17α-Allyl-19-nortestosterone

17α-Allyl-19-nortestosterone, also known as 3-ketoallylestrenol or as 17α-allylestr-4-en-17β-ol-3-one, is a progestin which was never marketed.^[1][2][3][4] It is a combined derivative of the anabolic–androgenic steroid and progestogen nandrolone (19-nortestosterone) and the antiandrogen allyltestosterone (17α-allyltestosterone).^[1][2][3] The drug is a major active metabolite of allylestrenol, which is thought to be a prodrug of 17α-allyl-19-nortestosterone.^[4][5]

17α-Allyl-19-nortestosterone

Clinical data
Other names	Allylnortestosterone; Allylestrenolone; Allylnandrolone; 3-Ketoallylestrenol; 17α-Allylestr-4-en-17β-ol-3-one; Allylestrenolone
Drug class	Progestogen
Identifiers
IUPAC name (8R,9S,10R,13S,14S,17R)-17-hydroxy-13-methyl-17-prop-2-enyl-1,2,6,7,8,9,10,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-3-one
CAS Number	7358-46-5 Y
PubChem CID	22790929
ChemSpider	22270
UNII	EH9MJ5WS79
Chemical and physical data
Formula	C21H30O2
Molar mass	314.469 g·mol−1
3D model (JSmol)	Interactive image
SMILES C[C@]12CC[C@H]3[C@H]([C@@H]1CC[C@]2(CC=C)O)CCC4=CC(=O)CC[C@H]34
InChI InChI=1S/C21H30O2/c1-3-10-21(23)12-9-19-18-6-4-14-13-15(22)5-7-16(14)17(18)8-11-20(19,21)2/h3,13,16-19,23H,1,4-12H2,2H3/t16-,17+,18+,19-,20-,21-/m0/s1 Key:NXGWVXNWOIYZLE-XUDSTZEESA-N

17α-Allyl-19-nortestosterone has 24% of the affinity of ORG-2058 and 186% of the affinity of progesterone for the progesterone receptor, 4.5% of the affinity of testosterone for the androgen receptor, 9.8% of the affinity of dexamethasone for the glucocorticoid receptor, 2.8% of the affinity of testosterone for sex hormone-binding globulin, and less than 0.2% of the affinity of estradiol for the estrogen receptor.^[6][7] The affinity of 17α-allyl-19-nortestosterone for the androgen receptor was less than that of norethisterone and medroxyprogesterone acetate and its affinity for sex hormone-binding globulin was much lower than that of norethisterone.^[6] These findings may help to explain the absence of teratogenic effects of allylestrenol on the external genitalia of female and male rat fetuses.^[6]

Relative affinities (%) of allylestrenol and metabolites^[6]

Compound	PRTooltip Progesterone receptor	ARTooltip Androgen receptor	ERTooltip Estrogen receptor	GRTooltip Glucocorticoid receptor	MRTooltip Mineralocorticoid receptor	SHBGTooltip Sex hormone-binding globulin	CBGTooltip Corticosteroid binding globulin
Allylestrenol	0	0	0	0	?	1	?
17α-Allyl-19-NT	186	5	0	10	?	3	?
Values are percentages (%). Reference ligands (100%) were P4Tooltip progesterone (medication) for the PRTooltip progesterone receptor, TTooltip testosterone (medication) for the ARTooltip androgen receptor, E2 for the ERTooltip estrogen receptor, DEXATooltip dexamethasone for the GRTooltip glucocorticoid receptor, aldosterone for the MRTooltip mineralocorticoid receptor, TTooltip testosterone (medication) for SHBGTooltip sex hormone-binding globulin, and cortisol for CBGTooltip Corticosteroid-binding globulin.

See also

• Altrenogest
• Ethinyltestosterone
• Vinyltestosterone