABCG2 transports sulfated conjugates of steroids and xenobiotics. J Biol Chem. 2003 Jun 20;278(25):22644-9. Epub 2003 Apr 7. [Article]
- Imai Y, Asada S, Tsukahara S, Ishikawa E, Tsuruo T, Sugimoto Y: Breast cancer resistance protein exports sulfated estrogens but not free estrogens. Mol Pharmacol. 2003 Sep;64(3):610-8. [Article]
- Miwa M, Tsukahara S, Ishikawa E, Asada S, Imai Y, Sugimoto Y: Single amino acid substitutions in the transmembrane domains of breast cancer resistance protein (BCRP) alter cross resistance patterns in transfectants. Int J Cancer. 2003 Dec 10;107(5):757-63. [Article]
- Imai Y, Tsukahara S, Ishikawa E, Tsuruo T, Sugimoto Y: Estrone and 17beta-estradiol reverse breast cancer resistance protein-mediated multidrug resistance. Jpn J Cancer Res. 2002 Mar;93(3):231-5. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- 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
- Tamai I, Nozawa T, Koshida M, Nezu J, Sai Y, Tsuji A: Functional characterization of human organic anion transporting polypeptide B (OATP-B) in comparison with liver-specific OATP-C. Pharm Res. 2001 Sep;18(9):1262-9. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- Sodium-independent organic anion transmembrane transporter activity
- Specific Function
- Plays an important role in the excretion/detoxification of endogenous and exogenous organic anions, especially from the brain and kidney. Involved in the transport basolateral of steviol, fexofenad...
- Gene Name
- SLC22A8
- Uniprot ID
- Q8TCC7
- Uniprot Name
- Solute carrier family 22 member 8
- Molecular Weight
- 59855.585 Da
References
- FDA Drug Development and Drug Interactions: Table of Substrates, Inhibitors and Inducers [Link]
Drug created at June 13, 2005 13:24 / Updated at February 20, 2024 23:55