4290. Fungichromin
Nomenclature
Description and references
Antifungal polyene macrolide antibiotic, related structurally to filipin, q.v. Isoln from Streptomyces cellulosae: A. A. Tytell et al., Antibiot. Annu. 1954-1955, 716. Isoln (as pentamycin) from S. penticus: S. Umezawa, Y. Tanaka, J. Antibiot. 11A, 26 (1958). Isoln (as lagosin) from S. roseoluteus: C. J. Bessel et al., US 3013947 (1961 to Glaxo). Isoln from S. griseus (FCRC-21): R. C. Pandey et al., Biomed. Mass Spectrom. 7, 93 (1980). Structures: A. C. Cope, H. E. Johnson, J. Am. Chem. Soc. 80, 1504 (1958); A. C. Cope et al., ibid. 84, 2170 (1962); M. L. Dhar et al., J. Chem. Soc. 1964, 842; M. P. Berry, M. C. Whiting, ibid. 862; V. Pozgay et al., J. Antibiot. 29, 472 (1976). Identity of fungichromin with lagosin and cogomycin and comparison of reported physico-chemical constants: R. C. Pandey et al., J. Antibiot. 35, 988 (1982). Biosynthesis and NMR assignment: H. Noguchi et al., J. Am. Chem. Soc. 110, 2938 (1988).
Properties
Light yellow cryst. mp 157-162° (dec). [α]D20 227.7° (c = 0.53 in DMF). uv max (methanol): 357, 338, 322 nm (E1%1cm 1231, 1250, 786). LD50 in mice (mg/kg): 1624 orally; 33.3 i.p. (Umezawa, Tanaka).Therapeutic Category
Antifungal (topical).
Keywords
Antifungal (Antibiotics); Polyenes