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Identification
Name Candicidin
Accession Number DB01152 (APRD00843)
Type small molecule
Groups approved
Description

Candicidin is an antibiotic obtained from a streptomyces (Streptomyces griseus) and active against some fungi of the genus Candida (C. albicans). Candicidin is administered intravaginally in the treatment of vulvovaginal candidiasis.
Structure Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms Not Available
Brand names
  • Candicidin A
  • Candicidin D
  • FR-008-III
  • Vanobid
Brand name mixtures Not Available
Categories
  • Anti-Bacterial Agents
  • Antifungal Agents
  • Macrolides
CAS number 1403-17-4
Weight Average: 1109.3009
Monoisotopic: 1108.571913894
Chemical Formula C59H84N2O18
InChI Key InChIKey=YKSVGLFNJPQDJE-WDANKXQLSA-N
InChI
InChI=1S/C59H84N2O18/c1-35-18-15-13-11-9-7-5-6-8-10-12-14-16-21-46(77-58-55(72)53(61)54(71)38(4)76-58)31-50-52(57(73)74)49(69)34-59(75,79-50)33-45(66)29-44(65)28-43(64)27-41(62)19-17-20-42(63)30-51(70)78-56(35)37(3)26-36(2)47(67)32-48(68)39-22-24-40(60)25-23-39/h5-16,18,21-25,35-38,43-47,49-50,52-56,58,64-67,69,71-72,75H,17,19-20,26-34,60-61H2,1-4H3,(H,73,74)/b6-5-,9-7-,10-8-,13-11-,14-12-,18-15-,21-16-/t35?,36?,37?,38-,43?,44?,45?,46?,47?,49?,50?,52?,53+,54-,55+,56?,58?,59?/m1/s1
Plain Text
IUPAC Name
(19Z,21Z,23Z,25Z,27Z,29Z,31Z)-33-{[(3S,4S,5S,6R)-4-amino-3,5-dihydroxy-6-methyloxan-2-yl]oxy}-17-[7-(4-aminophenyl)-5-hydroxy-4-methyl-7-oxoheptan-2-yl]-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
SMILES
CC(CC(C)C1OC(=O)CC(=O)CCCC(=O)CC(O)CC(O)CC(O)CC2(O)CC(O)C(C(CC(OC3O[C@H](C)[C@@H](O)[C@H](N)[C@@H]3O)\C=C/C=C\C=C/C=C\C=C/C=C\C=C/C1C)O2)C(O)=O)C(O)CC(=O)C1=CC=C(N)C=C1
Plain Text
Mass Spec Not Available
Taxonomy
Kingdom Organic
Classes
  • Aminoglycosides
  • Butyrophenones
Substructures
  • Carboxylic Acids and Derivatives
  • Aminoglycosides
  • Hydroxy Compounds
  • Alkanes and Alkenes
  • Pyrans
  • Acetates
  • Acetals and Derivatives
  • Keto-Acids
  • Lactones
  • Aliphatic and Aryl Amines
  • Ethers
  • Benzene and Derivatives
  • Butyrophenones
  • Amino Alcohols
  • Heterocyclic compounds
  • Aromatic compounds
  • Benzoyl Derivatives
  • Alcohols and Polyols
  • Acetophenones and Derivatives
  • Anilines
  • Ketones
Pharmacology
Indication Used in the topical treatment of vulvovaginal candidiasis.
Pharmacodynamics Candicidin is a polyene antifungal antibiotic produced by a strain of Streptomyces griseus. It is especially effective against Candida albicans (more effective than amphotericin B), and is administered intravaginally in the treatment of vulvovaginal candidiasis.
Mechanism of action Ergosterol, the principal sterol in the fungal cytoplasmic membrane, is the target site of action of Candicidin. Candicidin binds irreversibly to ergosterol, resulting in disruption of membrane integrity and ultimately cell death. There is some evidence that the binding site in the cell wall may be to fatty acids or fatty acid esters and that this binding capacity must be satisfied before candicidin can bring about its lethal effect by binding to sterol in the cell membrane.
Absorption Not Available
Volume of distribution Not Available
Protein binding Not Available
Metabolism
Route of elimination Not Available
Half life Not Available
Clearance Not Available
Toxicity Not Available
Affected organisms
  • Various Fungus Species
Pathways Not Available
Pharmacoeconomics
Manufacturers
  • Sanofi aventis us llc
Packagers Not Available
Dosage forms Not Available
Prices Not Available
Patents Not Available
Properties
State solid
Melting point Not Available
Experimental Properties
Property Value Source
logP 1.7 PhysProp
Predicted Properties
Property Value Source
water solubility 9.34e-03 g/l ALOGPS
logP -0.94 ALOGPS
logP -1.35 ChemAxon Molconvert
logS -5.07 ALOGPS
pKa 10.87 ChemAxon Molconvert
hydrogen acceptor count 19 ChemAxon Molconvert
hydrogen donor count 11 ChemAxon Molconvert
polar surface area 356.38 ChemAxon Molconvert
rotatable bond count 10 ChemAxon Molconvert
refractivity 300.50 ChemAxon Molconvert
polarizability 119.88 ChemAxon Molconvert
References
Synthesis Reference Not Available
General Reference Not Available
External Links
Resource Link
KEGG Compound C06690 Link_out
PubChem Compound 441142 Link_out
PubChem Substance 46504812 Link_out
ChemSpider 10128184 Link_out
Therapeutic Targets Database DAP001325 Link_out
Drug Product Database 0 Link_out
Wikipedia http://en.wikipedia.org/wiki/Candicidin Link_out
ATC Codes
  • G01AA04
AHFS Codes Not Available
PDB Entries Not Available
FDA label Not Available
MSDS Not Available
Interactions
Drug Interactions
Drug Interaction
Food Interactions Not Available
Targets

1. Ergosterol, Candida albicans

Pharmacological action: yes
Actions: antagonist

References:
  1. Hammond SM, Kliger BN: Mode of action of the polyene antibiotic candicidin: binding factors in the wall of Candida albicans. Antimicrob Agents Chemother. 1976 Apr;9(4):561-8. Pubmed
  2. Brajtburg J, Elberg S, Kobayashi GS, Medoff G: Effects of serum lipoproteins on damage to erythrocytes and Candida albicans cells by polyene antibiotics. J Infect Dis. 1986 Mar;153(3):623-6. Pubmed
  3. Borgers M: Mechanism of action of antifungal drugs, with special reference to the imidazole derivatives. Rev Infect Dis. 1980 Jul-Aug;2(4):520-34. Pubmed
Comments
Drug created on June 13, 2005 07:24 / Updated on November 10, 2010 13:46

This project is supported by Genome Alberta & Genome Canada, a not-for-profit organization that is leading Canada's national genomics strategy with $600 million in funding from the federal government. This project is also supported in part by GenomeQuest, Inc., an enterprise genomic information company serving the life science community.