Title: Fusidic Acid
CAS Registry Number: 6990-06-3
CAS Name: (3a,4a,8a,9b,11a,13a,14b,16b,17Z)-16-(Acetyloxy)-3,11-dihydroxy-29-nordammara-17(20),24-dien-21-oic acid
Additional Names: 3a,11a,16b-trihydroxy-29-nor-8a,9b,13a,14b-dammara-17(20),24-dien-21-oic acid 16-acetate; 3a,11a,16b-trihydroxy-4a,8,14-trimethyl-18-nor-5a,8a,9b,13a,14b-cholesta-17(20),24-dien-21-oic acid 16-acetate; 3,11,16-trihydroxy-4,8,10,14-tetramethyl-17-(1¢-carboxyisohept-4¢-enylidene)cyclopentanoperhydrophenanthrene 16-acetate; ramycin
Trademarks: Fucithalmic (Leo Pharm)
Molecular Formula: C31H48O6
Molecular Weight: 516.71
Percent Composition: C 72.06%, H 9.36%, O 18.58%
Literature References: Antibiotic isolated from the fermentation broth of Fusidium coccineum; structurally similar to cephalosporin P1, q.v. Inhibits bacterial protein synthesis by interference with elongation factor G. Isoln and structure: W. O. Godtfredsen et al., Nature 193, 987 (1962); Lancet I, 928 (1962); W. O. Godtfredsen, S. Vangedal, Tetrahedron 18, 1029 (1962). Identity with ramycin: H. Vanderhaeghe et al., Nature 205, 710 (1965). Structure: D. Arigoni et al., Experientia 19, 521 (1963). Stereochemistry: W. O. Godtfredsen et al., Tetrahedron 21, 3505 (1965). Synthetic studies: W. G. Dauben et al., J. Am. Chem. Soc. 94, 8593 (1972); R. E. Ireland, U. Hengartner, ibid. 3652; M. Tanabe et al., Tetrahedron Lett. 1977, 1481. Total synthesis: W. G. Dauben et al., J. Am. Chem. Soc. 104, 303 (1982). Review of structure-activity relationships: W. von Daehne et al., Adv. Appl. Microbiol. 25, 95-146 (1979). Series of articles on pharmacology and clinical experience: Int. J. Antimicrob. Ag. 12, Suppl. 2, S1-S93 (1999). Review of use in Staphylococcus aureus infections: D. Dobie, J. Gray, Arch. Dis. Child. 89, 74-77 (2004).
Properties: Crystals from ether or benzene, mp 192-193°. [a]D20 -9° (chloroform). uv max: 204 nm (e 9900). pK: 5.35 in water. Sol in alc, acetone, chloroform, pyridine, dioxane; sparingly sol in water, ether, hexane. LD50 in mice (g/kg): 1.2 s.c.; 1.5 orally (Godtfredsen).
Melting point: mp 192-193°
pKa: pK: 5.35 in water
Optical Rotation: [a]D20 -9° (chloroform)
Absorption maximum: uv max: 204 nm (e 9900)
Toxicity data: LD50 in mice (g/kg): 1.2 s.c.; 1.5 orally (Godtfredsen)
Derivative Type: Sodium salt
CAS Registry Number: 751-94-0
Additional Names: Sodium fusidate
Manufacturers' Codes: ZN-6
Trademarks: Fucidin (Leo Pharm); Fucidine (Leo Pharm)
Molecular Formula: C31H47NaO6
Molecular Weight: 538.69
Percent Composition: C 69.12%, H 8.79%, Na 4.27%, O 17.82%
Properties: Crystals, sol in water. LD50 in mice (g/kg): 0.2 i.v. (Godtfredsen, Nature 1962).
Toxicity data: LD50 in mice (g/kg): 0.2 i.v. (Godtfredsen, Nature 1962)
Therap-Cat: Antibacterial.
Therap-Cat-Vet: Antibacterial.
Keywords: Antibacterial (Antibiotics). |