13-05586. Lonapalene [Archived]

Nomenclature

CAS number: 91431-42-4
6-Chloro-2,3-dimethoxy-1,4-naphthalenediol diacetate; 6-chloro-1,4-diacetoxy-2,3-dimethoxynaphthalene; RS-43179.
C16H15ClO6; mol wt 338.74.
C 56.73%, H 4.46%, Cl 10.47%, O 28.34%.

Description and 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).

Chemical structure

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.

Therapeutic Category

Antipsoriatic.

Keywords

Antipsoriatic; 5-Lipoxygenase Inhibitor

Status

This monograph has been retired and is no longer subject to revision or update.