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Version 2.5
Creation Date 2005-06-13 13:24:05
Update Date 2009-05-06 16:53:15
Primary Accession Number DB01152
Secondary Accession Number
  • APRD00843
Name Candicidin
Drug Type
  • Approved
  • Small Molecule
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.
Synonyms Not Available
Brand Names
  1. Candicidin A
  2. Candicidin D
  3. FR-008-III
  4. Vanobid
Brand Mixtures Not Available
Chemical IUPAC Name (19E,21E,23E,25E,27E,29E,31E)-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
Chemical Formula C59H84N2O18
Chemical Structure Structure
CAS Registry Number 1403-17-4
InChI Identifier InChI=1/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/f/h73H
InChI Key YKSVGLFNJPQDJE-SHYPQKOXDP
KEGG Drug Not Available
KEGG Compound C06690 Link Image
PubChem Compound 11953885 Link Image
PubChem Substance 8915 Link Image
ChEBI ID Not Available
PharmGKB ID Not Available
HET ID Not Available
GenBank ID Not Available
Drug ID Number [DIN] Not Available
RxList Link Not Available
PDRhealth Link Not Available
Wikipedia Link http://en.wikipedia.org/wiki/Candicidin Link Image
FDA Label Not Available
Material Safety Data Sheet (MSDS) Not Available
Synthesis Reference Not Available
Average Molecular Weight 1109.3009
Monoisotopic Molecular Weight 1108.5719
State Solid
Melting Point Not Available
Experimental Water Solubility Not Available Source: PhysProp
Predicted Water Solubility 9.34e-03 mg/mL Calculated using ALOGPS
Experimental LogP/Hydrophobicity 1.7 Source: PhysProp
Predicted LogP -0.93 Calculated using ALOGPS
Experimental LogS Not Available
Predicted LogS -5.07 Calculated using ALOGPS
Experimental Caco2 Permeability Not Available
pKa/Isoelectric Point Not Available
Mass Spectrum Not Available
MOL File Show Link Image | Download Link Image
SDF File Show Link Image | Download Link Image
PDB File Show Link Image | Download Link Image
2D Structure
3D Structure
Experimental PDB ID Not Available
Isomeric SMILES C[C@@H](C[C@H](C)[C@H]1OC(=O)CC(=O)CCCC(=O)C[C@@H](O)C[C@@H](O)C[C@@H](O)C[C@]2(O)C[C@@H](O)[C@H]([C@@H](C[C@H](O[C@@H]3O[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/[C@@H]1C)O2)C(O)=O)[C@@H](O)CC(=O)C1=CC=C(N)C=C1
Canonical SMILES CC(CC(C)C1OC(=O)CC(=O)CCCC(=O)CC(O)CC(O)CC(O)CC2(O)CC(O)C(C(CC(OC3OC(C)C(O)C(N)C3O)C=CC=CC=CC=CC=CC=CC=CC1C)O2)C(O)=O)C(O)CC(=O)C1=CC=C(N)C=C1
Drug Category
  • Anti-Bacterial Agents
  • Antifungal Agents
  • Macrolides
ATC Codes
AHFS Codes Not Available
Indication Used in the topical treatment of vulvovaginal candidiasis.
Pharmacology 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
Toxicity Not Available
Protein Binding Not Available
Biotransformation Not Available
Half Life Not Available
Dosage Forms Not Available
Patient Information Not Available
Contraindications Not Available
Interactions Not Available
Drug Interactions Not Available
Food Interactions Not Available
Pathways Not Available
General References
  1. Wikipedia Link Image
Organisms Affected
  • Various Fungus Species
Targets
  1. Ergosterol biosynthetic protein 28
Drug Target 1 [top]
Target 1 ID 344
Target 1 Name Ergosterol biosynthetic protein 28
Target 1 Synonyms Not Available
Target 1 Gene Name ERG28
Target 1 Protein Sequence >Ergosterol biosynthetic protein 28 
MFSLQDVITTTKTTLAAMPKGYLPKWLLFISIVSVFNSIQTYVSGLELTRKVYERKPTET
THLSARTFGTWTFISCVIRFYGAMYLNEPHIFELVFMSYMVALFHFGSELLIFRTCKLGK
GFMGPLVVSTTSLVWMYKQREYYTGVAW
Target 1 Number of Residues 150
Target 1 Molecular Weight 17135
Target 1 Theoretical pI 9.71
Target 1 GO Classification
Function
molecular function unknown
Process
Not Available
Component
cell
membrane
intrinsic to membrane
integral to membrane
Target 1 General Function Involved in protein binding, bridging
Target 1 Specific Function Has a role as a scaffold to help anchor ERG25, ERG26 and ERG27 to the endoplasmic reticulum. May also be responsible for facilitating their interaction
Target 1 Pathways Not Available
Target 1 Reactions Not Available
Target 1 Pfam Domain Function
Target 1 Signals
  • None
Target 1 Transmembrane Regions
  • 26-46
  • 93-113
  • 121-136
Target 1 Essentiality Essential
Target 1 GenBank ID Protein 603277 Link Image
Target 1 UniProtKB/Swiss-Prot ID P40030 Link Image
Target 1 UniProtKB/Swiss-Prot Entry Name ERG28_YEAST Link Image
Target 1 PDB ID Not Available
Target 1 Cellular Location
  • Endoplasmic reticulum
  • endoplasmic reticulum membrane
  • multi-pass membrane protein (Probable)
Target 1 Gene Sequence >447 bp 
TTACCAAGCAACACCAGTGTAGTATTCTCTTTGTTTGTACATCCAAACCAAAGAGGTGGT
TGAGACAACCAATGGACCCATGAATCCCTTTCCCAACTTACAAGTTCTAAAGATCAATAA
TTCAGAGCCGAAGTGGAATAGGGCAACCATATAAGACATGAAGACCAATTCGAAAATGTG
TGGTTCATTCAAGTACATAGCCCCATAGAATCTGATAACACAGGAAATAAAGGTCCAAGT
ACCGAAAGTTCTTGCACTCAAATGGGTTGTTTCAGTGGGTTTTCTTTCGTAGACTTTACG
TGTCAATTCTAAACCAGAAACGTAAGTCTGGATAGAATTGAAGACTGATACAATGGAAAT
GAAAAGTAACCATTTTGGTAAGTAACCTTTTGGCATTGCTGCCAAGGTGGTCTTGGTTGT
AGTTATTACGTCTTGTAGGCTGAACAT
Target 1 GenBank Gene ID
Target 1 GeneCard ID Not Available
Target 1 GenAtlas ID Not Available
Target 1 HGNC ID Not Available
Target 1 Chromosome Location Not Available
Target 1 Locus Not Available
Target 1 SNPs SNPJam Report Link Image
Target 1 General References
  1. Ghaemmaghami S, Huh WK, Bower K, Howson RW, Belle A, Dephoure N, O'Shea EK, Weissman JS: Global analysis of protein expression in yeast. Nature. 2003 Oct 16;425(6959):737-41. [PubMed Link Image]
  2. Dietrich FS, Mulligan J, Hennessy K, Yelton MA, Allen E, Araujo R, Aviles E, Berno A, Brennan T, Carpenter J, Chen E, Cherry JM, Chung E, Duncan M, Guzman E, Hartzell G, Hunicke-Smith S, Hyman RW, Kayser A, Komp C, Lashkari D, Lew H, Lin D, Mosedale D, Davis RW, et al.: The nucleotide sequence of Saccharomyces cerevisiae chromosome V. Nature. 1997 May 29;387(6632 Suppl):78-81. [PubMed Link Image]
Target 1 Drug References
  1. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed Link Image]
  2. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed Link Image]

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.