Bexlosteride

Bexlosteride

Systematic (IUPAC) name
(4aS,10bR)-8-chloro-4-methyl-1,2,4a,5,6,10b-hexahydrobenzo[f]quinolin-
Clinical data
Routes of administration	Oral
Legal status	Uncontrolled
Identifiers
CAS Number	202189-78-4
ATC code	none
PubChem	CID 166562
ChemSpider	145762
UNII	36X732P4P0
ChEMBL	CHEMBL24955
Chemical data
Formula	C14H16ClNO
Molar mass	249.73594 g/mol
SMILES CN1C2CCC3=C(C2CCC1=O)C=CC(=C3)Cl
InChI InChI=1S/C14H16ClNO/c1-16-13-6-2-9-8-10(15)3-4-11(9)12(13)5-7-14(16)17/h3-4,8,12-13H,2,5-7H2,1H3/t12-,13-/m1/s1 Key:WQBIOEFDDDEARX-CHWSQXEVSA-N
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Bexlosteride (LY-191,704) is a potent and noncompetitive inhibitor of the enzyme 5α-reductase related to finasteride and dutasteride.^[1][2] It is selective for the type I isoform of the enzyme.^[1] It was never marketed.

Synthesis

Preparation of Bexlosteride:^[3]

Notes

A QSAR model was developed (1993):^[4]

See also

• 5α-Reductase inhibitor

References

1. Chang, Chawnshang (2002). Androgens and androgen receptor : mechanisms, functions, and clinical application. Boston: Kluwer Academic Publishers. ISBN 1-4020-7188-4.
2. Lednicer, Daniel (2008). Strategies for Organic Drug Synthesis and Design. New York: Wiley-Interscience. ISBN 0-470-19039-6.
3. Astleford, B. A.; Audia, J. E.; Deeter, J.; Heath, P. C.; Janisse, S. K.; Kress, T. J.; Wepsiec, J. P.; Weigel, L. O. (1996). "Resolution of δ-Lactams Provides Access to Nonracemic Benzoquinolinones: The Synthesis of LY300502 and LY300503". The Journal of Organic Chemistry 61 (13): 4450–4454. doi:10.1021/jo9601425. PMID 11667351.
4. Wikel, J. H.; Bemis, K. G.; Audia, J. E.; McQuaid, L. A.; Jones, C. D.; Pennington, P. A.; Lawhorn, D. E.; Hirsch, K. R.; Stamm, N. B. (1993). "QSAR study of benzoquinolinones as inhibitors of human type 1 5-α-reductase". Bioorganic & Medicinal Chemistry Letters 3 (6): 1157. doi:10.1016/S0960-894X(00)80306-6.