DU-41165

DU-41165

Clinical data
Other names	6-Fluoro-16-methylene-17α-acetoxy-δ^6-retroprogesterone; 6-Fluoro-16-methylene-17α-hydroxy-9β,10α-pregna-4,6-diene-3,20-dione 17α-acetate; 6-Fluoro-16-methylene-3,20-dioxo-9β,10α-pregna-4,6-dien-17α-yl acetate
Routes of administration	By mouth
Drug class	Progestin; Progestogen
Identifiers
IUPAC name [(8R,9R,10S,13S,14S,17R)-17-Acetyl-6-fluoro-10,13-dimethyl-16-methylidene-3-oxo-1,2,8,9,11,12,14,15-octahydrocyclopenta[a]phenanthren-17-yl] acetate
CAS Number	34184-58-2^Y
PubChem CID	169573
ChemSpider	148298
UNII	5M4PL394K5
CompTox Dashboard (EPA)	DTXSID60955729
Chemical and physical data
Formula	C24H29FO4
Molar mass	400.490 g·mol^−1
3D model (JSmol)	Interactive image
SMILES CC(=O)[C@]1(C(=C)C[C@@H]2[C@@]1(CC[C@@H]3[C@H]2C=C(C4=CC(=O)CC[C@@]34C)F)C)OC(=O)C
InChI InChI=1S/C24H29FO4/c1-13-10-19-17-12-21(25)20-11-16(28)6-8-22(20,4)18(17)7-9-23(19,5)24(13,14(2)26)29-15(3)27/h11-12,17-19H,1,6-10H2,2-5H3/t17-,18-,19+,22+,23+,24+/m1/s1 Key:XSSIGSNQDKHHLD-JBARXXBASA-N

DU-41165, also known as 6-fluoro-16-methylene-17α-acetoxy-δ⁶-retroprogesterone, is a progestin which was developed by Philips-Duphar in the 1970s and was never marketed.^[1][2] It is a combined derivative of 17α-hydroxyprogesterone and retroprogesterone.^[1][2] The drug shows extremely high potency as a progestogen in animals.^[1] It has been found to possess 158% of the relative binding affinity of promegestone for the progesterone receptor expressed in rat uterus (relative to 74% for the closely related progestin DU-41164).^[1] DU-41165 also showed 28% of the affinity of RU-28362 for the glucocorticoid receptor expressed in rat liver, but no affinity for the mineralocorticoid receptor expressed in rat kidney (<0.003% of that of RU-26752).^[1] The drug showed no androgenic, anabolic, or estrogenic activity in animals, but did show some antiandrogenic and glucocorticoid activity at high doses.^[1] Although highly potent in animals, DU-41165 produced little or no progestogenic effect at dosages of 50 and 200 μg/day in women, suggesting major species differences.^[1] DU-41165 has been studied as a potential photoaffinity label for the progesterone receptor.^[1]

References

1. Morsink L, de Wachter AM, Brenner P, Cekan SZ, Guerrero R, Hagenfeldt K, Diczfalusy E (May 1976). "Endocrine effects of two new retro-steroids in animal models and in women". Acta Endocrinol. 82 (1): 193–212. doi:10.1530/acta.0.0820193. PMID 57688.
2. Pinney KG, Carlson KE, Katzenellenbogen JA (February 1990). "[3H]DU41165: a high affinity ligand and novel photoaffinity labeling reagent for the progesterone receptor". J. Steroid Biochem. 35 (2): 179–89. doi:10.1016/0022-4731(90)90272-T. PMID 2308335.