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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

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

Description

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

1939
25
Targets

Targets

Primary TargetPharmacologyConditionPotency
Agonist
2361
Endometriosis
Modulator
769
Binding Agent
965
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Progesterone receptor
Approved
7883
Pranone
Primary
Progesterone receptor
Approved
7883
Pranone
Primary
Progesterone receptor
Approved
7883
Prone
PubMed

PubMed

TitleDatePubMed
The effect of structural QSAR parameters on skin penetration.
2001 Apr 17
Pharmacokinetics of norelgestromin and ethinyl estradiol from two consecutive contraceptive patches.
2001 Nov
Contraceptive efficacy and cycle control with the Ortho Evra/Evra transdermal system: the analysis of pooled data.
2002 Feb
Pharmacokinetic overview of Ortho Evra/Evra.
2002 Feb
The transdermal contraceptive patch: a new approach to hormonal contraception.
2002 Mar-Apr
New hormonal contraceptives: a comprehensive review of the literature.
2003 Dec
Serum distribution of the major metabolites of norgestimate in relation to its pharmacological properties.
2003 Feb
Norelgestromin as selective estrogen enzyme modulator in human breast cancer cell lines. Effect on sulfatase activity in comparison to medroxyprogesterone acetate.
2003 Feb
New drugs 2003, part II.
2003 Jul
Transdermal contraceptive patch delivering norelgestromin and ethinyl estradiol. Effects on the lipid profile.
2003 Mar
CD spectrometric methods for the simultaneous determination of ethisterone and its delta5-isomer.
2003 Mar
[Medication of the month. Evra: first contraceptive transdermal patch].
2003 Nov
Matrix metalloproteinase 2 and tissue inhibitor of metalloproteinase 2 expression is not regulated by norgestimate or norelgestromin.
2004 Jan
Induction of androgen receptor activity by norgestimate and norelgestromin in MDA-MB 231 breast cancer cells.
2004 Jul
Effects of nitric oxide on aldosterone synthesis and nitric oxide synthase activity in glomerulosa cells from bovine adrenal gland.
2004 Jun
An evaluation of the use of the transdermal contraceptive patch in adolescents.
2004 May
Nondaily hormonal contraception: establishing a fit between product characteristics and patient preferences.
2004 Nov
New contraception options.
2004 Sep-Oct
Effect of oral versus transdermal steroidal contraceptives on androgenic markers.
2005 Jun
[Safety evaluation of a transdermal contraceptive system with an oral contraceptive].
2005 Nov
Hormonal contraception: recent advances.
2006
How should we advise patients about the contraceptive patch, given the FDA warning?
2006 Jan
The Evra (ethinyl estradiol/norelgestromin) contraceptive patch: estrogen exposure concerns.
2006 Jan 17
Secondary sex ratio among women exposed to diethylstilbestrol in utero.
2007 Sep
[The applications of chiroptical spectroscopy for the determination and the detection of steroids and for the examination of their cyclodextrin-mediated enantioselective solubility].
2008
HT update: spotlight on estradiol/norethindrone acetate combination therapy.
2008
Testicular dysgenesis syndrome and the estrogen hypothesis: a quantitative meta-analysis.
2008 Feb
Genetic and chemical modifiers of a CUG toxicity model in Drosophila.
2008 Feb 13
Structure-activity relationships of synthetic progestins in a yeast-based in vitro androgen bioassay.
2008 May
Evaluation of extended and continuous use oral contraceptives.
2008 Oct
Prediction of pharmacological and xenobiotic responses to drugs based on time course gene expression profiles.
2009 Dec 2
Cytotoxicity, cellular localisation and biomolecular interaction of non-covalent metallo-intercalators with appended sex hormone steroid vectors.
2009 Dec 28
Vitellogenin induction by a mixture of steroidal estrogens in freshwater fishes and relevant risk assessment.
2009 Oct
Synthesis and solid state characterization of molecular rotors with steroidal stators: ethisterone and norethisterone.
2010 Jun 28
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
Patents

Patents

JPS588095A
1

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
INN   MART.   MI   WHO-DD  
INN  
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 [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 Tue Oct 22 00:36:44 UTC 2019 , Edited by admin on Tue Oct 22 00:36:44 UTC 2019
WHO-VATC QG03DC04
Created by admin on Tue Oct 22 00:36:44 UTC 2019 , Edited by admin on Tue Oct 22 00:36:44 UTC 2019
WHO-ATC G03FA03
Created by admin on Tue Oct 22 00:36:44 UTC 2019 , Edited by admin on Tue Oct 22 00:36:44 UTC 2019
WHO-ATC G03DC04
Created by admin on Tue Oct 22 00:36:44 UTC 2019 , Edited by admin on Tue Oct 22 00:36:44 UTC 2019
WHO-VATC QG03FA03
Created by admin on Tue Oct 22 00:36:44 UTC 2019 , Edited by admin on Tue Oct 22 00:36:44 UTC 2019
Code System Code Type Description
NCI_THESAURUS
C77012
Created by admin on Tue Oct 22 00:36:44 UTC 2019 , Edited by admin on Tue Oct 22 00:36:44 UTC 2019
PRIMARY
WIKIPEDIA
ETHISTERONE
Created by admin on Tue Oct 22 00:36:44 UTC 2019 , Edited by admin on Tue Oct 22 00:36:44 UTC 2019
PRIMARY
MESH
D005003
Created by admin on Tue Oct 22 00:36:44 UTC 2019 , Edited by admin on Tue Oct 22 00:36:44 UTC 2019
PRIMARY
EVMPD
SUB07279MIG
Created by admin on Tue Oct 22 00:36:44 UTC 2019 , Edited by admin on Tue Oct 22 00:36:44 UTC 2019
PRIMARY
ChEMBL
CHEMBL241694
Created by admin on Tue Oct 22 00:36:44 UTC 2019 , Edited by admin on Tue Oct 22 00:36:44 UTC 2019
PRIMARY
EPA CompTox
434-03-7
Created by admin on Tue Oct 22 00:36:44 UTC 2019 , Edited by admin on Tue Oct 22 00:36:44 UTC 2019
PRIMARY
RXCUI
4129
Created by admin on Tue Oct 22 00:36:44 UTC 2019 , Edited by admin on Tue Oct 22 00:36:44 UTC 2019
PRIMARY RxNorm
CAS
434-03-7
Created by admin on Tue Oct 22 00:36:44 UTC 2019 , Edited by admin on Tue Oct 22 00:36:44 UTC 2019
PRIMARY
MERCK INDEX
M5065
Created by admin on Tue Oct 22 00:36:44 UTC 2019 , Edited by admin on Tue Oct 22 00:36:44 UTC 2019
PRIMARY Merck Index
ECHA (EC/EINECS)
207-096-5
Created by admin on Tue Oct 22 00:36:44 UTC 2019 , Edited by admin on Tue Oct 22 00:36:44 UTC 2019
PRIMARY
PUBCHEM
5284557
Created by admin on Tue Oct 22 00:36:44 UTC 2019 , Edited by admin on Tue Oct 22 00:36:44 UTC 2019
PRIMARY
INN
374
Created by admin on Tue Oct 22 00:36:44 UTC 2019 , Edited by admin on Tue Oct 22 00:36:44 UTC 2019
PRIMARY
ACTIVE MOIETY
Structure of ETHISTERONE
PARENT (METABOLITE)
Structure of DANAZOL
NIH
NCATS
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ACCESSIBILITY
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