Title: Candicidin
CAS Registry Number: 1403-17-4
Additional Names: Levorin
Trademarks: Vanobid
Literature References: Heptaene macrolide antifungal antibiotic complex composed of candicidins A, B, C and D (major component). Produced by a strain of Streptomyces griseus (Rutgers no. 3570): Lechevalier et al., Mycologia 45, 155 (1953). Methods of isoln: Siminoff, US 2872373 (1959 to Penick); Waksman, Lechevalier, US 2992162 (1961 to Rutgers Res. & Ed. Found.). Activity: Kligman, Lewis, Proc. Soc. Exp. Biol. Med. 82, 399 (1953); Lancet 1, 507 (1954); Lechevalier, Presse Med. 61, 1327 (1953). Structure of candicidin D: J. Zielinski et al., Tetrahedron Lett. 1979, 1791. Biosynthesis studies: Liu et al., J. Antibiot. 25, 116 (1972). Anticholesteremic property and mode of action studies: I. H. Kwon, H. Fisher, Nutr. Rep. Int. 9, 245 (1974); A. K. Singhal et al., Lipids 16, 423 (1981). HPLC comparison of candicidin, hamycin, trichomycin, q.q.v.: P. Helboe et al., J. Chromatogr. 189, 249 (1980). Toxicity study: L. C. Vining et al., Antibiot. Annu. 1954-55, 980.
Properties: Small yellow needles or rosettes from aq tetrahydrofuran or pyridine/acetic acid/water soln (when pure). Absorption max: 403, 380 (E1%1cm 1150), 360 nm. Practically insol in water, alcohols, ketones, esters, ethers, hydrocarbons, and other lipophilic solvents. Sol in DMSO, DMF, and lower aliphatic acids. Very sol in 80% aq tetrahydofuran soln. The addn of 5%-25% water to alcohols greatly increases soly. Forms sol salts in alkaline solns. Soly: Marsh, Weiss, J. Assoc. Off. Anal. Chem. 50, 457 (1967). LD50 i.p. in mice: 14 mg/kg (Vining).
Absorption maximum: Absorption max: 403, 380 (E1%1cm 1150), 360 nm
Toxicity data: LD50 i.p. in mice: 14 mg/kg (Vining)
Derivative Type: Candicidin D
Additional Names: Levorin A2
Molecular Formula: C59H84N2O18
Molecular Weight: 1109.30
Percent Composition: C 63.88%, H 7.63%, N 2.53%, O 25.96%
Properties: Identity with levorin A2: Bosshardt, Bickel, Experientia 24, 422 (1968); J. Zielinski et al., loc. cit.
Therap-Cat: Antifungal (topical).
Keywords: Antifungal (Antibiotics); Polyenes. |