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

Details

Stereochemistry ABSOLUTE
Molecular Formula C21H28O2
Molecular Weight 312.4466
Optical Activity UNSPECIFIED
Defined Stereocenters 6 / 6
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ETHISTERONE

SMILES

C#C[C@@]1(CC[C@@]2([H])[C@]3([H])CCC4=CC(=O)CC[C@]4(C)[C@@]3([H])CC[C@@]21C)O

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
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

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

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
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
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
Prone

Approved Use

Endometriosis
PubMed

PubMed

TitleDatePubMed
GC-MS characterization of urinary metabolites and changes of ethisterone and testosterone profile after oral administration of danazol in equine.
2001 Apr
Pharmacokinetics of norelgestromin and ethinyl estradiol delivered by a contraceptive patch (Ortho Evra/Evra) under conditions of heat, humidity, and exercise.
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
Pharmacokinetic overview of Ortho Evra/Evra.
2002 Feb
Transdermal ethinylestradiol/norelgestromin: a review of its use in hormonal contraception.
2003
Ortho Evra, a new contraceptive patch.
2003 Apr
New hormonal contraceptives: a comprehensive review of the literature.
2003 Dec
Evra--a patch on oral contraception?
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
Ortho Evra/Evra versus oral contraceptives: follicular development and ovulation in normal cycles and after an intentional dosing error.
2003 Jul
Transdermal delivery of sex steroids for hormone replacement therapy and contraception. A review of principles and practice.
2003 Jul
New drugs 2003, part II.
2003 Jul
Progress in contraception: new technology.
2003 Jul-Aug
Transdermal contraceptive patch delivering norelgestromin and ethinyl estradiol. Effects on the lipid profile.
2003 Mar
[A transdermal form of combined hormonal contraceptives (EVRA)].
2003 Oct
Women prefer Ortho Evra patch.
2003 Oct-Nov
Matrix metalloproteinase 2 and tissue inhibitor of metalloproteinase 2 expression is not regulated by norgestimate or norelgestromin.
2004 Jan
Long-term evaluation of the use of the transdermal contraceptive patch in adolescents.
2004 Jul 8
Effects of nitric oxide on aldosterone synthesis and nitric oxide synthase activity in glomerulosa cells from bovine adrenal gland.
2004 Jun
Nondaily hormonal contraception: establishing a fit between product characteristics and patient preferences.
2004 Nov
[Hormonal contraceptive patch].
2004 Oct 4
New contraception options.
2004 Sep-Oct
Adolescents' experience with the combined estrogen and progestin transdermal contraceptive method Ortho Evra.
2005 Apr
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
Suppression of estrogen-withdrawal headache with extended transdermal contraception.
2005 Jun
Effect of oral versus transdermal steroidal contraceptives on androgenic markers.
2005 Jun
Steroids' transformations in Penicillium notatum culture.
2005 Mar
[Safety evaluation of a transdermal contraceptive system with an oral contraceptive].
2005 Nov
Hormonal contraception: recent advances.
2006
[Advances in the study of steroidogenic acute regulatory protein].
2006 Aug
The Evra (ethinyl estradiol/norelgestromin) contraceptive patch: estrogen exposure concerns.
2006 Jan 17
Gas chromatography/mass spectrometry characterization of urinary metabolites of danazol after oral administration in human.
2006 Jan 2
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
Secondary sex ratio among women exposed to diethylstilbestrol in utero.
2007 Sep
HT update: spotlight on estradiol/norethindrone acetate combination therapy.
2008
Genetic and chemical modifiers of a CUG toxicity model in Drosophila.
2008 Feb 13
Membranous nephropathy in a patient with hereditary angioedema: a case report.
2008 Oct 13
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
Synthesis and solid state characterization of molecular rotors with steroidal stators: ethisterone and norethisterone.
2010 Jun 28
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

Sample Use Guides

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.
Name Type Language
ETHISTERONE
INN   MART.   MI   WHO-DD  
INN  
Official Name English
ETHISTERONE [INN]
Common Name English
ETHISTERONE [WHO-DD]
Common Name English
SYNGESTROTABS
Brand Name English
NSC-9565
Code English
ETHISTERONE [MI]
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 Sat Jun 26 15:02:29 UTC 2021 , Edited by admin on Sat Jun 26 15:02:29 UTC 2021
WHO-VATC QG03DC04
Created by admin on Sat Jun 26 15:02:29 UTC 2021 , Edited by admin on Sat Jun 26 15:02:29 UTC 2021
WHO-ATC G03FA03
Created by admin on Sat Jun 26 15:02:29 UTC 2021 , Edited by admin on Sat Jun 26 15:02:29 UTC 2021
WHO-ATC G03DC04
Created by admin on Sat Jun 26 15:02:29 UTC 2021 , Edited by admin on Sat Jun 26 15:02:29 UTC 2021
WHO-VATC QG03FA03
Created by admin on Sat Jun 26 15:02:29 UTC 2021 , Edited by admin on Sat Jun 26 15:02:29 UTC 2021
Code System Code Type Description
NCI_THESAURUS
C77012
Created by admin on Sat Jun 26 15:02:29 UTC 2021 , Edited by admin on Sat Jun 26 15:02:29 UTC 2021
PRIMARY
DRUG CENTRAL
1084
Created by admin on Sat Jun 26 15:02:29 UTC 2021 , Edited by admin on Sat Jun 26 15:02:29 UTC 2021
PRIMARY
WIKIPEDIA
ETHISTERONE
Created by admin on Sat Jun 26 15:02:29 UTC 2021 , Edited by admin on Sat Jun 26 15:02:29 UTC 2021
PRIMARY
MESH
D005003
Created by admin on Sat Jun 26 15:02:29 UTC 2021 , Edited by admin on Sat Jun 26 15:02:29 UTC 2021
PRIMARY
EVMPD
SUB07279MIG
Created by admin on Sat Jun 26 15:02:29 UTC 2021 , Edited by admin on Sat Jun 26 15:02:29 UTC 2021
PRIMARY
ChEMBL
CHEMBL241694
Created by admin on Sat Jun 26 15:02:29 UTC 2021 , Edited by admin on Sat Jun 26 15:02:29 UTC 2021
PRIMARY
FDA UNII
P201BVY1MJ
Created by admin on Sat Jun 26 15:02:29 UTC 2021 , Edited by admin on Sat Jun 26 15:02:29 UTC 2021
PRIMARY
EPA CompTox
434-03-7
Created by admin on Sat Jun 26 15:02:29 UTC 2021 , Edited by admin on Sat Jun 26 15:02:29 UTC 2021
PRIMARY
USP_CATALOG
1261117
Created by admin on Sat Jun 26 15:02:29 UTC 2021 , Edited by admin on Sat Jun 26 15:02:29 UTC 2021
PRIMARY USP-RS
RXCUI
4129
Created by admin on Sat Jun 26 15:02:29 UTC 2021 , Edited by admin on Sat Jun 26 15:02:29 UTC 2021
PRIMARY RxNorm
CAS
434-03-7
Created by admin on Sat Jun 26 15:02:29 UTC 2021 , Edited by admin on Sat Jun 26 15:02:29 UTC 2021
PRIMARY
MERCK INDEX
M5065
Created by admin on Sat Jun 26 15:02:29 UTC 2021 , Edited by admin on Sat Jun 26 15:02:29 UTC 2021
PRIMARY Merck Index
ECHA (EC/EINECS)
207-096-5
Created by admin on Sat Jun 26 15:02:29 UTC 2021 , Edited by admin on Sat Jun 26 15:02:29 UTC 2021
PRIMARY
PUBCHEM
5284557
Created by admin on Sat Jun 26 15:02:29 UTC 2021 , Edited by admin on Sat Jun 26 15:02:29 UTC 2021
PRIMARY
INN
374
Created by admin on Sat Jun 26 15:02:29 UTC 2021 , Edited by admin on Sat Jun 26 15:02:29 UTC 2021
PRIMARY