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

Details

Stereochemistry ABSOLUTE
Molecular Formula C18H24O2
Molecular Weight 272.382
Optical Activity ( + )
Defined Stereocenters 5 / 5
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ESTRADIOL

SMILES

C[C@]12CC[C@H]3[C@@H](CCC4=CC(O)=CC=C34)[C@@H]1CC[C@@H]2O

InChI

InChIKey=VOXZDWNPVJITMN-ZBRFXRBCSA-N
InChI=1S/C18H24O2/c1-18-9-8-14-13-5-3-12(19)10-11(13)2-4-15(14)16(18)6-7-17(18)20/h3,5,10,14-17,19-20H,2,4,6-9H2,1H3/t14-,15-,16+,17+,18+/m1/s1

HIDE SMILES / InChI

Molecular Formula C18H24O2
Molecular Weight 272.382
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 Mon Mar 31 17:51:25 GMT 2025
Edited
by admin
on Mon Mar 31 17:51:25 GMT 2025
Record UNII
4TI98Z838E
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
ESTRADIOL
GREEN BOOK   HSDB   INCI   INN   JAN   MI   ORANGE BOOK   USP   VANDF   WHO-DD  
INN   INCI  
Official Name English
ACTIVELLA COMPONENT ESTRADIOL
Preferred Name English
VAGIFEM
Brand Name English
ESTRADIOL IMPURITY A [IP]
Common Name English
WC3011
Code English
ESTRADIOL [VANDF]
Common Name English
INNOFEM
Brand Name English
ESTRA-1,3,5(10)-TRIENE-3,17-DIOL (17.BETA.)-
Common Name English
17-.BETA.-OESTRADIOL
Common Name English
ETHINYLESTRADIOL IMPURITY D [EP IMPURITY]
Common Name English
DIVIGEL
Brand Name English
ESTRADIOL [ORANGE BOOK]
Common Name English
17BETA-ESTRADIOL
Common Name English
FEMPATCH
Brand Name English
ESTRADIOL [USP MONOGRAPH]
Common Name English
ESTRADIOL [GREEN BOOK]
Common Name English
OESTRADIOL
Common Name English
IMVEXXY
Brand Name English
ESTRADIOL [JAN]
Common Name English
Aerodiol
Brand Name English
ELESTRIM
Brand Name English
CLIMARA
Brand Name English
NSC-20293
Code English
ALORA
Brand Name English
ORIAHNN COMPONENT ESTRADIOL
Brand Name English
13.BETA.-METHYL-1,3,5(10)-GONATRIENE-3,17.BETA.-OL
Systematic Name English
E2
Common Name English
estradiol [INN]
Common Name English
ESCLIM
Brand Name English
ESTRING
Brand Name English
EVAMIST
Brand Name English
ESTRACE
Brand Name English
PREFEST COMPONENT ESTRADIOL
Common Name English
COMBIPATCH COMPONENT ESTRADIOL
Common Name English
ESTRADIOL VALERATE IMPURITY A [EP IMPURITY]
Common Name English
BIJUVA COMPONENT ESTRADIOL
Common Name English
ESTROGEL
Brand Name English
NSC-9895
Code English
WC-3011
Code English
ESTRADIOL [HSDB]
Common Name English
ESTRADIOL VALERATE METABOLITE E2
Common Name English
MENOSTAR
Brand Name English
S21400 (INTRANASAL)
Code English
ESTRADIOL ANHYDROUS
Common Name English
S 21400
Code English
17.BETA.-ESTRADIOL
Common Name English
ESTRADERM
Brand Name English
3,17.BETA.-DIHYDROXYESTRA-1,3,5(10)-TRIENE
Systematic Name English
GYNODIOL
Brand Name English
ESTRADIOL 17-BETA
VANDF  
Common Name English
ESTRADIOL 17-BETA [VANDF]
Common Name English
ESTRADIOL [MI]
Common Name English
CLIMARA PRO COMPONENT ESTRADIOL
Common Name English
(+)-3,17.BETA.-ESTRADIOL
Systematic Name English
17 ?-estradiol
Common Name English
Estra-1,3,5(10)-triene-3,17?-diol
Systematic Name English
ESTRADIOL BENZOATE IMPURITY A [EP IMPURITY]
Common Name English
VIVELLE
Brand Name English
S21400
Code English
Estradiol [WHO-DD]
Common Name English
17-BETA-OESTRADIOL
Common Name English
ANGELIQ COMPONENT ESTRADIOL
Common Name English
ESTRADIOL [USP-RS]
Common Name English
Classification Tree Code System Code
LOINC 35384-7
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LOINC 34290-7
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LOINC 2239-2
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WHO-ATC G03CA03
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WHO-VATC QG03CA03
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CFR 21 CFR 522.840
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LOINC 34288-1
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FDA ORPHAN DRUG 231706
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WHO-VATC QG03CA53
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LOINC 25401-1
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CFR 21 CFR 310.527
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WHO-VATC QG03AB08
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NDF-RT N0000011402
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WHO-ATC G03AA14
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LOINC 13883-4
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LOINC 2246-7
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WHO-VATC QG03AA14
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CFR 21 CFR 556.240
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LOINC 72873-3
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LOINC 21263-9
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LIVERTOX 372
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LOINC 2243-4
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WHO-ATC G03CA53
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WHO-ATC G03AB08
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LOINC 14960-9
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LOINC 2241-8
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EMA ASSESSMENT REPORTS IOA (WITHDRAWN: CONTRACEPTION)
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NDF-RT N0000000100
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LOINC 12213-5
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LOINC 34291-5
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CFR 21 CFR 522.2477
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NDF-RT N0000175825
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LOINC 44730-0
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LOINC 34289-9
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CFR 21 CFR 862.1430
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CFR 21 CFR 862.1260
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NCI_THESAURUS C2293
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Code System Code Type Description
IUPHAR
1013
Created by admin on Mon Mar 31 17:51:25 GMT 2025 , Edited by admin on Mon Mar 31 17:51:25 GMT 2025
PRIMARY
ECHA (EC/EINECS)
200-023-8
Created by admin on Mon Mar 31 17:51:25 GMT 2025 , Edited by admin on Mon Mar 31 17:51:25 GMT 2025
PRIMARY
WIKIPEDIA
ESTRADIOL
Created by admin on Mon Mar 31 17:51:25 GMT 2025 , Edited by admin on Mon Mar 31 17:51:25 GMT 2025
PRIMARY
LACTMED
Estradiol
Created by admin on Mon Mar 31 17:51:25 GMT 2025 , Edited by admin on Mon Mar 31 17:51:25 GMT 2025
PRIMARY
DRUG BANK
DB00783
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PRIMARY
EVMPD
SUB96040
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PRIMARY
CHEBI
23965
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PRIMARY
MERCK INDEX
m5028
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PRIMARY Merck Index
WIKIPEDIA
Estradiol (medication)
Created by admin on Mon Mar 31 17:51:25 GMT 2025 , Edited by admin on Mon Mar 31 17:51:25 GMT 2025
PRIMARY
MESH
D004958
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PRIMARY
NSC
20293
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PRIMARY
EPA CompTox
DTXSID0020573
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PRIMARY
INN
406
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PRIMARY
NCI_THESAURUS
C478
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PRIMARY
ChEMBL
CHEMBL135
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PRIMARY
DRUG CENTRAL
1057
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PRIMARY
CAS
50-28-2
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PRIMARY
SMS_ID
100000091739
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PRIMARY
NSC
9895
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PRIMARY
DAILYMED
4TI98Z838E
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PRIMARY
CHEBI
16469
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PRIMARY
RS_ITEM_NUM
1250008
Created by admin on Mon Mar 31 17:51:25 GMT 2025 , Edited by admin on Mon Mar 31 17:51:25 GMT 2025
PRIMARY
EVMPD
SUB07242MIG
Created by admin on Mon Mar 31 17:51:25 GMT 2025 , Edited by admin on Mon Mar 31 17:51:25 GMT 2025
PRIMARY
FDA UNII
4TI98Z838E
Created by admin on Mon Mar 31 17:51:25 GMT 2025 , Edited by admin on Mon Mar 31 17:51:25 GMT 2025
PRIMARY
RXCUI
4083
Created by admin on Mon Mar 31 17:51:25 GMT 2025 , Edited by admin on Mon Mar 31 17:51:25 GMT 2025
PRIMARY RxNorm
EVMPD
SUB21195
Created by admin on Mon Mar 31 17:51:25 GMT 2025 , Edited by admin on Mon Mar 31 17:51:25 GMT 2025
PRIMARY
HSDB
3589
Created by admin on Mon Mar 31 17:51:25 GMT 2025 , Edited by admin on Mon Mar 31 17:51:25 GMT 2025
PRIMARY
PUBCHEM
5757
Created by admin on Mon Mar 31 17:51:25 GMT 2025 , Edited by admin on Mon Mar 31 17:51:25 GMT 2025
PRIMARY
Related Record Type Details
SALT/SOLVATE -> PARENT
BINDER->LIGAND
BINDING
SALT/SOLVATE -> PARENT
TARGET -> INHIBITOR
BINDING
IC50
SOLVATE->ANHYDROUS
METABOLIC ENZYME -> INHIBITOR
IC50
BASIS OF STRENGTH->SUBSTANCE
ASSAY (HPLC)
USP
TARGET -> AGONIST
BINDING
IC50
METABOLIC ENZYME -> SUBSTRATE
METABOLIC ENZYME -> SUBSTRATE
LABELED -> NON-LABELED
SUBSTANCE->BASIS OF STRENGTH
METABOLIC ENZYME -> SUBSTRATE
BINDER->LIGAND
BINDING
TARGET -> AGONIST
Binding Assay
IC50
TRANSPORTER -> INHIBITOR
Related Record Type Details
PRODRUG -> METABOLITE ACTIVE
METABOLITE -> PARENT
E2 is then extensively metabolized to estrone (E1) (15%), estrone sulfate (E1S) (65%), and other compounds.
METABOLITE -> PARENT
PRODRUG -> METABOLITE ACTIVE
PRODRUG -> METABOLITE ACTIVE
METABOLITE -> PARENT
METABOLITE -> PARENT
E2 is then extensively metabolized to estrone (E1) (15%), estrone sulfate (E1S) (65%), and other compounds.
METABOLITE LESS ACTIVE -> PARENT
PRODRUG -> METABOLITE ACTIVE
PRODRUG -> METABOLITE ACTIVE
METABOLITE -> PARENT
PARENT -> METABOLITE ACTIVE
PARENT -> METABOLITE
Metabolite produced by hydrolysis. Estramustine,s primary mechanism of antineoplastic action is inhibition of mitosis.
PLASMA
METABOLITE -> PARENT
MAJOR
METABOLITE -> PARENT
METABOLITE -> PARENT
PRODRUG -> METABOLITE ACTIVE
Related Record Type Details
PARENT -> IMPURITY
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
PARENT -> IMPURITY
CHROMATOGRAPHIC PURITY (TLC)
USP
IMPURITY -> PARENT
IMPURITY -> PARENT
PARENT -> IMPURITY
IMPURITY -> PARENT
Related Record Type Details
ACTIVE MOIETY
Name Property Type Amount Referenced Substance Defining Parameters References
Tmax PHARMACOKINETIC ESTRADIOL VALERATE

Single Dose

Volume of Distribution PHARMACOKINETIC
Biological Half-life PHARMACOKINETIC ESTRADIOL VALERATE

Single Dose