U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ABSOLUTE
Molecular Formula C23H32O3
Molecular Weight 356.4984
Optical Activity UNSPECIFIED
Defined Stereocenters 5 / 5
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ESTRADIOL VALERATE

SMILES

[H][C@@]12CC[C@H](OC(=O)CCCC)[C@@]1(C)CC[C@]3([H])C4=C(CC[C@@]23[H])C=C(O)C=C4

InChI

InChIKey=RSEPBGGWRJCQGY-RBRWEJTLSA-N
InChI=1S/C23H32O3/c1-3-4-5-22(25)26-21-11-10-20-19-8-6-15-14-16(24)7-9-17(15)18(19)12-13-23(20,21)2/h7,9,14,18-21,24H,3-6,8,10-13H2,1-2H3/t18-,19-,20+,21+,23+/m1/s1

HIDE SMILES / InChI

Molecular Formula C23H32O3
Molecular Weight 356.4984
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 5 / 5
E/Z Centers 0
Optical Activity UNSPECIFIED

Description
Curator's Comment: Description was created based on several sources, including http://www.accessdata.fda.gov/drugsatfda_docs/label/2013/020375s027lbl.pdf

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. 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. Estradiol is used 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). Estradiol is marketed under the brand name Climara (among others), indicated for: the treatment of moderate to severe vasomotor symptoms due to menopause, treatment of symptoms of vulvar and vaginal atrophy due to menopause, treatment of hypoestrogenism due to hypogonadism, castration or primary ovarian failure and prevention of postmenopausal osteoporosis.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Target ID: P08842
Gene ID: 412.0
Gene Symbol: STS
Target Organism: Homo sapiens (Human)
0.0084 nM [EC50]
1.4 nM [EC50]
19.1 nM [IC50]
0.13 nM [Ki]
0.09 nM [Kd]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
CLIMARA

Approved Use

Climara is an estrogen indicated for: •Treatment of Moderate to Severe Vasomotor Symptoms due to Menopause •Treatment of Moderate to Severe Symptoms of Vulvar and Vaginal Atrophy due to Menopause •Treatment of Hypoestrogenism due to Hypogonadism, Castration or Primary Ovarian Failure •Prevention of Postmenopausal Osteoporosis

Launch Date

1974
Preventing
CLIMARA

Approved Use

Climara is an estrogen indicated for: •Treatment of Moderate to Severe Vasomotor Symptoms due to Menopause •Treatment of Moderate to Severe Symptoms of Vulvar and Vaginal Atrophy due to Menopause •Treatment of Hypoestrogenism due to Hypogonadism, Castration or Primary Ovarian Failure •Prevention of Postmenopausal Osteoporosis

Launch Date

1974
Primary
CLIMARA

Approved Use

Climara is an estrogen indicated for: •Treatment of Moderate to Severe Vasomotor Symptoms due to Menopause •Treatment of Moderate to Severe Symptoms of Vulvar and Vaginal Atrophy due to Menopause •Treatment of Hypoestrogenism due to Hypogonadism, Castration or Primary Ovarian Failure •Prevention of Postmenopausal Osteoporosis

Launch Date

1974
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
14.7 pg/mL
0.25 mg 1 times / day steady-state, topical
dose: 0.25 mg
route of administration: Topical
experiment type: STEADY-STATE
co-administered:
ESTRADIOL plasma
Homo sapiens
population: UNKNOWN
age: ADULT
sex: FEMALE
food status: UNKNOWN
92 pg/mL
0.05 mg 1 times / day multiple, topical
dose: 0.05 mg
route of administration: Topical
experiment type: MULTIPLE
co-administered:
ESTRADIOL plasma
Homo sapiens
population: UNKNOWN
age: ADULT
sex: FEMALE
food status: UNKNOWN
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
236 pg × h/mL
0.25 mg 1 times / day steady-state, topical
dose: 0.25 mg
route of administration: Topical
experiment type: STEADY-STATE
co-administered:
ESTRADIOL plasma
Homo sapiens
population: UNKNOWN
age: ADULT
sex: FEMALE
food status: UNKNOWN
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
10 h
0.25 mg 1 times / day steady-state, topical
dose: 0.25 mg
route of administration: Topical
experiment type: STEADY-STATE
co-administered:
ESTRADIOL plasma
Homo sapiens
population: UNKNOWN
age: ADULT
sex: FEMALE
food status: UNKNOWN
1.75 h
0.05 mg 1 times / day multiple, topical
dose: 0.05 mg
route of administration: Topical
experiment type: MULTIPLE
co-administered:
ESTRADIOL plasma
Homo sapiens
population: UNKNOWN
age: ADULT
sex: FEMALE
food status: UNKNOWN
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG



Drug as perpetrator​

Drug as perpetrator​

Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
minor
minor
minor
minor
minor
minor
no
no
no
no
no
no
no
no
no
yes [Km 7 uM]
yes
yes
yes
yes
yes
yes
yes
yes
yes
yes
yes
yes
yes
yes
Sourcing

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

TitleDatePubMed
An increase of pituitary 3', 5' cyclic adenosine monophosphate produced by estradiol benzoate in vitro: possible implication of this increase in the secretion of luteinizing hormone.
1978 May
Sulfation of estrone and 17 beta-estradiol in human liver. Catalysis by thermostable phenol sulfotransferase and by dehydroepiandrosterone sulfotransferase.
1992 May-Jun
Interaction of estrogenic chemicals and phytoestrogens with estrogen receptor beta.
1998 Oct
Inhibition of the neuronal insulin receptor causes Alzheimer-like disturbances in oxidative/energy brain metabolism and in behavior in adult rats.
1999
Estrogen-induced pituitary tumor development in the ACI rat not inhibited by dietary energy restriction.
1999 Dec
Sex steroids and odorants modulate gonadotropin-releasing hormone secretion in primary cultures of human olfactory cells.
1999 Nov
Effects of environmental estrogens on tumor necrosis factor alpha-mediated apoptosis in MCF-7 cells.
1999 Nov
Steroid feedback on gonadotropin release and pituitary gonadotropin subunit mRNA in mice lacking a functional estrogen receptor alpha.
1999 Oct
Involvement of cyclooxygenase 2 in the protective effect of 17beta-estradiol on hypercholesterolemic rabbit aorta.
2000 Aug 28
Indole-3-carbinol is a negative regulator of estrogen receptor-alpha signaling in human tumor cells.
2000 Dec
High concentrations of bisphenol A induce cell growth and prolactin secretion in an estrogen-responsive pituitary tumor cell line.
2000 Feb 1
Proteinase inhibitor 9, an inhibitor of granzyme B-mediated apoptosis, is a primary estrogen-inducible gene in human liver cells.
2000 Feb 25
The aryl hydrocarbon receptor interacts with estrogen receptor alpha and orphan receptors COUP-TFI and ERRalpha1.
2000 Jan 1
Induction of uterine adenocarcinoma in CD-1 mice by catechol estrogens.
2000 Jan 15
Dramatic suppression of plasma and urinary prostate specific antigen and human glandular kallikrein by antiandrogens in male-to-female transsexuals.
2000 Mar
Estradiol acts as a germ cell survival factor in the human testis in vitro.
2000 May
Female sex steroids: effects upon microglial cell activation.
2000 Nov 1
Changes in serum and tissue zinc levels in sex hormone-induced prostatic carcinogenesis in the noble rat.
2000 Nov-Dec
Resveratrol acts as a mixed agonist/antagonist for estrogen receptors alpha and beta.
2000 Oct
Effects of arsenite on estrogen receptor-alpha expression and activity in MCF-7 breast cancer cells.
2000 Oct
NADPH- and hydroperoxide-supported 17beta-estradiol hydroxylation catalyzed by a variant form (432L, 453S) of human cytochrome P450 1B1.
2000 Sep
Constitutive expression of the steroid sulfatase gene supports the growth of MCF-7 human breast cancer cells in vitro and in vivo.
2001 Apr
Vitellogenin-induced pathology in male summer flounder (Paralichthys dentatus).
2001 Feb
Use of salivary biomarkers in biobehavioral research: cotton-based sample collection methods can interfere with salivary immunoassay results.
2001 Feb
Estrogen induces the Akt-dependent activation of endothelial nitric-oxide synthase in vascular endothelial cells.
2001 Feb 2
Unique protein determinants of the subtype-selective ligand responses of the estrogen receptors (ERalpha and ERbeta ) at AP-1 sites.
2001 Feb 9
Pregnancy stimulates secretion of adrenocorticotropin and nitric oxide from peripheral bovine lymphocytes.
2001 Jan
Follicle selection in cattle: role of luteinizing hormone.
2001 Jan
Lysyl oxidase and MMP-2 expression in dehydroepiandrosterone-induced polycystic ovary in rats.
2001 Jan
Changes in follicle-stimulating hormone and follicle populations during the ovarian cycle of the common marmoset.
2001 Jan
Estradiol-induced attenuation of pulmonary hypertension is not associated with altered eNOS expression.
2001 Jan
Metabolism of estradiol, ethynylestradiol, and moxestrol in rat uterus, vagina, and aorta: influence of sex steroid treatment.
2001 Jan
Sex steroid hormones enhance immune function in male and female Siberian hamsters.
2001 Jan
Stimulatory effect of clofibrate and gemfibrozil administration on the formation of fatty acid esters of estradiol by rat liver microsomes.
2001 Jan
Influence of gender and sex hormones on nicotine acute pharmacological effects in mice.
2001 Jan
Gender-related distinctions in protein kinase C activity in rat vascular smooth muscle.
2001 Jan
Dose-response relationships and pharmacokinetics of vitellogenin in rainbow trout after intravascular administration of 17alpha-ethynylestradiol.
2001 Jan
Neuroprotection by estradiol.
2001 Jan
Affinity labeling of rat glutathione S-transferase isozyme 1-1 by 17beta -iodoacetoxy-estradiol-3-sulfate.
2001 Jan 19
Reduction of gamma-aminobutyric acid-ergic neurotransmission as a putative mechanism of radiation induced activation of the gonadotropin releasing-hormone-pulse generator leading to precocious puberty in female rats.
2001 Jan 5
Hormone binding by protein disulfide isomerase, a high capacity hormone reservoir of the endoplasmic reticulum.
2001 Jan 5
Acquisition of Lubrol insolubility, a common step for growth hormone and prolactin in the secretory pathway of neuroendocrine cells.
2001 Jan 5
In vivo regulation of syndecan-3 expression in the rat uterus by 17 beta-estradiol.
2001 Jan 5
Glutathione stimulates sulfated estrogen transport by multidrug resistance protein 1.
2001 Mar 2
Estrogen decreases osteoclast formation by down-regulating receptor activator of NF-kappa B ligand (RANKL)-induced JNK activation.
2001 Mar 23
Enhanced multispecificity of arabidopsis vacuolar multidrug resistance-associated protein-type ATP-binding cassette transporter, AtMRP2.
2001 Mar 23
The unusual binding properties of the third distinct teleost estrogen receptor subtype ERbetaa are accompanied by highly conserved amino acid changes in the ligand binding domain.
2004 Jun
[Study of gonadal hormone drugs in blocking filovirus entry of cells in vitro].
2015 Dec
Evaluation of Effects of Topical Estradiol Benzoate Application on Cutaneous Wound Healing in Ovariectomized Female Mice.
2016
Effects of Exposure to Estradiol Benzoate or Flutamide at the Weaning Age on Expression of Connexins in the Caudal Epididymis of Adult Rat.
2016 Dec
Patents

Sample Use Guides

In Vivo Use Guide
Curator's Comment: Estradiol benzoate is not approved by the FDA for use in humans in the United States.
Unknown
Route of Administration: Unknown
Estradiol-3-sulfate (E2SO4) infused intracerebroventricularly (icv) significantly increased plasma adrenocorticotropic hormone (ACTH) and cortisol concentrations. All minipumps in the treated fetuses were filled with E2SO4 in the vehicle (water) and minipumps in the control fetuses were filled with vehicle only. These minipumps deliver a constant infusion of 5 μL/h; the concentration of E2SO4 in infusates was therefore 8.33 μg/μL. It was concluded, that E2SO4 had complex actions on the fetal brain, which might involve deconjugation by steroid sulfatase. But that the net result of direct E2SO4 icv infusion was more complex than could be accounted for by infusion of E2 alone.
Substance Class Chemical
Created
by admin
on Fri Dec 15 15:13:14 GMT 2023
Edited
by admin
on Fri Dec 15 15:13:14 GMT 2023
Record UNII
OKG364O896
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
ESTRADIOL VALERATE
EP   GREEN BOOK   INN   JAN   MART.   ORANGE BOOK   USP   USP-RS   VANDF   WHO-DD  
INN  
Official Name English
Estradiol 17-valerate
MI  
Common Name English
OESTRADIOL VALERATE
Common Name English
Estradiol valerate [WHO-DD]
Common Name English
ESTRA-1,3,5(10)-TRIENE-3,17-DIOL(17.BETA.)-, 17-PENTANOATE
Common Name English
ESTRADIOL VALERATE [GREEN BOOK]
Common Name English
ESTRADIOL VALERATE [USP MONOGRAPH]
Common Name English
ESTRADIOL VALERATE [MART.]
Common Name English
ESTRADIOL VALERATE [JAN]
Common Name English
estradiol valerate [INN]
Common Name English
ESTRADIOL VALERATE [EP MONOGRAPH]
Common Name English
DELADUMONE
Brand Name English
ESTRADIOL VALERATE COMPONENT OF DITATE-DS
Common Name English
ESTRADIOL 17-VALERATE [MI]
Common Name English
DITATE-DS COMPONENT ESTRADIOL VALERATE
Common Name English
DELESTROGEN
Brand Name English
ESTRADIOL VALERATE [USP-RS]
Common Name English
ESTRADIOL VALERATE [ORANGE BOOK]
Common Name English
NSC-17590
Code English
.BETA.-ESTRADIOL 17-VALERATE
Common Name English
ESTRADIOL VALERATE [VANDF]
Common Name English
Classification Tree Code System Code
CFR 21 CFR 522.850
Created by admin on Fri Dec 15 15:13:14 GMT 2023 , Edited by admin on Fri Dec 15 15:13:14 GMT 2023
NCI_THESAURUS C478
Created by admin on Fri Dec 15 15:13:14 GMT 2023 , Edited by admin on Fri Dec 15 15:13:14 GMT 2023
Code System Code Type Description
EVMPD
SUB07245MIG
Created by admin on Fri Dec 15 15:13:14 GMT 2023 , Edited by admin on Fri Dec 15 15:13:14 GMT 2023
PRIMARY
CAS
979-32-8
Created by admin on Fri Dec 15 15:13:14 GMT 2023 , Edited by admin on Fri Dec 15 15:13:14 GMT 2023
PRIMARY
LACTMED
Estradiol Valerate
Created by admin on Fri Dec 15 15:13:14 GMT 2023 , Edited by admin on Fri Dec 15 15:13:14 GMT 2023
PRIMARY
EPA CompTox
DTXSID8023004
Created by admin on Fri Dec 15 15:13:14 GMT 2023 , Edited by admin on Fri Dec 15 15:13:14 GMT 2023
PRIMARY
IUPHAR
7655
Created by admin on Fri Dec 15 15:13:14 GMT 2023 , Edited by admin on Fri Dec 15 15:13:14 GMT 2023
PRIMARY
ChEMBL
CHEMBL1511
Created by admin on Fri Dec 15 15:13:14 GMT 2023 , Edited by admin on Fri Dec 15 15:13:14 GMT 2023
PRIMARY
MERCK INDEX
m5028
Created by admin on Fri Dec 15 15:13:14 GMT 2023 , Edited by admin on Fri Dec 15 15:13:14 GMT 2023
PRIMARY Merck Index
NCI_THESAURUS
C1090
Created by admin on Fri Dec 15 15:13:14 GMT 2023 , Edited by admin on Fri Dec 15 15:13:14 GMT 2023
PRIMARY
PUBCHEM
13791
Created by admin on Fri Dec 15 15:13:14 GMT 2023 , Edited by admin on Fri Dec 15 15:13:14 GMT 2023
PRIMARY
RS_ITEM_NUM
1254009
Created by admin on Fri Dec 15 15:13:14 GMT 2023 , Edited by admin on Fri Dec 15 15:13:14 GMT 2023
PRIMARY
NSC
17590
Created by admin on Fri Dec 15 15:13:14 GMT 2023 , Edited by admin on Fri Dec 15 15:13:14 GMT 2023
PRIMARY
FDA UNII
OKG364O896
Created by admin on Fri Dec 15 15:13:14 GMT 2023 , Edited by admin on Fri Dec 15 15:13:14 GMT 2023
PRIMARY
DRUG BANK
DB13956
Created by admin on Fri Dec 15 15:13:14 GMT 2023 , Edited by admin on Fri Dec 15 15:13:14 GMT 2023
PRIMARY
ECHA (EC/EINECS)
213-559-2
Created by admin on Fri Dec 15 15:13:14 GMT 2023 , Edited by admin on Fri Dec 15 15:13:14 GMT 2023
PRIMARY
DAILYMED
OKG364O896
Created by admin on Fri Dec 15 15:13:14 GMT 2023 , Edited by admin on Fri Dec 15 15:13:14 GMT 2023
PRIMARY
MESH
C015854
Created by admin on Fri Dec 15 15:13:14 GMT 2023 , Edited by admin on Fri Dec 15 15:13:14 GMT 2023
PRIMARY
INN
3921
Created by admin on Fri Dec 15 15:13:14 GMT 2023 , Edited by admin on Fri Dec 15 15:13:14 GMT 2023
PRIMARY
RXCUI
24395
Created by admin on Fri Dec 15 15:13:14 GMT 2023 , Edited by admin on Fri Dec 15 15:13:14 GMT 2023
PRIMARY RxNorm
SMS_ID
100000090493
Created by admin on Fri Dec 15 15:13:14 GMT 2023 , Edited by admin on Fri Dec 15 15:13:14 GMT 2023
PRIMARY
WIKIPEDIA
Estradiol valerate
Created by admin on Fri Dec 15 15:13:14 GMT 2023 , Edited by admin on Fri Dec 15 15:13:14 GMT 2023
PRIMARY
DRUG CENTRAL
1064
Created by admin on Fri Dec 15 15:13:14 GMT 2023 , Edited by admin on Fri Dec 15 15:13:14 GMT 2023
PRIMARY
Related Record Type Details
BASIS OF STRENGTH->SUBSTANCE
ASSAY (UV)
EP
BASIS OF STRENGTH->SUBSTANCE
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
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