- Overview
- Properties
- Genetics
- Related Genes
- Pathways
- Related Drugs
- Related Diseases
- Datasets
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Overview
| Generic Names: | 17-beta; Beta-Estradiol; Cis-Estradiol; Cis-Oestradiol; D-Estradiol; D-Oestradiol; Dihydrofollicular Hormone; Dihydrofolliculin; Dihydroxyesterin; Dihydroxyestrin; Dihydroxyoestrin; Estradiol Cypionate; Estradiol Valerate; Estradiol-17beta; estradiol |
|---|---|
| Trade Names: | Aerodiol; Agofollin; Alora; Altrad; Amnestrogen; Aquadiol; Bardiol; Climaderm; Climara; Combipatch; Compudose; Compudose 200; Compudose 365; Corpagen; Delestrogen; Depo-Estradiol; Dermestril; Dihydromenformon; Dihydrotheelin; Dimenformon; Dimenformon Prolongatum; Diogyn; Diogynets; Divigel; Elestrin; Encore; Esclim; Estinyl; Estrace; Estraderm; Estraderm Tts; Estradurin; Estrasorb; Estreva; Estrifam; Estring; Estring Vaginal Ring; Estroclim; Estroclim 50; Estrofem 2; Estrofem Forte; Estrogel; Estrogens, Esterified; Estrovite; Evamist; Evorel; Extrasorb; Femestral; Femestrol; Feminone; Femogen; Fempatch; Femring; Femtrace; Femtran; Follicyclin; Ginedisc; Ginosedol; Gynergon; Gynestrel; Gynodiol; Gynoestryl; Gynpolar; Innofem; Lamdiol; Lynoral; Macrodiol; Macrol; Menest; Menorest; Menostar; Microdiol; Nordicol; Oestergon; Oestradiol; Oestradiol R; Oestrogel; Oestroglandol; Oestrogynal; Ovahormon; Ovasterol; Ovastevol; Ovociclina; Ovocyclin; Ovocycline; Ovocylin; Perlatanol; Primofol; Profoliol; Profoliol B; Progynon; Progynon Dh; Progynon-Dh; Ricifon; Ritsifon; Sandrena Gel; Sisare Gel; Sk-Estrogens; Soldep; Sotipox; Syndiol; Systen; Tradelia; Trial Sat; Trocosone; Vagifem; Vivelle; Zerella; Zumenon |
| Brand Mixtures: | Alesse 21 Tablets (Ethinyl Estradiol + Levonorgestrel); Alesse 28 Tablets (Ethinyl Estradiol + Levonorgestrel); Brevicon 0.5/35 21 Tab (Ethinyl Estradiol + Norethindrone); Brevicon 0.5/35 28 Tab (Ethinyl Estradiol + Norethindrone); Brevicon 1/35 21 Tab (Ethinyl Estradiol + Norethindrone); Brevicon 1/35 28 Tab (Ethinyl Estradiol + Norethindrone); Calf-Oid Implant (Estradiol Benzoate + Progesterone); Climacteron Injection (Estradiol Benzoate + Estradiol Dienanthate + Testosterone Enanthate Benzilic Acid Hydrazone); Demulen 50 (21 Day Pack) (Ethinyl Estradiol + Ethynodiol Diacetate); Demulen 50 (28 Day Pack) (Ethinyl Estradiol + Ethynodiol Diacetate); Min-Ovral 21 Tab (Ethinyl Estradiol + Levonorgestrel); Min-Ovral 28 Tab (Ethinyl Estradiol + Levonorgestrel); Neo Mens Tab (Ethinyl Estradiol + Ethisterone); Ortho 10/11 Tablets (21 Day) (Ethinyl Estradiol + Norethindrone); Ortho 10/11 Tablets (28 Day) (Ethinyl Estradiol + Norethindrone); Ovral 21 Tab (Ethinyl Estradiol + Norgestrel (Norgestrel)); Ovral 28tab (Ethinyl Estradiol + Norgestrel); Preven Tablets (Ethinyl Estradiol + Levonorgestrel); Synphasic 21 Tablets (Ethinyl Estradiol + Norethindrone); Synphasic-28 Tablets (Ethinyl Estradiol + Norethindrone); Tri-Cyclen Lo (Ethinyl Estradiol + Norgestimate); Triphasil 21 Tab (Ethinyl Estradiol + Levonorgestrel); Triphasil 28 Tab (Ethinyl Estradiol + Levonorgestrel); Triquilar 21 (Ethinyl Estradiol + Levonorgestrel) |
| PharmGKB Accession Id: | PA449503 |
Description
Generally refers to the 17-beta-isomer of estradiol, an aromatized C18 steroid with hydroxyl group at 3-beta- and 17-beta-position. Estradiol-17-beta is the most potent form of mammalian estrogenic steroids. In humans, it is produced primarily by the cyclic ovaries and the placenta. It is also produced by the adipose tissue of men and postmenopausal women. The 17-alpha-isomer of estradiol binds weakly to estrogen receptors (receptors, estrogen) and exhibits little estrogenic activity in estrogen-responsive tissues. Various isomers can be synthesized. PubChem (source: Drug Bank)
Indication
For the treatment of urogenital symptoms associated with post-menopausal atrophy of the vagina (such as dryness, burning, pruritus and dyspareunia) and/or the lower urinary tract (urinary urgency and dysuria). (source: Drug Bank)
ATC Therapeutic Categories
- G03CA:Natural and semisynthetic estrogens, plain
- L02AA:Estrogens
Pharmacology, Interactions, and Contraindications
Mechanism Of Action
Estradiol enters target cells freely (e.g., female organs, breasts, hypothalamus, pituitary) and interacts with a target cell receptor. When the estrogen receptor has bound its ligand it can enter the nucleus of the target cell, and regulate gene transcription which leads to formation of messenger RNA. The mRNA interacts with ribosomes to produce specific proteins that express the effect of estradiol upon the target cell. 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) from the anterior pituitary. (source: Drug Bank)
Pharmacology
Estradiol, the principal intracellular human estrogen, is substantially more active than its metabolites, estrone and estriol, at the cellular level. (source: Drug Bank)
Food Interactions
Take with food to decrease nausea. (source: Drug Bank)
Absorption, Distribution, Metabolism, Elimination & Toxicity
Biotransformation
Exogenous estrogens are metabolized using the same mechanism as endogenous estrogens. Estrogens are partially metabolized by cytochrome P450. (source: Drug Bank)
Protein Binding
>95% (source: Drug Bank)
Absorption
43% (source: Drug Bank)
Toxicity
Can cause nausea and vomiting, and withdrawal bleeding may occur in females. (source: Drug Bank)
Isomeric SMILES Code:
C[C@]12CC[C@@H]3c4ccc(cc4CC[C@H]3[C@@H]1CC[C@@H]2O)O (source: Drug Bank)
Curated Annotations (
)
-
rs45511401
at chr16:16080733
in
ABCC1
system: membrane vessicles from HEK cells transfected with WT and variant; FA: transport of leukotriene C4, 17beta-estradiol 17beta-(D)-glucuronide, and estrone sulfate were the same for WT and variant- Variant Name:
- G671V
- Related Drugs:
- estradiol, estrone
- Evidence:
-
PMID:11721885
-
rs35529209
at chr16:16112826
in
ABCC1
system: membrane vessicles from HEK cells transfected with WT or variant; FA: variant had approx 50% decrease in transport of tritium labelled 17[beta]-estradiol-17[beta]-D-glucuronide (17E2b-g) due to decrease in Km- Variant Name:
- Ala989Thr
- Related Drugs:
- estradiol
- Evidence:
-
PMID:16041243
The following genes are in curated knowledge about this drug.
| Gene | Relationship | Evidence | |
|---|---|---|---|
|
ABCC1 |
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Variants |
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ADORA1 |
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Publications |
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CYP19A1 |
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Publications |
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CYP1A2 |
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Publications |
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ERBB2 |
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Publications |
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ESR1 |
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Publications |
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G6PD |
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Publications |
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GPX1 |
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Publications |
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JAG1 |
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Publications |
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KRT13 |
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Publications |
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NR1I2 |
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Publications |
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OGG1 |
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Publications |
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PAPSS1 |
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Publications |
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SLC7A11 |
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Publications |
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SLCO1B1 |
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Publications |
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SOD1 |
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Publications |
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SOD2 |
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Publications |
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SPINK4 |
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Publications |
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SULT1A1 |
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Publications |
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SULT1A2 |
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Publications |
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SULT1A3 |
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Publications |
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SULT1A4 |
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Publications |
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SULT1B1 |
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Publications |
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SULT1C4 |
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Publications |
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SULT1E1 |
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Publications |
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SULT2A1 |
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Publications |
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SULT2B1 |
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Publications |
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SULT4A1 |
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Publications |
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SULT6B1 |
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Publications |
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UGT1A1 |
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Publications |
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UGT1A10 |
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Publications |
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UGT1A3 |
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Publications |
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UGT1A6 |
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Publications |
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UGT2B17 |
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Publications |
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XRCC4 |
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Publications |
A list of non-curated publications that mention this drug along with other genes is available.
Drug Targets
| Gene | Description | |
|---|---|---|
| ESR1 |
|
(source: Drug Bank) |
| ESR2 |
|
(source: Drug Bank) |
| NR1I2 |
|
(source: Drug Bank) |
| SHBG |
|
(source: Drug Bank) |
PharmGKB Curated Pathways
- Anti-estrogen Pathway (Aromatase Inhibitor)
- Anti-estrogen Pathway (Estrogen metabolism)
- Anti-estrogen Pathway (Summary)
BioCarta Pathways†
- carm1 and regulation of the estrogen receptor - (BioCarta via Pathway Interaction Database)
- downregulated of mta-3 in er-negative breast tumors - (BioCarta via Pathway Interaction Database)
- estrogen responsive protein efp controls cell cycle and breast tumors growth - (BioCarta via Pathway Interaction Database)
- overview of telomerase protein component gene htert transcriptional regulation - (BioCarta via Pathway Interaction Database)
- pelp1 modulation of estrogen receptor activity - (BioCarta via Pathway Interaction Database)
Reactome Pathways†
The following drugs are in curated knowledge about this drug.
| Drug | Relationship | Evidence | |
|---|---|---|---|
|
|
anastrozole |
|
Publications |
|
|
letrozole |
|
Publications |
|
|
tamoxifen |
|
Publications |
A list of non-curated publications that mention this drug along with other drugs is available.
Drug Interactions
| Drug | Description | |
|---|---|---|
| amobarbital |
|
The enzyme inducer decreases the effect of hormones (source: Drug Bank) |
| aprobarbital |
|
The enzyme inducer decreases the effect of hormones (source: Drug Bank) |
| butabarbital |
|
The enzyme inducer decreases the effect of hormones (source: Drug Bank) |
| butalbital |
|
The enzyme inducer decreases the effect of hormones (source: Drug Bank) |
| butethal |
|
The enzyme inducer decreases the effect of hormones (source: Drug Bank) |
| ethotoin |
|
The enzyme inducer decreases the effect of hormones (source: Drug Bank) |
| fosphenytoin |
|
The enzyme inducer decreases the effect of hormones (source: Drug Bank) |
| griseofulvin |
|
The enzyme inducer decreases the effect of hormones (source: Drug Bank) |
| heptabarbital |
|
The enzyme inducer decreases the effect of hormones (source: Drug Bank) |
| hexobarbital |
|
The enzyme inducer decreases the effect of hormones (source: Drug Bank) |
| mephenytoin |
|
The enzyme inducer decreases the effect of hormones (source: Drug Bank) |
| methohexital |
|
The enzyme inducer decreases the effect of hormones (source: Drug Bank) |
| methylphenobarbital |
|
The enzyme inducer decreases the effect of hormones (source: Drug Bank) |
| pentobarbital |
|
The enzyme inducer decreases the effect of hormones (source: Drug Bank) |
| phenobarbital |
|
The enzyme inducer decreases the effect of hormones (source: Drug Bank) |
| phenytoin |
|
The enzyme inducer decreases the effect of hormones (source: Drug Bank) |
| prednisolone |
|
The estrogenic agent increases the effect of corticosteroid (source: Drug Bank) |
| prednisone |
|
The estrogenic agent increases the effect of corticosteroid (source: Drug Bank) |
| primidone |
|
The enzyme inducer decreases the effect of hormones (source: Drug Bank) |
| raloxifene |
|
Association not recommended (source: Drug Bank) |
| secobarbital |
|
The enzyme inducer decreases the effect of hormones (source: Drug Bank) |
| talbutal |
|
The enzyme inducer decreases the effect of hormones (source: Drug Bank) |
| ursodeoxycholic acid |
|
Estrogens decreases the effect of ursodiol (source: Drug Bank) |
Curated Information
The following diseases are in curated knowledge about this drug.
| Disease | Relationship | Evidence | |
|---|---|---|---|
|
|
Breast Neoplasms |
|
Publications |
|
|
Crigler-Najjar Syndrome |
|
Publications |
|
|
estrogen-dependent carcinogenesis |
|
Publications |
Non-Curated Information
A list of non-curated publications that mention this drug along with other diseases is available.
Additional Datasets
These datasets are minimally curated and are sorted alphabetically by title.
LinkOuts
Common Searches
Search PubMed
Search Medline Plus
Search PubChem
Search CTD
Non-Curated Publications
A list of non-curated publications that mention this drug is available.