5584. Loteprednol Etabonate

Nomenclature

CAS number: 82034-46-6
(11β,17α)-17-[(Ethoxycarbonyl)oxy]-11-hydroxy-3-oxoandrosta-1,4-diene-17-carboxylic acid chloromethyl ester; chloromethyl 17α-ethoxycarbonyloxy-11β-hydroxyandrosta-1,4-diene-3-one-17β-carboxylate; 17α-ethoxycarbonyloxy-Δ′-cortienic acid chloromethyl ester; CDDD-5604; HGP-1; P-5604; Alrex (Bausch & Lomb); Lotemax (Bausch & Lomb).
C24H31ClO7; mol wt 466.95.
C 61.73%, H 6.69%, Cl 7.59%, O 23.98%.

Description and references

Ophthalmic corticosteroid. Prepn: N. S. Bodor, BE 889563 (1981 to Otsuka); idem, US 4996335 (1991). Physicochemical properties: M. Alberth et al., J. Biopharm. Sci. 2, 115 (1991). HPLC determn in plasma and urine: G. Hochhaus et al., J. Pharm. Sci. 81, 1210 (1992). NMR structural studies: S. Rachwal et al., Steroids 61, 524 (1996); idem et al., ibid. 63, 193 (1998). Metabolism and transdermal permeability: N. Bodor et al., Pharm. Res. 9, 1275 (1992). Evaluation of effect on intraocular pressure: J. D. Bartlett et al., J. Ocul. Pharmacol. 9, 157 (1993). Clinical trial in keratoconjunctivitis sicca: S. C. Pflugfelder et al., Am. J. Ophthalmol. 138, 444 (2004). Review of ophthalmic clinical studies: J. F. Howes, Pharmazie 55, 178-183 (2000).

Chemical structure

Properties

Crystals from THF + hexane, mp 220.5-223.5°. Soly at 25° (mg/ml): 0.0005 in water; 0.037 in 50% propylene glycol + water. Lipophilicity (log K): 3.04.

Therapeutic Category

Anti-inflammatory (topical).

Keywords

Glucocorticoid