Loteprednol Etabonate
Structural Formula Vector Image
Title: Loteprednol Etabonate
CAS Registry Number: 82034-46-6
CAS Name: (11b,17a)-17-[(Ethoxycarbonyl)oxy]-11-hydroxy-3-oxoandrosta-1,4-diene-17-carboxylic acid chloromethyl ester
Additional Names: chloromethyl 17a-ethoxycarbonyloxy-11b-hydroxyandrosta-1,4-diene-3-one-17b-carboxylate; 17a-ethoxycarbonyloxy--cortienic acid chloromethyl ester
Manufacturers' Codes: CDDD-5604; HGP-1; P-5604
Trademarks: Alrex (Bausch & Lomb); Lotemax (Bausch & Lomb)
Molecular Formula: C24H31ClO7
Molecular Weight: 466.95
Percent Composition: C 61.73%, H 6.69%, Cl 7.59%, O 23.98%
Literature 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).
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.
Melting point: mp 220.5-223.5°
Therap-Cat: Anti-inflammatory (topical).
Keywords: Glucocorticoid.

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