Structural Formula Vector Image
Title: Lonapalene
CAS Registry Number: 91431-42-4
CAS Name: 6-Chloro-2,3-dimethoxy-1,4-naphthalenediol diacetate
Additional Names: 6-chloro-1,4-diacetoxy-2,3-dimethoxynaphthalene
Manufacturers' Codes: RS-43179
Molecular Formula: C16H15ClO6
Molecular Weight: 338.74
Percent Composition: C 56.73%, H 4.46%, Cl 10.47%, O 28.34%
Literature References: Selective 5-lipoxygenase inhibitor. Prepn: G. H. Jones et al., EP 107512; eidem, US 4466981 (both 1984 to Syntex); eidem, J. Med. Chem. 29, 1504 (1986); S. T. Perri, H. W. Moore, Tetrahedron Lett. 28, 4507 (1987). Clinical pharmacology: A. K. Black et al., J. Invest. Dermatol. 95, 50 (1990). Percutaneous absorption and metabolism: P. A. Lehman et al., Pharm. Res. 9, 1145 (1992). HPLC determn in pharmaceutical prepns: R. A. Kenley et al., Drug Dev. Ind. Pharm. 11, 1781 (1985); of metabolites in urine: C.-H. Kiang, C. Lee, J. Chromatogr. 565, 339 (1991). Clinical evaluation in psoriasis: A. Lassus, S. Forsstrom, Br. J. Dermatol. 113, 103 (1985).
Properties: Crystals from ether-petroleum ether, mp 93-94° (Jones); also reported as mp 87.5-89.5° (Perri, Moore). Partition coefficient (n-octanol/water): 3.26.
Melting point: mp 93-94° (Jones); mp 87.5-89.5° (Perri, Moore)
Log P: Partition coefficient (n-octanol/water): 3.26
Therap-Cat: Antipsoriatic.
Keywords: Antipsoriatic; 5-Lipoxygenase Inhibitor.
Status: This monograph has been retired and is no longer subject to revision or update.

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