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
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
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 |
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
Sources: http://www.hmdb.ca/metabolites/HMDB60580
Curator's Comment: Ethisterone was synthesized in 1938 by Hans Herloff Inhoffen, Willy Logemann, Walter Hohlweg, and Arthur Serini at Schering AG in Berlin and marketed in Germany in 1939 as Proluton C and by Schering in the U.S. in 1945 as Pranone.
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL3305 Sources: https://www.ncbi.nlm.nih.gov/pubmed/3641693 |
|||
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | Pranone Approved UseFor 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. |
|||
Primary | Pranone Approved UseFor 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. |
|||
Primary | Prone Approved UseEndometriosis |
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 |
|
The effect of structural QSAR parameters on skin penetration. | 2001 Apr 17 |
|
Pharmacokinetics of norelgestromin and ethinyl estradiol delivered by a contraceptive patch (Ortho Evra/Evra) under conditions of heat, humidity, and exercise. | 2001 Dec |
|
Transdermal contraception. | 2001 Dec |
|
Pharmacokinetics of norelgestromin and ethinyl estradiol from two consecutive contraceptive patches. | 2001 Nov |
|
The introduction of a transdermal hormonal contraceptive (Ortho Evra/Evra). | 2002 Feb |
|
Assessment of compliance with a weekly contraceptive patch (Ortho Evra/Evra) among North American women. | 2002 Feb |
|
Integrated summary of Ortho Evra/Evra contraceptive patch adhesion in varied climates and conditions. | 2002 Feb |
|
Pharmacokinetic overview of Ortho Evra/Evra. | 2002 Feb |
|
The transdermal contraceptive patch: a new approach to hormonal contraception. | 2002 Mar-Apr |
|
Transdermal ethinylestradiol/norelgestromin: a review of its use in hormonal contraception. | 2003 |
|
Ortho Evra, a new contraceptive patch. | 2003 Apr |
|
New hormonal contraceptives: a comprehensive review of the literature. | 2003 Dec |
|
Evra--a patch on oral contraception? | 2003 Dec |
|
Ortho Evra/Evra versus oral contraceptives: follicular development and ovulation in normal cycles and after an intentional dosing error. | 2003 Jul |
|
Transdermal delivery of sex steroids for hormone replacement therapy and contraception. A review of principles and practice. | 2003 Jul |
|
Progress in contraception: new technology. | 2003 Jul-Aug |
|
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 |
|
Women prefer Ortho Evra patch. | 2003 Oct-Nov |
|
[Transdermal contraception--a new beginning]. | 2004 |
|
Matrix metalloproteinase 2 and tissue inhibitor of metalloproteinase 2 expression is not regulated by norgestimate or norelgestromin. | 2004 Jan |
|
New Product Review (September 2003). Norelgestromin/ethinyl oestradiol transdermal contraceptive system (Evra). | 2004 Jan |
|
Induction of androgen receptor activity by norgestimate and norelgestromin in MDA-MB 231 breast cancer cells. | 2004 Jul |
|
Long-term evaluation of the use of the transdermal contraceptive patch in adolescents. | 2004 Jul 8 |
|
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 |
|
[Hormonal contraceptive patch]. | 2004 Oct 4 |
|
Adolescents' experience with the combined estrogen and progestin transdermal contraceptive method Ortho Evra. | 2005 Apr |
|
Extended use of transdermal norelgestromin/ethinyl estradiol: a randomized trial. | 2005 Jun |
|
Suppression of estrogen-withdrawal headache with extended transdermal contraception. | 2005 Jun |
|
Steroids' transformations in Penicillium notatum culture. | 2005 Mar |
|
[Safety evaluation of a transdermal contraceptive system with an oral contraceptive]. | 2005 Nov |
|
Microbial transformation of 17alpha-ethynyl- and 17alpha-ethylsteroids, and tyrosinase inhibitory activity of transformed products. | 2005 Nov |
|
[Advances in the study of steroidogenic acute regulatory protein]. | 2006 Aug |
|
How should we advise patients about the contraceptive patch, given the FDA warning? | 2006 Jan |
|
Gas chromatography/mass spectrometry characterization of urinary metabolites of danazol after oral administration in human. | 2006 Jan 2 |
|
New warning on birth control patch. | 2006 Jan-Feb |
|
Mortality in women given diethylstilbestrol during pregnancy. | 2006 Jul 3 |
|
Secondary sex ratio among women exposed to diethylstilbestrol in utero. | 2007 Sep |
|
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 |
|
Evaluation of extended and continuous use oral contraceptives. | 2008 Oct |
|
Membranous nephropathy in a patient with hereditary angioedema: a case report. | 2008 Oct 13 |
|
Cytotoxicity, cellular localisation and biomolecular interaction of non-covalent metallo-intercalators with appended sex hormone steroid vectors. | 2009 Dec 28 |
|
Danazol for uterine fibroids. | 2009 Jul 8 |
|
(20S,2''S)-20-[4'-(3''-Hydroxy-2''-methyl-prop-yl)-3'-methylisoxazol-5-yl]-5β-preg-nan-3β,16β-diol. | 2009 Nov 28 |
|
Vitellogenin induction by a mixture of steroidal estrogens in freshwater fishes and relevant risk assessment. | 2009 Oct |
|
Treatment of Hereditary Angioedema: items that need to be addressed in practice parameter. | 2010 May 25 |
|
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
Sample Use Guides
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/3641693
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
Edited
Fri Dec 15 15:09:56 GMT 2023
by
admin
on
Fri Dec 15 15:09:56 GMT 2023
|
Record UNII |
P201BVY1MJ
|
Record Status |
Validated (UNII)
|
Record Version |
|
-
Download
Name | Type | Language | ||
---|---|---|---|---|
|
Official Name | English | ||
|
Common Name | English | ||
|
Brand Name | English | ||
|
Code | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Brand Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Brand Name | English | ||
|
Systematic Name | English | ||
|
Brand Name | English |
Classification Tree | Code System | Code | ||
---|---|---|---|---|
|
NCI_THESAURUS |
C776
Created by
admin on Fri Dec 15 15:09:56 GMT 2023 , Edited by admin on Fri Dec 15 15:09:56 GMT 2023
|
||
|
WHO-VATC |
QG03DC04
Created by
admin on Fri Dec 15 15:09:56 GMT 2023 , Edited by admin on Fri Dec 15 15:09:56 GMT 2023
|
||
|
WHO-ATC |
G03FA03
Created by
admin on Fri Dec 15 15:09:56 GMT 2023 , Edited by admin on Fri Dec 15 15:09:56 GMT 2023
|
||
|
WHO-ATC |
G03DC04
Created by
admin on Fri Dec 15 15:09:56 GMT 2023 , Edited by admin on Fri Dec 15 15:09:56 GMT 2023
|
||
|
WHO-VATC |
QG03FA03
Created by
admin on Fri Dec 15 15:09:56 GMT 2023 , Edited by admin on Fri Dec 15 15:09:56 GMT 2023
|
Code System | Code | Type | Description | ||
---|---|---|---|---|---|
|
C77012
Created by
admin on Fri Dec 15 15:09:56 GMT 2023 , Edited by admin on Fri Dec 15 15:09:56 GMT 2023
|
PRIMARY | |||
|
1084
Created by
admin on Fri Dec 15 15:09:56 GMT 2023 , Edited by admin on Fri Dec 15 15:09:56 GMT 2023
|
PRIMARY | |||
|
ETHISTERONE
Created by
admin on Fri Dec 15 15:09:56 GMT 2023 , Edited by admin on Fri Dec 15 15:09:56 GMT 2023
|
PRIMARY | |||
|
D005003
Created by
admin on Fri Dec 15 15:09:56 GMT 2023 , Edited by admin on Fri Dec 15 15:09:56 GMT 2023
|
PRIMARY | |||
|
34749
Created by
admin on Fri Dec 15 15:09:56 GMT 2023 , Edited by admin on Fri Dec 15 15:09:56 GMT 2023
|
PRIMARY | |||
|
SUB07279MIG
Created by
admin on Fri Dec 15 15:09:56 GMT 2023 , Edited by admin on Fri Dec 15 15:09:56 GMT 2023
|
PRIMARY | |||
|
CHEMBL241694
Created by
admin on Fri Dec 15 15:09:56 GMT 2023 , Edited by admin on Fri Dec 15 15:09:56 GMT 2023
|
PRIMARY | |||
|
P201BVY1MJ
Created by
admin on Fri Dec 15 15:09:56 GMT 2023 , Edited by admin on Fri Dec 15 15:09:56 GMT 2023
|
PRIMARY | |||
|
DTXSID2023016
Created by
admin on Fri Dec 15 15:09:56 GMT 2023 , Edited by admin on Fri Dec 15 15:09:56 GMT 2023
|
PRIMARY | |||
|
9565
Created by
admin on Fri Dec 15 15:09:56 GMT 2023 , Edited by admin on Fri Dec 15 15:09:56 GMT 2023
|
PRIMARY | |||
|
100000082618
Created by
admin on Fri Dec 15 15:09:56 GMT 2023 , Edited by admin on Fri Dec 15 15:09:56 GMT 2023
|
PRIMARY | |||
|
4129
Created by
admin on Fri Dec 15 15:09:56 GMT 2023 , Edited by admin on Fri Dec 15 15:09:56 GMT 2023
|
PRIMARY | RxNorm | ||
|
434-03-7
Created by
admin on Fri Dec 15 15:09:56 GMT 2023 , Edited by admin on Fri Dec 15 15:09:56 GMT 2023
|
PRIMARY | |||
|
1261117
Created by
admin on Fri Dec 15 15:09:56 GMT 2023 , Edited by admin on Fri Dec 15 15:09:56 GMT 2023
|
PRIMARY | |||
|
m5065
Created by
admin on Fri Dec 15 15:09:56 GMT 2023 , Edited by admin on Fri Dec 15 15:09:56 GMT 2023
|
PRIMARY | Merck Index | ||
|
207-096-5
Created by
admin on Fri Dec 15 15:09:56 GMT 2023 , Edited by admin on Fri Dec 15 15:09:56 GMT 2023
|
PRIMARY | |||
|
5284557
Created by
admin on Fri Dec 15 15:09:56 GMT 2023 , Edited by admin on Fri Dec 15 15:09:56 GMT 2023
|
PRIMARY | |||
|
374
Created by
admin on Fri Dec 15 15:09:56 GMT 2023 , Edited by admin on Fri Dec 15 15:09:56 GMT 2023
|
PRIMARY |
Related Record | Type | Details | ||
---|---|---|---|---|
|
PARENT -> METABOLITE |
Related Record | Type | Details | ||
---|---|---|---|---|
|
ACTIVE MOIETY |