Title: Griseofulvin
CAS Registry Number: 126-07-8
CAS Name: (1¢S,6¢R)-7-Chloro-2¢,4,6-trimethoxy-6¢-methylspiro[benzofuran-2(3H),1¢-[2]cyclohexene]-3,4¢-dione
Additional Names: 7-chloro-4,6-dimethoxycoumaran-3-one-2-spiro-1¢-(2¢-methoxy-6¢-methylcyclohex-2¢-en-4¢-one); amudane; Curling factor
Trademarks: Fulcin (Zeneca); Fulvicin (Schering); Grifulvin (McNeil); Grisactin (Ayerst); Griséfuline (Sanofi Winthrop); Grisovin (GSK); Gris-PEG (Herbert); Grysio (Ayerst); Lamoryl (Leo Pharm); Likuden (HMR); Polygris (Essex); Poncyl-FP (Takeda); Spirofulvin; Sporostatin (Schering)
Molecular Formula: C17H17ClO6
Molecular Weight: 352.77
Percent Composition: C 57.88%, H 4.86%, Cl 10.05%, O 27.21%
Literature References: Antibiotic substance produced by Penicillium griseofulvum Dierckx and by P. janczewskii Zal. [same as P. nigricans (Banier)Thom]. Isoln: Oxford et al., Biochem. J. 33, 240 (1939); Brian et al., Trans. Br. Mycol. Soc. 29, 173 (1946); Hockenhull, Dorey et al., US 3069328, US 3069329 (both 1962 to Glaxo). Structure: Grove et al., Chem. Ind. (London) 1951, 219; J. Chem. Soc. 1952, 3977. Stereochemistry: MacMillan, ibid. 1959, 1823; Brown, Sim, ibid. 1963, 1050. Total synthesis: Brossi et al., Helv. Chim. Acta 43, 1444, 2071 (1960); Taub et al., Tetrahedron 19, 1 (1963); Stork, Tomasz, J. Am. Chem. Soc. 86, 471 (1964); S. Danishefsky, F. J. Walker, ibid. 101, 7018 (1979). Conformation: Levine, Hicks, Tetrahedron Lett. 1971, 311. Crystal structure: G. Malmros et al., Cryst. Struct. Commun. 6, 463 (1977). Review and evaluation of studies of carcinogenic action in laboratory animals: IARC Monographs 10, 153-161 (1976). Review: Grove, Q. Rev. Chem. Soc. 17, 1 (1963); Huber in Antibiotics vol. 3, J. W. Corcoran, F. E. Hahn, Eds. (Springer-Verlag, New York, 1975) pp 606-613. Comprehensive description: E. R. Townley, Anal. Profiles Drug Subs. 8, 219-249 (1979).
Properties: Stout octahedra or rhombs from benzene, mp 220°. [a]D17 +370° (satd CHCl3 soln). uv max: 286, 325 nm. Soly in DMF at 25°: 12 to 14 g/100 ml. Slightly sol in ethanol, methanol, acetone, benzene, CHCl3, ethyl acetate, acetic acid. Practically insol in water, petr ether.
Melting point: mp 220°
Optical Rotation: [a]D17 +370° (satd CHCl3 soln)
Absorption maximum: uv max: 286, 325 nm
Therap-Cat: Antifungal.
Therap-Cat-Vet: Antifungal.
Keywords: Antifungal (Antibiotics). |