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

Details

Stereochemistry ABSOLUTE
Molecular Formula C18H24O2
Molecular Weight 272.3826
Optical Activity ( + )
Defined Stereocenters 5 / 5
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ESTRADIOL

SMILES

C[C@@]12CC[C@]3([H])c4ccc(cc4CC[C@@]3([H])[C@]2([H])CC[C@]1([H])O)O

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

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 3-sulfate or 17beta-estradiol 3-sulfate is a biologically inactive metabolite of estradiol, which can be converted by steryl sulfatase again to the parent estrogen.

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

1.57679993E11
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

1.57679993E11
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

1.57679993E11
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
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
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
Growth stimulation of a rat pituitary cell line MtT/E-2 by environmental estrogens in vitro and in vivo.
1999 Aug
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
Inhibitory effect of natural and environmental estrogens on thymic hormone production in thymus epithelial cell culture.
1999 Dec
[Physiology and exploration of the gonadotropic axis].
1999 Jun 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
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
WISP-2 as a novel estrogen-responsive gene in human breast cancer cells.
2000 Aug 18
Involvement of cyclooxygenase 2 in the protective effect of 17beta-estradiol on hypercholesterolemic rabbit aorta.
2000 Aug 28
Indole-3-carbinol is a negative regulator of estrogen receptor-alpha signaling in human tumor cells.
2000 Dec
High concentrations of bisphenol A induce cell growth and prolactin secretion in an estrogen-responsive pituitary tumor cell line.
2000 Feb 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
Estradiol and pesticide methoxychlor do not exhibit additivity or synergism in the reproductive tract of adult ovariectomized mice.
2000 Jul 28
Crosstalk between estrogen receptor alpha and the aryl hydrocarbon receptor in breast cancer cells involves unidirectional activation of proteasomes.
2000 Jul 28
Endocrine disrupting chemicals, phthalic acid and nonylphenol, activate Pregnane X receptor-mediated transcription.
2000 Mar
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
Estradiol enhances the resistance of LDL to oxidation by stabilizing apoB-100 conformation.
2000 Nov 14
Differential effects of xenoestrogens on coactivator recruitment by estrogen receptor (ER) alpha and ERbeta.
2000 Nov 17
Changes in serum and tissue zinc levels in sex hormone-induced prostatic carcinogenesis in the noble rat.
2000 Nov-Dec
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
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
Repression of chick multidrug resistance-associated protein 1 (chMRP1) gene expression by estrogen.
2000 Oct 31
NADPH- and hydroperoxide-supported 17beta-estradiol hydroxylation catalyzed by a variant form (432L, 453S) of human cytochrome P450 1B1.
2000 Sep
Estrogen induces the Akt-dependent activation of endothelial nitric-oxide synthase in vascular endothelial cells.
2001 Feb 2
Unique protein determinants of the subtype-selective ligand responses of the estrogen receptors (ERalpha and ERbeta ) at AP-1 sites.
2001 Feb 9
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
Increased expression of a novel heat shock protein transcript in the mouse uterus during decidualization and in response to progesterone.
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
Estradiol-induced attenuation of pulmonary hypertension is not associated with altered eNOS expression.
2001 Jan
Heat-shock factor-1, steroid hormones, and regulation of heat-shock protein expression in the heart.
2001 Jan
Gender-related distinctions in protein kinase C activity in rat vascular smooth muscle.
2001 Jan
Evaluation of an EIA method for measuring serum levels of the estrogen metabolite 2-hydroxyestrone in adults.
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
Acquisition of Lubrol insolubility, a common step for growth hormone and prolactin in the secretory pathway of neuroendocrine cells.
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
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.
Start therapy with Climara (estradiol) 0.025 mg per day applied to the skin onceweekly. Transdermal system 0.025 mg per day, 0.0375 mg per day, 0.05 mg per day, 0.06 mg per day, 0.075 mg per day and 0.1 mg per day
Route of Administration: Transdermal
1 nM estradiol (E2) treatment of cultured fallopian tube epithelium enhanced cilia beating rate (~25% increase) and increased OVGP1 secretion.
Name Type Language
ESTRADIOL
GREEN BOOK   HSDB   INCI   INN   JAN   MI   ORANGE BOOK   USP   VANDF   WHO-DD  
INN   INCI  
Official Name English
VAGIFEM
Brand Name English
ESTRADIOL IMPURITY A [IP]
Common Name English
WC3011
Code English
ESTRADIOL [VANDF]
Common Name English
ETHINYLESTRADIOL IMPURITY D [EP]
Common Name English
ESTRADIOL [WHO-DD]
Common Name English
INNOFEM
Brand Name English
ESTRA-1,3,5(10)-TRIENE-3,17-DIOL (17.BETA.)-
Common Name English
ESTRADIOL BENZOATE SPECIFIED IMPURITY A [EP]
Common Name English
17-.BETA.-OESTRADIOL
Common Name English
DIVIGEL
Brand Name English
ESTRADIOL [ORANGE BOOK]
Common Name English
17BETA-ESTRADIOL
Common Name English
ESTRADIOL COMPONENT OF COMBIPATCH
Common Name English
FEMPATCH
Brand Name English
ESTRADIOL COMPONENT OF CLIMARA PRO
Common Name English
ESTRADIOL [GREEN BOOK]
Common Name English
OESTRADIOL
Common Name English
IMVEXXY
Brand Name English
ESTRADIOL [JAN]
Common 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
ESTRADIOL COMPONENT OF BIJUVA
Common Name English
E2
Common Name English
ESTRADIOL [INN]
Common Name English
ESTRADIOL BENZOATE IMPURITY A [EP]
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 COMPONENT OF ANGELIQ
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
ESTRADIOL COMPONENT OF ACTIVELLA
Common Name English
ESTRADIOL ANHYDROUS
Common Name English
17.BETA.-ESTRADIOL
Common Name English
ESTRADIOL [USP]
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
ESTRADIOL [INCI]
Common Name English
CLIMARA PRO COMPONENT ESTRADIOL
Common Name English
ESTRADIOL VALERATE IMPURITY A [EP]
Common Name English
(+)-3,17.BETA.-ESTRADIOL
Systematic Name English
ESTRA-1,3,5(10)-TRIENE-3,17.BETA.-DIOL
Systematic Name English
VIVELLE
Brand Name English
ESTRADIOL COMPONENT OF ORIAHNN
Brand Name English
17-BETA-OESTRADIOL
Common Name English
ANGELIQ COMPONENT ESTRADIOL
Common Name English
ESTRADIOL [USP-RS]
Common Name English
ACTIVELLA COMPONENT ESTRADIOL
Common Name English
ESTRADIOL COMPONENT OF PREFEST
Common Name English
Classification Tree Code System Code
LOINC 35384-7
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LOINC 34290-7
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LOINC 12595-5
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LOINC 2239-2
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WHO-ATC G03CA03
Created by admin on Fri Jun 25 21:35:35 UTC 2021 , Edited by admin on Fri Jun 25 21:35:35 UTC 2021
WHO-VATC QG03CA03
Created by admin on Fri Jun 25 21:35:36 UTC 2021 , Edited by admin on Fri Jun 25 21:35:36 UTC 2021
CFR 21 CFR 522.840
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LOINC 83097-6
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LOINC 2240-0
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LOINC 14715-7
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LOINC 12214-3
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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
Created by admin on Fri Jun 25 21:35:36 UTC 2021 , Edited by admin on Fri Jun 25 21:35:36 UTC 2021
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
Created by admin on Fri Jun 25 21:35:36 UTC 2021 , Edited by admin on Fri Jun 25 21:35:36 UTC 2021
CFR 21 CFR 556.240
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LOINC 72873-3
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LOINC 34287-3
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LOINC 55857-7
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LOINC 35207-0
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LOINC 21263-9
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LIVERTOX 372
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LOINC 2243-4
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LOINC 2245-9
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LOINC 2238-4
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LOINC 31176-1
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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)
Created by admin on Fri Jun 25 21:35:35 UTC 2021 , Edited by admin on Fri Jun 25 21:35:35 UTC 2021
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
Created by admin on Fri Jun 25 21:35:35 UTC 2021 , Edited by admin on Fri Jun 25 21:35:35 UTC 2021
NCI_THESAURUS C2293
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LOINC 13736-4
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LOINC 2242-6
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Code System Code Type Description
IUPHAR
1013
Created by admin on Fri Jun 25 21:35:35 UTC 2021 , Edited by admin on Fri Jun 25 21:35:35 UTC 2021
PRIMARY
ECHA (EC/EINECS)
200-023-8
Created by admin on Fri Jun 25 21:35:35 UTC 2021 , Edited by admin on Fri Jun 25 21:35:35 UTC 2021
PRIMARY
WIKIPEDIA
ESTRADIOL
Created by admin on Fri Jun 25 21:35:36 UTC 2021 , Edited by admin on Fri Jun 25 21:35:36 UTC 2021
PRIMARY
LACTMED
Estradiol
Created by admin on Fri Jun 25 21:35:35 UTC 2021 , Edited by admin on Fri Jun 25 21:35:35 UTC 2021
PRIMARY
DRUG BANK
DB00783
Created by admin on Fri Jun 25 21:35:35 UTC 2021 , Edited by admin on Fri Jun 25 21:35:35 UTC 2021
PRIMARY
EVMPD
SUB96040
Created by admin on Fri Jun 25 21:35:35 UTC 2021 , Edited by admin on Fri Jun 25 21:35:35 UTC 2021
PRIMARY
MERCK INDEX
M5028
Created by admin on Fri Jun 25 21:35:35 UTC 2021 , Edited by admin on Fri Jun 25 21:35:35 UTC 2021
PRIMARY Merck Index
MESH
D004958
Created by admin on Fri Jun 25 21:35:35 UTC 2021 , Edited by admin on Fri Jun 25 21:35:35 UTC 2021
PRIMARY
EPA CompTox
50-28-2
Created by admin on Fri Jun 25 21:35:35 UTC 2021 , Edited by admin on Fri Jun 25 21:35:35 UTC 2021
PRIMARY
INN
406
Created by admin on Fri Jun 25 21:35:35 UTC 2021 , Edited by admin on Fri Jun 25 21:35:35 UTC 2021
PRIMARY
NCI_THESAURUS
C478
Created by admin on Fri Jun 25 21:35:36 UTC 2021 , Edited by admin on Fri Jun 25 21:35:36 UTC 2021
PRIMARY
ChEMBL
CHEMBL135
Created by admin on Fri Jun 25 21:35:35 UTC 2021 , Edited by admin on Fri Jun 25 21:35:35 UTC 2021
PRIMARY
DRUG CENTRAL
1057
Created by admin on Fri Jun 25 21:35:35 UTC 2021 , Edited by admin on Fri Jun 25 21:35:35 UTC 2021
PRIMARY
CAS
50-28-2
Created by admin on Fri Jun 25 21:35:35 UTC 2021 , Edited by admin on Fri Jun 25 21:35:35 UTC 2021
PRIMARY
EVMPD
SUB07242MIG
Created by admin on Fri Jun 25 21:35:35 UTC 2021 , Edited by admin on Fri Jun 25 21:35:35 UTC 2021
PRIMARY
FDA UNII
4TI98Z838E
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PRIMARY
RXCUI
4083
Created by admin on Fri Jun 25 21:35:36 UTC 2021 , Edited by admin on Fri Jun 25 21:35:36 UTC 2021
PRIMARY RxNorm
EVMPD
SUB21195
Created by admin on Fri Jun 25 21:35:35 UTC 2021 , Edited by admin on Fri Jun 25 21:35:35 UTC 2021
PRIMARY
HSDB
3589
Created by admin on Fri Jun 25 21:35:35 UTC 2021 , Edited by admin on Fri Jun 25 21:35:35 UTC 2021
PRIMARY
USP_CATALOG
1250008
Created by admin on Fri Jun 25 21:35:36 UTC 2021 , Edited by admin on Fri Jun 25 21:35:36 UTC 2021
PRIMARY USP-RS
PUBCHEM
5757
Created by admin on Fri Jun 25 21:35:36 UTC 2021 , Edited by admin on Fri Jun 25 21:35:36 UTC 2021
PRIMARY