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Details

Stereochemistry ABSOLUTE
Molecular Formula C29H34O4
Molecular Weight 446.5779
Optical Activity UNSPECIFIED
Defined Stereocenters 5 / 5
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ESTRA-1,3,5(10)-TRIENE-3,17-DIOL (17.BETA.)-, 3-BENZOATE 17-BUTANOATE

SMILES

CCCC(=O)O[C@H]1CC[C@H]2[C@@H]3CCC4=CC(OC(=O)C5=CC=CC=C5)=CC=C4[C@H]3CC[C@]12C

InChI

InChIKey=MKYFGNOOEKZNPW-ZRJUGLEFSA-N
InChI=1S/C29H34O4/c1-3-7-27(30)33-26-15-14-25-24-12-10-20-18-21(32-28(31)19-8-5-4-6-9-19)11-13-22(20)23(24)16-17-29(25,26)2/h4-6,8-9,11,13,18,23-26H,3,7,10,12,14-17H2,1-2H3/t23-,24-,25+,26+,29+/m1/s1

HIDE SMILES / InChI

Molecular Formula C29H34O4
Molecular Weight 446.5779
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 https://books.google.ru/books?id=68n6f1Nw6EEC&pg=PA64&redir_esc=y#v=onepage&q&f=false | https://www.fda.gov/downloads/AnimalVeterinary/Products/ApprovedAnimalDrugProducts/FOIADrugSummaries/ucm116143.pdf | https://www.fda.gov/downloads/AnimalVeterinary/Products/ApprovedAnimalDrugProducts/FOIADrugSummaries/UCM338208.pdf

Estradiol benzoate is the synthetic benzoate ester of estradiol, a steroid sex hormone vital to the maintenance of fertility and secondary sexual characteristics in females. As the primary, most potent estrogen hormone produced by the ovaries, estradiol binds to and activates specific nuclear receptors. This agent exhibits mild anabolic and metabolic properties, and increases blood coagulability. Although estradiol benzoate is not approved by the FDA for use in humans in the United States, it is approved for veterinary use as a subdermal implant both alone (CELERIN®) and in combination with the anabolic steroid trenbolone acetate (SYNOVEX® Plus).

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
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 serum
Homo sapiens
population: UNKNOWN
age: ADULT
sex: FEMALE
food status: UNKNOWN
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 serum
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 serum
Homo sapiens
population: UNKNOWN
age: ADULT
sex: FEMALE
food status: UNKNOWN
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
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 serum
Homo sapiens
population: UNKNOWN
age: ADULT
sex: FEMALE
food status: UNKNOWN
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 serum
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
[The effect of adrenaline and 17beta-estradiol sulfate on transmembrane potentials of guinea pig cardiomyocytes].
1996 Dec
Inhibition of the neuronal insulin receptor causes Alzheimer-like disturbances in oxidative/energy brain metabolism and in behavior in adult rats.
1999
Estrogen and aryl hydrocarbon responsiveness of ECC-1 endometrial cancer cells.
1999 Apr 25
Methoxychlor stimulates estrogen-responsive messenger ribonucleic acids in mouse uterus through a non-estrogen receptor (non-ER) alpha and non-ER beta mechanism.
1999 Aug
Estrogen-induced pituitary tumor development in the ACI rat not inhibited by dietary energy restriction.
1999 Dec
Low-dose bioactivity of xenoestrogens in animals: fetal exposure to low doses of methoxychlor and other xenoestrogens increases adult prostate size in mice.
1999 Jan-Mar
[Physiology and exploration of the gonadotropic axis].
1999 Jun 15
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
Effects of environmental estrogens on tumor necrosis factor alpha-mediated apoptosis in MCF-7 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
Perinatal exposure to estrogenic compounds and the subsequent effects on the prostate of the adult rat: evaluation of inflammation in the ventral and lateral lobes.
1999 Nov-Dec
Acute activation of Maxi-K channels (hSlo) by estradiol binding to the beta subunit.
1999 Sep 17
Estrogen and aryl hydrocarbon receptor expression and crosstalk in human Ishikawa endometrial cancer cells.
2000 Apr
Effect of chlorinated hydrocarbons on expression of cytochrome P450 1A1, 1A2 and 1B1 and 2- and 4-hydroxylation of 17beta-estradiol in female Sprague-Dawley rats.
2000 Aug
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 pregnane X receptor: a promiscuous xenobiotic receptor that has diverged during evolution.
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
Atheroprotective effect of estriol and estrone sulfate on human vascular smooth muscle cells.
2000 Jan-Feb
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
Estrogen activation of the nuclear orphan receptor CAR (constitutive active receptor) in induction of the mouse Cyp2b10 gene.
2000 Nov
Changes in serum and tissue zinc levels in sex hormone-induced prostatic carcinogenesis in the noble rat.
2000 Nov-Dec
Effects of arsenite on estrogen receptor-alpha expression and activity in MCF-7 breast cancer cells.
2000 Oct
Antiestrogenic effects of 2,3,7,8-tetrachlorodibenzo-p-dioxin in mouse uterus: critical role of the aryl hydrocarbon receptor in stromal tissue.
2000 Oct
NADPH- and hydroperoxide-supported 17beta-estradiol hydroxylation catalyzed by a variant form (432L, 453S) of human cytochrome P450 1B1.
2000 Sep
Use of salivary biomarkers in biobehavioral research: cotton-based sample collection methods can interfere with salivary immunoassay results.
2001 Feb
Effects of follicle-stimulating hormone with and without luteinizing hormone on serum hormone concentrations, follicle growth, and intrafollicular estradiol and aromatase activity in gonadotropin-releasing hormone-immunized heifers.
2001 Jan
Female steroid hormones modulate receptors for nerve growth factor in rat dorsal root ganglia.
2001 Jan
Regulation and role of vascular endothelial growth factor in the corpus luteum during mid-pregnancy in rats.
2001 Jan
Dose-response relationships and pharmacokinetics of vitellogenin in rainbow trout after intravascular administration of 17alpha-ethynylestradiol.
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
Estrogen decreases osteoclast formation by down-regulating receptor activator of NF-kappa B ligand (RANKL)-induced JNK activation.
2001 Mar 23
Sulfonation of 17beta-estradiol and inhibition of sulfotransferase activity by polychlorobiphenylols and celecoxib in channel catfish, Ictalurus punctatus.
2007 Mar 10
Complex actions of estradiol-3-sulfate in late gestation fetal brain.
2011 Jul
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 Wed Apr 02 06:26:27 GMT 2025
Edited
by admin
on Wed Apr 02 06:26:27 GMT 2025
Record UNII
ZE4IGI4UMH
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
BETA-ESTRADIOL 3-BENZOATE 17-N-BUTYRATE
Preferred Name English
ESTRA-1,3,5(10)-TRIENE-3,17-DIOL (17.BETA.)-, 3-BENZOATE 17-BUTANOATE
Systematic Name English
ESTRADIOL BENZOATE BUTYRATE
Common Name English
ESTRADIOL-3-BENZOATE-17-BUTYRATE
Common Name English
Code System Code Type Description
WIKIPEDIA
Estradiol_benzoate_butyrate
Created by admin on Wed Apr 02 06:26:27 GMT 2025 , Edited by admin on Wed Apr 02 06:26:27 GMT 2025
PRIMARY
ECHA (EC/EINECS)
263-807-9
Created by admin on Wed Apr 02 06:26:27 GMT 2025 , Edited by admin on Wed Apr 02 06:26:27 GMT 2025
PRIMARY
CAS
63042-18-2
Created by admin on Wed Apr 02 06:26:27 GMT 2025 , Edited by admin on Wed Apr 02 06:26:27 GMT 2025
PRIMARY
FDA UNII
ZE4IGI4UMH
Created by admin on Wed Apr 02 06:26:27 GMT 2025 , Edited by admin on Wed Apr 02 06:26:27 GMT 2025
PRIMARY
EPA CompTox
DTXSID20978979
Created by admin on Wed Apr 02 06:26:27 GMT 2025 , Edited by admin on Wed Apr 02 06:26:27 GMT 2025
PRIMARY
SMS_ID
100000184196
Created by admin on Wed Apr 02 06:26:27 GMT 2025 , Edited by admin on Wed Apr 02 06:26:27 GMT 2025
PRIMARY
PUBCHEM
67081
Created by admin on Wed Apr 02 06:26:27 GMT 2025 , Edited by admin on Wed Apr 02 06:26:27 GMT 2025
PRIMARY
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