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Details

Stereochemistry ABSOLUTE
Molecular Formula C21H28O2
Molecular Weight 312.4458
Optical Activity UNSPECIFIED
Defined Stereocenters 6 / 6
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ETHISTERONE

SMILES

[H][C@@]12CC[C@@](O)(C#C)[C@@]1(C)CC[C@@]3([H])[C@@]2([H])CCC4=CC(=O)CC[C@]34C

InChI

InChIKey=CHNXZKVNWQUJIB-CEGNMAFCSA-N
InChI=1S/C21H28O2/c1-4-21(23)12-9-18-16-6-5-14-13-15(22)7-10-19(14,2)17(16)8-11-20(18,21)3/h1,13,16-18,23H,5-12H2,2-3H3/t16-,17+,18+,19+,20+,21+/m1/s1

HIDE SMILES / InChI
Molecular Formula C21H28O2
Molecular Weight 312.4458
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 6 / 6
E/Z Centers 0
Optical Activity UNSPECIFIED

Description

Ethisterone is a metabolite of danazol. Ethisterone is a progestogen hormone. The first orally active progestin, Ethisterone (brand names Pranone, Progestoral, Lutocylol, Proluton C), also known as 17α-ethinyltestosterone, pregneninolone, or anhydrohydroxyprogesterone, is a steroidal progestin with androgenic activity which is derived from testosterone and was introduced for medical use in 1939. Ethisterone is indicated for progesterone supplementation or replacement as part of an Assisted Reproductive Technology (ART) treatment for infertile women with progesterone deficiency and for the treatment of secondary amenorrhea. Also used as a female contraceptive.

Originator

Schering
47
Curator's Comment: Ethisterone was synthesized in 1938 by Hans Herloff Inhoffen, Willy Logemann, Walter Hohlweg, and Arthur Serini at Schering AG in Berlin and marketed in Germany in 1939 as Proluton C and by Schering in the U.S. in 1945 as Pranone.

Approval Year

1939
35
Targets

Targets

Primary TargetPharmacologyConditionPotency
Binding Agent
1064
Agonist
2678
Modulator
828
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Approved
8429
Pranone

Approved Use

For progesterone supplementation or replacement as part of an Assisted Reproductive Technology (ART) treatment for infertile women with progesterone deficiency and for the treatment of secondary amenorrhea. Also used as a female contraceptive.
Primary
Approved
8429
Pranone

Approved Use

For progesterone supplementation or replacement as part of an Assisted Reproductive Technology (ART) treatment for infertile women with progesterone deficiency and for the treatment of secondary amenorrhea. Also used as a female contraceptive.
Primary
Approved
8429
Prone

Approved Use

Endometriosis
Sourcing

Sourcing

Vendor/AggregatorIDURL
ChEBI
CHEBI:34749
https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:34749
ChemicalBook
CB1207877
https://www.chemicalbook.com/ChemicalProductProperty_EN_CB1207877
MolPort
MolPort-002-507-150
https://www.molport.com/shop/molecule-link/MolPort-002-507-150
Selleck Chemicals
ethisterone
http://www.selleckchem.com/products/ethisterone.html
ZINC
ZINC000003881635
http://zinc15.docking.org/substances/ZINC000003881635
eMolecules
29549882
https://www.emolecules.com/cgi-bin/more?vid=29549882
eMolecules
31708439
https://www.emolecules.com/cgi-bin/more?vid=31708439
eMolecules
511134
https://www.emolecules.com/cgi-bin/more?vid=511134
PubMed

PubMed

TitleDatePubMed
The effect of structural QSAR parameters on skin penetration.
2001 Apr 17
Pharmacokinetics of norelgestromin and ethinyl estradiol delivered by a contraceptive patch (Ortho Evra/Evra) under conditions of heat, humidity, and exercise.
2001 Dec
Transdermal contraception.
2001 Dec
Pharmacokinetics of norelgestromin and ethinyl estradiol from two consecutive contraceptive patches.
2001 Nov
Pharmacokinetics of a contraceptive patch (Evra/Ortho Evra) containing norelgestromin and ethinyloestradiol at four application sites.
2002 Feb
The introduction of a transdermal hormonal contraceptive (Ortho Evra/Evra).
2002 Feb
Assessment of compliance with a weekly contraceptive patch (Ortho Evra/Evra) among North American women.
2002 Feb
Integrated summary of Ortho Evra/Evra contraceptive patch adhesion in varied climates and conditions.
2002 Feb
New hormonal contraceptives: a comprehensive review of the literature.
2003 Dec
Norelgestromin as selective estrogen enzyme modulator in human breast cancer cell lines. Effect on sulfatase activity in comparison to medroxyprogesterone acetate.
2003 Feb
Transdermal delivery of sex steroids for hormone replacement therapy and contraception. A review of principles and practice.
2003 Jul
Progress in contraception: new technology.
2003 Jul-Aug
CD spectrometric methods for the simultaneous determination of ethisterone and its delta5-isomer.
2003 Mar
[A transdermal form of combined hormonal contraceptives (EVRA)].
2003 Oct
[Transdermal contraception--a new beginning].
2004
Matrix metalloproteinase 2 and tissue inhibitor of metalloproteinase 2 expression is not regulated by norgestimate or norelgestromin.
2004 Jan
Induction of androgen receptor activity by norgestimate and norelgestromin in MDA-MB 231 breast cancer cells.
2004 Jul
Nondaily hormonal contraception: establishing a fit between product characteristics and patient preferences.
2004 Nov
[Hormonal contraceptive patch].
2004 Oct 4
Preference for and satisfaction of Canadian women with the transdermal contraceptive patch versus previous contraceptive method: an open-label, multicentre study.
2005 Apr
Extended use of transdermal norelgestromin/ethinyl estradiol: a randomized trial.
2005 Jun
Steroids' transformations in Penicillium notatum culture.
2005 Mar
[Safety evaluation of a transdermal contraceptive system with an oral contraceptive].
2005 Nov
Microbial transformation of 17alpha-ethynyl- and 17alpha-ethylsteroids, and tyrosinase inhibitory activity of transformed products.
2005 Nov
[Advances in the study of steroidogenic acute regulatory protein].
2006 Aug
How should we advise patients about the contraceptive patch, given the FDA warning?
2006 Jan
The Evra (ethinyl estradiol/norelgestromin) contraceptive patch: estrogen exposure concerns.
2006 Jan 17
Mortality in women given diethylstilbestrol during pregnancy.
2006 Jul 3
A full conformational characterization of 13-ethylprogestogens through theoretical calculations and nuclear magnetic resonance spectroscopy.
2007 Feb
Testicular dysgenesis syndrome and the estrogen hypothesis: a quantitative meta-analysis.
2008 Feb
Evaluation of extended and continuous use oral contraceptives.
2008 Oct
Membranous nephropathy in a patient with hereditary angioedema: a case report.
2008 Oct 13
Prediction of pharmacological and xenobiotic responses to drugs based on time course gene expression profiles.
2009 Dec 2
Danazol for uterine fibroids.
2009 Jul 8
(20S,2''S)-20-[4'-(3''-Hydroxy-2''-methyl-prop-yl)-3'-methylisoxazol-5-yl]-5β-preg-nan-3β,16β-diol.
2009 Nov 28
Vitellogenin induction by a mixture of steroidal estrogens in freshwater fishes and relevant risk assessment.
2009 Oct
Treatment of Hereditary Angioedema: items that need to be addressed in practice parameter.
2010 May 25
Luminescent Au(I)/Cu(I) alkynyl clusters with an ethynyl steroid and related aliphatic ligands: an octanuclear Au4Cu4 cluster and luminescence polymorphism in Au3Cu2 clusters.
2010 Sep 8
Patents

Patents

JPS588095A
1

Sample Use Guides

In Vivo Use Guide
200 to 800 mg, single dose 500mg, 12 hourly, PO
Route of Administration: Oral
In Vitro Use Guide
A pool of normal female serum was incubated with Ethisterone (3 x 10(-7) mol/l and 3 x 10(-6) mol/l). In vitro ethisterone (a major metabolite of danazol) competed with testosterone for SHBG binding sites.
Substance Class Chemical
Created
by admin
on Fri Dec 15 15:09:56 GMT 2023
Edited
by admin
on Fri Dec 15 15:09:56 GMT 2023
Record UNII
P201BVY1MJ
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
ETHISTERONE
INN   MART.   MI   WHO-DD  
INN  
Official Name English
ethisterone [INN]
Common Name English
SYNGESTROTABS
Brand Name English
NSC-9565
Code English
ETHISTERONE [MI]
Common Name English
Ethisterone [WHO-DD]
Common Name English
PREGNENINOLONE
Common Name English
PRANONE
Brand Name English
ETHISTERONE [USP-RS]
Common Name English
ETHISTERONE [MART.]
Common Name English
TROSINONE
Brand Name English
17-ETHYNYL-17.BETA.-HYDROXYANDROST-4-EN-3-ONE
Systematic Name English
ORA-LUTIN
Brand Name English
Classification Tree Code System Code
NCI_THESAURUS C776
Created by admin on Fri Dec 15 15:09:56 GMT 2023 , Edited by admin on Fri Dec 15 15:09:56 GMT 2023
WHO-VATC QG03DC04
Created by admin on Fri Dec 15 15:09:56 GMT 2023 , Edited by admin on Fri Dec 15 15:09:56 GMT 2023
WHO-ATC G03FA03
Created by admin on Fri Dec 15 15:09:56 GMT 2023 , Edited by admin on Fri Dec 15 15:09:56 GMT 2023
WHO-ATC G03DC04
Created by admin on Fri Dec 15 15:09:56 GMT 2023 , Edited by admin on Fri Dec 15 15:09:56 GMT 2023
WHO-VATC QG03FA03
Created by admin on Fri Dec 15 15:09:56 GMT 2023 , Edited by admin on Fri Dec 15 15:09:56 GMT 2023
Code System Code Type Description
NCI_THESAURUS
C77012
Created by admin on Fri Dec 15 15:09:56 GMT 2023 , Edited by admin on Fri Dec 15 15:09:56 GMT 2023
PRIMARY
DRUG CENTRAL
1084
Created by admin on Fri Dec 15 15:09:56 GMT 2023 , Edited by admin on Fri Dec 15 15:09:56 GMT 2023
PRIMARY
WIKIPEDIA
ETHISTERONE
Created by admin on Fri Dec 15 15:09:56 GMT 2023 , Edited by admin on Fri Dec 15 15:09:56 GMT 2023
PRIMARY
MESH
D005003
Created by admin on Fri Dec 15 15:09:56 GMT 2023 , Edited by admin on Fri Dec 15 15:09:56 GMT 2023
PRIMARY
CHEBI
34749
Created by admin on Fri Dec 15 15:09:56 GMT 2023 , Edited by admin on Fri Dec 15 15:09:56 GMT 2023
PRIMARY
EVMPD
SUB07279MIG
Created by admin on Fri Dec 15 15:09:56 GMT 2023 , Edited by admin on Fri Dec 15 15:09:56 GMT 2023
PRIMARY
ChEMBL
CHEMBL241694
Created by admin on Fri Dec 15 15:09:56 GMT 2023 , Edited by admin on Fri Dec 15 15:09:56 GMT 2023
PRIMARY
FDA UNII
P201BVY1MJ
Created by admin on Fri Dec 15 15:09:56 GMT 2023 , Edited by admin on Fri Dec 15 15:09:56 GMT 2023
PRIMARY
EPA CompTox
DTXSID2023016
Created by admin on Fri Dec 15 15:09:56 GMT 2023 , Edited by admin on Fri Dec 15 15:09:56 GMT 2023
PRIMARY
NSC
9565
Created by admin on Fri Dec 15 15:09:56 GMT 2023 , Edited by admin on Fri Dec 15 15:09:56 GMT 2023
PRIMARY
SMS_ID
100000082618
Created by admin on Fri Dec 15 15:09:56 GMT 2023 , Edited by admin on Fri Dec 15 15:09:56 GMT 2023
PRIMARY
RXCUI
4129
Created by admin on Fri Dec 15 15:09:56 GMT 2023 , Edited by admin on Fri Dec 15 15:09:56 GMT 2023
PRIMARY RxNorm
CAS
434-03-7
Created by admin on Fri Dec 15 15:09:56 GMT 2023 , Edited by admin on Fri Dec 15 15:09:56 GMT 2023
PRIMARY
RS_ITEM_NUM
1261117
Created by admin on Fri Dec 15 15:09:56 GMT 2023 , Edited by admin on Fri Dec 15 15:09:56 GMT 2023
PRIMARY
MERCK INDEX
m5065
Created by admin on Fri Dec 15 15:09:56 GMT 2023 , Edited by admin on Fri Dec 15 15:09:56 GMT 2023
PRIMARY Merck Index
ECHA (EC/EINECS)
207-096-5
Created by admin on Fri Dec 15 15:09:56 GMT 2023 , Edited by admin on Fri Dec 15 15:09:56 GMT 2023
PRIMARY
PUBCHEM
5284557
Created by admin on Fri Dec 15 15:09:56 GMT 2023 , Edited by admin on Fri Dec 15 15:09:56 GMT 2023
PRIMARY
INN
374
Created by admin on Fri Dec 15 15:09:56 GMT 2023 , Edited by admin on Fri Dec 15 15:09:56 GMT 2023
PRIMARY
Related Record Type Details
Structure of DANAZOL
PARENT -> METABOLITE
Related Record Type Details
Structure of ETHISTERONE
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