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
Pharmacokinetics of norelgestromin and ethinyl estradiol delivered by a contraceptive patch (Ortho Evra/Evra) under conditions of heat, humidity, and exercise.	2001 Dec	11762557
Pharmacokinetic overview of Ortho Evra/Evra.	2002 Feb	11849630
Serum distribution of the major metabolites of norgestimate in relation to its pharmacological properties.	2003 Feb	12586319
An evaluation of the use of the transdermal contraceptive patch in adolescents.	2004 May	15093794
New contraception options.	2004 Sep-Oct	15586908
Mortality in women given diethylstilbestrol during pregnancy.	2006 Jul 3	16786044

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