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
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
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 |
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Target ID: CHEMBL3305 Sources: https://www.ncbi.nlm.nih.gov/pubmed/3641693 |
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Conditions
Condition | Modality | Targets | Highest Phase | Product |
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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. |
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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. |
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Primary | Prone Approved UseEndometriosis |
PubMed
Title | Date | PubMed |
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GC-MS characterization of urinary metabolites and changes of ethisterone and testosterone profile after oral administration of danazol in equine. | 2001 Apr |
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Pharmacokinetics of norelgestromin and ethinyl estradiol delivered by a contraceptive patch (Ortho Evra/Evra) under conditions of heat, humidity, and exercise. | 2001 Dec |
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Pharmacokinetics of norelgestromin and ethinyl estradiol from two consecutive contraceptive patches. | 2001 Nov |
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Pharmacokinetics of a contraceptive patch (Evra/Ortho Evra) containing norelgestromin and ethinyloestradiol at four application sites. | 2002 Feb |
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The introduction of a transdermal hormonal contraceptive (Ortho Evra/Evra). | 2002 Feb |
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Pharmacokinetic overview of Ortho Evra/Evra. | 2002 Feb |
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Transdermal ethinylestradiol/norelgestromin: a review of its use in hormonal contraception. | 2003 |
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Ortho Evra, a new contraceptive patch. | 2003 Apr |
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New hormonal contraceptives: a comprehensive review of the literature. | 2003 Dec |
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Evra--a patch on oral contraception? | 2003 Dec |
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Norelgestromin as selective estrogen enzyme modulator in human breast cancer cell lines. Effect on sulfatase activity in comparison to medroxyprogesterone acetate. | 2003 Feb |
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Ortho Evra/Evra versus oral contraceptives: follicular development and ovulation in normal cycles and after an intentional dosing error. | 2003 Jul |
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Transdermal delivery of sex steroids for hormone replacement therapy and contraception. A review of principles and practice. | 2003 Jul |
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New drugs 2003, part II. | 2003 Jul |
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Progress in contraception: new technology. | 2003 Jul-Aug |
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Transdermal contraceptive patch delivering norelgestromin and ethinyl estradiol. Effects on the lipid profile. | 2003 Mar |
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[A transdermal form of combined hormonal contraceptives (EVRA)]. | 2003 Oct |
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Women prefer Ortho Evra patch. | 2003 Oct-Nov |
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Matrix metalloproteinase 2 and tissue inhibitor of metalloproteinase 2 expression is not regulated by norgestimate or norelgestromin. | 2004 Jan |
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Long-term evaluation of the use of the transdermal contraceptive patch in adolescents. | 2004 Jul 8 |
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Effects of nitric oxide on aldosterone synthesis and nitric oxide synthase activity in glomerulosa cells from bovine adrenal gland. | 2004 Jun |
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Nondaily hormonal contraception: establishing a fit between product characteristics and patient preferences. | 2004 Nov |
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[Hormonal contraceptive patch]. | 2004 Oct 4 |
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New contraception options. | 2004 Sep-Oct |
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Adolescents' experience with the combined estrogen and progestin transdermal contraceptive method Ortho Evra. | 2005 Apr |
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Preference for and satisfaction of Canadian women with the transdermal contraceptive patch versus previous contraceptive method: an open-label, multicentre study. | 2005 Apr |
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Extended use of transdermal norelgestromin/ethinyl estradiol: a randomized trial. | 2005 Jun |
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Suppression of estrogen-withdrawal headache with extended transdermal contraception. | 2005 Jun |
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Effect of oral versus transdermal steroidal contraceptives on androgenic markers. | 2005 Jun |
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Steroids' transformations in Penicillium notatum culture. | 2005 Mar |
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[Safety evaluation of a transdermal contraceptive system with an oral contraceptive]. | 2005 Nov |
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Hormonal contraception: recent advances. | 2006 |
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[Advances in the study of steroidogenic acute regulatory protein]. | 2006 Aug |
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The Evra (ethinyl estradiol/norelgestromin) contraceptive patch: estrogen exposure concerns. | 2006 Jan 17 |
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Gas chromatography/mass spectrometry characterization of urinary metabolites of danazol after oral administration in human. | 2006 Jan 2 |
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Mortality in women given diethylstilbestrol during pregnancy. | 2006 Jul 3 |
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A full conformational characterization of 13-ethylprogestogens through theoretical calculations and nuclear magnetic resonance spectroscopy. | 2007 Feb |
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Secondary sex ratio among women exposed to diethylstilbestrol in utero. | 2007 Sep |
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HT update: spotlight on estradiol/norethindrone acetate combination therapy. | 2008 |
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Genetic and chemical modifiers of a CUG toxicity model in Drosophila. | 2008 Feb 13 |
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Membranous nephropathy in a patient with hereditary angioedema: a case report. | 2008 Oct 13 |
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Danazol for uterine fibroids. | 2009 Jul 8 |
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(20S,2''S)-20-[4'-(3''-Hydroxy-2''-methyl-prop-yl)-3'-methylisoxazol-5-yl]-5β-preg-nan-3β,16β-diol. | 2009 Nov 28 |
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Vitellogenin induction by a mixture of steroidal estrogens in freshwater fishes and relevant risk assessment. | 2009 Oct |
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Synthesis and solid state characterization of molecular rotors with steroidal stators: ethisterone and norethisterone. | 2010 Jun 28 |
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Treatment of Hereditary Angioedema: items that need to be addressed in practice parameter. | 2010 May 25 |
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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.
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NCI_THESAURUS |
C776
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WHO-VATC |
QG03DC04
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WHO-ATC |
G03FA03
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WHO-ATC |
G03DC04
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WHO-VATC |
QG03FA03
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Code System | Code | Type | Description | ||
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C77012
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1084
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ETHISTERONE
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D005003
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SUB07279MIG
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CHEMBL241694
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P201BVY1MJ
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434-03-7
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1261117
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4129
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434-03-7
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M5065
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207-096-5
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5284557
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374
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ACTIVE MOIETY
PARENT (METABOLITE)