Identification

Name
Estradiol
Accession Number
DB00783
Description

Estradiol is a naturally occurring hormone circulating endogenously in females. It is commercially available in several hormone therapy products for managing conditions associated with reduced estrogen, such as vulvovaginal atrophy and hot flashes. Some available forms of estradiol include oral tablets, injections, vaginal rings, transdermal patches, sprays, gels, and creams.27,28,29,30,31,32,33

When used for oral or IM administration, estradiol is commonly synthesized as a pro-drug ester (such as Estradiol acetate, Estradiol benzoate, Estradiol cypionate, Estradiol dienanthate, and Estradiol valerate). Because it has a low oral bioavailability on its own, estradiol is commonly formulated with an ester side-chain. Ethinylestradiol (EE) is a synthetic form of estradiol commonly used as the estrogenic component of most combination oral contraceptive pills (OCPs). Ethinyl estradiol is different from estradiol due to its higher biovailability and increased resistance to metabolism, rendering it more suitable for oral administration.

Type
Small Molecule
Groups
Approved, Investigational, Vet approved
Structure
Thumb
Weight
Average: 272.382
Monoisotopic: 272.177630012
Chemical Formula
C18H24O2
Synonyms
  • (17β)-estra-1,3,5(10)-triene-3,17-diol
  • 17beta oestradiol
  • 17β-estra-1,3,5(10)-triene-3,17-diol
  • 17β-estradiol
  • 17β-oestradiol
  • beta-Estradiol
  • cis-Estradiol
  • Estradiol
  • Estradiol-17beta
  • Estradiolum
External IDs
  • E3A
  • NSC 17590
  • NSC-20293
  • NSC-9895
  • SQ 16150
  • WC-3011
  • WC3011

Pharmacology

Indication

Estradiol is indicated in various preparations for the treatment of moderate to severe vasomotor symptoms and vulvar and vaginal atrophy due to menopause, for the treatment of hypoestrogenism due to hypogonadism, castration, or primary ovarian failure, and for the prevention of postmenopausal osteoporosis. It is also used for the treatment of breast cancer (only for palliation therapy) in certain men or women with metastatic disease, and for the treatment of androgen-dependent prostate cancer (only for palliation therapy).27,30,31 It is also used in combination with other hormones as a component of oral contraceptive pills for preventing pregnancy (most commonly as Ethinylestradiol, a synthetic form of estradiol).

A note on duration of treatment

Recommendations for treatment of menopausal symptoms changed drastically following the release of results and early termination of the Women's Health Initiative (WHI) studies in 2002 as concerns were raised regarding estrogen use.11 Specifically, the combined estrogen–progestin group was discontinued after about 5 years of follow up due to a statistically significant increase in invasive breast cancer and in cardiovascular events.12

Following extensive critique of the WHI results, Hormone Replacement Therapy (HRT) is now recommended to be used only for a short period (for 3-5 years postmenopause) in low doses, and in women without a history of breast cancer or increased risk of cardiovascular or thromboembolic disease.13 Estrogen for postmenopausal symptoms should always be given with a progestin component due to estrogen's stimulatory effects on the endometrium; in women with an intact uterus, unopposed estrogen has been shown to promote the growth of the endometrium which can lead to endometrial hyperplasia and possibly cancer over the long-term.

Associated Conditions
Associated Therapies
Contraindications & Blackbox Warnings
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Pharmacodynamics

Estradiol acts on the on the estrogen receptors to relieve vasomotor systems (such as hot flashes) and urogenital symptoms (such as vaginal dryness and dyspareunia).18,19,20

Estradiol has also been shown to exert favorable effects on bone density by inhibiting bone resorption. Estrogen appears to inhibit bone resorption 18,35 and may have beneficial effects on the plasma lipid profile.19,34 Estrogens cause an increase in hepatic synthesis of various proteins, which include sex hormone binding globulin (SHBG), and thyroid-binding globulin (TBG). Estrogens are known to suppress the formation of follicle-stimulating hormone (FSH) in the anterior pituitary gland.27

A note on hyper-coagulable state, cardiovascular health, and blood pressure

Estradiol may cause an increased risk of cardiovascular disease, DVT, and stroke, and its use should be avoided in patients at high risk of these conditions.35 Estrogen induces a hyper-coagulable state, which is also associated with both estrogen-containing oral contraceptive (OC) use and pregnancy. Although estrogen causes an increase in levels of plasma renin and angiotensin. Estrogen-induced increases in angiotensin, causing sodium retention, which is likely to be the mechanism causing hypertension after oral contraceptive treatment.18

Mechanism of action

Estrogen is found in the the breast, uterine, ovarian, skin, prostate, bone, fat, and brain tissues. The main source of estrogen in adult women during the reproductive period of life is the ovarian follicle, which secretes 70 to 500 mcg of estradiol each day. After menopause, however, the majority of endogenous estrogen is produced by transformation of androstenedione (which is secreted by the adrenal cortex) to estrone in the peripheral tissues. Both estrone and its sulphate conjugated form, estrone sulphate, represent the most abundant estrogens found in postmenopausal women.34

Estradiol, however, is considerably more potent than estrone and estriol at the estrogen receptor (ER). As a result, the higher estrone concentration in postmenopausal population, can cause various undesirable effects. These effects may include hot flashes, chills, vaginal dryness, mood swings, irregular menstruation, and chills, in addition to sleep problems.34

Estradiol workings by binding to subtypes of the estrogen receptor: estrogen receptor alpha (ERα) and estrogen receptor beta (ERβ). It also exerts potent agonism of G Protein-coupled estrogen receptor (GPER), which is recognized an important regulator of this drug's rapid effects. Once the estrogen receptor has bound to its ligand, it enters the nucleus of the target cell, regulating gene transcription and formation of of messenger RNA. This mRNA makes contact with ribosomes producing specific proteins that express the effect of estradiol upon the target cell. Agonism of estrogen receptors increases pro-estrogenic effects, leading to the relief of vasomotor and urogenital symptoms of a postmenopausal or low estradiol state.9,27,31

TargetActionsOrganism
AEstrogen receptor alpha
agonist
Humans
AEstrogen receptor beta
agonist
Humans
UNuclear receptor subfamily 1 group I member 2
binder
Humans
UNeuronal acetylcholine receptor subunit alpha-4
binder
Humans
UG-protein coupled estrogen receptor 1
binder
Humans
UATP synthase subunit a
inhibitor
Humans
UBeclin-1
binder
Humans
Absorption

The absorption of several formulations of estradiol is described below:

Oral tablets and injections

First-pass metabolism in the gastrointestinal tract rapidly breaks down estradiol tablets before entering the systemic circulation.10,27 The bioavailability of oral estrogens is said to be 2-10% due to significant first-pass effects.10 The esterification of estradiol improves the administration (such as with estradiol valerate) or to sustain release from intramuscular depot injections (including estradiol cypionate29) via higher lipophilicity.26 After absorption, the esters are cleaved, which leads to the release of endogenous estradiol, or 17β-estradiol.

Transdermal preparations

The transdermal preparations slowly release estradiol through intact skin, which sustains circulating levels of estradiol during a 1 week period of time. Notably, the bioavailability of estradiol after transdermal administration is about 20 times higher than after oral administration. Transdermal estradiol avoids first pass metabolism effects that reduce bioavailability. Administration via the buttock leads to a Cmax of about 174 pg/mL compared to 147 pg/mL via the abdomen.34

Spray preparations

After daily administration, the spray formulations of estradiol reach steady state within 7-8 days. After 3 sprays daily, Cmax is about 54 pg/mL with a Tmax of 20 hours. AUC is about 471 pg•hr/mL.28

Vaginal ring and cream preparations

Estradiol is efficiently absorbed through the mucous membranes of the vagina. The vaginal administration of estrogens evades first-pass metabolism. Tmax after vaginal ring delivery ranges from 0.5 to 1 hour. Cmax is about 63 pg/mL.30 The vaginal cream preparation has a Cmax of estradiol (a component of Premarin vaginal estrogen conjugate cream) was a Cmax of 12.8 ± 16.6 pg/mL, Tmax of 8.5 ± 6.2 hours, with an AUC of 231 ± 285 pg•hr/mL.38

Volume of distribution

Estrogens administered exogenously distribute in a similar fashion to endogenous estrogens. They can be found throughout the body, especially in the sex hormone target organs, such as the breast, ovaries and uterus.10,21,27

Protein binding

More than 95% of estrogens are found to circulate in the blood bound to sex hormone binding globulin (SHBG) and albumin.10,27

Metabolism

Exogenously administered estrogens are metabolized in the same fashion as endogenous estrogens. Metabolic transformation occurs primarily in the liver and intestine.15 Estradiol is metabolized to estrone, and both are converted to estriol, which is later excreted in the urine. Sulfate and glucuronide conjugation estrogens also take place in the liver. Biliary secretion of metabolic conjugates are released into the intestine, and estrogen hydrolysis in the gut occurs, followed by reabsorption.10,34 The CYP3A4 hepatic cytochrome enzyme is heavily involved in the metabolism of estradiol. CYP1A2 also plays a role.24,25

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Route of elimination

Estradiol is excreted in the urine with both glucuronide and sulfate conjugates.27,34,38

Half-life

The terminal half-lives for various estrogen products post oral or intravenous administration has been reported to range from 1-12 hours.10 One pharmacokinetic study of oral estradiol valerate administration in postmenopausal women revealed a terminal elimination half-life of 16.9 ± 6.0 h.22 A pharmacokinetic study of intravenous estradiol administration in postmenopausal women showed an elimination half-life of 27.45 ± 5.65 minutes.23 The half-life of estradiol appears to vary by route of administration.

Clearance

In one pharmacokinetic study, the clearance of orally administered micronized estradiol in postmenopausal women was 29.9±15.5 mL/min/kg.10 Another study revealed a clearance of intravenously administered estradiol was 1.3 mL/min/kg.23

Adverse Effects
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Toxicity

The NOAEL (no-observed-adverse-effect-level) oral toxicity of estradiol after 90 day in rats was 0.003 mg/kg/day for blood, female reproductive, and male reproductive, endocrine, and liver toxicity.36 Oral TDLO of ethinyl estradiol is 21 mg/kg/21D intermittent, woman) with an oral LD50 of 960 mg/kg in the rat.37

There is limited information in the literature regarding estrogen overdose. Estradiol overdose likely leads to the occurrence of estrogen-associated adverse effects, including nausea, vomiting, abdominal pain, breast tenderness, venous thrombosis, and vaginal bleeding.35 It is generally recommend to discontinue estradiol treatment and offer supportive care in the case of an overdose.30

Affected organisms
  • Humans and other mammals
Pathways
PathwayCategory
Estrone MetabolismMetabolic
17-beta Hydroxysteroid Dehydrogenase III DeficiencyDisease
Androgen and Estrogen MetabolismMetabolic
Aromatase DeficiencyDisease
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.
DrugInteraction
AbacavirEstradiol may decrease the excretion rate of Abacavir which could result in a higher serum level.
AbametapirThe serum concentration of Estradiol can be increased when it is combined with Abametapir.
AbataceptThe metabolism of Estradiol can be increased when combined with Abatacept.
AbciximabEstradiol may decrease the anticoagulant activities of Abciximab.
AbemaciclibEstradiol may decrease the excretion rate of Abemaciclib which could result in a higher serum level.
AbirateroneThe serum concentration of Estradiol can be increased when it is combined with Abiraterone.
AcalabrutinibThe metabolism of Estradiol can be decreased when combined with Acalabrutinib.
AcarboseAcarbose may decrease the excretion rate of Estradiol which could result in a higher serum level.
AceclofenacAceclofenac may decrease the excretion rate of Estradiol which could result in a higher serum level.
AcemetacinAcemetacin may decrease the excretion rate of Estradiol which could result in a higher serum level.
Additional Data Available
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  • Severity
    Severity
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  • Evidence Level
    Evidence Level
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  • Action
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Food Interactions
No interactions found.

Products

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Product Ingredients
IngredientUNIICASInChI Key
Estradiol hemihydrateCXY7B3Q98Z35380-71-3ZVVGLAMWAQMPDR-WVEWYJOQSA-N
Product Images
International/Other Brands
Estraderm MX (Novartis) / Estraderm TTS (Novartis) / Estrofem (Novo Nordisk) / Femtrace (Warner Chilcott)
Brand Name Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
AloraPatch0.05 mg/1dTransdermalAllergan, Inc.1996-12-20Not applicableUS flag
AloraPatch0.075 mg/1dTransdermalActavis Pharma, Inc.1996-12-202020-12-31US flag
AloraPatch0.1 mg/1dTransdermalAllergan, Inc.1996-12-20Not applicableUS flag
AloraPatch0.025 mg/1dTransdermalAllergan, Inc.2002-04-05Not applicableUS flag
AloraPatch0.05 mg/1dTransdermalActavis Pharma, Inc.1996-12-202020-12-31US flag
AloraPatch0.1 mg/1dTransdermalActavis Pharma, Inc.1996-12-202020-12-31US flag
AloraPatch0.075 mg/1dTransdermalAllergan, Inc.1996-12-20Not applicableUS flag
AloraPatch0.025 mg/1dTransdermalActavis Pharma, Inc.2002-04-052020-12-21US flag
ClimaraPatch0.06 mg/1dTransdermalBayer HealthCare Pharmaceuticals Inc.2008-01-03Not applicableUS flag
ClimaraPatch0.025 mg/1dTransdermalBayer HealthCare Pharmaceuticals Inc.1999-03-05Not applicableUS flag
Additional Data Available
  • Application Number
    Application Number
    Available for Purchase

    A unique ID assigned by the FDA when a product is submitted for approval by the labeller.

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  • Product Code
    Product Code
    Available for Purchase

    A governmentally-recognized ID which uniquely identifies the product within its regulatory market.

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Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
DottiPatch, extended release0.1 mg/1dTransdermalAmneal Pharmaceuticals LLC2019-02-04Not applicableUS flag
DottiPatch, extended release0.0375 mg/1dTransdermalAmneal Pharmaceuticals LLC2019-02-04Not applicableUS flag
DottiPatch, extended release0.075 mg/1dTransdermalAmneal Pharmaceuticals LLC2019-02-04Not applicableUS flag
DottiPatch, extended release0.025 mg/1dTransdermalAmneal Pharmaceuticals LLC2019-02-04Not applicableUS flag
DottiPatch, extended release0.05 mg/1dTransdermalAmneal Pharmaceuticals LLC2019-02-04Not applicableUS flag
EstraceTablet0.5 mg/1OralAllergan, Inc.2011-12-26Not applicableUS flag
EstraceTablet1 mg/1OralPhysicians Total Care, Inc.1996-04-162012-06-30US flag
EstraceTablet2 mg/1OralWarner Chilcott2009-06-012012-10-15US flag
EstraceTablet2 mg/1OralAllergan, Inc.2011-12-26Not applicableUS flag
EstraceCream0.1 mg/1gVaginalA-S Medication Solutions2001-07-01Not applicableUS flag
Additional Data Available
  • Application Number
    Application Number
    Available for Purchase

    A unique ID assigned by the FDA when a product is submitted for approval by the labeller.

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  • Product Code
    Product Code
    Available for Purchase

    A governmentally-recognized ID which uniquely identifies the product within its regulatory market.

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Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
ActivellaEstradiol (0.5 mg/1) + Norethisterone acetate (0.1 mg/1)Tablet, film coatedOralAmneal Pharmaceuticals LLC2019-05-01Not applicableUS flag
ActivellaEstradiol (0.5 mg/1) + Norethisterone acetate (0.1 mg/1)Tablet, film coatedOralGemini Laboratories, LLC2016-05-122019-08-31US flag
ActivellaEstradiol (0.5 mg/1) + Norethisterone acetate (0.1 mg/1)Tablet, film coatedOralNovo Nordisk2007-04-092017-04-30US flag
ActivellaEstradiol (1 mg/1) + Norethisterone acetate (0.5 mg/1)Tablet, film coatedOralAmneal Pharmaceuticals LLC2019-05-01Not applicableUS flag
ActivellaEstradiol (1 mg/1) + Norethisterone acetate (0.5 mg/1)Tablet, film coatedOralNovo Nordisk2003-07-222018-10-31US flag
ActivellaEstradiol (1 mg/1) + Norethisterone acetate (0.5 mg/1)Tablet, film coatedOralGemini Laboratories, LLC2016-05-122020-07-31US flag
ActivelleEstradiol (1.0 mg) + Norethisterone acetate (0.5 mg)TabletOralNovo Nordisk2008-05-16Not applicableCanada flag
Activelle LdEstradiol (0.5 mg) + Norethisterone acetate (0.1 mg)TabletOralNovo Nordisk2008-05-16Not applicableCanada flag
AmabelzEstradiol (0.5 mg/1) + Norethisterone (0.1 mg/1)TabletOralLupin Pharmaceuticals, Inc.2020-10-08Not applicableUS flag
AmabelzEstradiol (1 mg/1) + Norethisterone (0.5 mg/1)TabletOralLupin Pharmaceuticals, Inc.2020-10-08Not applicableUS flag
Unapproved/Other Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
EstradiolEstradiol (18 mg/1)PelletOralQualgen Llc2015-09-01Not applicableUS flag
EstradiolEstradiol (22 mg/1)PelletOralQualgen Llc2015-09-01Not applicableUS flag
EstradiolEstradiol (10 mg/1)PelletOralQualgen Llc2015-09-01Not applicableUS flag
EstradiolEstradiol (12.5 mg/1)PelletOralQualgen Llc2015-09-01Not applicableUS flag
EstradiolEstradiol (20 mg/1)PelletOralQualgen Llc2015-09-01Not applicableUS flag
EstradiolEstradiol (6 mg/1)PelletOralQualgen Llc2015-09-01Not applicableUS flag
EstradiolEstradiol (15 mg/1)PelletOralQualgen Llc2015-09-01Not applicableUS flag
EstradiolEstradiol (25 mg/1)PelletOralQualgen Llc2015-09-01Not applicableUS flag

Categories

ATC Codes
G03FA16 — Trimegestone and estrogenG03FA06 — Etynodiol and estrogenG03FA09 — Noretynodrel and estrogenG03FA14 — Dydrogesterone and estrogenG03CA53 — Estradiol, combinationsG03FA12 — Medroxyprogesterone and estrogenG03FB12 — Nomegestrol and estrogenG03FB03 — Chlormadinone and estrogenG03FA15 — Dienogest and estrogenG03FB02 — Lynestrenol and estrogenG03FB10 — Desogestrel and estrogenG03FA10 — Norgestrel and estrogenG03EA01 — Methyltestosterone and estrogenG03FA04 — Progesterone and estrogenG03FB11 — Trimegestone and estrogenG03FA01 — Norethisterone and estrogenG03FB09 — Levonorgestrel and estrogenG03FB08 — Dydrogesterone and estrogenG03EA03 — Prasterone and estrogenG03AA14 — Nomegestrol and estradiolG03AB08 — Dienogest and estradiolG03FB01 — Norgestrel and estrogenG03FA03 — Ethisterone and estrogenG03FA08 — Megestrol and estrogenG03FB06 — Medroxyprogesterone and estrogenG03EA02 — Testosterone and estrogenG03FA11 — Levonorgestrel and estrogenG03AA17 — Medroxyprogesterone and estradiolG03FB07 — Medrogestone and estrogenG03FA17 — Drospirenone and estrogenG03FA07 — Lynestrenol and estrogenG03FA02 — Hydroxyprogesterone and estrogenG03HB01 — Cyproterone and estrogenG03FB04 — Megestrol and estrogenG03FA13 — Norgestimate and estrogenG02BB01 — Vaginal ring with progestogen and estrogenG03CA03 — EstradiolG03FA05 — Methylnortestosterone and estrogenG03FB05 — Norethisterone and estrogen
Drug Categories
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-hydroxysteroids / Phenanthrenes and derivatives / Tetralins / 1-hydroxy-2-unsubstituted benzenoids / Secondary alcohols / Cyclic alcohols and derivatives / Hydrocarbon derivatives
Substituents
1-hydroxy-2-unsubstituted benzenoid / 17-hydroxysteroid / 3-hydroxysteroid / Alcohol / Aromatic homopolycyclic compound / Benzenoid / Cyclic alcohol / Estrogen-skeleton / Hydrocarbon derivative / Hydroxysteroid
Molecular Framework
Aromatic homopolycyclic compounds
External Descriptors
17beta-hydroxy steroid, estradiol (CHEBI:16469) / C18 steroids (estrogens) and derivatives, Estrane and derivatives, Estrogens (C00951) / C18 steroids (estrogens) and derivatives (LMST02010001)

Chemical Identifiers

UNII
4TI98Z838E
CAS number
50-28-2
InChI Key
VOXZDWNPVJITMN-ZBRFXRBCSA-N
InChI
InChI=1S/C18H24O2/c1-18-9-8-14-13-5-3-12(19)10-11(13)2-4-15(14)16(18)6-7-17(18)20/h3,5,10,14-17,19-20H,2,4,6-9H2,1H3/t14-,15-,16+,17+,18+/m1/s1
IUPAC Name
(1S,10R,11S,14S,15S)-15-methyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-2(7),3,5-triene-5,14-diol
SMILES

References

Synthesis Reference

Akira Nakagawa, Munehiko Hirano, Miyuki Shinmura, "Estradiol percutaneous administration preparations." U.S. Patent US5248676, issued November, 1980.

US5248676
General References
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  2. Sharpe RM, Skakkebaek NE: Are oestrogens involved in falling sperm counts and disorders of the male reproductive tract? Lancet. 1993 May 29;341(8857):1392-5. [PubMed:8098802]
  3. Raman JD, Schlegel PN: Aromatase inhibitors for male infertility. J Urol. 2002 Feb;167(2 Pt 1):624-9. [PubMed:11792932]
  4. Carani C, Qin K, Simoni M, Faustini-Fustini M, Serpente S, Boyd J, Korach KS, Simpson ER: Effect of testosterone and estradiol in a man with aromatase deficiency. N Engl J Med. 1997 Jul 10;337(2):91-5. [PubMed:9211678]
  5. Behl C, Widmann M, Trapp T, Holsboer F: 17-beta estradiol protects neurons from oxidative stress-induced cell death in vitro. Biochem Biophys Res Commun. 1995 Nov 13;216(2):473-82. [PubMed:7488136]
  6. Schmidt JW, Wollner D, Curcio J, Riedlinger J, Kim LS: Hormone replacement therapy in menopausal women: Past problems and future possibilities. Gynecol Endocrinol. 2006 Oct;22(10):564-77. [PubMed:17135036]
  7. Foresta C, Zuccarello D, Biagioli A, De Toni L, Prana E, Nicoletti V, Ambrosini G, Ferlin A: Oestrogen stimulates endothelial progenitor cells via oestrogen receptor-alpha. Clin Endocrinol (Oxf). 2007 Oct;67(4):520-5. Epub 2007 Jun 15. [PubMed:17573901]
  8. Garcia-Segura LM, Sanz A, Mendez P: Cross-talk between IGF-I and estradiol in the brain: focus on neuroprotection. Neuroendocrinology. 2006;84(4):275-9. Epub 2006 Nov 23. [PubMed:17124377]
  9. Prossnitz ER, Barton M: Estrogen biology: new insights into GPER function and clinical opportunities. Mol Cell Endocrinol. 2014 May 25;389(1-2):71-83. doi: 10.1016/j.mce.2014.02.002. Epub 2014 Feb 12. [PubMed:24530924]
  10. O'Connell MB: Pharmacokinetic and pharmacologic variation between different estrogen products. J Clin Pharmacol. 1995 Sep;35(9S):18S-24S. doi: 10.1002/j.1552-4604.1995.tb04143.x. [PubMed:8530713]
  11. Rossouw JE, Anderson GL, Prentice RL, LaCroix AZ, Kooperberg C, Stefanick ML, Jackson RD, Beresford SA, Howard BV, Johnson KC, Kotchen JM, Ockene J: Risks and benefits of estrogen plus progestin in healthy postmenopausal women: principal results From the Women's Health Initiative randomized controlled trial. JAMA. 2002 Jul 17;288(3):321-33. [PubMed:12117397]
  12. Speroff L: Clinical appraisal of the Women's Health Initiative. J Obstet Gynaecol Res. 2005 Apr;31(2):80-93. doi: 10.1111/j.1447-0756.2005.00251.x. [PubMed:15771632]
  13. Marjoribanks J, Farquhar C, Roberts H, Lethaby A, Lee J: Long-term hormone therapy for perimenopausal and postmenopausal women. Cochrane Database Syst Rev. 2017 Jan 17;1:CD004143. doi: 10.1002/14651858.CD004143.pub5. [PubMed:28093732]
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  16. del Carmen Cravioto M, Larrea F, Delgado NE, Escobar AR, Diaz-Sanchez V, Dominguez J, de Leon RP: Pharmacokinetics and pharmacodynamics of 25-mg estradiol implants in postmenopausal Mexican women. Menopause. 2001 Sep-Oct;8(5):353-60. doi: 10.1097/00042192-200109000-00010. [PubMed:11528362]
  17. Lievertz RW: Pharmacology and pharmacokinetics of estrogens. Am J Obstet Gynecol. 1987 May;156(5):1289-93. doi: 10.1016/0002-9378(87)90166-9. [PubMed:3578450]
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  19. Krause M, Wheeler TL 2nd, Richter HE, Snyder TE: Systemic effects of vaginally administered estrogen therapy: a review. Female Pelvic Med Reconstr Surg. 2010 May;16(3):188-95. doi: 10.1097/SPV.0b013e3181d7e86e. [PubMed:22453284]
  20. Sojo-Aranda I, Cortes-Gallegos V: [Pharmacodynamics of synthetic estrogens. Review article]. Ginecol Obstet Mex. 1990 Oct;58:277-83. [PubMed:2292429]
  21. Ruggiero RJ, Likis FE: Estrogen: physiology, pharmacology, and formulations for replacement therapy. J Midwifery Womens Health. 2002 May-Jun;47(3):130-8. doi: 10.1016/s1526-9523(02)00233-7. [PubMed:12071379]
  22. Zimmermann H, Koytchev R, Mayer O, Borner A, Mellinger U, Breitbarth H: Pharmacokinetics of orally administered estradiol valerate. Results of a single-dose cross-over bioequivalence study in postmenopausal women. Arzneimittelforschung. 1998 Sep;48(9):941-7. [PubMed:9793623]
  23. White CM, Ferraro-Borgida MJ, Fossati AT, McGill CC, Ahlberg AW, Feng YJ, Heller GV, Chow MS: The pharmacokinetics of intravenous estradiol--a preliminary study. Pharmacotherapy. 1998 Nov-Dec;18(6):1343-6. [PubMed:9855336]
  24. 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. [PubMed:12865317]
  25. Ren J, Chen GG, Liu Y, Su X, Hu B, Leung BC, Wang Y, Ho RL, Yang S, Lu G, Lee CG, Lai PB: Cytochrome P450 1A2 Metabolizes 17beta-Estradiol to Suppress Hepatocellular Carcinoma. PLoS One. 2016 Apr 19;11(4):e0153863. doi: 10.1371/journal.pone.0153863. eCollection 2016. [PubMed:27093553]
  26. W. KuhnzH. BlodeH. Zimmermann (1993). Pharmacokinetics of Exogenous Natural and Synthetic Estrogens and Antiestrogens. In: Estrogens and Antiestrogens II.. Springer, Berlin, Heidelberg. [ISBN:978-3-642-60107-1]
  27. FDA Approved Products: Estrace (Estradiol) oral tablets [Link]
  28. FDA Approved Products: Evamist (Estradiol) transdermal spray [Link]
  29. FDA Approved Products: Depo-Estradiol (estradiol cypionate) for injection [Link]
  30. FDA Approved Products: Estring (Estradiol vaginal ring) [Link]
  31. FDA Approved Products: Climara (estradiol) transdermal system [Link]
  32. FDA approved products: Estrace (estradiol vaginal cream) [Link]
  33. Estra-50 (Estradiol pellet) implantable [Link]
  34. FDA Approved Products: Esclim (Estradiol) transdermal system [Link]
  35. NIH StatPearls: Estradiol [Link]
  36. Pfizer MSDS: Estradiol tablets MSDS [Link]
  37. CaymanChem: Ethinyl estradiol safety data sheet [Link]
  38. FDA Approved Products: Premarin (conjugated estrogens) vaginal cream [Link]
Human Metabolome Database
HMDB0000151
KEGG Drug
D00105
KEGG Compound
C00951
PubChem Compound
5757
PubChem Substance
46508115
ChemSpider
5554
BindingDB
17292
RxNav
4083
ChEBI
16469
ChEMBL
CHEMBL135
ZINC
ZINC000013520815
Therapeutic Targets Database
DAP000854
PharmGKB
PA449503
Guide to Pharmacology
GtP Drug Page
PDBe Ligand
EST
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
Wikipedia
Estradiol_(medication)
AHFS Codes
  • 68:16.04 — Estrogens
PDB Entries
1a27 / 1a52 / 1aqu / 1e6w / 1ere / 1fds / 1fdt / 1fdu / 1fdw / 1g50
show 36 more
FDA label
Download (89.1 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
4Active Not RecruitingBasic ScienceSuicidal Thoughts1
4Active Not RecruitingOtherPelvic Floor Disorders1
4Active Not RecruitingTreatmentCystocele / Pelvic Floor Disorders / Pelvic Organ Prolapse (POP) / Urogenital Prolapse / Uterine Prolapse / Vaginal Prolapse / Vaginal Vault Prolapse1
4Active Not RecruitingTreatmentPainful Intercourse1
4CompletedBasic ScienceContraception / Fertility1
4CompletedBasic ScienceMenopause1
4CompletedBasic ScienceMenopause / Pelvic Organ Prolapse (POP)1
4CompletedBasic SciencePerimenopausal Depression1
4CompletedBasic ScienceSuicidal Thoughts1
4CompletedBasic ScienceTranssexualism1

Pharmacoeconomics

Manufacturers
  • Warner chilcott inc
  • Watson laboratories inc
  • Bayer healthcare pharmaceuticals inc
  • Women first healthcare inc
  • Novartis pharmaceuticals corp
  • Mylan technologies inc
  • Ortho mcneil pharmaceutical inc
  • Parke davis pharmaceutical research div warner lambert co
  • Azur pharma international ii ltd
  • Ascend therapeutics inc
  • Upsher smith laboratories inc
  • Pharmacia and upjohn co
  • Kv pharmaceutical co
  • Bristol myers squibb co
  • Bristol myers squibb co pharmaceutical research institute
  • Aai pharma inc
  • Barr laboratories inc
  • Heritage pharmaceuticals inc
  • Mylan pharmaceuticals inc
  • Usl pharma inc
  • Duramed pharmaceuticals inc sub barr laboratories inc
  • Novo nordisk inc
  • Galen ltd
  • Graceway pharmaceuticals llc
  • Jhp pharmaceuticals llc
  • Pharmaforce inc
  • Sandoz canada inc
  • Private formulations inc
  • Monarch pharmaceuticals inc
  • Wyeth ayerst laboratories
Packagers
  • Apotheca Inc.
  • Ascend Therapeutics
  • AzurPharma Inc.
  • Bayer Healthcare
  • Carlisle Laboratories Inc.
  • Clint Pharmaceutical Inc.
  • Consolidated Midland Corp.
  • Darby Dental Supply Co. Inc.
  • Direct Dispensing Inc.
  • Dispensing Solutions
  • E.R. Squibb and Sons LLC
  • Gallipot
  • Graceway Pharmaceuticals
  • Group Health Cooperative
  • JHP Pharmaceuticals LLC
  • King Pharmaceuticals Inc.
  • Lunsco Inc.
  • Martica Enterprises Inc.
  • Martin Surgical Supply
  • Medisca Inc.
  • Merit Pharmaceuticals
  • Monarch Pharmacy
  • Murfreesboro Pharmaceutical Nursing Supply
  • Mylan
  • National Pharmaceuticals
  • Novartis AG
  • Novavax Inc.
  • Novo Nordisk Inc.
  • Paddock Labs
  • PD-Rx Pharmaceuticals Inc.
  • Pharmacia Inc.
  • Physicians Total Care Inc.
  • Prepackage Specialists
  • Primedics Laboratories
  • Professional Co.
  • San Jose Surgical Supply Inc.
  • Sandhills Packaging Inc.
  • Sandoz
  • Spectrum Pharmaceuticals
  • Ther-Rx Corp.
  • Upsher Smith Laboratories
  • Watson Pharmaceuticals
  • WC Pharmaceuticals
Dosage Forms
FormRouteStrength
Tablet, film coatedOral0.1 mg
Tablet, coatedOral1 mg
InjectionIntramuscular5 mg/mL
Tablet, film coatedOral
TabletOral0.5 mg
CapsuleOral
PatchTransdermal0.05 mg/1
PatchTransdermal2 mg
PatchTransdermal3.8 mg
PlasterTransdermal50 Mikrogramm/24h
PatchTransdermal7.8 mg
PatchTransdermal3.9 mg
PatchTransdermal
Patch, extended releaseTransdermal
Kit; patchTransdermal10 mcg
PatchTransdermal25 MCG
PatchTransdermal50 MCG
PlasterCutaneous0.025 mg/1
PlasterCutaneous0.05 mg/1
PlasterCutaneous25 UG
PlasterCutaneous50 UG
PlasterCutaneous75 UG
GelTopical.25 mg/.25g
GelTopical.5 mg/.5g
GelTopical.75 mg/.75g
GelTopical0.25 mg/1g
GelTopical0.5 mg/1g
GelTopical1 mg/1g
GelTopical1.0 mg/1g
GelTopical1.25 mg/1.25g
GelTopical100 mg/100g
GelTransdermal0.1 %
GelTopical0.1 %
GelTransdermal0.6 mg/1g
Gel, meteredTopical0.52 mg/0.87g
Gel, meteredTopical0.52 mg/1g
PlasterTransdermal50 mcg/24h
PatchTransdermal240 MCG
PatchTransdermal250 MCG
CreamVaginal0.1 g
Pellet, implantableSubcutaneous25 mg/1
Pellet, implantableSubcutaneous50 mg/1
CreamVaginal0.1 mg/1g
TabletOral1 mg
TabletOral
Patch, extended releaseTransdermal4 mg/1
Patch, extended releaseTransdermal8 mg/1
Patch, extended releaseTransdermal
Film, extended releaseTransdermal0.025 mg/1d
Film, extended releaseTransdermal0.0375 mg/1d
Film, extended releaseTransdermal0.050 mg/1d
Film, extended releaseTransdermal0.075 mg/1d
Film, extended releaseTransdermal0.10 mg/1d
InsertVaginal10 ug/1
PatchTransdermal0.025 mg/1d
PatchTransdermal0.0375 mg/1d
PatchTransdermal0.05 mg/1d
PatchTransdermal0.06 mg/1d
PatchTransdermal0.075 mg/1d
PatchTransdermal0.1 mg/1d
PatchTransdermal0.97 mg/48[USP'U]
PatchTransdermal1.46 mg/48[USP'U]
PatchTransdermal1.94 mg/48[USP'U]
PelletOral10 mg/1
PelletOral12.5 mg/1
PelletOral15 mg/1
PelletOral18 mg/1
PelletOral20 mg/1
PelletOral22 mg/1
PelletOral25 mg/1
PelletOral6 mg/1
TabletOral0.5 mg/1
TabletOral1 mg/1
TabletOral2 mg/1
PowderNot applicable1 g/1g
TabletOral
PlasterTransdermal100 Mikrogramm/24stunde
PlasterCutaneous
PlasterTransdermal25 Mikrogramm/24stunde
PlasterTransdermal37.5 Mikrogramm/24stunde
PlasterTransdermal50 Mikrogramm/24stunde
PlasterTransdermal75 Mikrogramm/24stunde
PlasterCutaneous0.1 mg
PatchTransdermal100 μg/24h
PlasterCutaneous0.025 mg
PatchTransdermal25 μg/24h
PlasterCutaneous0.0375 mg
PlasterCutaneous0.05 mg
PatchTransdermal50 μg/24h
PlasterCutaneous0.075 mg
EmulsionTopical.025 mg/1d
EmulsionTopical2.5 mg/1g
Tablet, film coatedOral1 MG
Tablet, film coatedOral2 MG
RingVaginal2 mg
RingVaginal2 mg/1
RingVaginal7.5 mcg/24h
GelTransdermal0.06 %
GelTransdermal0.75 mg/1.25g
Gel, meteredTopical0.75 mg/1.25g
Gel, meteredTransdermal0.75 mg/1.25g
CapsuleOral; Transdermal
SprayTransdermal1.53 mg/1
Spray, meteredTransdermal1.53 mg/1
Tablet, coatedOral1.5 mg
Gel1.5 mg/2.5gr
PatchTransdermal1.5 MG
TabletOral10 mg
TabletOral20 mg
Tablet, coatedOral0.5 MG
Tablet, film coatedOral5 mg
Kit; tablet, film coatedOral1 mg
Kit; tablet, film coatedOral2 mg
Tablet, film coatedOral0.5 mg
Tablet, film coatedOral10 mg
Tablet, coatedOral5 mg
Tablet, coatedOral10 mg
PatchTransdermal100 MCG
PatchTransdermal75 MCG
Patch, extended releaseTransdermal50 µg/24h
Patch, extended releaseTransdermal50 mcg/24hr
GelTransdermal1.5 MG
GelTopical60 mg
Tablet2 MG
InsertVaginal10 mcg
InsertVaginal4 mcg
InsertVaginal4 ug/1
Tablet, film coatedOral0.5 mg/1
Tablet, film coatedOral1 mg/1
Tablet, film coatedOral2 mg/1
TabletOral2 mg
Tablet, coatedOral2 mg
SprayTransdermal1.58 mg
EmulsionVaginal100 μg/g
PatchTransdermal14 ug/1d
Film, extended releaseTransdermal0.05 mg/1d
Film, extended releaseTransdermal0.1 mg/1d
CreamTopical100 Mikrogramm/g
TabletOral1.5 MG
Tablet, coatedOral2.5 mg
Gel60 mg/100g
GelTopical0.06 %
Gel
Tablet, sugar coatedOral2 mg
Tablet, sugar coatedOral1 mg
GelTransdermal0.5 mg
PatchTransdermal0.53 mg
SolutionIntramuscular0.5 mg
TabletVaginal25 mcg
Tablet, film coatedVaginal10 ug/1
Tablet, film coatedVaginal25 ug/1
TabletVaginal
SuppositoryVaginal10 mcg
Tablet25 mcg
Tablet, film coatedOral0.76 mg
Patch, extended releaseTransdermal2.17 mg/1
Patch, extended releaseTransdermal3.28 mg/1
Patch, extended releaseTransdermal4.33 mg/1
Patch, extended releaseTransdermal6.57 mg/1
Patch, extended releaseTransdermal8.66 mg/1
PatchTransdermal
Patch, extended releaseTransdermal0.025 mg/1d
Patch, extended releaseTransdermal0.0375 mg/1d
Patch, extended releaseTransdermal0.05 mg/1d
Patch, extended releaseTransdermal0.075 mg/1d
Patch, extended releaseTransdermal0.1 mg/1d
Tablet, coatedOral3 mg
TabletVaginal10 ug/1
Tablet, film coatedOral2.5 mg
Prices
Unit descriptionCostUnit
Femring 0.1 mg/24hr Ring218.6USD ring
Estring 2 mg Ring Box210.39USD box
Femring 0.10 mg vaginal ring210.19USD ring
Femring 0.05 mg/24hr Ring205.15USD ring
Estring 2 mg vaginal ring202.3USD ring
Femring 0.05 mg vaginal ring197.26USD ring
Elestrin 0.52 mg/0.87 gm(0.06%) Gel 144 gm Bottle162.06USD bottle
Ethinyl estradiol powder140.0USD g
Vagifem 18 25 mcg tablet Box139.78USD box
Estrace 0.1 mg/gm Cream 42.5 gm Tube133.27USD tube
Estradiol cypionate powder88.74USD g
Delestrogen 10 mg/ml Oil 5ml Vial88.04USD vial
Evamist 1.53 mg/spray Solution 8.1ml Bottle87.18USD bottle
Divigel 1 mg/gm Gel Box Of 30 gm85.53USD box
Estrogel 0.75 mg/1.25 gm(0.06%) Gel 50 gm Bottle84.24USD bottle
Divigel 30 0.25 mg/0.25 gm Gel 30 Patches/box81.24USD box
Climara 4 0.025 mg/24hr Patches Box75.58USD box
Climara 4 0.05 mg/24hr Patches Box75.58USD box
Climara 4 0.1 mg/24hr Patches Box75.58USD box
Menostar 4 14 mcg/24hr Patches Box73.18USD box
Divigel 0.5 mg/0.5 gm Gel Box72.99USD box
Estraderm 8 0.1 mg/24hr Patches Box72.47USD box
Vivelle-Dot 8 0.1 mg/24hr Patches Box72.46USD box
Vivelle-Dot 8 0.025 mg/24hr Patches Box70.69USD box
Climara 4 0.075 mg/24hr Patches Box69.04USD box
Climara Pro 4 0.045-0.015 mg/day Patches Box69.04USD box
Vivelle-Dot 8 0.0375 mg/24hr Patches Box68.84USD box
Vivelle-Dot 8 0.075 mg/24hr Patches Box66.89USD box
CombiPatch 8 0.05-0.25 mg/day Patches Box66.45USD box
Estraderm 8 0.05 mg/24hr Patches Box66.35USD box
Vivelle-Dot 8 0.05 mg/24hr Patches Box65.99USD box
Estring 2 mg Slow-Release Ring65.39USD ring
Alora 8 0.1 mg/24hr Patches Box62.99USD box
Alora 8 0.05 mg/24hr Patches Box60.99USD box
Alora 8 0.075 mg/24hr Patches Box58.27USD box
Vagifem 8 25 mcg tablet Box58.23USD box
Vagifem 8 10 mcg tablet Box54.99USD box
Vivelle 8 0.05 mg/24hr Patches Box49.99USD box
Estradiol benzoate powder42.0USD g
Estradiol 4 0.025 mg/24hr Patches Box40.92USD box
Estradiol 4 0.05 mg/24hr Patches Box40.92USD box
Estradiol 4 0.075 mg/24hr Patches Box40.92USD box
Estradiol 4 0.1 mg/24hr Patches Box40.92USD box
Estradiol 4 0.06 mg/24hr Patches Box39.99USD box
Delestrogen 40 mg/ml Oil39.52USD ml
Estradiol 4 0.0375 mg/24hr Patches Box39.35USD box
Delestrogen 40 mg/ml vial38.0USD ml
Estradiol valerate 40 mg/ml vial35.62USD ml
Estradiol valerate powder32.13USD g
Delestrogen 20 mg/ml Oil23.82USD ml
Delestrogen 20 mg/ml vial22.91USD ml
Estradiol valerate 20 mg/ml vial21.25USD ml
Estradiol 0.1 mg/day patch20.55USD patch
Estradiol powder17.86USD g
Climara 0.0375 mg/24hr Patches17.26USD patch
Climara 0.06 mg/24hr Patches17.26USD patch
Estradiol 0.05 mg/day patch16.91USD patch
Delestrogen 10 mg/ml vial16.25USD ml
Climara 0.025 mg/day patch15.77USD patch
Climara 0.0375 mg/day patch15.77USD patch
Climara 0.05 mg/day patch15.77USD patch
Climara 0.06/mg day patch15.77USD patch
Climara 0.075 mg/day patch15.77USD patch
Climara 0.1 mg/day patch15.77USD patch
Climara pro patch15.77USD patch
Estradiol valerate 10 mg/ml vial15.24USD ml
Evamist 1.53 mg/spray10.43USD ml
Estradiol tds 0.025 mg/day9.84USD each
Estradiol tds 0.0375 mg/day9.84USD each
Estradiol tds 0.06 mg/day9.84USD each
Estradiol tds 0.075 mg/day9.84USD each
Depo-Estradiol 5 mg/ml Oil9.66USD ml
Estraderm 0.1 mg patch8.66USD patch
CombiPatch 0.05-0.14 mg/day Patches8.65USD patch
Vivelle-dot 0.075 mg patch8.49USD patch
Estraderm 0.05 mg patch8.07USD patch
Combipatch 0.05-0.14 mg ptch7.92USD patch
Combipatch 0.05-0.25 mg ptch7.91USD patch
Depo-estradiol 5 mg/ml vial7.89USD ml
Vivelle-dot 0.1 mg patch7.89USD patch
Vivelle-dot 0.05 mg patch7.61USD patch
Vivelle-dot 0.0375 mg patch7.54USD patch
Vivelle-dot 0.025 mg patch7.53USD patch
Alora 0.1 mg patch7.16USD patch
Alora 0.075 mg patch7.0USD patch
Alora 0.05 mg patch6.86USD patch
Vagifem 10 mcg vaginal tab6.78USD each
Vagifem 25 mcg vaginal tab6.78USD each
Climara 100 (7.8 Mg/Pth) 100 mcg/day Patch6.67USD patch
Climara 75 (5.7 Mg/Pth) 75 mcg/day Patch6.31USD patch
Alora 0.025 mg patch6.26USD patch
Vivelle 0.1 mg patch5.94USD patch
Climara 50 (3.9 Mg/Pth) 50 mcg/day Patch5.91USD patch
Vivelle 0.05 mg patch5.74USD patch
Climara 25 (2 Mg/Pth) 25 mcg/day Patch5.54USD patch
Estraderm-100 (8.0 Mg/Pth) 100 mcg/day Patch4.52USD patch
Estraderm-25 (2 Mg/Pth) 25 mcg/day Patch3.74USD patch
Estradot 100 (1.56 Mg/Pth) 100 mcg/day Patch3.49USD patch
Estradot 75 (1.17 Mg/Pth) 75 mcg/day Patch3.3USD patch
Vagifem 25 mcg Tablet3.21USD tablet
Estradot 50 (0.78 Mg/Pth) 50 mcg/day Patch3.07USD patch
Oesclim 50 (10 Mg/Pth) 50 mcg/day Patch3.06USD patch
Estrace 0.01% cream3.05USD g
Estrace 2 mg tablet2.98USD tablet
Estradot 37.5 (0.585 Mg/Pth) 37.5 mcg/day Patch2.88USD patch
Estradot 25 (0.39 Mg/Pth) 25 mcg/day Patch2.86USD patch
Estrasorb 4.35 mg/1.74 gm Emulsion 1.74 gm Packet2.83USD packet
Oesclim 25 (5 Mg/Pth) 25 mcg/day Patch2.83USD patch
Divigel 0.25 mg gel packet2.74USD each
Divigel 0.5 mg gel packet2.74USD each
Divigel 1 mg gel packet2.74USD g
Sandoz Estradiol Derm 100 (8 Mg/Pth) 100 mcg/day Patch2.64USD patch
Menest 2.5 mg tablet2.6USD tablet
Femtrace 1.8 mg tablet2.59USD tablet
Sandoz Estradiol Derm 75 (6 Mg/Pth) 75 mcg/day Patch2.5USD patch
Sandoz Estradiol Derm 50 (4 Mg/Pth) 50 mcg/day Patch2.34USD patch
Estrace 0.5 mg tablet2.29USD tablet
Femtrace 0.45 mg tablet2.02USD tablet
Femtrace 0.9 mg tablet2.02USD tablet
Estrace 1 mg tablet1.93USD tablet
Estrogel 0.06% gel1.63USD g
Menest 1.25 mg tablet1.56USD tablet
Menest 0.625 mg tablet1.41USD tablet
Estrasorb packet1.21USD g
Elestrin 0.06% gel0.94USD g
Menest 0.3 mg tablet0.89USD tablet
Gynodiol 1.5 mg tablet0.5USD tablet
Estradiol 2 mg tablet0.49USD tablet
Estrace 2 mg Tablet0.44USD tablet
Estradiol 1 mg tablet0.42USD tablet
Estradiol 0.5 mg tablet0.36USD tablet
Estrogel 0.06 % Gel0.31USD g
Estrace 1 mg Tablet0.25USD tablet
Estrace 0.5 mg Tablet0.13USD tablet
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)Region
US5223261No1993-06-292010-06-29US flag
CA2306881No2008-09-022018-11-19Canada flag
CA1338660No1996-10-222013-10-22Canada flag
US7018992No2006-03-282022-09-17US flag
US5860946No1999-01-192017-07-01US flag
US6299900No2001-10-092017-02-19US flag
US6818226No2004-11-162017-02-19US flag
US6923983No2005-08-022017-02-19US flag
US6978945No2005-12-272022-07-31US flag
US6747019No2004-06-082020-03-20US flag
US7320970No2008-01-222020-03-30US flag
US6933395No2005-08-232017-08-11US flag
US8906890No2014-12-092031-10-22US flag
US5855906No1999-01-052015-12-19US flag
US7572779No2009-08-112025-10-02US flag
US6962908No2005-11-082021-12-21US flag
US7799771No2010-09-212021-12-21US flag
US5891868No1999-04-062017-11-21US flag
US6692763No2004-02-172017-11-21US flag
US7470433No2008-12-302021-08-03US flag
US7198801No2007-04-032022-06-25US flag
US6133251No2000-10-172016-10-25US flag
US8071577No2011-12-062026-05-13US flag
US8153616No2012-04-102028-01-30US flag
US6884793No2005-04-262016-10-25US flag
US8231906No2012-07-312030-07-04US flag
US6841716No2005-01-112020-04-27US flag
US9730900No2017-08-152028-07-10US flag
US9724310No2017-08-082028-07-10US flag
US9833419No2017-12-052028-07-10US flag
US9180091No2015-11-102033-12-20US flag
US9289382No2016-03-222032-11-21US flag
US7419983No2008-09-022024-07-06US flag
US7462625No2008-12-092021-01-25US flag
US7179815No2007-02-202021-03-07US flag
US7056927No2006-06-062024-09-10US flag
US6872728No2005-03-292021-01-25US flag
US9006222No2015-04-142032-11-21US flag
US9114145No2015-08-252032-11-21US flag
US8846649No2014-09-302032-11-21US flag
US9301920No2016-04-052032-11-21US flag
US8846648No2014-09-302032-11-21US flag
US9114146No2015-08-252032-11-21US flag
US8633178No2014-01-212032-11-21US flag
US10052386No2018-08-212032-11-21US flag
US8993548No2015-03-312032-11-21US flag
US8987237No2015-03-242032-11-21US flag
US8993549No2015-03-312032-11-21US flag
US10206932No2019-02-192032-11-21US flag
US10258630No2019-04-162033-12-20US flag
US10398708No2019-09-032033-12-20US flag
US10471072No2019-11-122033-06-18US flag
US10537581No2012-11-212032-11-21US flag
US10568891No2013-06-182033-06-18US flag
US10639375No2012-11-212032-11-21US flag
US10668082No2013-06-182033-06-18US flag
US10675288No2012-11-212032-11-21US flag
US10806697No2012-11-212032-11-21US flag
Additional Data Available
  • Filed On
    Filed On
    Available for Purchase

    The date on which a patent was filed with the relevant government.

    Learn more

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)173https://www.chemsrc.com/en/cas/50-28-2_757059.html
boiling point (°C)445.9±45.0Not Available
water solubility3.6 mg/L (at 27 °C)YALKOWSKY,SH & DANNENFELSER,RM (1992)
logP4.01HANSCH,C ET AL. (1995)
Caco2 permeability-4.77ADME Research, USCD
pKa10.46±0.03Profiles of Drug Substances, Excipients and Related Methodology Volume 33
Predicted Properties
PropertyValueSource
Water Solubility0.0213 mg/mLALOGPS
logP3.57ALOGPS
logP3.75ChemAxon
logS-4.1ALOGPS
pKa (Strongest Acidic)10.33ChemAxon
pKa (Strongest Basic)-0.88ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area40.46 Å2ChemAxon
Rotatable Bond Count0ChemAxon
Refractivity79.9 m3·mol-1ChemAxon
Polarizability32.13 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+1.0
Blood Brain Barrier+0.8917
Caco-2 permeable+0.8867
P-glycoprotein substrateSubstrate0.7058
P-glycoprotein inhibitor INon-inhibitor0.9147
P-glycoprotein inhibitor IINon-inhibitor0.9403
Renal organic cation transporterNon-inhibitor0.8008
CYP450 2C9 substrateNon-substrate0.727
CYP450 2D6 substrateNon-substrate0.801
CYP450 3A4 substrateSubstrate0.7132
CYP450 1A2 substrateInhibitor0.9106
CYP450 2C9 inhibitorNon-inhibitor0.939
CYP450 2D6 inhibitorNon-inhibitor0.9574
CYP450 2C19 inhibitorNon-inhibitor0.9025
CYP450 3A4 inhibitorNon-inhibitor0.8309
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.7887
Ames testNon AMES toxic0.9198
CarcinogenicityNon-carcinogens0.8829
BiodegradationNot ready biodegradable0.9746
Rat acute toxicity2.2272 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.8647
hERG inhibition (predictor II)Inhibitor0.6624
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Download (9.34 KB)
Spectra
SpectrumSpectrum TypeSplash Key
GC-MS Spectrum - GC-MS (2 TMS)GC-MSsplash10-017r-1791100000-7b16254894cdcb8ee86d
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
GC-MS Spectrum - EI-BGC-MSsplash10-00di-1980000000-b2dec84718861de189ec
GC-MS Spectrum - EI-BGC-MSsplash10-00di-3940000000-f3692a81f624f15d3e0b
GC-MS Spectrum - EI-BGC-MSsplash10-00di-0960000000-be4e96105398cb805cd9
GC-MS Spectrum - EI-BGC-MSsplash10-00di-0790000000-5c858378c15135811824
GC-MS Spectrum - GC-MSGC-MSsplash10-017r-1791100000-7b16254894cdcb8ee86d
Mass Spectrum (Electron Ionization)MSsplash10-075a-2920000000-10218bfa5b56f829853e
MS/MS Spectrum - Quattro_QQQ 10V, PositiveLC-MS/MSsplash10-05fr-0590000000-1dd83cbcb3d21edfbdbd
MS/MS Spectrum - Quattro_QQQ 25V, PositiveLC-MS/MSsplash10-0a4i-2900000000-f3279d6cdab9cf3800fd
MS/MS Spectrum - Quattro_QQQ 40V, PositiveLC-MS/MSsplash10-0a4i-8900000000-0efe28378f612aab8c3d
MS/MS Spectrum - EI-B (JEOL JMS-01-SG-2) , PositiveLC-MS/MSsplash10-00di-1980000000-b2dec84718861de189ec
MS/MS Spectrum - EI-B (HITACHI RMU-6E) , PositiveLC-MS/MSsplash10-00di-3940000000-f3692a81f624f15d3e0b
MS/MS Spectrum - EI-B (HITACHI M-52) , PositiveLC-MS/MSsplash10-00di-0960000000-be4e96105398cb805cd9
MS/MS Spectrum - EI-B (HITACHI M-80) , PositiveLC-MS/MSsplash10-00di-0790000000-5c83456da6e28375ad51
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
MS/MS Spectrum - Linear Ion Trap , negativeLC-MS/MSsplash10-00di-0490000000-c3c4658cfae36bedff30
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0a4i-1900000000-51d28e077b0aefa6aa1c
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0a4i-2900000000-a22a9233ffbb9eb05a1b
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0002-0960000000-d2ee002f4c0363c04e83
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0002-0960000000-2ad7c6e17386448419df
1H NMR Spectrum1D NMRNot Applicable
[1H,13C] 2D NMR Spectrum2D NMRNot Applicable

Targets

Details
1. Estrogen receptor alpha
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
  1. Brama M, Gnessi L, Basciani S, Cerulli N, Politi L, Spera G, Mariani S, Cherubini S, Scotto d'Abusco A, Scandurra R, Migliaccio S: Cadmium induces mitogenic signaling in breast cancer cell by an ERalpha-dependent mechanism. Mol Cell Endocrinol. 2007 Jan 29;264(1-2):102-8. Epub 2006 Nov 27. [PubMed:17125913]
  2. 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. [PubMed:2011412]
  3. Paterni I, Granchi C, Katzenellenbogen JA, Minutolo F: Estrogen receptors alpha (ERalpha) and beta (ERbeta): subtype-selective ligands and clinical potential. Steroids. 2014 Nov;90:13-29. doi: 10.1016/j.steroids.2014.06.012. Epub 2014 Jun 24. [PubMed:24971815]
  4. Banerjee M, Robbins D, Chen T: Modulation of xenobiotic receptors by steroids. Molecules. 2013 Jun 24;18(7):7389-406. doi: 10.3390/molecules18077389. [PubMed:23884115]
  5. FDA Approved Products: Estrace (Estradiol) oral tablets [Link]
Details
2. Estrogen receptor beta
Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Agonist
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
  1. Vijayanathan V, Greenfield NJ, Thomas TJ, Ivanova MM, Tyulmenkov VV, Klinge CM, Gallo MA, Thomas T: Effects of estradiol and 4-hydroxytamoxifen on the conformation, thermal stability, and DNA recognition of estrogen receptor beta. Biochem Cell Biol. 2007 Feb;85(1):1-10. [PubMed:17464340]
  2. 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. [PubMed:2011412]
  3. Paterni I, Granchi C, Katzenellenbogen JA, Minutolo F: Estrogen receptors alpha (ERalpha) and beta (ERbeta): subtype-selective ligands and clinical potential. Steroids. 2014 Nov;90:13-29. doi: 10.1016/j.steroids.2014.06.012. Epub 2014 Jun 24. [PubMed:24971815]
  4. Jiang Y, Gong P, Madak-Erdogan Z, Martin T, Jeyakumar M, Carlson K, Khan I, Smillie TJ, Chittiboyina AG, Rotte SC, Helferich WG, Katzenellenbogen JA, Katzenellenbogen BS: Mechanisms enforcing the estrogen receptor beta selectivity of botanical estrogens. FASEB J. 2013 Nov;27(11):4406-18. doi: 10.1096/fj.13-234617. Epub 2013 Jul 23. [PubMed:23882126]
  5. FDA Approved Products: Estrace (Estradiol) oral tablets [Link]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Binder
General Function
Zinc ion binding
Specific Function
Nuclear receptor that binds and is activated by variety of endogenous and xenobiotic compounds. Transcription factor that activates the transcription of multiple genes involved in the metabolism an...
Gene Name
NR1I2
Uniprot ID
O75469
Uniprot Name
Nuclear receptor subfamily 1 group I member 2
Molecular Weight
49761.245 Da
References
  1. Xue Y, Moore LB, Orans J, Peng L, Bencharit S, Kliewer SA, Redinbo MR: Crystal structure of the pregnane X receptor-estradiol complex provides insights into endobiotic recognition. Mol Endocrinol. 2007 May;21(5):1028-38. Epub 2007 Feb 27. [PubMed:17327420]
  2. Banerjee M, Robbins D, Chen T: Modulation of xenobiotic receptors by steroids. Molecules. 2013 Jun 24;18(7):7389-406. doi: 10.3390/molecules18077389. [PubMed:23884115]
  3. Wang J, Dai S, Guo Y, Xie W, Zhai Y: Biology of PXR: role in drug-hormone interactions. EXCLI J. 2014 Jul 7;13:728-39. eCollection 2014. [PubMed:26417296]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Binder
General Function
Ligand-gated ion channel activity
Specific Function
After binding acetylcholine, the AChR responds by an extensive change in conformation that affects all subunits and leads to opening of an ion-conducting channel across the plasma membrane permeabl...
Gene Name
CHRNA4
Uniprot ID
P43681
Uniprot Name
Neuronal acetylcholine receptor subunit alpha-4
Molecular Weight
69956.47 Da
References
  1. Paradiso K, Zhang J, Steinbach JH: The C terminus of the human nicotinic alpha4beta2 receptor forms a binding site required for potentiation by an estrogenic steroid. J Neurosci. 2001 Sep 1;21(17):6561-8. [PubMed:11517245]
  2. Jin X, Steinbach JH: A portable site: a binding element for 17beta-estradiol can be placed on any subunit of a nicotinic alpha4beta2 receptor. J Neurosci. 2011 Mar 30;31(13):5045-54. doi: 10.1523/JNEUROSCI.4802-10.2011. [PubMed:21451042]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Binder
General Function
Steroid hormone binding
Specific Function
G-protein coupled estrogen receptor that binds to 17-beta-estradiol (E2) with high affinity, leading to rapid and transient activation of numerous intracellular signaling pathways. Stimulates cAMP ...
Gene Name
GPER1
Uniprot ID
Q99527
Uniprot Name
G-protein coupled estrogen receptor 1
Molecular Weight
42247.12 Da
References
  1. Thomas P, Dong J: Binding and activation of the seven-transmembrane estrogen receptor GPR30 by environmental estrogens: a potential novel mechanism of endocrine disruption. J Steroid Biochem Mol Biol. 2006 Dec;102(1-5):175-9. Epub 2006 Nov 7. [PubMed:17088055]
  2. Prossnitz ER, Arterburn JB, Sklar LA: GPR30: A G protein-coupled receptor for estrogen. Mol Cell Endocrinol. 2007 Feb;265-266:138-42. doi: 10.1016/j.mce.2006.12.010. Epub 2007 Jan 11. [PubMed:17222505]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Mitochondrial membrane ATP synthase (F(1)F(0) ATP synthase or Complex V) produces ATP from ADP in the presence of a proton gradient across the membrane which is generated by electron transport complexes of the respiratory chain. F-type ATPases consist of two structural domains, F(1) - containing the extramembraneous catalytic core and F(0) - containing the membrane proton channel, linked together by a central stalk and a peripheral stalk. During catalysis, ATP synthesis in the catalytic domain of F(1) is coupled via a rotary mechanism of the central stalk subunits to proton translocation. Key component of the proton channel; it may play a direct role in the translocation of protons across the membrane.
Specific Function
Hydrogen ion transmembrane transporter activity
Gene Name
MT-ATP6
Uniprot ID
P00846
Uniprot Name
ATP synthase subunit a
Molecular Weight
24816.865 Da
References
  1. Van Dorst B, Mehta J, Rouah-Martin E, De Coen W, Blust R, Robbens J: The identification of cellular targets of 17beta estradiol using a lytic (T7) cDNA phage display approach. Toxicol In Vitro. 2011 Feb;25(1):388-93. doi: 10.1016/j.tiv.2010.10.012. Epub 2010 Oct 27. [PubMed:21034808]
  2. Massart F, Paolini S, Piscitelli E, Brandi ML, Solaini G: Dose-dependent inhibition of mitochondrial ATP synthase by 17 beta-estradiol. Gynecol Endocrinol. 2002 Oct;16(5):373-7. [PubMed:12587531]
  3. Moreno AJ, Moreira PI, Custodio JB, Santos MS: Mechanism of inhibition of mitochondrial ATP synthase by 17beta-estradiol. J Bioenerg Biomembr. 2013 Jun;45(3):261-70. doi: 10.1007/s10863-012-9497-1. Epub 2012 Dec 29. [PubMed:23274738]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Binder
Curator comments
This is a possible target due to its location on the estrogen receptor, which binds to estradiol.
General Function
Plays a central role in autophagy (PubMed:23184933). Acts as core subunit of the PI3K complex that mediates formation of phosphatidylinositol 3-phosphate; different complex forms are believed to play a role in multiple membrane trafficking pathways: PI3KC3-C1 is involved in initiation of autophagosomes and PI3KC3-C2 in maturation of autophagosomes and endocytosis. Involved in regulation of degradative endocytic trafficking and required for the abcission step in cytokinesis, probably in the context of PI3KC3-C2 (PubMed:20643123, PubMed:20208530). Essential for the formation of PI3KC3-C2 but not PI3KC3-C1 PI3K complex forms. Involved in endocytosis (PubMed:25275521). Protects against infection by a neurovirulent strain of Sindbis virus (PubMed:9765397). May play a role in antiviral host defense.
Specific Function
Phosphatidylinositol 3-kinase binding
Gene Name
BECN1
Uniprot ID
Q14457
Uniprot Name
Beclin-1
Molecular Weight
51895.945 Da
References
  1. Van Dorst B, Mehta J, Rouah-Martin E, De Coen W, Blust R, Robbens J: The identification of cellular targets of 17beta estradiol using a lytic (T7) cDNA phage display approach. Toxicol In Vitro. 2011 Feb;25(1):388-93. doi: 10.1016/j.tiv.2010.10.012. Epub 2010 Oct 27. [PubMed:21034808]
  2. Moreno AJ, Moreira PI, Custodio JB, Santos MS: Mechanism of inhibition of mitochondrial ATP synthase by 17beta-estradiol. J Bioenerg Biomembr. 2013 Jun;45(3):261-70. doi: 10.1007/s10863-012-9497-1. Epub 2012 Dec 29. [PubMed:23274738]

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
  1. 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. [PubMed:12865317]
  2. Tsuchiya Y, Nakajima M, Yokoi T: Cytochrome P450-mediated metabolism of estrogens and its regulation in human. Cancer Lett. 2005 Sep 28;227(2):115-24. doi: 10.1016/j.canlet.2004.10.007. Epub 2004 Nov 19. [PubMed:16112414]
  3. Cheng ZN, Shu Y, Liu ZQ, Wang LS, Ou-Yang DS, Zhou HH: Role of cytochrome P450 in estradiol metabolism in vitro. Acta Pharmacol Sin. 2001 Feb;22(2):148-54. [PubMed:11741520]
  4. 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. [PubMed:22837389]
  5. O'Connell MB: Pharmacokinetic and pharmacologic variation between different estrogen products. J Clin Pharmacol. 1995 Sep;35(9S):18S-24S. doi: 10.1002/j.1552-4604.1995.tb04143.x. [PubMed:8530713]
  6. Flockhart Table of Drug Interactions [Link]
  7. FDA Approved Products: Estrace (Estradiol) oral tablets [Link]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
Inhibitor
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
  1. 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. [PubMed:12865317]
  2. Hong CC, Tang BK, Hammond GL, Tritchler D, Yaffe M, Boyd NF: Cytochrome P450 1A2 (CYP1A2) activity and risk factors for breast cancer: a cross-sectional study. Breast Cancer Res. 2004;6(4):R352-65. doi: 10.1186/bcr798. Epub 2004 May 7. [PubMed:15217502]
  3. Ren J, Chen GG, Liu Y, Su X, Hu B, Leung BC, Wang Y, Ho RL, Yang S, Lu G, Lee CG, Lai PB: Cytochrome P450 1A2 Metabolizes 17beta-Estradiol to Suppress Hepatocellular Carcinoma. PLoS One. 2016 Apr 19;11(4):e0153863. doi: 10.1371/journal.pone.0153863. eCollection 2016. [PubMed:27093553]
  4. Pollock BG, Wylie M, Stack JA, Sorisio DA, Thompson DS, Kirshner MA, Folan MM, Condifer KA: Inhibition of caffeine metabolism by estrogen replacement therapy in postmenopausal women. J Clin Pharmacol. 1999 Sep;39(9):936-40. [PubMed:10471985]
  5. Flockhart Table of Drug Interactions [Link]
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
  1. Flockhart Table of Drug Interactions [Link]
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
CYP3A7
Uniprot ID
P24462
Uniprot Name
Cytochrome P450 3A7
Molecular Weight
57525.03 Da
References
  1. Flockhart Table of Drug Interactions [Link]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Steroid binding
Specific Function
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the...
Gene Name
UGT1A1
Uniprot ID
P22309
Uniprot Name
UDP-glucuronosyltransferase 1-1
Molecular Weight
59590.91 Da
References
  1. Hanioka N, Tanabe N, Jinno H, Tanaka-Kagawa T, Nagaoka K, Naito S, Koeda A, Narimatsu S: Functional characterization of human and cynomolgus monkey UDP-glucuronosyltransferase 1A1 enzymes. Life Sci. 2010 Aug 14;87(7-8):261-8. doi: 10.1016/j.lfs.2010.07.001. Epub 2010 Jul 8. [PubMed:20620155]
  2. Guillemette C, Belanger A, Lepine J: Metabolic inactivation of estrogens in breast tissue by UDP-glucuronosyltransferase enzymes: an overview. Breast Cancer Res. 2004;6(6):246-54. Epub 2004 Sep 27. [PubMed:15535854]
  3. Zhou J, Tracy TS, Remmel RP: Correlation between bilirubin glucuronidation and estradiol-3-gluronidation in the presence of model UDP-glucuronosyltransferase 1A1 substrates/inhibitors. Drug Metab Dispos. 2011 Feb;39(2):322-9. doi: 10.1124/dmd.110.035030. Epub 2010 Oct 28. [PubMed:21030469]
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
  1. Dubey RK, Jackson EK, Gillespie DG, Rosselli M, Barchiesi F, Krust A, Keller H, Zacharia LC, Imthurn B: Cytochromes 1A1/1B1- and catechol-O-methyltransferase-derived metabolites mediate estradiol-induced antimitogenesis in human cardiac fibroblast. J Clin Endocrinol Metab. 2005 Jan;90(1):247-55. doi: 10.1210/jc.2003-032154. Epub 2004 Oct 26. [PubMed:15507517]
  2. Dubey RK, Gillespie DG, Zacharia LC, Barchiesi F, Imthurn B, Jackson EK: CYP450- and COMT-derived estradiol metabolites inhibit activity of human coronary artery SMCs. Hypertension. 2003 Mar;41(3 Pt 2):807-13. doi: 10.1161/01.HYP.0000048862.28501.72. Epub 2002 Dec 23. [PubMed:12624000]
  3. Flockhart Table of Drug Interactions [Link]
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
  1. Dubey RK, Jackson EK, Gillespie DG, Rosselli M, Barchiesi F, Krust A, Keller H, Zacharia LC, Imthurn B: Cytochromes 1A1/1B1- and catechol-O-methyltransferase-derived metabolites mediate estradiol-induced antimitogenesis in human cardiac fibroblast. J Clin Endocrinol Metab. 2005 Jan;90(1):247-55. doi: 10.1210/jc.2003-032154. Epub 2004 Oct 26. [PubMed:15507517]
  2. Dubey RK, Gillespie DG, Zacharia LC, Barchiesi F, Imthurn B, Jackson EK: CYP450- and COMT-derived estradiol metabolites inhibit activity of human coronary artery SMCs. Hypertension. 2003 Mar;41(3 Pt 2):807-13. doi: 10.1161/01.HYP.0000048862.28501.72. Epub 2002 Dec 23. [PubMed:12624000]
  3. Nishida CR, Everett S, Ortiz de Montellano PR: Specificity determinants of CYP1B1 estradiol hydroxylation. Mol Pharmacol. 2013 Sep;84(3):451-8. doi: 10.1124/mol.113.087700. Epub 2013 Jul 2. [PubMed:23821647]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
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
  1. Mwinyi J, Cavaco I, Pedersen RS, Persson A, Burkhardt S, Mkrtchian S, Ingelman-Sundberg M: Regulation of CYP2C19 expression by estrogen receptor alpha: implications for estrogen-dependent inhibition of drug metabolism. Mol Pharmacol. 2010 Nov;78(5):886-94. doi: 10.1124/mol.110.065540. Epub 2010 Jul 30. [PubMed:20675569]
  2. Justenhoven C, Hamann U, Pierl CB, Baisch C, Harth V, Rabstein S, Spickenheuer A, Pesch B, Bruning T, Winter S, Ko YD, Brauch H: CYP2C19*17 is associated with decreased breast cancer risk. Breast Cancer Res Treat. 2009 May;115(2):391-6. doi: 10.1007/s10549-008-0076-4. Epub 2008 Jun 3. [PubMed:18521743]
  3. Cheng ZN, Shu Y, Liu ZQ, Wang LS, Ou-Yang DS, Zhou HH: Role of cytochrome P450 in estradiol metabolism in vitro. Acta Pharmacol Sin. 2001 Feb;22(2):148-54. [PubMed:11741520]
  4. Tervasmaki A, Winqvist R, Jukkola-Vuorinen A, Pylkas K: Recurrent CYP2C19 deletion allele is associated with triple-negative breast cancer. BMC Cancer. 2014 Dec 2;14:902. doi: 10.1186/1471-2407-14-902. [PubMed:25466287]
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
CYP2C8
Uniprot ID
P10632
Uniprot Name
Cytochrome P450 2C8
Molecular Weight
55824.275 Da
References
  1. Cheng ZN, Shu Y, Liu ZQ, Wang LS, Ou-Yang DS, Zhou HH: Role of cytochrome P450 in estradiol metabolism in vitro. Acta Pharmacol Sin. 2001 Feb;22(2):148-54. [PubMed:11741520]
  2. Delaforge M, Pruvost A, Perrin L, Andre F: Cytochrome P450-mediated oxidation of glucuronide derivatives: example of estradiol-17beta-glucuronide oxidation to 2-hydroxy-estradiol-17beta-glucuronide by CYP 2C8. Drug Metab Dispos. 2005 Mar;33(3):466-73. doi: 10.1124/dmd.104.002097. Epub 2004 Dec 17. [PubMed:15608133]
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
  1. 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. [PubMed:9625734]
  2. Schmider J, Greenblatt DJ, von Moltke LL, Karsov D, Vena R, Friedman HL, Shader RI: Biotransformation of mestranol to ethinyl estradiol in vitro: the role of cytochrome P-450 2C9 and metabolic inhibitors. J Clin Pharmacol. 1997 Mar;37(3):193-200. [PubMed:9089421]
  3. Cheng ZN, Shu Y, Liu ZQ, Wang LS, Ou-Yang DS, Zhou HH: Role of cytochrome P450 in estradiol metabolism in vitro. Acta Pharmacol Sin. 2001 Feb;22(2):148-54. [PubMed:11741520]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inducer
General Function
Glucuronosyltransferase activity
Specific Function
UDPGTs are of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isozyme displays activity toward several classes of xeno...
Gene Name
UGT2B15
Uniprot ID
P54855
Uniprot Name
UDP-glucuronosyltransferase 2B15
Molecular Weight
61035.815 Da
References
  1. Harrington WR, Sengupta S, Katzenellenbogen BS: Estrogen regulation of the glucuronidation enzyme UGT2B15 in estrogen receptor-positive breast cancer cells. Endocrinology. 2006 Aug;147(8):3843-50. Epub 2006 May 11. [PubMed:16690804]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
O-methyltransferase activity
Specific Function
Catalyzes the O-methylation, and thereby the inactivation, of catecholamine neurotransmitters and catechol hormones. Also shortens the biological half-lives of certain neuroactive drugs, like L-DOP...
Gene Name
COMT
Uniprot ID
P21964
Uniprot Name
Catechol O-methyltransferase
Molecular Weight
30036.77 Da
References
  1. Dubey RK, Jackson EK, Gillespie DG, Rosselli M, Barchiesi F, Krust A, Keller H, Zacharia LC, Imthurn B: Cytochromes 1A1/1B1- and catechol-O-methyltransferase-derived metabolites mediate estradiol-induced antimitogenesis in human cardiac fibroblast. J Clin Endocrinol Metab. 2005 Jan;90(1):247-55. doi: 10.1210/jc.2003-032154. Epub 2004 Oct 26. [PubMed:15507517]
  2. Worda C, Sator MO, Schneeberger C, Jantschev T, Ferlitsch K, Huber JC: Influence of the catechol-O-methyltransferase (COMT) codon 158 polymorphism on estrogen levels in women. Hum Reprod. 2003 Feb;18(2):262-6. doi: 10.1093/humrep/deg059. [PubMed:12571159]
  3. Dubey RK, Gillespie DG, Zacharia LC, Barchiesi F, Imthurn B, Jackson EK: CYP450- and COMT-derived estradiol metabolites inhibit activity of human coronary artery SMCs. Hypertension. 2003 Mar;41(3 Pt 2):807-13. doi: 10.1161/01.HYP.0000048862.28501.72. Epub 2002 Dec 23. [PubMed:12624000]
Kind
Protein group
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
Inducer
General Function
Steroid binding
Specific Function
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the...

Components:
References
  1. Cho SJ, Ning M, Zhang Y, Rubin LH, Jeong H: 17beta-Estradiol up-regulates UDP-glucuronosyltransferase 1A9 expression via estrogen receptor alpha. Acta Pharm Sin B. 2016 Sep;6(5):504-509. doi: 10.1016/j.apsb.2016.04.005. Epub 2016 May 20. [PubMed:27709019]
  2. Williams JA, Ring BJ, Cantrell VE, Campanale K, Jones DR, Hall SD, Wrighton SA: Differential modulation of UDP-glucuronosyltransferase 1A1 (UGT1A1)-catalyzed estradiol-3-glucuronidation by the addition of UGT1A1 substrates and other compounds to human liver microsomes. Drug Metab Dispos. 2002 Nov;30(11):1266-73. doi: 10.1124/dmd.30.11.1266. [PubMed:12386134]
  3. Chen H, Yang K, Choi S, Fischer JH, Jeong H: Up-regulation of UDP-glucuronosyltransferase (UGT) 1A4 by 17beta-estradiol: a potential mechanism of increased lamotrigine elimination in pregnancy. Drug Metab Dispos. 2009 Sep;37(9):1841-7. doi: 10.1124/dmd.109.026609. Epub 2009 Jun 22. [PubMed:19546240]
  4. Ebner T, Remmel RP, Burchell B: Human bilirubin UDP-glucuronosyltransferase catalyzes the glucuronidation of ethinylestradiol. Mol Pharmacol. 1993 Apr;43(4):649-54. [PubMed:8474433]

Carriers

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Binder
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
  1. Campusano M C, Brusco G F, Campino J C, Rodriguez P L, Arteaga U E: [Assessment of androgenic decline in the elderly]. Rev Med Chil. 2006 Sep;134(9):1123-8. Epub 2006 Dec 12. [PubMed:17171213]
  2. Kuba R, Pohanka M, Zakopcan J, Novotna I, Rektor I: Sexual dysfunctions and blood hormonal profile in men with focal epilepsy. Epilepsia. 2006 Dec;47(12):2135-40. [PubMed:17201714]
  3. Bendlova B, Zavadilova J, Vankova M, Vejrazkova D, Lukasova P, Vcelak J, Hill M, Cibula D, Vondra K, Starka L, Vrbikova J: Role of D327N sex hormone-binding globulin gene polymorphism in the pathogenesis of polycystic ovary syndrome. J Steroid Biochem Mol Biol. 2007 Apr;104(1-2):68-74. Epub 2007 Jan 26. [PubMed:17258903]
  4. Sablik Z, Samborska-Sablik A, Bolinska-Soltysiak H, Goch JH, Kula K: [Hyperandrogenism as a risk factor of coronary artery disease in young women]. Pol Arch Med Wewn. 2006 Feb;115(2):118-24. [PubMed:17274467]
  5. Mohamad MJ, Mohammad MA, Karayyem M, Hairi A, Hader AA: Serum levels of sex hormones in men with acute myocardial infarction. Neuro Endocrinol Lett. 2007 Apr;28(2):182-6. [PubMed:17435665]
  6. O'Connell MB: Pharmacokinetic and pharmacologic variation between different estrogen products. J Clin Pharmacol. 1995 Sep;35(9S):18S-24S. doi: 10.1002/j.1552-4604.1995.tb04143.x. [PubMed:8530713]
  7. Pardridge WM: Serum bioavailability of sex steroid hormones. Clin Endocrinol Metab. 1986 May;15(2):259-78. [PubMed:3521955]
  8. Ropponen A, Aittomaki K, Vihma V, Tikkanen MJ, Ylikorkala O: Effects of oral and transdermal estradiol administration on levels of sex hormone-binding globulin in postmenopausal women with and without a history of intrahepatic cholestasis of pregnancy. J Clin Endocrinol Metab. 2005 Jun;90(6):3431-4. doi: 10.1210/jc.2005-0352. Epub 2005 Mar 22. [PubMed:15784702]
  9. Knochenhauer ES, Boots LR, Potter HD, Azziz R: Differential binding of estradiol and testosterone to SHBG. Relation to circulating estradiol levels. J Reprod Med. 1998 Aug;43(8):665-70. [PubMed:9749416]
  10. FDA Approved Products: Estring (Estradiol vaginal ring) [Link]
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
  1. O'Connell MB: Pharmacokinetic and pharmacologic variation between different estrogen products. J Clin Pharmacol. 1995 Sep;35(9S):18S-24S. doi: 10.1002/j.1552-4604.1995.tb04143.x. [PubMed:8530713]
  2. FDA Approved Products: Estring (Estradiol vaginal ring) [Link]
Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
Binder
General Function
Transporter activity
Specific Function
FABP are thought to play a role in the intracellular transport of long-chain fatty acids and their acyl-CoA esters. FABP2 is probably involved in triglyceride-rich lipoprotein synthesis. Binds satu...
Gene Name
FABP2
Uniprot ID
P12104
Uniprot Name
Fatty acid-binding protein, intestinal
Molecular Weight
15207.165 Da
References
  1. Rowland A, Knights KM, Mackenzie PI, Miners JO: Characterization of the binding of drugs to human intestinal fatty acid binding protein (IFABP): potential role of IFABP as an alternative to albumin for in vitro-in vivo extrapolation of drug kinetic parameters. Drug Metab Dispos. 2009 Jul;37(7):1395-403. doi: 10.1124/dmd.109.027656. Epub 2009 Apr 27. [PubMed:19398502]

Transporters

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
Downregulator
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
  1. 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. [PubMed:12110607]
  2. Urakami Y, Okuda M, Saito H, Inui K: Hormonal regulation of organic cation transporter OCT2 expression in rat kidney. FEBS Lett. 2000 May 12;473(2):173-6. doi: 10.1016/s0014-5793(00)01525-8. [PubMed:10812069]
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
  1. 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. [PubMed:9830022]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Atpase activity, coupled to transmembrane movement of substances
Specific Function
ATP-dependent transporter probably involved in cellular detoxification through lipophilic anion extrusion.
Gene Name
ABCC10
Uniprot ID
Q5T3U5
Uniprot Name
Multidrug resistance-associated protein 7
Molecular Weight
161627.375 Da
References
  1. Chen ZS, Hopper-Borge E, Belinsky MG, Shchaveleva I, Kotova E, Kruh GD: Characterization of the transport properties of human multidrug resistance protein 7 (MRP7, ABCC10). Mol Pharmacol. 2003 Feb;63(2):351-8. [PubMed:12527806]
  2. Hopper-Borge E, Chen ZS, Shchaveleva I, Belinsky MG, Kruh GD: Analysis of the drug resistance profile of multidrug resistance protein 7 (ABCC10): resistance to docetaxel. Cancer Res. 2004 Jul 15;64(14):4927-30. [PubMed:15256465]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Sodium-independent organic anion transmembrane transporter activity
Specific Function
Mediates saturable uptake of estrone sulfate, dehydroepiandrosterone sulfate and related compounds.
Gene Name
SLC22A11
Uniprot ID
Q9NSA0
Uniprot Name
Solute carrier family 22 member 11
Molecular Weight
59970.945 Da
References
  1. Cha SH, Sekine T, Kusuhara H, Yu E, Kim JY, Kim DK, Sugiyama Y, Kanai Y, Endou H: Molecular cloning and characterization of multispecific organic anion transporter 4 expressed in the placenta. J Biol Chem. 2000 Feb 11;275(6):4507-12. [PubMed:10660625]
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
  1. 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. [PubMed:12920197]
  2. 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. [PubMed:11927002]
  3. 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. [PubMed:25236865]
  4. Hartz AM, Mahringer A, Miller DS, Bauer B: 17-beta-Estradiol: a powerful modulator of blood-brain barrier BCRP activity. J Cereb Blood Flow Metab. 2010 Oct;30(10):1742-55. doi: 10.1038/jcbfm.2010.36. Epub 2010 Mar 10. [PubMed:20216549]
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
  1. 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. [PubMed:11683238]
  2. Kullak-Ublick GA, Ismair MG, Stieger B, Landmann L, Huber R, Pizzagalli F, Fattinger K, Meier PJ, Hagenbuch B: Organic anion-transporting polypeptide B (OATP-B) and its functional comparison with three other OATPs of human liver. Gastroenterology. 2001 Feb;120(2):525-33. [PubMed:11159893]
  3. FDA Drug Development and Drug Interactions: Table of Substrates, Inhibitors and Inducers [Link]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
Downregulator
Regulator
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
  1. 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. [PubMed:15290871]
  2. Zampieri L, Bianchi P, Ruff P, Arbuthnot P: Differential modulation by estradiol of P-glycoprotein drug resistance protein expression in cultured MCF7 and T47D breast cancer cells. Anticancer Res. 2002 Jul-Aug;22(4):2253-9. [PubMed:12174911]
  3. Mutoh K, Tsukahara S, Mitsuhashi J, Katayama K, Sugimoto Y: Estrogen-mediated post transcriptional down-regulation of P-glycoprotein in MDR1-transduced human breast cancer cells. Cancer Sci. 2006 Nov;97(11):1198-204. Epub 2006 Aug 22. [PubMed:16925584]
  4. Kanado Y, Tsurudome Y, Omata Y, Yasukochi S, Kusunose N, Akamine T, Matsunaga N, Koyanagi S, Ohdo S: Estradiol regulation of P-glycoprotein expression in mouse kidney and human tubular epithelial cells, implication for renal clearance of drugs. Biochem Biophys Res Commun. 2019 Nov 12;519(3):613-619. doi: 10.1016/j.bbrc.2019.09.021. Epub 2019 Sep 17. [PubMed:31540689]
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
  1. Cha SH, Sekine T, Fukushima JI, Kanai Y, Kobayashi Y, Goya T, Endou H: Identification and characterization of human organic anion transporter 3 expressing predominantly in the kidney. Mol Pharmacol. 2001 May;59(5):1277-86. [PubMed:11306713]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
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
  1. Kullak-Ublick GA, Ismair MG, Stieger B, Landmann L, Huber R, Pizzagalli F, Fattinger K, Meier PJ, Hagenbuch B: Organic anion-transporting polypeptide B (OATP-B) and its functional comparison with three other OATPs of human liver. Gastroenterology. 2001 Feb;120(2):525-33. [PubMed:11159893]
  2. FDA Drug Development and Drug Interactions: Table of Substrates, Inhibitors and Inducers [Link]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Thyroid hormone transmembrane transporter activity
Specific Function
Mediates the Na(+)-independent high affinity transport of organic anions such as the thyroid hormones thyroxine (T4) and rT3. Other potential substrates, such as triiodothyronine (T3), 17-beta-gluc...
Gene Name
SLCO1C1
Uniprot ID
Q9NYB5
Uniprot Name
Solute carrier organic anion transporter family member 1C1
Molecular Weight
78695.625 Da
References
  1. Pizzagalli F, Hagenbuch B, Stieger B, Klenk U, Folkers G, Meier PJ: Identification of a novel human organic anion transporting polypeptide as a high affinity thyroxine transporter. Mol Endocrinol. 2002 Oct;16(10):2283-96. [PubMed:12351693]

Drug created on June 13, 2005 07:24 / Updated on November 30, 2020 13:38

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