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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
Complex actions of estradiol-3-sulfate in late gestation fetal brain.
2011-07
Sulfonation of 17beta-estradiol and inhibition of sulfotransferase activity by polychlorobiphenylols and celecoxib in channel catfish, Ictalurus punctatus.
2007-03-10
Hormone status selects for spontaneous somatic androgen receptor variants that demonstrate specific ligand and cofactor dependent activities in autochthonous prostate cancer.
2001-04-06
Constitutive expression of the steroid sulfatase gene supports the growth of MCF-7 human breast cancer cells in vitro and in vivo.
2001-04
Estrogen decreases osteoclast formation by down-regulating receptor activator of NF-kappa B ligand (RANKL)-induced JNK activation.
2001-03-23
Enhanced multispecificity of arabidopsis vacuolar multidrug resistance-associated protein-type ATP-binding cassette transporter, AtMRP2.
2001-03-23
Glutathione stimulates sulfated estrogen transport by multidrug resistance protein 1.
2001-03-02
Unique protein determinants of the subtype-selective ligand responses of the estrogen receptors (ERalpha and ERbeta ) at AP-1 sites.
2001-02-09
Estrogen induces the Akt-dependent activation of endothelial nitric-oxide synthase in vascular endothelial cells.
2001-02-02
Vitellogenin-induced pathology in male summer flounder (Paralichthys dentatus).
2001-02
Use of salivary biomarkers in biobehavioral research: cotton-based sample collection methods can interfere with salivary immunoassay results.
2001-02
Affinity labeling of rat glutathione S-transferase isozyme 1-1 by 17beta -iodoacetoxy-estradiol-3-sulfate.
2001-01-19
Effects of heterocyclic amines with mammary gland carcinogenic potential on estrogenic response of uterus in ovariectomized rats.
2001-01-10
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.
2001-01-05
Hormone binding by protein disulfide isomerase, a high capacity hormone reservoir of the endoplasmic reticulum.
2001-01-05
Acquisition of Lubrol insolubility, a common step for growth hormone and prolactin in the secretory pathway of neuroendocrine cells.
2001-01-05
In vivo regulation of syndecan-3 expression in the rat uterus by 17 beta-estradiol.
2001-01-05
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.
2001-01
Female steroid hormones modulate receptors for nerve growth factor in rat dorsal root ganglia.
2001-01
Regulation and role of vascular endothelial growth factor in the corpus luteum during mid-pregnancy in rats.
2001-01
Increased expression of a novel heat shock protein transcript in the mouse uterus during decidualization and in response to progesterone.
2001-01
Regulation of progesterone receptors and decidualization in uterine stroma of the estrogen receptor-alpha knockout mouse.
2001-01
Pregnancy stimulates secretion of adrenocorticotropin and nitric oxide from peripheral bovine lymphocytes.
2001-01
Follicle selection in cattle: role of luteinizing hormone.
2001-01
Lysyl oxidase and MMP-2 expression in dehydroepiandrosterone-induced polycystic ovary in rats.
2001-01
Changes in follicle-stimulating hormone and follicle populations during the ovarian cycle of the common marmoset.
2001-01
Estradiol-induced attenuation of pulmonary hypertension is not associated with altered eNOS expression.
2001-01
Comparison of histological compositions and apoptosis in canine spontaneous benign prostatic hyperplasia treated with androgen suppressive agents chlormadinone acetate and finasteride.
2001-01
Metabolism of estradiol, ethynylestradiol, and moxestrol in rat uterus, vagina, and aorta: influence of sex steroid treatment.
2001-01
Sex steroid hormones enhance immune function in male and female Siberian hamsters.
2001-01
Rapid and reversible inhibition of brain aromatase activity.
2001-01
Oestrogen-induced changes in the synaptology of the monkey (Cercopithecus aethiops) arcuate nucleus during gonadotropin feedback.
2001-01
Stimulatory effect of clofibrate and gemfibrozil administration on the formation of fatty acid esters of estradiol by rat liver microsomes.
2001-01
Influence of gender and sex hormones on nicotine acute pharmacological effects in mice.
2001-01
Heat-shock factor-1, steroid hormones, and regulation of heat-shock protein expression in the heart.
2001-01
Gender-related distinctions in protein kinase C activity in rat vascular smooth muscle.
2001-01
Dose-response relationships and pharmacokinetics of vitellogenin in rainbow trout after intravascular administration of 17alpha-ethynylestradiol.
2001-01
Evaluation of an EIA method for measuring serum levels of the estrogen metabolite 2-hydroxyestrone in adults.
2001-01
Estradiol levels in psychotic disorders.
2001-01
Neuroprotection by estradiol.
2001-01
Indole-3-carbinol is a negative regulator of estrogen receptor-alpha signaling in human tumor cells.
2000-12
Estradiol enhances the resistance of LDL to oxidation by stabilizing apoB-100 conformation.
2000-11-14
Female sex steroids: effects upon microglial cell activation.
2000-11-01
Estrogen activation of the nuclear orphan receptor CAR (constitutive active receptor) in induction of the mouse Cyp2b10 gene.
2000-11
Repression of chick multidrug resistance-associated protein 1 (chMRP1) gene expression by estrogen.
2000-10-31
Relative binding affinity does not predict biological response to xenoestrogens in rat endometrial adenocarcinoma cells.
2000-10
Resveratrol acts as a mixed agonist/antagonist for estrogen receptors alpha and beta.
2000-10
NADPH- and hydroperoxide-supported 17beta-estradiol hydroxylation catalyzed by a variant form (432L, 453S) of human cytochrome P450 1B1.
2000-09
[The effect of adrenaline and 17beta-estradiol sulfate on transmembrane potentials of guinea pig cardiomyocytes].
1996-12
Sulfation of estrone and 17 beta-estradiol in human liver. Catalysis by thermostable phenol sulfotransferase and by dehydroepiandrosterone sulfotransferase.
1992-05-01
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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