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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

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

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

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

Approval Year

1939
26
Targets

Targets

Primary TargetPharmacologyConditionPotency
Agonist
2314
Endometriosis
Modulator
720
Binding Agent
942
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Progesterone receptor
Approved
7777
Pranone
Primary
Progesterone receptor
Approved
7777
Pranone
Primary
Progesterone receptor
Approved
7777
Prone
PubMed

PubMed

TitleDatePubMed
The effect of structural QSAR parameters on skin penetration.
2001 Apr 17
Transdermal contraception.
2001 Dec
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
Pharmacokinetic overview of Ortho Evra/Evra.
2002 Feb
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
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
New Product Review (September 2003). Norelgestromin/ethinyl oestradiol transdermal contraceptive system (Evra).
2004 Jan
Induction of androgen receptor activity by norgestimate and norelgestromin in MDA-MB 231 breast cancer cells.
2004 Jul
Long-term evaluation of the use of the transdermal contraceptive patch in adolescents.
2004 Jul 8
[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
Extended use of transdermal norelgestromin/ethinyl estradiol: a randomized trial.
2005 Jun
Suppression of estrogen-withdrawal headache with extended transdermal contraception.
2005 Jun
[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
Hormonal contraception: recent advances.
2006
[Advances in the study of steroidogenic acute regulatory protein].
2006 Aug
New warning on birth control patch.
2006 Jan-Feb
Mortality in women given diethylstilbestrol during pregnancy.
2006 Jul 3
HT update: spotlight on estradiol/norethindrone acetate combination therapy.
2008
Genetic and chemical modifiers of a CUG toxicity model in Drosophila.
2008 Feb 13
Structure-activity relationships of synthetic progestins in a yeast-based in vitro androgen bioassay.
2008 May
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
Cytotoxicity, cellular localisation and biomolecular interaction of non-covalent metallo-intercalators with appended sex hormone steroid vectors.
2009 Dec 28
(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
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.
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 [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 Tue Oct 22 00:36:44 UTC 2019 , Edited by admin on Tue Oct 22 00:36:44 UTC 2019
WHO-VATC QG03DC04
Created by admin on Tue Oct 22 00:36:44 UTC 2019 , Edited by admin on Tue Oct 22 00:36:44 UTC 2019
WHO-ATC G03FA03
Created by admin on Tue Oct 22 00:36:44 UTC 2019 , Edited by admin on Tue Oct 22 00:36:44 UTC 2019
WHO-ATC G03DC04
Created by admin on Tue Oct 22 00:36:44 UTC 2019 , Edited by admin on Tue Oct 22 00:36:44 UTC 2019
WHO-VATC QG03FA03
Created by admin on Tue Oct 22 00:36:44 UTC 2019 , Edited by admin on Tue Oct 22 00:36:44 UTC 2019
Code System Code Type Description
NCI_THESAURUS
C77012
Created by admin on Tue Oct 22 00:36:44 UTC 2019 , Edited by admin on Tue Oct 22 00:36:44 UTC 2019
PRIMARY
WIKIPEDIA
ETHISTERONE
Created by admin on Tue Oct 22 00:36:44 UTC 2019 , Edited by admin on Tue Oct 22 00:36:44 UTC 2019
PRIMARY
MESH
D005003
Created by admin on Tue Oct 22 00:36:44 UTC 2019 , Edited by admin on Tue Oct 22 00:36:44 UTC 2019
PRIMARY
EVMPD
SUB07279MIG
Created by admin on Tue Oct 22 00:36:44 UTC 2019 , Edited by admin on Tue Oct 22 00:36:44 UTC 2019
PRIMARY
ChEMBL
CHEMBL241694
Created by admin on Tue Oct 22 00:36:44 UTC 2019 , Edited by admin on Tue Oct 22 00:36:44 UTC 2019
PRIMARY
EPA CompTox
434-03-7
Created by admin on Tue Oct 22 00:36:44 UTC 2019 , Edited by admin on Tue Oct 22 00:36:44 UTC 2019
PRIMARY
RXCUI
4129
Created by admin on Tue Oct 22 00:36:44 UTC 2019 , Edited by admin on Tue Oct 22 00:36:44 UTC 2019
PRIMARY RxNorm
CAS
434-03-7
Created by admin on Tue Oct 22 00:36:44 UTC 2019 , Edited by admin on Tue Oct 22 00:36:44 UTC 2019
PRIMARY
MERCK INDEX
M5065
Created by admin on Tue Oct 22 00:36:44 UTC 2019 , Edited by admin on Tue Oct 22 00:36:44 UTC 2019
PRIMARY Merck Index
ECHA (EC/EINECS)
207-096-5
Created by admin on Tue Oct 22 00:36:44 UTC 2019 , Edited by admin on Tue Oct 22 00:36:44 UTC 2019
PRIMARY
PUBCHEM
5284557
Created by admin on Tue Oct 22 00:36:44 UTC 2019 , Edited by admin on Tue Oct 22 00:36:44 UTC 2019
PRIMARY
INN
374
Created by admin on Tue Oct 22 00:36:44 UTC 2019 , Edited by admin on Tue Oct 22 00:36:44 UTC 2019
PRIMARY
ACTIVE MOIETY
Structure of ETHISTERONE
PARENT (METABOLITE)
Structure of DANAZOL
NIH
NCATS
PRIVACY ACT
ACCESSIBILITY
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