ETHISTERONE

US Previously Marketed

First approved in 1939

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 Search

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

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
Sources: http://www.druginfosys.com/drug.aspx?drugcode=2232&type=1 | https://edudrugs.com/P/Pranone/more.html

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

Targets

Primary Target	Pharmacology	Condition	Potency
Testis-specific androgen-binding protein 6 Target ID: CHEMBL3305 Sources: https://www.ncbi.nlm.nih.gov/pubmed/3641693	Binding Agent 1076
Progesterone receptor 61 Target ID: CHEMBL208 Sources: https://books.google.ru/books?id=J3VxihGDh9wC&pg=PA554&lpg=PA554&dq=ethisterone retrieved from Sex and Gender Differences in Pharmacology edited by Vera Regitz-Zagrosek, p.554	Agonist 2752
Androgen Receptor 169 Target ID: CHEMBL1871 Sources: https://www.ncbi.nlm.nih.gov/pubmed/22871957 \| https://www.ncbi.nlm.nih.gov/pubmed/3501955 \| https://www.ncbi.nlm.nih.gov/pubmed/18395441	Modulator 846

Conditions

Condition	Modality	Highest Phase	Product
Infertility 14 Sources: https://edudrugs.com/P/Pranone/more.html	Primary	Approved 8583	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.
Secondary amenorrhea 6 Sources: https://edudrugs.com/P/Pranone/more.html http://www.druginfosys.com/drug.aspx?drugcode=2232&type=1	Primary	Approved 8583	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.
Endometriosis 32 Sources: http://www.druginfosys.com/drug.aspx?drugcode=2232&type=1	Primary	Approved 8583	Prone Approved Use Endometriosis

Sourcing

Vendor/Aggregator	ID	URL
ChEBI	CHEBI:34749	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:34749
ChemicalBook	CB1207877	https://www.chemicalbook.com/ChemicalProductProperty_EN_CB1207877
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
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

PubMed

Title	Date	PubMed
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.	2010-09-08	20704268
Synthesis and solid state characterization of molecular rotors with steroidal stators: ethisterone and norethisterone.	2010-06-28	20464000
Treatment of Hereditary Angioedema: items that need to be addressed in practice parameter.	2010-05-25	20497583
Cytotoxicity, cellular localisation and biomolecular interaction of non-covalent metallo-intercalators with appended sex hormone steroid vectors.	2009-12-28	20023906
Prediction of pharmacological and xenobiotic responses to drugs based on time course gene expression profiles.	2009-12-02	19956587
(20S,2''S)-20-[4'-(3''-Hydroxy-2''-methyl-prop-yl)-3'-methylisoxazol-5-yl]-5β-preg-nan-3β,16β-diol.	2009-11-28	21578960
Vitellogenin induction by a mixture of steroidal estrogens in freshwater fishes and relevant risk assessment.	2009-10	19016308
Danazol for uterine fibroids.	2009-07-08	19588442
Membranous nephropathy in a patient with hereditary angioedema: a case report.	2008-10-13	18851753
[The applications of chiroptical spectroscopy for the determination and the detection of steroids and for the examination of their cyclodextrin-mediated enantioselective solubility].	2008	18476368
HT update: spotlight on estradiol/norethindrone acetate combination therapy.	2008	18488874
Secondary sex ratio among women exposed to diethylstilbestrol in utero.	2007-09	17805421
A full conformational characterization of 13-ethylprogestogens through theoretical calculations and nuclear magnetic resonance spectroscopy.	2007-02	17084626
[Advances in the study of steroidogenic acute regulatory protein].	2006-08	16970168
Mortality in women given diethylstilbestrol during pregnancy.	2006-07-03	16786044
Gas chromatography/mass spectrometry characterization of urinary metabolites of danazol after oral administration in human.	2006-01-02	16288903
[Safety evaluation of a transdermal contraceptive system with an oral contraceptive].	2005-11	16566363
Microbial transformation of 17alpha-ethynyl- and 17alpha-ethylsteroids, and tyrosinase inhibitory activity of transformed products.	2005-11	16054181
Extended use of transdermal norelgestromin/ethinyl estradiol: a randomized trial.	2005-06	15932834
Suppression of estrogen-withdrawal headache with extended transdermal contraception.	2005-06	15950671
Adolescents' experience with the combined estrogen and progestin transdermal contraceptive method Ortho Evra.	2005-04	15897103
Preference for and satisfaction of Canadian women with the transdermal contraceptive patch versus previous contraceptive method: an open-label, multicentre study.	2005-04	15937609
Steroids' transformations in Penicillium notatum culture.	2005-03	15763598
[Hormonal contraceptive patch].	2004-10-04	15515462
Long-term evaluation of the use of the transdermal contraceptive patch in adolescents.	2004-07-08	15258678
Induction of androgen receptor activity by norgestimate and norelgestromin in MDA-MB 231 breast cancer cells.	2004-07	15625768
Effects of nitric oxide on aldosterone synthesis and nitric oxide synthase activity in glomerulosa cells from bovine adrenal gland.	2004-06	15249705
An evaluation of the use of the transdermal contraceptive patch in adolescents.	2004-05	15093794
Matrix metalloproteinase 2 and tissue inhibitor of metalloproteinase 2 expression is not regulated by norgestimate or norelgestromin.	2004-01	15106361
New Product Review (September 2003). Norelgestromin/ethinyl oestradiol transdermal contraceptive system (Evra).	2004-01	15006313
[Transdermal contraception--a new beginning].	2004	15323313
New hormonal contraceptives: a comprehensive review of the literature.	2003-12	14695038
Evra--a patch on oral contraception?	2003-12	14723093
[A transdermal form of combined hormonal contraceptives (EVRA)].	2003-10	14692356
Progress in contraception: new technology.	2003-09-19	13677551
Ortho Evra/Evra versus oral contraceptives: follicular development and ovulation in normal cycles and after an intentional dosing error.	2003-07	12849799
Transdermal delivery of sex steroids for hormone replacement therapy and contraception. A review of principles and practice.	2003-07	12953327
Ortho Evra, a new contraceptive patch.	2003-04	12680477
Transdermal contraceptive patch delivering norelgestromin and ethinyl estradiol. Effects on the lipid profile.	2003-03	12698776
Transdermal ethinylestradiol/norelgestromin: a review of its use in hormonal contraception.	2003	15966567
Pharmacokinetics of a contraceptive patch (Evra/Ortho Evra) containing norelgestromin and ethinyloestradiol at four application sites.	2002-02	11851637
The introduction of a transdermal hormonal contraceptive (Ortho Evra/Evra).	2002-02	11849629
Assessment of compliance with a weekly contraceptive patch (Ortho Evra/Evra) among North American women.	2002-02	11849633
Integrated summary of Ortho Evra/Evra contraceptive patch adhesion in varied climates and conditions.	2002-02	11849634
Contraceptive efficacy and cycle control with the Ortho Evra/Evra transdermal system: the analysis of pooled data.	2002-02	11849631
Pharmacokinetics of norelgestromin and ethinyl estradiol delivered by a contraceptive patch (Ortho Evra/Evra) under conditions of heat, humidity, and exercise.	2001-12	11762557
Transdermal contraception.	2001-12	11727179
Pharmacokinetics of norelgestromin and ethinyl estradiol from two consecutive contraceptive patches.	2001-11	11697756
The effect of structural QSAR parameters on skin penetration.	2001-04-17	11292537
GC-MS characterization of urinary metabolites and changes of ethisterone and testosterone profile after oral administration of danazol in equine.	2001-04	11442791

Patents

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 `Mon Mar 31 17:48:42 GMT 2025` Edited by `admin` on `Mon Mar 31 17:48:42 GMT 2025`
Record UNII	P201BVY1MJ
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

ETHISTERONE

Official Name

English

ETHISTERONE [MI]

Preferred Name

English

ethisterone [INN]

Common Name

English

SYNGESTROTABS

Brand Name

English

NSC-9565

Code

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