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Details

Stereochemistry ABSOLUTE
Molecular Formula C26H36O3
Molecular Weight 396.5622
Optical Activity UNSPECIFIED
Defined Stereocenters 5 / 5
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ESTRADIOL CYPIONATE

SMILES

[H][C@@]12CC[C@H](OC(=O)CCC3CCCC3)[C@@]1(C)CC[C@]4([H])C5=C(CC[C@@]24[H])C=C(O)C=C5

InChI

InChIKey=UOACKFBJUYNSLK-XRKIENNPSA-N
InChI=1S/C26H36O3/c1-26-15-14-21-20-10-8-19(27)16-18(20)7-9-22(21)23(26)11-12-24(26)29-25(28)13-6-17-4-2-3-5-17/h8,10,16-17,21-24,27H,2-7,9,11-15H2,1H3/t21-,22-,23+,24+,26+/m1/s1

HIDE SMILES / InChI

Molecular Formula C26H36O3
Molecular Weight 396.5622
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
Suppressive effects of estradiol on 2,3,7,8-tetrachlorodibenzo-p-dioxin-mediated transcriptional activation of murine Cyp1a-1 in mouse hepatoma Hepa 1c1c7 cells.
1998 Nov 27
Estrogenicity of bisphenol A in a human endometrial carcinoma cell line.
1999 Apr 25
Estrogen and aryl hydrocarbon responsiveness of ECC-1 endometrial cancer cells.
1999 Apr 25
Comparison of the pharmacokinetics of 17 beta-estradiol after a single 4-day application of Oesclim 50, Oesclim 100, and Vivelle 0.05 (Menorest 50) transdermal delivery systems.
1999 Aug
Lack of mutations in DNA polymerase beta of estradiol-induced hamster kidney tumors: sequence of hamster DNA polymerase beta cDNA.
1999 Aug
Inhibitory effect of natural and environmental estrogens on thymic hormone production in thymus epithelial cell culture.
1999 Dec
Rapid inhibition of rat brain mitochondrial proton F0F1-ATPase activity by estrogens: comparison with Na+, K+ -ATPase of porcine cortex.
1999 Feb 26
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
Short-term effects of high-dose 17beta-estradiol in postmenopausal PD patients: a crossover study.
1999 Jul 13
Endometrial cancer after combined hormone replacement therapy.
1999 Mar 15
The aryl hydrocarbon receptor (AHR)/AHR nuclear translocator (ARNT) heterodimer interacts with naturally occurring estrogen response elements.
1999 Nov 25
Circadian expression of the steroid 15 alpha-hydroxylase (Cyp2a4) and coumarin 7-hydroxylase (Cyp2a5) genes in mouse liver is regulated by the PAR leucine zipper transcription factor DBP.
1999 Oct
Transcriptional activation of c-fos protooncogene by 17beta-estradiol: mechanism of aryl hydrocarbon receptor-mediated inhibition.
1999 Sep
Involvement of genotoxic effects in the initiation of estrogen-induced cellular transformation: studies using Syrian hamster embryo cells treated with 17beta-estradiol and eight of its metabolites.
2000 Apr 1
Indole-3-carbinol is a negative regulator of estrogen receptor-alpha signaling in human tumor cells.
2000 Dec
Intrinsic alcohol dehydrogenase and hydroxysteroid dehydrogenase activities of human mitochondrial short-chain L-3-hydroxyacyl-CoA dehydrogenase.
2000 Jan 1
Endocrine disrupting chemicals, phthalic acid and nonylphenol, activate Pregnane X receptor-mediated transcription.
2000 Mar
Six high-priority organochlorine pesticides, either singly or in combination, are nonestrogenic in transfected HeLa cells.
2000 Mar-Apr
Estrogen activation of the nuclear orphan receptor CAR (constitutive active receptor) in induction of the mouse Cyp2b10 gene.
2000 Nov
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
Constitutive expression of the steroid sulfatase gene supports the growth of MCF-7 human breast cancer cells in vitro and in vivo.
2001 Apr
Hormone status selects for spontaneous somatic androgen receptor variants that demonstrate specific ligand and cofactor dependent activities in autochthonous prostate cancer.
2001 Apr 6
Use of salivary biomarkers in biobehavioral research: cotton-based sample collection methods can interfere with salivary immunoassay results.
2001 Feb
Unique protein determinants of the subtype-selective ligand responses of the estrogen receptors (ERalpha and ERbeta ) at AP-1 sites.
2001 Feb 9
Regulation and role of vascular endothelial growth factor in the corpus luteum during mid-pregnancy in rats.
2001 Jan
Regulation of progesterone receptors and decidualization in uterine stroma of the estrogen receptor-alpha knockout mouse.
2001 Jan
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
Comparison of histological compositions and apoptosis in canine spontaneous benign prostatic hyperplasia treated with androgen suppressive agents chlormadinone acetate and finasteride.
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
Rapid and reversible inhibition of brain aromatase activity.
2001 Jan
Oestrogen-induced changes in the synaptology of the monkey (Cercopithecus aethiops) arcuate nucleus during gonadotropin feedback.
2001 Jan
Stimulatory effect of clofibrate and gemfibrozil administration on the formation of fatty acid esters of estradiol by rat liver microsomes.
2001 Jan
Heat-shock factor-1, steroid hormones, and regulation of heat-shock protein expression in the heart.
2001 Jan
Effects of heterocyclic amines with mammary gland carcinogenic potential on estrogenic response of uterus in ovariectomized rats.
2001 Jan 10
Hormone binding by protein disulfide isomerase, a high capacity hormone reservoir of the endoplasmic reticulum.
2001 Jan 5
Glutathione stimulates sulfated estrogen transport by multidrug resistance protein 1.
2001 Mar 2
Complex actions of estradiol-3-sulfate in late gestation fetal brain.
2011 Jul
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 17:21:01 GMT 2023
Edited
by admin
on Fri Dec 15 17:21:01 GMT 2023
Record UNII
7E1DV054LO
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
ESTRADIOL CYPIONATE
ORANGE BOOK   USP   USP-RS   VANDF  
Common Name English
DEPO-TESTADIOL COMPONENT ESTRADIOL CYPIONATE
Common Name English
ESTRADIOL CYPIONATE [USP MONOGRAPH]
Common Name English
ESTRADIOLI CYPIONAS [WHO-IP]
Common Name English
ESTRADIOL CYPIONATE [USP-RS]
Common Name English
ESTRADIOL CIPIONATE
MART.   WHO-DD  
Common Name English
ESTRADIOL CYPIONATE [VANDF]
Common Name English
DEPO
Brand Name English
LUNELLE COMPONENT ESTRADIOL CYPIONATE
Common Name English
ESTRADIOL CIPIONATE [MART.]
Common Name English
ESTRADIOL CYPIONATE [ORANGE BOOK]
Common Name English
Estradiol cipionate [WHO-DD]
Common Name English
ESTRADIOL 17.BETA.-CYCLOPENTANEPROPANOATE [MI]
Common Name English
ESTRADIOL-17-CYCLOPENTANEPROPIONATE
Common Name English
.BETA.-ESTRADIOL 17-CYPIONATE
Common Name English
NSC-3354
Code English
ESTRADIOL CYPIONATE COMPONENT OF DEPO-TESTADIOL
Common Name English
ESTRADIOL CYPIONATE COMPONENT OF LUNELLE
Common Name English
ESTRADIOL 17.BETA.-CYCLOPENTANEPROPANOATE
MI  
Common Name English
ESTRA-1,3,5(10)-TRIENE-3,17-DIOL, (17.BETA.)-, 17-CYCLOPENTANEPROPANOATE
Systematic Name English
Classification Tree Code System Code
WHO-ESSENTIAL MEDICINES LIST 18.3.2 (EST/MED)
Created by admin on Fri Dec 15 17:21:01 GMT 2023 , Edited by admin on Fri Dec 15 17:21:01 GMT 2023
NCI_THESAURUS C478
Created by admin on Fri Dec 15 17:21:01 GMT 2023 , Edited by admin on Fri Dec 15 17:21:01 GMT 2023
Code System Code Type Description
ECHA (EC/EINECS)
206-237-8
Created by admin on Fri Dec 15 17:21:01 GMT 2023 , Edited by admin on Fri Dec 15 17:21:01 GMT 2023
PRIMARY
RS_ITEM_NUM
1252003
Created by admin on Fri Dec 15 17:21:01 GMT 2023 , Edited by admin on Fri Dec 15 17:21:01 GMT 2023
PRIMARY
ChEMBL
CHEMBL1200973
Created by admin on Fri Dec 15 17:21:01 GMT 2023 , Edited by admin on Fri Dec 15 17:21:01 GMT 2023
PRIMARY
MERCK INDEX
m5028
Created by admin on Fri Dec 15 17:21:01 GMT 2023 , Edited by admin on Fri Dec 15 17:21:01 GMT 2023
PRIMARY Merck Index
RXCUI
1000146
Created by admin on Fri Dec 15 17:21:01 GMT 2023 , Edited by admin on Fri Dec 15 17:21:01 GMT 2023
PRIMARY RxNorm
DAILYMED
7E1DV054LO
Created by admin on Fri Dec 15 17:21:01 GMT 2023 , Edited by admin on Fri Dec 15 17:21:01 GMT 2023
PRIMARY
DRUG BANK
DB13954
Created by admin on Fri Dec 15 17:21:01 GMT 2023 , Edited by admin on Fri Dec 15 17:21:01 GMT 2023
PRIMARY
FDA UNII
7E1DV054LO
Created by admin on Fri Dec 15 17:21:01 GMT 2023 , Edited by admin on Fri Dec 15 17:21:01 GMT 2023
PRIMARY
WIKIPEDIA
Estradiol cypionate
Created by admin on Fri Dec 15 17:21:01 GMT 2023 , Edited by admin on Fri Dec 15 17:21:01 GMT 2023
PRIMARY
NCI_THESAURUS
C47991
Created by admin on Fri Dec 15 17:21:01 GMT 2023 , Edited by admin on Fri Dec 15 17:21:01 GMT 2023
PRIMARY
LACTMED
Estradiol Cypionate
Created by admin on Fri Dec 15 17:21:01 GMT 2023 , Edited by admin on Fri Dec 15 17:21:01 GMT 2023
PRIMARY
NSC
3354
Created by admin on Fri Dec 15 17:21:01 GMT 2023 , Edited by admin on Fri Dec 15 17:21:01 GMT 2023
PRIMARY
PUBCHEM
9403
Created by admin on Fri Dec 15 17:21:01 GMT 2023 , Edited by admin on Fri Dec 15 17:21:01 GMT 2023
PRIMARY
CAS
313-06-4
Created by admin on Fri Dec 15 17:21:01 GMT 2023 , Edited by admin on Fri Dec 15 17:21:01 GMT 2023
PRIMARY
EVMPD
SUB01965MIG
Created by admin on Fri Dec 15 17:21:01 GMT 2023 , Edited by admin on Fri Dec 15 17:21:01 GMT 2023
PRIMARY
EPA CompTox
DTXSID4022999
Created by admin on Fri Dec 15 17:21:01 GMT 2023 , Edited by admin on Fri Dec 15 17:21:01 GMT 2023
PRIMARY
DRUG CENTRAL
1059
Created by admin on Fri Dec 15 17:21:01 GMT 2023 , Edited by admin on Fri Dec 15 17:21:01 GMT 2023
PRIMARY
SMS_ID
100000089397
Created by admin on Fri Dec 15 17:21:01 GMT 2023 , Edited by admin on Fri Dec 15 17:21:01 GMT 2023
PRIMARY
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