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
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
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
PubMed
Title | Date | PubMed |
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The effect of structural QSAR parameters on skin penetration. | 2001 Apr 17 |
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Pharmacokinetics of norelgestromin and ethinyl estradiol from two consecutive contraceptive patches. | 2001 Nov |
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Contraceptive efficacy and cycle control with the Ortho Evra/Evra transdermal system: the analysis of pooled data. | 2002 Feb |
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Pharmacokinetic overview of Ortho Evra/Evra. | 2002 Feb |
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The transdermal contraceptive patch: a new approach to hormonal contraception. | 2002 Mar-Apr |
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New hormonal contraceptives: a comprehensive review of the literature. | 2003 Dec |
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Serum distribution of the major metabolites of norgestimate in relation to its pharmacological properties. | 2003 Feb |
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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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New drugs 2003, part II. | 2003 Jul |
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Transdermal contraceptive patch delivering norelgestromin and ethinyl estradiol. Effects on the lipid profile. | 2003 Mar |
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CD spectrometric methods for the simultaneous determination of ethisterone and its delta5-isomer. | 2003 Mar |
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[Medication of the month. Evra: first contraceptive transdermal patch]. | 2003 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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Induction of androgen receptor activity by norgestimate and norelgestromin in MDA-MB 231 breast cancer cells. | 2004 Jul |
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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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An evaluation of the use of the transdermal contraceptive patch in adolescents. | 2004 May |
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Nondaily hormonal contraception: establishing a fit between product characteristics and patient preferences. | 2004 Nov |
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New contraception options. | 2004 Sep-Oct |
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Effect of oral versus transdermal steroidal contraceptives on androgenic markers. | 2005 Jun |
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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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How should we advise patients about the contraceptive patch, given the FDA warning? | 2006 Jan |
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The Evra (ethinyl estradiol/norelgestromin) contraceptive patch: estrogen exposure concerns. | 2006 Jan 17 |
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Secondary sex ratio among women exposed to diethylstilbestrol in utero. | 2007 Sep |
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[The applications of chiroptical spectroscopy for the determination and the detection of steroids and for the examination of their cyclodextrin-mediated enantioselective solubility]. | 2008 |
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HT update: spotlight on estradiol/norethindrone acetate combination therapy. | 2008 |
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Testicular dysgenesis syndrome and the estrogen hypothesis: a quantitative meta-analysis. | 2008 Feb |
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Genetic and chemical modifiers of a CUG toxicity model in Drosophila. | 2008 Feb 13 |
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Structure-activity relationships of synthetic progestins in a yeast-based in vitro androgen bioassay. | 2008 May |
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Evaluation of extended and continuous use oral contraceptives. | 2008 Oct |
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Prediction of pharmacological and xenobiotic responses to drugs based on time course gene expression profiles. | 2009 Dec 2 |
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Cytotoxicity, cellular localisation and biomolecular interaction of non-covalent metallo-intercalators with appended sex hormone steroid vectors. | 2009 Dec 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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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
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Classification Tree | Code System | Code | ||
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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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admin on Tue Oct 22 00:36:44 UTC 2019 , Edited by admin on Tue Oct 22 00:36:44 UTC 2019
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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
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Code System | Code | Type | Description | ||
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C77012
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PRIMARY | |||
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ETHISTERONE
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admin on Tue Oct 22 00:36:44 UTC 2019 , Edited by admin on Tue Oct 22 00:36:44 UTC 2019
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D005003
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SUB07279MIG
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CHEMBL241694
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434-03-7
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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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PRIMARY |
ACTIVE MOIETY
PARENT (METABOLITE)