Candicidin Chemical Properties

Boiling point:

878.79°C (rough estimate)

Density 

1.1100 (rough estimate)

refractive index 

1.6200 (estimate)

storage temp. 

Store at -20°C

solubility 

DMSO:4.9(Max Conc. mg/mL);10.08(Max Conc. mM)
Ethanol:12.5(Max Conc. mg/mL);25.72(Max Conc. mM)

form 

A solid

Water Solubility 

13.47g/L(21 ºC)

Safety Information

Toxicity

LD50 i.p. in mice: 14 mg/kg (Vining)

Candicidin Usage And Synthesis

Originator

Candeptin,Schmidt,US,1964

Uses

Candicidin is a macrocyclic heptaene antifungal complex produced by Streptomyces griseus and isolated by Lechevalier and colleagues in 1953. The candicidin complex comprises analogues A, B, C and D, with candicidin D as the major component. Candicidin is active against fungi, in particular Candida albicans, and is used clinically to treat vaginal candidiasis. Like all polyene antifungal metabolites, candicidin acts by binding to ergosterol and disrupting the fungal membrane.

Definition

ChEBI: Candicidin D is a 38-membered ring lactone containing seven (E)-double bonds between positions 22 and 35 and substituted by hydroxy groups at positions 9, 11, 13, 17 and 19, oxo groups at positions 3, 7 and 15, a carboxy group at position 18, a 3-amino-3,6-dideoxymannopyranosyloxy group at position 21, a methyl group at position 36 and a 7-(4-aminophenyl)-5-hydroxy-4-methyl-7-oxoheptan-2-yl group at position 37. It is the major component of candicidin, a mixture of antifungal heptaene macrolides obtained from a strain of Streptomyces griseus. It has a role as a bacterial metabolite and an antifungal drug. It is a macrolide antibiotic and a polyene antibiotic.

Manufacturing Process

Hubert Lechevalier et al were the first to describe "Candicidin, a New Antifungal Antibiotic," in Mycologia XLV, No. 2, 155-171, March-April 1953. They produced candicidin by growing a culture of the organism streptomyces griseus No. 3570 on a yeast-glucose medium, isolating a "crude candicidin" from the resulting broth and purifying it. An improved extraction and purification method is described in US Patent 2,872,373 and is shown in the flow diagram below.
Another extraction and separation process is described in US Patent 2,992,162.

brand name

Vanobid (Sanofi Aventis).

Therapeutic Function

Topical antifungal

Candicidin(1403-17-4)Related Product Information

• TRIS(2,2,6,6-TETRAMETHYL-3,5-HEPTANEDIONATO)DYSPROSIUM(III)
• N-BUTYLISOCYANIDE
• Benzyl isocyanide
• Ethyl isocyanoacetate
• TRIS(2,2,6,6-TETRAMETHYL-3,5-HEPTANEDIONATO)EUROPIUM(III)
• Cupric acetylacetonate
• 1,1,3,3-TETRAMETHYLBUTYL ISOCYANIDE
• Tosylmethyl isocyanide
• TERT-BUTYL ISOCYANIDE
• Carboprost tromethamine
• COBALT(II) ACETYLACETONATE
• Aluminum acetylacetonate
• PHENYLSELENOL
• 2,4-PENTANEDIONE, SILVER DERIVATIVE
• SALCOMINE
• Candicidin
• METHYL ISOCYANOACETATE
• 15(S)-15-Methyl prostaglandin