Ethynerone

Ethynerone

Systematic (IUPAC) name
(8S,13S,14S,17S)-17-(2-Chloroethynyl)-17-hydroxy-13-methyl-1,2,6,7,8,11,12,14,15,16-decahydrocyclopenta[a]phenanthren-3-one
Clinical data
Routes of administration	Oral
Identifiers
CAS Number	3124-93-4
PubChem	CID: 18403
ChemSpider	8512249
Chemical data
Formula	C20H23ClO2
Molecular mass	330.84842 g/mol
SMILES CC12CCC3=C4CCC(=O)C=C4CCC3C1CCC2(C#CCl)O
InChI InChI=1S/C20H23ClO2/c1-19-8-6-16-15-5-3-14(22)12-13(15)2-4-17(16)18(19)7-9-20(19,23)10-11-21/h12,17-18,23H,2-9H2,1H3/t17-,18+,19+,20-/m1/s1 Key:KEOBKPHJNAILCW-FUMNGEBKSA-N

Ethynerone (INN, USAN) is a steroidal progestin of the 19-nortestosterone group that was developed in the 1960s but was never marketed. Under the developmental code name MK-665, it was studied in combination with mestranol as an oral contraceptive. Development of the drug was discontinued due to concerns surrounding toxicity findings in dogs. It is a chloro-ethynyl derivative of norethisterone.

In 1966, during its clinical development, ethynerone was found to produce mammary gland tumors in dogs treated with it at very high doses for prolonged periods of time. Subsequent investigation found that 17α-hydroxyprogesterone derivatves included anagestone acetate, chlormadinone acetate, medroxyprogesterone acetate, and megestrol acetate produced similar mammary gland tumors, and that their ability to do so correlated directly with their progestogenic actions. In contrast, the non-halogenated 19-nortestosterone derivatives norgestrel, norethisterone, noretynodrel, and etynodiol diacetate, which are much less potent as progestogens, did not produce such effects at the dosages tested. Clinical development of ethynerone was discontinued, and many of the 17α-hydroxyprogesterone derivatives were withdrawn for the indication of hormonal contraception. Research later on revealed species differences between dogs and humans and established that there is no similar risk in humans.