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

Details

Stereochemistry ABSOLUTE
Molecular Formula C21H28O2
Molecular Weight 312.4458
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

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
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 a contraceptive patch (Evra/Ortho Evra) containing norelgestromin and ethinyloestradiol at four application sites.
2002 Feb
Contraceptive efficacy and cycle control with the Ortho Evra/Evra transdermal system: the analysis of pooled data.
2002 Feb
A comparative and pooled analysis of the safety and tolerability of the contraceptive patch (Ortho Evra/Evra).
2002 Feb
Pharmacokinetic overview of Ortho Evra/Evra.
2002 Feb
Ortho Evra, a new contraceptive patch.
2003 Apr
New hormonal contraceptives: a comprehensive review of the literature.
2003 Dec
Ortho Evra/Evra versus oral contraceptives: follicular development and ovulation in normal cycles and after an intentional dosing error.
2003 Jul
[Transdermal contraception--a new beginning].
2004
New Product Review (September 2003). Norelgestromin/ethinyl oestradiol transdermal contraceptive system (Evra).
2004 Jan
Nondaily hormonal contraception: establishing a fit between product characteristics and patient preferences.
2004 Nov
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
Steroids' transformations in Penicillium notatum culture.
2005 Mar
A full conformational characterization of 13-ethylprogestogens through theoretical calculations and nuclear magnetic resonance spectroscopy.
2007 Feb
Structure-activity relationships of synthetic progestins in a yeast-based in vitro androgen bioassay.
2008 May
Prediction of pharmacological and xenobiotic responses to drugs based on time course gene expression profiles.
2009 Dec 2
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.
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
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