Anagestone acetate

Anagestone acetate

a steroidal progestin
Systematic (IUPAC) name
(17-Acetyl-6,10,13-trimethyl-1,2,3,6,7,8,9,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-17-yl) acetate
Clinical data
Routes of administration	Oral
Identifiers
CAS Number	3137-73-3
PubChem	CID: 18443
ChemSpider	221058
Synonyms	Anapregnone acetate; 17α-hydroxy-6α-methylpregn-4-en-20-one acetate
Chemical data
Formula	C24H36O3
Molecular mass	372.54084 g/mol
SMILES CC1CC2C(CCC3(C2CCC3(C(=O)C)OC(=O)C)C)C4(C1=CCCC4)C
InChI InChI=1S/C24H36O3/c1-15-14-18-20(22(4)11-7-6-8-19(15)22)9-12-23(5)21(18)10-13-24(23,16(2)25)27-17(3)26/h8,15,18,20-21H,6-7,9-14H2,1-5H3 Key:KDLNOQQQEBKBQM-UHFFFAOYSA-N

Anagestone acetate (USAN) (brand name Anatropin; former developmental code name ORF-1658), also known as 17α-hydroxy-6α-methylpregn-4-en-20-one acetate, is a steroidal progestin that was formerly marketed by Ortho Pharmaceutical. Under the brand name Neo-Novum and in combination with the estrogen mestranol, it was introduced in 1968 as an oral contraceptive in the United States. Anagestone acetate is the acetate ester of anagestone, which, in contrast to anagestone acetate, was never marketed.

In 1969, along with a variety of other progestogens including progesterone, chlormadinone acetate, megestrol acetate, medroxyprogesterone acetate, ethynerone, and chloroethynyl norgestrel, anagestone acetate was found to induce the development of mammary gland tumors in Beagle dogs after extensive treatment (2–7 years) with very high doses (10–25 times the recommended human dose), though notably not with 1–2 times the human dosage. In contrast, the non-halogenated 19-nortestosterone derivatives norgestrel, norethisterone, noretynodrel, and etynodiol diacetate were not found to produce such nodules. Because of these findings, anagestone acetate was withdrawn from the U.S. market in 1969, and this was followed by its subsequent discontinuation worldwide by the manufacturer. The findings also led to the virtual disappearance of most 17α-hydroxyprogesterone derivatives as hormonal contraceptives from the market (though medroxyprogesterone acetate has continued to be used). According to Hughes et al., "It is still doubtful how much relevance these findings have for humans as the dog mammary gland seems to be the only one which can be directly maintained by progestogens." Subsequent research revealed species differences between dogs and humans and established that there is no similar risk in humans.

See also

• Algestone acetophenide
• Cyproterone acetate
• Delmadinone acetate
• Hydroxyprogesterone acetate
• Hydroxyprogesterone caproate
• Hydroxyprogesterone heptanoate
• Melengestrol acetate