Ursodiol
Title: Ursodiol
CAS Registry Number: 128-13-2
CAS Name: (3a,5b,7b)-3,7-Dihydroxycholan-24-oic acid
Additional Names: 17b-(1-methyl-3-carboxypropyl)etiocholane-3a,7b-diol; 3a,7b-dioxycholanic acid; ursodeoxycholic acid
Trademarks: Actigall (Novartis); Arsacol (Zambon); Cholit-Ursan (Fresenius); Delursan (Houd?; Desol (CT); Destolit (Norgine); Deursil (Midy); Litursol (Alfa); Lyeton (Leben's); Peptarom (Fresenius); Solutrat (Labinca); Urdes (Errekappa); Ursacol (Zambon); Urso (Tokyo Tanabe); Ursochol (Zambon); Ursofalk (Falk); Ursolvan (Synthelabo)
Molecular Formula: C24H40O4
Molecular Weight: 392.57
Percent Composition: C 73.43%, H 10.27%, O 16.30%
Literature References: Epimeric with chenodiol, q.v., with respect to the hydroxyl group at C7. Found in bear bile (combined with taurine). Isoln: Shoda, J. Biochem. (Tokyo) 7, 505 (1927). Structure: Kaziro, Z. Physiol. Chem. 185, 151 (1929); 197, 206 (1931); Iwasaki, ibid. 244, 181 (1936). Toxicity data: M. Ardenne, P. G. Reitnauer, Arzneim.-Forsch. 20, 323 (1970). Effect on cholesterol and bile acid metabolism: G. S. Tint et al., Gastroenterology 91, 1007 (1986). Clinical trial in primary biliary cirrhosis: R. E. Poupon et al., N. Engl. J. Med. 324, 1548 (1991). Review of pharmacology, toxicology, efficacy: A. Ward et al., Drugs 27, 95-131 (1984). Brief review of clinical effects and comparison with chenodiol: H. Fromm, Gastroenterology 87, 229-233 (1984).
Properties: Bitter plates from alc. mp 203°. [a]D20 +57° (c = 2 in abs ethanol). Freely sol in ethanol, glacial acetic acid; slightly sol in chloroform, sparingly sol in ether. Practically insol in water. LD50 in mice (g/kg): 0.1 i.v. (Ardenne, Reitnauer); in rats, mice (mg/kg): 2000, 6000 s.c.; 1000, 1200 i.p., 310, 260 i.v. (Ward).
Melting point: mp 203°
Optical Rotation: [a]D20 +57° (c = 2 in abs ethanol)
Toxicity data: LD50 in mice (g/kg): 0.1 i.v. (Ardenne, Reitnauer); in rats, mice (mg/kg): 2000, 6000 s.c.; 1000, 1200 i.p., 310, 260 i.v. (Ward)
 
Derivative Type: Diformate
Molecular Formula: C26H40O6
Molecular Weight: 448.59
Percent Composition: C 69.61%, H 8.99%, O 21.40%
Properties: Crystals, mp 170°.
Melting point: mp 170°
 
Derivative Type: Diacetate
Molecular Formula: C28H44O6
Molecular Weight: 476.65
Percent Composition: C 70.55%, H 9.30%, O 20.14%
Properties: Crystals, mp 98-102°.
Melting point: mp 98-102°
 
Therap-Cat: Anticholelithogenic.
Keywords: Cholelitholytic Agent.

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