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

[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

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 1059
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 2662
Androgen Receptor 167 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 822

Conditions

Condition	Modality	Highest Phase	Product
Infertility 14 Sources: https://edudrugs.com/P/Pranone/more.html	Primary	Approved 8360	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 8360	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 8360	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
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
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

PubMed

Title	Date	PubMed
GC-MS characterization of urinary metabolites and changes of ethisterone and testosterone profile after oral administration of danazol in equine.	2001 Apr	11442791
The effect of structural QSAR parameters on skin penetration.	2001 Apr 17	11292537
Pharmacokinetics of norelgestromin and ethinyl estradiol delivered by a contraceptive patch (Ortho Evra/Evra) under conditions of heat, humidity, and exercise.	2001 Dec	11762557
Transdermal contraception.	2001 Dec	11727179
Pharmacokinetics of norelgestromin and ethinyl estradiol from two consecutive contraceptive patches.	2001 Nov	11697756
Pharmacokinetics of a contraceptive patch (Evra/Ortho Evra) containing norelgestromin and ethinyloestradiol at four application sites.	2002 Feb	11851637
The introduction of a transdermal hormonal contraceptive (Ortho Evra/Evra).	2002 Feb	11849629
Assessment of compliance with a weekly contraceptive patch (Ortho Evra/Evra) among North American women.	2002 Feb	11849633
A comparative and pooled analysis of the safety and tolerability of the contraceptive patch (Ortho Evra/Evra).	2002 Feb	11849632
Pharmacokinetic overview of Ortho Evra/Evra.	2002 Feb	11849630
Transdermal ethinylestradiol/norelgestromin: a review of its use in hormonal contraception.	2003	15966567
Ortho Evra, a new contraceptive patch.	2003 Apr	12680477
New hormonal contraceptives: a comprehensive review of the literature.	2003 Dec	14695038
Evra--a patch on oral contraception?	2003 Dec	14723093
Serum distribution of the major metabolites of norgestimate in relation to its pharmacological properties.	2003 Feb	12586319
Ortho Evra/Evra versus oral contraceptives: follicular development and ovulation in normal cycles and after an intentional dosing error.	2003 Jul	12849799
Transdermal delivery of sex steroids for hormone replacement therapy and contraception. A review of principles and practice.	2003 Jul	12953327
Progress in contraception: new technology.	2003 Jul-Aug	13677551
Transdermal contraceptive patch delivering norelgestromin and ethinyl estradiol. Effects on the lipid profile.	2003 Mar	12698776
CD spectrometric methods for the simultaneous determination of ethisterone and its delta5-isomer.	2003 Mar	12638059
[A transdermal form of combined hormonal contraceptives (EVRA)].	2003 Oct	14692356
[Transdermal contraception--a new beginning].	2004	15323313
Matrix metalloproteinase 2 and tissue inhibitor of metalloproteinase 2 expression is not regulated by norgestimate or norelgestromin.	2004 Jan	15106361
New Product Review (September 2003). Norelgestromin/ethinyl oestradiol transdermal contraceptive system (Evra).	2004 Jan	15006313
Long-term evaluation of the use of the transdermal contraceptive patch in adolescents.	2004 Jul 8	15258678
Effects of nitric oxide on aldosterone synthesis and nitric oxide synthase activity in glomerulosa cells from bovine adrenal gland.	2004 Jun	15249705
Nondaily hormonal contraception: establishing a fit between product characteristics and patient preferences.	2004 Nov	15527729
Adolescents' experience with the combined estrogen and progestin transdermal contraceptive method Ortho Evra.	2005 Apr	15897103
Preference for and satisfaction of Canadian women with the transdermal contraceptive patch versus previous contraceptive method: an open-label, multicentre study.	2005 Apr	15937609
Extended use of transdermal norelgestromin/ethinyl estradiol: a randomized trial.	2005 Jun	15932834
Steroids' transformations in Penicillium notatum culture.	2005 Mar	15763598
[Safety evaluation of a transdermal contraceptive system with an oral contraceptive].	2005 Nov	16566363
Microbial transformation of 17alpha-ethynyl- and 17alpha-ethylsteroids, and tyrosinase inhibitory activity of transformed products.	2005 Nov	16054181
[Advances in the study of steroidogenic acute regulatory protein].	2006 Aug	16970168
How should we advise patients about the contraceptive patch, given the FDA warning?	2006 Jan	16444915
A full conformational characterization of 13-ethylprogestogens through theoretical calculations and nuclear magnetic resonance spectroscopy.	2007 Feb	17084626
Secondary sex ratio among women exposed to diethylstilbestrol in utero.	2007 Sep	17805421
[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
Testicular dysgenesis syndrome and the estrogen hypothesis: a quantitative meta-analysis.	2008 Feb	18288311
Genetic and chemical modifiers of a CUG toxicity model in Drosophila.	2008 Feb 13	18270582
Structure-activity relationships of synthetic progestins in a yeast-based in vitro androgen bioassay.	2008 May	18395441
Evaluation of extended and continuous use oral contraceptives.	2008 Oct	19209272
Membranous nephropathy in a patient with hereditary angioedema: a case report.	2008 Oct 13	18851753
Prediction of pharmacological and xenobiotic responses to drugs based on time course gene expression profiles.	2009 Dec 2	19956587
Danazol for uterine fibroids.	2009 Jul 8	19588442
(20S,2''S)-20-[4'-(3''-Hydroxy-2''-methyl-prop-yl)-3'-methylisoxazol-5-yl]-5β-preg-nan-3β,16β-diol.	2009 Nov 28	21578960
Vitellogenin induction by a mixture of steroidal estrogens in freshwater fishes and relevant risk assessment.	2009 Oct	19016308
Synthesis and solid state characterization of molecular rotors with steroidal stators: ethisterone and norethisterone.	2010 Jun 28	20464000
Treatment of Hereditary Angioedema: items that need to be addressed in practice parameter.	2010 May 25	20497583
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	20704268

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 `Wed Jul 05 22:41:39 UTC 2023` Edited by `admin` on `Wed Jul 05 22:41:39 UTC 2023`
Record UNII	P201BVY1MJ
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

ETHISTERONE

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