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Identification
NameCandicidin
Accession NumberDB01152  (APRD00843)
TypeSmall Molecule
GroupsWithdrawn
DescriptionCandicidin 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 KeyYKSVGLFNJPQDJE-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
Pharmacology
IndicationUsed in the topical treatment of vulvovaginal candidiasis.
Structured Indications Not Available
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.
TargetKindPharmacological actionActionsOrganismUniProt ID
ErgosterolSmall moleculeyes
antagonist
Candida albicansnot applicabledetails
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
Interactions
Drug Interactions
DrugInteractionDrug group
AmlodipineThe risk or severity of adverse effects can be increased when Candicidin is combined with Amlodipine.Approved
Amphotericin BThe therapeutic efficacy of Amphotericin B can be decreased when used in combination with Candicidin.Approved, Investigational
AmrinoneThe risk or severity of adverse effects can be increased when Candicidin is combined with Amrinone.Approved
AzelnidipineThe risk or severity of adverse effects can be increased when Candicidin is combined with Azelnidipine.Approved
AzimilideThe risk or severity of adverse effects can be increased when Candicidin is combined with Azimilide.Investigational
BarnidipineThe risk or severity of adverse effects can be increased when Candicidin is combined with Barnidipine.Approved
BcgThe therapeutic efficacy of Bcg can be decreased when used in combination with Candicidin.Investigational
BenidipineThe risk or severity of adverse effects can be increased when Candicidin is combined with Benidipine.Approved
BepridilThe risk or severity of adverse effects can be increased when Candicidin is combined with Bepridil.Approved, Withdrawn
BuspironeThe metabolism of Buspirone can be decreased when combined with Candicidin.Approved, Investigational
BusulfanThe serum concentration of Busulfan can be increased when it is combined with Candicidin.Approved, Investigational
CaiThe risk or severity of adverse effects can be increased when Candicidin is combined with Cai.Investigational
CilnidipineThe risk or severity of adverse effects can be increased when Candicidin is combined with Cilnidipine.Approved
CinnarizineThe risk or severity of adverse effects can be increased when Candicidin is combined with Cinnarizine.Approved
CisaprideThe serum concentration of Cisapride can be increased when it is combined with Candicidin.Approved, Investigational, Withdrawn
ClevidipineThe risk or severity of adverse effects can be increased when Candicidin is combined with Clevidipine.Approved
ConivaptanThe metabolism of Conivaptan can be decreased when combined with Candicidin.Approved, Investigational
CyclosporineThe metabolism of Cyclosporine can be decreased when combined with Candicidin.Approved, Investigational, Vet Approved
DarodipineThe risk or severity of adverse effects can be increased when Candicidin is combined with Darodipine.Experimental
DidanosineDidanosine can cause a decrease in the absorption of Candicidin resulting in a reduced serum concentration and potentially a decrease in efficacy.Approved
DiltiazemThe risk or severity of adverse effects can be increased when Candicidin is combined with Diltiazem.Approved
DocetaxelThe metabolism of Docetaxel can be decreased when combined with Candicidin.Approved, Investigational
DofetilideThe metabolism of Dofetilide can be decreased when combined with Candicidin.Approved
DotarizineThe risk or severity of adverse effects can be increased when Candicidin is combined with Dotarizine.Investigational
EfonidipineThe risk or severity of adverse effects can be increased when Candicidin is combined with Efonidipine.Approved
EperisoneThe risk or severity of adverse effects can be increased when Candicidin is combined with Eperisone.Approved, Investigational
EtravirineThe serum concentration of Etravirine can be increased when it is combined with Candicidin.Approved
FelodipineThe risk or severity of adverse effects can be increased when Candicidin is combined with Felodipine.Approved, Investigational
FendilineThe risk or severity of adverse effects can be increased when Candicidin is combined with Fendiline.Withdrawn
FlunarizineThe risk or severity of adverse effects can be increased when Candicidin is combined with Flunarizine.Approved
FosphenytoinThe serum concentration of Candicidin can be decreased when it is combined with Fosphenytoin.Approved
GabapentinThe risk or severity of adverse effects can be increased when Candicidin is combined with Gabapentin.Approved, Investigational
GallopamilThe risk or severity of adverse effects can be increased when Candicidin is combined with Gallopamil.Investigational
IsradipineThe risk or severity of adverse effects can be increased when Candicidin is combined with Isradipine.Approved
LacidipineThe risk or severity of adverse effects can be increased when Candicidin is combined with Lacidipine.Approved
LamotrigineThe risk or severity of adverse effects can be increased when Candicidin is combined with Lamotrigine.Approved, Investigational
LercanidipineThe risk or severity of adverse effects can be increased when Candicidin is combined with Lercanidipine.Approved, Investigational
LosartanThe metabolism of Losartan can be decreased when combined with Candicidin.Approved
Magnesium SulfateThe risk or severity of adverse effects can be increased when Candicidin is combined with Magnesium Sulfate.Approved, Vet Approved
ManidipineThe risk or severity of adverse effects can be increased when Candicidin is combined with Manidipine.Approved
MibefradilThe risk or severity of adverse effects can be increased when Candicidin is combined with Mibefradil.Withdrawn
NaftopidilThe risk or severity of adverse effects can be increased when Candicidin is combined with Naftopidil.Investigational
NicardipineThe risk or severity of adverse effects can be increased when Candicidin is combined with Nicardipine.Approved
NifedipineThe risk or severity of adverse effects can be increased when Candicidin is combined with Nifedipine.Approved
NiguldipineThe risk or severity of adverse effects can be increased when Candicidin is combined with Niguldipine.Experimental
NiludipineThe risk or severity of adverse effects can be increased when Candicidin is combined with Niludipine.Experimental
NilvadipineThe risk or severity of adverse effects can be increased when Candicidin is combined with Nilvadipine.Approved
NimesulideThe risk or severity of adverse effects can be increased when Candicidin is combined with Nimesulide.Approved, Withdrawn
NimodipineThe risk or severity of adverse effects can be increased when Candicidin is combined with Nimodipine.Approved
NisoldipineThe risk or severity of adverse effects can be increased when Candicidin is combined with Nisoldipine.Approved
NitrendipineThe risk or severity of adverse effects can be increased when Candicidin is combined with Nitrendipine.Approved
PerhexilineThe risk or severity of adverse effects can be increased when Candicidin is combined with Perhexiline.Approved
PhenytoinThe serum concentration of Phenytoin can be increased when it is combined with Candicidin.Approved, Vet Approved
Picosulfuric acidThe therapeutic efficacy of Picosulfuric acid can be decreased when used in combination with Candicidin.Approved
PimozideCandicidin may increase the arrhythmogenic activities of Pimozide.Approved
PinaveriumThe risk or severity of adverse effects can be increased when Candicidin is combined with Pinaverium.Approved
PregabalinThe risk or severity of adverse effects can be increased when Candicidin is combined with Pregabalin.Approved, Illicit, Investigational
PrenylamineThe risk or severity of adverse effects can be increased when Candicidin is combined with Prenylamine.Withdrawn
ProgesteroneThe therapeutic efficacy of Progesterone can be decreased when used in combination with Candicidin.Approved, Vet Approved
QuinidineThe metabolism of Quinidine can be decreased when combined with Candicidin.Approved
RanolazineThe metabolism of Ranolazine can be decreased when combined with Candicidin.Approved, Investigational
RifabutinThe serum concentration of Rifabutin can be increased when it is combined with Candicidin.Approved
RifampicinThe serum concentration of Rifampicin can be increased when it is combined with Candicidin.Approved
RifapentineThe serum concentration of Rifapentine can be increased when it is combined with Candicidin.Approved
RisedronateThe risk or severity of adverse effects can be increased when Candicidin is combined with Risedronate.Approved, Investigational
SolifenacinThe metabolism of Solifenacin can be decreased when combined with Candicidin.Approved
SucralfateSucralfate can cause a decrease in the absorption of Candicidin resulting in a reduced serum concentration and potentially a decrease in efficacy.Approved
SunitinibThe metabolism of Sunitinib can be decreased when combined with Candicidin.Approved, Investigational
TacrolimusThe metabolism of Tacrolimus can be decreased when combined with Candicidin.Approved, Investigational
Tolfenamic AcidThe risk or severity of adverse effects can be increased when Candicidin is combined with Tolfenamic Acid.Approved
TranilastThe risk or severity of adverse effects can be increased when Candicidin is combined with Tranilast.Approved, Investigational
VerapamilThe risk or severity of adverse effects can be increased when Candicidin is combined with Verapamil.Approved
VinpocetineThe risk or severity of adverse effects can be increased when Candicidin is combined with Vinpocetine.Investigational
XylometazolineThe risk or severity of adverse effects can be increased when Candicidin is combined with Xylometazoline.Approved
ZiconotideThe risk or severity of adverse effects can be increased when Candicidin is combined with Ziconotide.Approved
ZolpidemThe serum concentration of Zolpidem can be increased when it is combined with Candicidin.Approved
Food InteractionsNot 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
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
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

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 ]
Comments
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Drug created on June 13, 2005 07:24 / Updated on August 17, 2016 12:23