Candicidin

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.
Candidin Candoxatril Canertinib Canfosfamide Cangrelor

Candicidin
Candicidin.png
Systematic (IUPAC) name
33-[(3-amino-3,6-dideoxy-D-mannopyranosyl)oxy]-17-[6-(4-aminophenyl)-4-hydroxy-1,3-dimethyl-6-oxohexyl]-1,3,5,7,37-pentahydroxy-18-methyl-9,13,15-trioxo-16,39-dioxabicyclo[33.3.1]nonatriaconta-19,21,23,25,27,29,31-heptaene-36-carboxylic acid
Clinical data
Legal status  ?
Identifiers
CAS number 1403-17-4 YesY
ATC code G01AA04
PubChem CID 441142
DrugBank DB01152
ChemSpider 10128184 YesY
UNII 48N2IYJ202 YesY
ChEMBL CHEMBL1200647 N
Chemical data
Formula C59H84N2O18 
Mol. mass 1109,32 g/mol
 N (what is this?)  (verify)

Candicidin is an antibiotic obtained from Streptomyces griseus and is active against some fungi of the Candida albicans. Candicidin is administered intravaginally in the treatment of vulvovaginal candidiasis.[1]