Ethisterone

Ethisterone, also known as ethinyltestosterone, pregneninolone, and anhydrohydroxyprogesterone and formerly sold under the brand names Proluton C and Pranone among others, is a progestin medication which was used in the treatment of gynecological disorders but is now no longer available. It was used alone and was not formulated in combination with an estrogen. The medication is taken by mouth.

Ethisterone
Clinical data
Trade namesProluton C, Pranone, others
Other namesEthinyltestosterone; Ethynyltestosterone; Pregneninolone; Anhydrohydroxyprogesterone; Etisteron; Pregnin; Ethindrone
Routes of
administration		By mouth, sublingual
Drug classProgestogen; Progestin; Androgen; Anabolic steroid
ATC code
Pharmacokinetic data
Metabolites• 5α-Dihydroethisterone
Identifiers
  • (8R,9S,10R,13R,14S,17R)-17-Ethynyl-17-hydroxy-10,13-dimethyl-2,6,7,8,9,11,12,14,15,16-decahydro-1H-cyclopenta[a]phenanthren-3-one
CAS Number
PubChem CID
ChemSpider
UNII
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.006.452
Chemical and physical data
FormulaC21H28O2
Molar mass312.453 g·mol−1
3D model (JSmol)
SMILES
  • C[C@]12CCC(=O)C=C1CC[C@@H]3[C@@H]2CC[C@]4([C@H]3CC[C@]4(C#C)O)C
  • 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 Y
  • Key:CHNXZKVNWQUJIB-CEGNMAFCSA-N Y
  (verify)

Side effects of ethisterone include masculinization among others. Ethisterone is a progestin, or a synthetic progestogen, and hence is an agonist of the progesterone receptor, the biological target of progestogens like progesterone. It has some androgenic and anabolic activity and no other important hormonal activity.

Ethisterone was discovered in 1938 and was introduced for medical use in Germany in 1939 and in the United States in 1945. It was the second progestogen to be marketed, following injected progesterone in 1934, and was both the first orally active progestogen and the first progestin to be introduced. Ethisterone was followed by the improved and much more widely used and known progestin norethisterone in 1957.

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