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
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 |
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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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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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Pharmacokinetic overview of Ortho Evra/Evra. | 2002 Feb |
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Serum distribution of the major metabolites of norgestimate in relation to its pharmacological properties. | 2003 Feb |
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An evaluation of the use of the transdermal contraceptive patch in adolescents. | 2004 May |
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New contraception options. | 2004 Sep-Oct |
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Mortality in women given diethylstilbestrol during pregnancy. | 2006 Jul 3 |
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
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Record UNII |
P201BVY1MJ
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Record Status |
Validated (UNII)
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Record Version |
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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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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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34749
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SUB07279MIG
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CHEMBL241694
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P201BVY1MJ
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DTXSID2023016
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9565
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100000082618
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4129
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434-03-7
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1261117
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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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PARENT -> METABOLITE |
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ACTIVE MOIETY |