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Identification
NameCandicidin
Accession NumberDB01152  (APRD00843)
TypeSmall Molecule
GroupsWithdrawn
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
SynonymsNot Available
External Identifiers Not Available
Approved Prescription ProductsNot Available
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International Brands
NameCompany
Candicidin ANot Available
Candicidin DNot Available
FR-008-IIINot Available
ProstatinNot Available
Brand mixturesNot Available
SaltsNot Available
Categories
UNII48N2IYJ202
CAS number1403-17-4
WeightAverage: 1109.3009
Monoisotopic: 1108.571913894
Chemical FormulaC59H84N2O18
InChI KeyInChIKey=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
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[[email protected]](C)[C@@H](O)[[email protected]](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
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as macrolides and analogues. These are organic compounds containing a lactone ring of at least twelve members.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassMacrolides and analogues
Sub ClassNot Available
Direct ParentMacrolides and analogues
Alternative Parents
Substituents
  • Macrolide
  • Glucosamine
  • Amino sugar
  • O-glycosyl compound
  • Glycosyl compound
  • Butyrophenone
  • Acetophenone
  • Substituted aniline
  • Aryl alkyl ketone
  • Aryl ketone
  • Benzoyl
  • Amino saccharide
  • Beta-hydroxy acid
  • Aniline
  • Benzenoid
  • 1,3-dicarbonyl compound
  • Primary aromatic amine
  • Oxane
  • Monosaccharide
  • Hydroxy acid
  • Dicarboxylic acid or derivatives
  • Beta-hydroxy ketone
  • Monocyclic benzene moiety
  • Cyclic ketone
  • Secondary alcohol
  • Polyol
  • Lactone
  • Ketone
  • Hemiacetal
  • Carboxylic acid ester
  • 1,2-aminoalcohol
  • Oxacycle
  • Organoheterocyclic compound
  • Carboxylic acid
  • Carboxylic acid derivative
  • Acetal
  • Hydrocarbon derivative
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Primary aliphatic amine
  • Carbonyl group
  • Amine
  • Alcohol
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Pharmacology
IndicationUsed in the topical treatment of vulvovaginal candidiasis.
PharmacodynamicsCandicidin 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 actionErgosterol, 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.
Related Articles
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
MetabolismNot Available
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityNot Available
Affected organisms
  • Various Fungus Species
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption-0.9509
Blood Brain Barrier-0.9398
Caco-2 permeable-0.7585
P-glycoprotein substrateSubstrate0.8004
P-glycoprotein inhibitor INon-inhibitor0.5359
P-glycoprotein inhibitor IIInhibitor0.6783
Renal organic cation transporterNon-inhibitor0.952
CYP450 2C9 substrateNon-substrate0.7747
CYP450 2D6 substrateNon-substrate0.8665
CYP450 3A4 substrateSubstrate0.5161
CYP450 1A2 substrateNon-inhibitor0.8668
CYP450 2C9 inhibitorNon-inhibitor0.9212
CYP450 2D6 inhibitorNon-inhibitor0.9092
CYP450 2C19 inhibitorNon-inhibitor0.8723
CYP450 3A4 inhibitorNon-inhibitor0.8064
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9525
Ames testNon AMES toxic0.8306
CarcinogenicityNon-carcinogens0.9559
BiodegradationNot ready biodegradable0.9959
Rat acute toxicity2.5750 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9748
hERG inhibition (predictor II)Non-inhibitor0.7767
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
StateSolid
Experimental Properties
PropertyValueSource
logP1.7Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.00934 mg/mLALOGPS
logP-0.94ALOGPS
logP0.93ChemAxon
logS-5.1ALOGPS
pKa (Strongest Acidic)3.68ChemAxon
pKa (Strongest Basic)9.07ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count19ChemAxon
Hydrogen Donor Count11ChemAxon
Polar Surface Area356.38 Å2ChemAxon
Rotatable Bond Count10ChemAxon
Refractivity300.5 m3·mol-1ChemAxon
Polarizability119.88 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
SpectraNot Available
References
Synthesis Reference

Siminoff, P.; U.S. Patent 2,872,373; February 3,1959; assigned to S.B. Penick & Company,
Inc.
Waksman, S.A. and Lechevalier, H.A.; U.S. Patent 2,992,162; July 11,1961; assigned to
Rutgers Research and Educational Foundation.

General ReferencesNot Available
External Links
ATC CodesG01AA04
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSNot Available
Interactions
Drug InteractionsNot Available
Food InteractionsNot Available

Targets

1. Ergosterol
Kind
Small molecule
Organism
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:773298 ]
  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:3512734 ]
  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:7003674 ]
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Drug created on June 13, 2005 07:24 / Updated on August 17, 2016 12:23