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

Details

Stereochemistry ABSOLUTE
Molecular Formula C18H22O2
Molecular Weight 270.3661
Optical Activity UNSPECIFIED
Defined Stereocenters 4 / 4
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ESTRONE

SMILES

[H][C@@]12CCC(=O)[C@@]1(C)CC[C@]3([H])C4=C(CC[C@@]23[H])C=C(O)C=C4

InChI

InChIKey=DNXHEGUUPJUMQT-CBZIJGRNSA-N
InChI=1S/C18H22O2/c1-18-9-8-14-13-5-3-12(19)10-11(13)2-4-15(14)16(18)6-7-17(18)20/h3,5,10,14-16,19H,2,4,6-9H2,1H3/t14-,15-,16+,18+/m1/s1

HIDE SMILES / InChI

Molecular Formula C18H22O2
Molecular Weight 270.3661
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 4 / 4
E/Z Centers 0
Optical Activity UNSPECIFIED

Estrone, one of the major mammalian estrogens, is an aromatized C18 steroid with a 3-hydroxyl group and a 17-ketone. It is produced in vivo from androstenedione or from testosterone via estradiol. It is produced primarily in the ovaries, placenta, and in peripheral tissues (especially adipose tissue) through conversion of adrostenedione. Estrone may be further metabolized to 16-alpha-hydroxyestrone, which may be reduced to estriol by estradiol dehydrogenase. It’s used as hameopatic in management of premenopausal and postmenopausal symptoms. In 1929, Butenandt isolated estrone from the urine of pregnant women. Estrone is known to be a carcinogen for human females as well as a cause of breast tenderness or pain, nausea, headache, hypertension, and leg cramps in the context of non-endogenous exposure. In men, estrone has been known to cause anorexia, nausea, vomiting, and erectile dysfunction. Estrone is relevant to health and disease states because of its conversion to estrone sulfate, a long-lived derivative. Estrone sulfate acts as a reservoir that can be converted as needed to the more active estradiol.

CNS Activity

Curator's Comment: Estrone sulfate crossed the blood brain barrier in rats.

Originator

Curator's Comment: Estrone is one of the hormones responsible for sexual development and function in females.

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Diagnostic
Unknown

Approved Use

Unknown
Diagnostic
Unknown

Approved Use

Unknown
Diagnostic
Unknown

Approved Use

Unknown
Diagnostic
Unknown

Approved Use

Unknown
Diagnostic
Unknown

Approved Use

Unknown
Diagnostic
Unknown

Approved Use

Unknown
Diagnostic
Unknown

Approved Use

Unknown
Diagnostic
Unknown

Approved Use

Unknown
Diagnostic
Unknown

Approved Use

Unknown
Primary
Estragyn

Approved Use

Estragyn Vaginal Cream is prescribed in the treatment of menopausal and post menopausal symptoms. Estragyn Vaginal Cream should be prescribed with an appropriate dosage of a progestin for women with intact uteri to prevent endometrial hyperplasia/carcinoma.
Primary
Estragyn

Approved Use

Estragyn Vaginal Cream is prescribed in the treatment of menopausal and post menopausal symptoms. Estragyn Vaginal Cream should be prescribed with an appropriate dosage of a progestin for women with intact uteri to prevent endometrial hyperplasia/carcinoma.
Primary
THEELIN

Approved Use

For management of Menopausal and postmenopausal disorders
Palliative
Unknown

Approved Use

Unknown
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
733 pg/mL
0.5 mg single, vaginal
dose: 0.5 mg
route of administration: Vaginal
experiment type: SINGLE
co-administered:
ESTRONE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE
food status: UNKNOWN
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
550 pg × h/mL
0.5 mg single, vaginal
dose: 0.5 mg
route of administration: Vaginal
experiment type: SINGLE
co-administered:
ESTRONE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE
food status: UNKNOWN
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
3 h
0.5 mg single, vaginal
dose: 0.5 mg
route of administration: Vaginal
experiment type: SINGLE
co-administered:
ESTRONE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE
food status: UNKNOWN
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG



OverviewOther

Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
yes
Drug as victimTox targets

Tox targets

TargetModalityActivityMetaboliteClinical evidence
PubMed

PubMed

TitleDatePubMed
Molecular cloning and characterization of a new multispecific organic anion transporter from rat brain.
1999 May 7
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
Molecular cloning and characterization of multispecific organic anion transporter 4 expressed in the placenta.
2000 Feb 11
Atheroprotective effect of estriol and estrone sulfate on human vascular smooth muscle cells.
2000 Jan-Feb
Estrogen activation of the nuclear orphan receptor CAR (constitutive active receptor) in induction of the mouse Cyp2b10 gene.
2000 Nov
Glucuronidation of estrogens and retinoic acid and expression of UDP-glucuronosyltransferase 2B7 in human intestinal mucosa.
2000 Oct
Identification of human multidrug resistance protein 1 (MRP1) mutations and characterization of a G671V substitution.
2001
15-ketodihydro-PGF2 alpha, progesterone and cortisol profiles in heifers after induction of parturition by injection of dexamethasone.
2001
Aromatase inhibition reduces specifically one display of the ring dove courtship behavior.
2001 Apr
Comparative study on reduction of bone loss and lipid metabolism abnormality in ovariectomized rats by soy isoflavones, daidzin, genistin, and glycitin.
2001 Apr
19-Oxygenation of C19-steroids with an A, B-ring enone structure, competitive inhibitors of estrogen biosynthesis, with human placental aromatase.
2001 Apr
Measurement of urinary and fecal steroid metabolites during the ovarian cycle in captive and wild Japanese macaques, Macaca fuscata.
2001 Apr
Do urinary estrogen metabolites reflect the differences in breast cancer risk between Singapore Chinese and United States African-American and white women?
2001 Apr 15
Estrogen replacement therapy after breast cancer: a 12-year follow-up.
2001 Dec
By the way, Doctor. Whenever I read about the effects of hormone replacement therapy (HRT), the researchers always seem to use 0.625 mg of Premarin. I'm taking 1 mg of Estrace daily. How does this compare to the standard dose of Premarin?
2001 Dec
Estrogenic activity of estradiol and its metabolites in the ER-CALUX assay with human T47D breast cells.
2001 Feb
Differential in vitro suppressive effects of steroids on leukocyte phagocytosis in two teleosts, tilapia and common carp.
2001 Feb
Effect of GnRH immunisation on hormonal levels, sexual behaviour, semen quality and testicular morphology in mature stallions.
2001 Jan
Bioequivalence and relative bioavailability of three estradiol and norethisterone acetate-containing hormone replacement therapy tablets.
2001 Jan
Metabolism of estradiol, ethynylestradiol, and moxestrol in rat uterus, vagina, and aorta: influence of sex steroid treatment.
2001 Jan
Estrogen metabolism and malignancy: analysis of the expression and function of 17beta-hydroxysteroid dehydrogenases in colonic cancer.
2001 Jan 22
Molecular mechanisms of estrogen recognition and 17-keto reduction by human 17beta-hydroxysteroid dehydrogenase 1.
2001 Jan 30
Mutagenic properties of estrogen quinone-derived DNA adducts in simian kidney cells.
2001 Jan 9
Influence of endogenous androgens on carotid wall in postmenopausal women.
2001 Jan-Feb
Synthesis and steroid sulphatase inhibitory activity of C19- and C21-steroidal derivatives bearing a benzyl-inhibiting group.
2001 Jul-Aug
Serum lipid profile improved by ultra-low doses of 17 beta-estradiol in elderly women.
2001 Jun
Oral gavage of oleoyl-oestrone has a stronger effect on body weight in male Zucker obese rats than in female.
2001 Jun
Identification of a new subfamily of sulphotransferases: cloning and characterization of canine SULT1D1.
2001 Jun 15
Postischemic estrogen reduces hypoperfusion and secondary ischemia after experimental stroke.
2001 Mar
Effect of soymilk consumption on serum estrogen and androgen concentrations in Japanese men.
2001 Mar
Investigations of the origins of estrogenic A-ring aromatic steroids in UK sewage treatment works effluents.
2001 Mar
Follicle-stimulating hormone regulates steroidogenic enzymes in cultured cells of the chick embryo ovary.
2001 Mar
Glutathione stimulates sulfated estrogen transport by multidrug resistance protein 1.
2001 Mar 2
Actions of the soy phytoestrogen genistein in models of human chronic disease: potential involvement of transforming growth factor beta.
2001 May
Pharmacologic, but not dietary, genistein supports endometriosis in a rat model.
2001 May
A polymorphism in CYP17 and endometrial cancer risk.
2001 May 15
An evolutionarily ancient Oatp: insights into conserved functional domains of these proteins.
2002 Apr
Endogenous sex hormones and breast cancer in postmenopausal women: reanalysis of nine prospective studies.
2002 Apr 17
Review of estrone sulfatase and its inhibitors--an important new target against hormone dependent breast cancer.
2002 Jan
Endocrine changes in late bovine pregnancy with special emphasis on fetal well-being.
2002 Jul
Estrogens affect endothelin-1 mRNA expression in LNCaP human prostate carcinoma cells.
2002 May
Endometrial thickness and uterine diameter not affected by ultralow doses of 17beta-estradiol in elderly women.
2002 May
Patents

Sample Use Guides

In Vivo Use Guide
Curator's Comment: Vaginal route is possible: The recommended dose is 2.0 to 4.0 g intravaginally per day, adjusted to the lowest amount that controls symptoms http://www.rxlist.com/estragyn-drug.htm
Estrone is available in the following doses: Estrone 2 Mg/ml Intramuscular Solution Estrone 5 Mg/ml Intramuscular Solution Estrone Compounding Powder Forms of Medication Estrone is available in the following forms: Injectable Solution Injectable Suspension Vaginal Suppository
Route of Administration: Intramuscular
At 1.0 x 10(-8) M, estrone promoted growth of MTW9/PL cells established from the carcinogen-induced hormone-responsive MT-W9A rat mammary tumor of a Wistar-Furth (W/Fu) rat.
Substance Class Chemical
Created
by admin
on Sat Dec 16 16:02:46 UTC 2023
Edited
by admin
on Sat Dec 16 16:02:46 UTC 2023
Record UNII
2DI9HA706A
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
ESTRONE
HSDB   INN   JAN   MART.   MI   ORANGE BOOK   USP   USP-RS   VANDF   WHO-DD  
INN  
Official Name English
ESTRONE [MI]
Common Name English
WAY 164397
Code English
1,3,5-ESTRATRIEN-3-OL-17-ONE
Common Name English
estrone [INN]
Common Name English
FOLLICULIN
Common Name English
ETHINYLESTRADIOL IMPURITY C [EP IMPURITY]
Common Name English
THEELIN
Brand Name English
FOLLICULAR-HORMONE
Common Name English
ESTRONE [VANDF]
Common Name English
FOLLICULINUM
HPUS  
Common Name English
OESTRONE
Common Name English
THELYKININ
Common Name English
KETOHYDROXYESTRIN
Common Name English
ESTRADIOL METABOLITE E1
Common Name English
FOLLICULAR HORMONE
Common Name English
TOKOKIN
Common Name English
ESTRONE [ORANGE BOOK]
Common Name English
FOLLICULINUM [HPUS]
Common Name English
ESTRONE [USP-RS]
Common Name English
ESTRONE [MART.]
Common Name English
ESTRONE [JAN]
Common Name English
3-HYDROXYESTRA-1,3,5(10)-TRIEN-17-ONE
Systematic Name English
ESTROGENIC SUBSTANCE
Brand Name English
ESTRADIOL HEMIHYDRATE IMPURITY A [EP IMPURITY]
Common Name English
Estrone [WHO-DD]
Common Name English
ESTRA-1,3,5(10)-TRIEN-17-ONE, 3-HYDROXY-
Systematic Name English
ESTRONE [USP MONOGRAPH]
Common Name English
ESTRONE [HSDB]
Common Name English
(8R,9S,13S,14S)-3-HYDROXY-13-METHYL-6,7,8,9,11,12,13,14,15,16-DECAHYDRO-17H-CYCLOPENTA(A)PHENANTHREN-17-ONE
Systematic Name English
NSC-9699
Code English
Classification Tree Code System Code
LOINC 25403-7
Created by admin on Sat Dec 16 16:02:48 UTC 2023 , Edited by admin on Sat Dec 16 16:02:48 UTC 2023
LOINC 2258-2
Created by admin on Sat Dec 16 16:02:48 UTC 2023 , Edited by admin on Sat Dec 16 16:02:48 UTC 2023
LIVERTOX 376
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LOINC 13739-8
Created by admin on Sat Dec 16 16:02:48 UTC 2023 , Edited by admin on Sat Dec 16 16:02:48 UTC 2023
WHO-ATC G03CA07
Created by admin on Sat Dec 16 16:02:47 UTC 2023 , Edited by admin on Sat Dec 16 16:02:47 UTC 2023
LOINC 22663-9
Created by admin on Sat Dec 16 16:02:48 UTC 2023 , Edited by admin on Sat Dec 16 16:02:48 UTC 2023
LOINC 34297-2
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LOINC 34299-8
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LOINC 31177-9
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CFR 21 CFR 862.1430
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LOINC 27998-4
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LOINC 2257-4
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LOINC 6776-9
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LOINC 35208-8
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LOINC 2261-6
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WHO-ATC G03CC04
Created by admin on Sat Dec 16 16:02:47 UTC 2023 , Edited by admin on Sat Dec 16 16:02:47 UTC 2023
LOINC 14160-6
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LOINC 34298-0
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LOINC 2260-8
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LOINC 2262-4
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LOINC 2259-0
Created by admin on Sat Dec 16 16:02:48 UTC 2023 , Edited by admin on Sat Dec 16 16:02:48 UTC 2023
WHO-VATC QG03CA07
Created by admin on Sat Dec 16 16:02:48 UTC 2023 , Edited by admin on Sat Dec 16 16:02:48 UTC 2023
CFR 21 CFR 862.1280
Created by admin on Sat Dec 16 16:02:47 UTC 2023 , Edited by admin on Sat Dec 16 16:02:47 UTC 2023
WHO-VATC QG03CC04
Created by admin on Sat Dec 16 16:02:48 UTC 2023 , Edited by admin on Sat Dec 16 16:02:48 UTC 2023
Code System Code Type Description
WIKIPEDIA
ESTRONE
Created by admin on Sat Dec 16 16:02:48 UTC 2023 , Edited by admin on Sat Dec 16 16:02:48 UTC 2023
PRIMARY
CAS
53-16-7
Created by admin on Sat Dec 16 16:02:47 UTC 2023 , Edited by admin on Sat Dec 16 16:02:47 UTC 2023
PRIMARY
FDA UNII
2DI9HA706A
Created by admin on Sat Dec 16 16:02:48 UTC 2023 , Edited by admin on Sat Dec 16 16:02:48 UTC 2023
PRIMARY
ChEMBL
CHEMBL1405
Created by admin on Sat Dec 16 16:02:48 UTC 2023 , Edited by admin on Sat Dec 16 16:02:48 UTC 2023
PRIMARY
DAILYMED
2DI9HA706A
Created by admin on Sat Dec 16 16:02:48 UTC 2023 , Edited by admin on Sat Dec 16 16:02:48 UTC 2023
PRIMARY
NCI_THESAURUS
C484
Created by admin on Sat Dec 16 16:02:48 UTC 2023 , Edited by admin on Sat Dec 16 16:02:48 UTC 2023
PRIMARY
EVMPD
SUB07251MIG
Created by admin on Sat Dec 16 16:02:47 UTC 2023 , Edited by admin on Sat Dec 16 16:02:47 UTC 2023
PRIMARY
NSC
9699
Created by admin on Sat Dec 16 16:02:48 UTC 2023 , Edited by admin on Sat Dec 16 16:02:48 UTC 2023
PRIMARY
DRUG CENTRAL
3188
Created by admin on Sat Dec 16 16:02:48 UTC 2023 , Edited by admin on Sat Dec 16 16:02:48 UTC 2023
PRIMARY
SMS_ID
100000082364
Created by admin on Sat Dec 16 16:02:48 UTC 2023 , Edited by admin on Sat Dec 16 16:02:48 UTC 2023
PRIMARY
ECHA (EC/EINECS)
200-164-5
Created by admin on Sat Dec 16 16:02:48 UTC 2023 , Edited by admin on Sat Dec 16 16:02:48 UTC 2023
PRIMARY
IUPHAR
2818
Created by admin on Sat Dec 16 16:02:48 UTC 2023 , Edited by admin on Sat Dec 16 16:02:48 UTC 2023
PRIMARY
WIKIPEDIA
Estrone (medication)
Created by admin on Sat Dec 16 16:02:48 UTC 2023 , Edited by admin on Sat Dec 16 16:02:48 UTC 2023
PRIMARY
HSDB
3324
Created by admin on Sat Dec 16 16:02:48 UTC 2023 , Edited by admin on Sat Dec 16 16:02:48 UTC 2023
PRIMARY
MESH
D004970
Created by admin on Sat Dec 16 16:02:48 UTC 2023 , Edited by admin on Sat Dec 16 16:02:48 UTC 2023
PRIMARY
PUBCHEM
5870
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PRIMARY
INN
407
Created by admin on Sat Dec 16 16:02:48 UTC 2023 , Edited by admin on Sat Dec 16 16:02:48 UTC 2023
PRIMARY
CHEBI
17263
Created by admin on Sat Dec 16 16:02:47 UTC 2023 , Edited by admin on Sat Dec 16 16:02:47 UTC 2023
PRIMARY
RXCUI
4103
Created by admin on Sat Dec 16 16:02:48 UTC 2023 , Edited by admin on Sat Dec 16 16:02:48 UTC 2023
PRIMARY RxNorm
MERCK INDEX
m5033
Created by admin on Sat Dec 16 16:02:48 UTC 2023 , Edited by admin on Sat Dec 16 16:02:48 UTC 2023
PRIMARY Merck Index
DRUG BANK
DB00655
Created by admin on Sat Dec 16 16:02:48 UTC 2023 , Edited by admin on Sat Dec 16 16:02:48 UTC 2023
PRIMARY
RS_ITEM_NUM
1255001
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PRIMARY
EPA CompTox
DTXSID4022367
Created by admin on Sat Dec 16 16:02:48 UTC 2023 , Edited by admin on Sat Dec 16 16:02:48 UTC 2023
PRIMARY
Related Record Type Details
TRANSPORTER -> INHIBITOR
Related Record Type Details
METABOLITE -> PARENT
IN-VITRO
Scientific Literature
PARENT -> METABOLITE
E2 is then extensively metabolized to estrone (E1) (15%), estrone sulfate (E1S) (65%), and other compounds.
METABOLITE LESS ACTIVE -> PARENT
IN-VITRO
Scientific Literature
METABOLITE -> PARENT
IN-VIVO
URINE
Related Record Type Details
PARENT -> IMPURITY
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
PARENT -> IMPURITY
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
PARENT -> IMPURITY
CHROMATOGRAPHIC PURITY (TLC)
USP
Related Record Type Details
ACTIVE MOIETY