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Details

Stereochemistry ABSOLUTE
Molecular Formula C21H28O3
Molecular Weight 328.4452
Optical Activity UNSPECIFIED
Defined Stereocenters 5 / 5
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ESTRADIOL 17-PROPIONATE

SMILES

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

InChI

InChIKey=PQCRZWCSVWBYSC-AGRFSFNASA-N
InChI=1S/C21H28O3/c1-3-20(23)24-19-9-8-18-17-6-4-13-12-14(22)5-7-15(13)16(17)10-11-21(18,19)2/h5,7,12,16-19,22H,3-4,6,8-11H2,1-2H3/t16-,17-,18+,19+,21+/m1/s1

HIDE SMILES / InChI

Molecular Formula C21H28O3
Molecular Weight 328.4452
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
Effect of estradiol benzoate on the proliferation of osteogenic cells in fetal rat fibulae cultured in vitro.
1978 Mar
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
Comparison of the ligand binding specificity and transcript tissue distribution of estrogen receptors alpha and beta.
1997 Mar
Estrogenic and antiestrogenic activities of 16alpha- and 2-hydroxy metabolites of 17beta-estradiol in MCF-7 and T47D human breast cancer cells.
1998 Dec
Inhibition of the neuronal insulin receptor causes Alzheimer-like disturbances in oxidative/energy brain metabolism and in behavior in adult rats.
1999
Estradiol prevents and testosterone promotes Fas-dependent apoptosis in CD4+ Th2 cells by altering Bcl 2 expression.
1999
Effects of 17beta-estradiol on tachycardia-induced changes of atrial refractoriness and cisapride-induced ventricular arrhythmia.
1999 Apr
Differential regulation of c-fos expression in estrogen-induced hamster renal tumors compared with kidney not due to creation of an estrogen-response element by point mutation in the gene's flanking sequence.
1999 Apr
Growth stimulation of a rat pituitary cell line MtT/E-2 by environmental estrogens in vitro and in vivo.
1999 Aug
Inhibitory effect of natural and environmental estrogens on thymic hormone production in thymus epithelial cell culture.
1999 Dec
Estrogen-induced pituitary tumor development in the ACI rat not inhibited by dietary energy restriction.
1999 Dec
Estrogen receptor activation via activation function 2 predicts agonism of xenoestrogens in normal and neoplastic cells of the uterine myometrium.
1999 Jul 1
Estrogenic potential of certain pyrethroid compounds in the MCF-7 human breast carcinoma cell line.
1999 Mar
Endometrial cancer after combined hormone replacement therapy.
1999 Mar 15
Sex steroids and odorants modulate gonadotropin-releasing hormone secretion in primary cultures of human olfactory cells.
1999 Nov
Estrogen directly respresses gonadotropin-releasing hormone (GnRH) gene expression in estrogen receptor-alpha (ERalpha)- and ERbeta-expressing GT1-7 GnRH neurons.
1999 Nov
Steroid feedback on gonadotropin release and pituitary gonadotropin subunit mRNA in mice lacking a functional estrogen receptor alpha.
1999 Oct
Estrogen and aryl hydrocarbon receptor expression and crosstalk in human Ishikawa endometrial cancer cells.
2000 Apr
WISP-2 as a novel estrogen-responsive gene in human breast cancer cells.
2000 Aug 18
Molecular analysis of the inhibition of monocyte chemoattractant protein-1 gene expression by estrogens and xenoestrogens in MCF-7 cells.
2000 Jan
The aryl hydrocarbon receptor interacts with estrogen receptor alpha and orphan receptors COUP-TFI and ERRalpha1.
2000 Jan 1
Intrinsic alcohol dehydrogenase and hydroxysteroid dehydrogenase activities of human mitochondrial short-chain L-3-hydroxyacyl-CoA dehydrogenase.
2000 Jan 1
Induction of uterine adenocarcinoma in CD-1 mice by catechol estrogens.
2000 Jan 15
Six high-priority organochlorine pesticides, either singly or in combination, are nonestrogenic in transfected HeLa cells.
2000 Mar-Apr
Assaying estrogenicity by quantitating the expression levels of endogenous estrogen-regulated genes.
2000 May
Estradiol enhances the resistance of LDL to oxidation by stabilizing apoB-100 conformation.
2000 Nov 14
Relative binding affinity does not predict biological response to xenoestrogens in rat endometrial adenocarcinoma cells.
2000 Oct
Resveratrol acts as a mixed agonist/antagonist for estrogen receptors alpha and beta.
2000 Oct
Repression of chick multidrug resistance-associated protein 1 (chMRP1) gene expression by estrogen.
2000 Oct 31
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
Regulation of progesterone receptors and decidualization in uterine stroma of the estrogen receptor-alpha knockout mouse.
2001 Jan
Estradiol-induced attenuation of pulmonary hypertension is not associated with altered eNOS expression.
2001 Jan
Influence of gender and sex hormones on nicotine acute pharmacological effects in mice.
2001 Jan
Dose-response relationships and pharmacokinetics of vitellogenin in rainbow trout after intravascular administration of 17alpha-ethynylestradiol.
2001 Jan
Evaluation of an EIA method for measuring serum levels of the estrogen metabolite 2-hydroxyestrone in adults.
2001 Jan
Estradiol levels in psychotic disorders.
2001 Jan
Effects of heterocyclic amines with mammary gland carcinogenic potential on estrogenic response of uterus in ovariectomized rats.
2001 Jan 10
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
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
Enhanced multispecificity of arabidopsis vacuolar multidrug resistance-associated protein-type ATP-binding cassette transporter, AtMRP2.
2001 Mar 23
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 15:04:07 GMT 2023
Edited
by admin
on Fri Dec 15 15:04:07 GMT 2023
Record UNII
K31PC34297
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
ESTRADIOL 17-PROPIONATE
Common Name English
1,3,5(10)-ESTRATRIENE-3,17.BETA.-DIOL 17-PROPIONATE
Systematic Name English
ESTRADIOL PROPIONATE
Common Name English
Code System Code Type Description
CAS
3758-34-7
Created by admin on Fri Dec 15 15:04:07 GMT 2023 , Edited by admin on Fri Dec 15 15:04:07 GMT 2023
PRIMARY
EPA CompTox
DTXSID4048985
Created by admin on Fri Dec 15 15:04:07 GMT 2023 , Edited by admin on Fri Dec 15 15:04:07 GMT 2023
PRIMARY
ECHA (EC/EINECS)
223-164-7
Created by admin on Fri Dec 15 15:04:07 GMT 2023 , Edited by admin on Fri Dec 15 15:04:07 GMT 2023
PRIMARY
FDA UNII
K31PC34297
Created by admin on Fri Dec 15 15:04:07 GMT 2023 , Edited by admin on Fri Dec 15 15:04:07 GMT 2023
PRIMARY
SMS_ID
100000089475
Created by admin on Fri Dec 15 15:04:07 GMT 2023 , Edited by admin on Fri Dec 15 15:04:07 GMT 2023
PRIMARY
PUBCHEM
19571
Created by admin on Fri Dec 15 15:04:07 GMT 2023 , Edited by admin on Fri Dec 15 15:04:07 GMT 2023
PRIMARY
EVMPD
SUB25453
Created by admin on Fri Dec 15 15:04:07 GMT 2023 , Edited by admin on Fri Dec 15 15:04:07 GMT 2023
PRIMARY
Related Record Type Details
ACTIVE MOIETY