ETHISTERONE

US Previously Marketed

First approved in 1939

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C21H28O2
Molecular Weight	312.4466
Optical Activity	UNSPECIFIED
Defined Stereocenters	6 / 6
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

C#C[C@@]1(CC[C@@]2([H])[C@]3([H])CCC4=CC(=O)CC[C@]4(C)[C@@]3([H])CC[C@@]21C)O

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
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 996
Progesterone receptor 59 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 2470
Androgen Receptor 163 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 780

Conditions

Condition	Modality	Highest Phase	Product
Infertility 14 Sources: https://edudrugs.com/P/Pranone/more.html	Primary	Approved 8043	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 8043	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 30 Sources: http://www.druginfosys.com/drug.aspx?drugcode=2232&type=1	Primary	Approved 8043	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
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
Integrated summary of Ortho Evra/Evra contraceptive patch adhesion in varied climates and conditions.	2002 Feb	11849634
Contraceptive efficacy and cycle control with the Ortho Evra/Evra transdermal system: the analysis of pooled data.	2002 Feb	11849631
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
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
New drugs 2003, part II.	2003 Jul	12851504
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
[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
Induction of androgen receptor activity by norgestimate and norelgestromin in MDA-MB 231 breast cancer cells.	2004 Jul	15625768
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
An evaluation of the use of the transdermal contraceptive patch in adolescents.	2004 May	15093794
[Hormonal contraceptive patch].	2004 Oct 4	15515462
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
Suppression of estrogen-withdrawal headache with extended transdermal contraception.	2005 Jun	15950671
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
Gas chromatography/mass spectrometry characterization of urinary metabolites of danazol after oral administration in human.	2006 Jan 2	16288903
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
HT update: spotlight on estradiol/norethindrone acetate combination therapy.	2008	18488874
Genetic and chemical modifiers of a CUG toxicity model in Drosophila.	2008 Feb 13	18270582
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
Cytotoxicity, cellular localisation and biomolecular interaction of non-covalent metallo-intercalators with appended sex hormone steroid vectors.	2009 Dec 28	20023906
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.

Name

Type

Language

ETHISTERONE

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 [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