FCE 28260

FCE 28260
Clinical data
Other names	PNU 156765
Routes of; administration	Oral
ATC code	none;
Identifiers
	IUPAC name (4aR,4bS,6aS,7S,9aS,9bS,11aR)-4a,6a-Dimethyl-2-oxo-N-((2RS)-1,1,1-trifluoro-2-phenyl-2-propanyl)-2,4a,4b,5,6,6a,7,8,9,9a,9b,10,11,11a-tetradecahydro-1H-indeno[5,4-f]quinoline-7-carboxamide;
CAS Number	155651-56-2 ;
ChemSpider	117369;
UNII	HP9C5LM7NX;
Chemical and physical data
Formula	C28H35F3N2O2
Molar mass	488.595 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES FC(F)(F)C(c1ccccc1)(NC(=O)[C@@H]3[C@]2(CC[C@H]4[C@H]([C@@H]2CC3)CC[C@H]5NC(=O)\C=C/[C@]45C)C)C;
	InChI InChI=1S/C28H35F3N2O2/c1-25-15-13-20-18(9-12-22-26(20,2)16-14-23(34)32-22)19(25)10-11-21(25)24(35)33-27(3,28(29,30)31)17-7-5-4-6-8-17/h4-8,14,16,18-22H,9-13,15H2,1-3H3,(H,32,34)(H,33,35)/t18-,19-,20-,21+,22+,25-,26+,27?/m0/s1; Key:FAIZUAWLKOHMOP-ZOIXLQFFSA-N;

FCE 28260 is an azasteroidal 5α-reductase inhibitor which was developed for the treatment of benign prostatic hyperplasia and androgenic alopecia (pattern hair loss) in the 1990s but was never marketed.^[1]^[2]^[3] FCE 28260 has been found to inhibit rat and human 5α-reductase with half-maximal inhibitory concentrations (IC₅₀) of 15 and 16 nM, respectively, while finasteride had values of 30 and 52 nM.^[1]

References

^ ^a ^b Giudici D, Briatico G, Cominato C, Zaccheo T, Iehlè C, Nesi M, et al. (June 1996). "FCE 28260, a new 5 alpha-reductase inhibitor: in vitro and in vivo effects". The Journal of Steroid Biochemistry and Molecular Biology. 58 (3): 299–305. doi:10.1016/0960-0760(96)00040-4. PMID 8836165. S2CID 140209512.
^ EP 0782582, di Salle E, Nesi M, Panzeri A, "Epimers of (22RS)-N-(1,1,1-trifluoro-2-phenylprop-2-yl)-3-oxo-4-aza-5α-androst-1-ene-17β-carboxamide", published 1997-07-09
^ "FCE 28260". AdisInsight. Springer Nature Switzerland AG.

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Clinical data

Other names	PNU 156765
Routes of administration	Oral
ATC code	none
Identifiers
IUPAC name (4aR,4bS,6aS,7S,9aS,9bS,11aR)-4a,6a-Dimethyl-2-oxo-N-((2RS)-1,1,1-trifluoro-2-phenyl-2-propanyl)-2,4a,4b,5,6,6a,7,8,9,9a,9b,10,11,11a-tetradecahydro-1H-indeno[5,4-f]quinoline-7-carboxamide
CAS Number	155651-56-2^Y
ChemSpider	117369
UNII	HP9C5LM7NX
Chemical and physical data
Formula	C₂₈H₃₅F₃N₂O₂
Molar mass	488.595 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES FC(F)(F)C(c1ccccc1)(NC(=O)[C@@H]3[C@]2(CC[C@H]4[C@H]([C@@H]2CC3)CC[C@H]5NC(=O)\C=C/[C@]45C)C)C
InChI InChI=1S/C28H35F3N2O2/c1-25-15-13-20-18(9-12-22-26(20,2)16-14-23(34)32-22)19(25)10-11-21(25)24(35)33-27(3,28(29,30)31)17-7-5-4-6-8-17/h4-8,14,16,18-22H,9-13,15H2,1-3H3,(H,32,34)(H,33,35)/t18-,19-,20-,21+,22+,25-,26+,27?/m0/s1 Key:FAIZUAWLKOHMOP-ZOIXLQFFSA-N