Identification

Name
Candicidin
Accession Number
DB01152
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.

Type
Small Molecule
Groups
Approved, Withdrawn
Structure
Thumb
Weight
Average: 1109.317
Monoisotopic: 1108.571913873
Chemical Formula
C59H84N2O18
Synonyms
  • Candicidin
  • Candicidina
  • Candicidine
  • Candicidinum
  • Candizidin
  • Levorin
  • Levorina
  • Levorine
  • Levorinum

Pharmacology

Indication

Used in the topical treatment of vulvovaginal candidiasis.

Contraindications & Blackbox Warnings
Learn about our commercial Contraindications & Blackbox Warnings data.
Learn More
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.

TargetActionsOrganism
AErgosterol
antagonist
Candida albicans
Absorption
Not Available
Volume of distribution
Not Available
Protein binding
Not Available
Metabolism
Not Available
Route of elimination
Not Available
Half-life
Not Available
Clearance
Not Available
Adverse Effects
Learn about our commercial Adverse Effects data.
Learn More
Toxicity
Not Available
Affected organisms
  • Various Fungus Species
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
AbirateroneThe metabolism of Abiraterone can be decreased when combined with Candicidin.
AcalabrutinibThe metabolism of Acalabrutinib can be decreased when combined with Candicidin.
AcenocoumarolThe serum concentration of Acenocoumarol can be increased when it is combined with Candicidin.
AcetyldigitoxinThe serum concentration of Acetyldigitoxin can be increased when it is combined with Candicidin.
AlbendazoleThe metabolism of Albendazole can be decreased when combined with Candicidin.
AlectinibThe metabolism of Alectinib can be decreased when combined with Candicidin.
AlfentanilThe serum concentration of Alfentanil can be increased when it is combined with Candicidin.
AlfuzosinThe metabolism of Alfuzosin can be decreased when combined with Candicidin.
AlpelisibThe metabolism of Alpelisib can be decreased when combined with Candicidin.
AlprazolamThe metabolism of Alprazolam can be decreased when combined with Candicidin.
Additional Data Available
  • Extended Description
    Extended Description

    Extended description of the mechanism of action and particular properties of each drug interaction.

    Learn more
  • Severity
    Severity

    A severity rating for each drug interaction, from minor to major.

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  • Evidence Level
    Evidence Level

    A rating for the strength of the evidence supporting each drug interaction.

    Learn more
  • Action
    Action

    An effect category for each drug interaction. Know how this interaction affects the subject drug.

    Learn more
Food Interactions
Not Available

Products

International/Other Brands
Vanobid

Categories

ATC Codes
G01AA04 — Candicidin
Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as aminoglycosides. These are molecules or a portion of a molecule composed of amino-modified sugars.
Kingdom
Organic compounds
Super Class
Organic oxygen compounds
Class
Organooxygen compounds
Sub Class
Carbohydrates and carbohydrate conjugates
Direct Parent
Aminoglycosides
Alternative Parents
Alkyl-phenylketones / Macrolides and analogues / Butyrophenones / O-glycosyl compounds / Aniline and substituted anilines / Aryl alkyl ketones / Benzoyl derivatives / Beta hydroxy acids and derivatives / 1,3-dicarbonyl compounds / Oxanes
show 17 more
Substituents
1,2-aminoalcohol / 1,3-dicarbonyl compound / Acetal / Alcohol / Alkyl-phenylketone / Amine / Amino acid / Amino acid or derivatives / Aminoglycoside core / Aniline or substituted anilines
show 35 more
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
macrolide antibiotic, polyene antibiotic (CHEBI:3349)

Chemical Identifiers

UNII
48N2IYJ202
CAS number
1403-17-4
InChI Key
OPGSFDUODIJJGF-JBUZINEHSA-N
InChI
InChI=1S/C59H84N2O18/c1-35-18-15-13-11-9-7-5-6-8-10-12-14-16-21-47(78-59-56(74)54(61)55(73)38(4)77-59)33-51(71)53(58(75)76)50(70)31-46(67)30-45(66)29-44(65)28-43(64)27-41(62)19-17-20-42(63)32-52(72)79-57(35)37(3)26-36(2)48(68)34-49(69)39-22-24-40(60)25-23-39/h5-16,18,21-25,35-38,43-45,47-48,50-51,53-57,59,64-66,68,70-71,73-74H,17,19-20,26-34,60-61H2,1-4H3,(H,75,76)/b6-5+,9-7+,10-8+,13-11+,14-12+,18-15+,21-16+/t35?,36?,37?,38-,43?,44?,45?,47?,48?,50?,51?,53?,54+,55-,56+,57?,59?/m1/s1
IUPAC Name
(23E,25E,27E,29E,31E,33E,35E)-22-{[(3S,4S,5S,6R)-4-amino-3,5-dihydroxy-6-methyloxan-2-yl]oxy}-38-[7-(4-aminophenyl)-5-hydroxy-4-methyl-7-oxoheptan-2-yl]-10,12,14,18,20-pentahydroxy-37-methyl-2,4,8,16-tetraoxo-1-oxacyclooctatriaconta-23,25,27,29,31,33,35-heptaene-19-carboxylic acid
SMILES
CC(CC(C)C1OC(=O)CC(=O)CCCC(=O)CC(O)CC(O)CC(O)CC(=O)CC(O)C(C(O)CC(OC2O[[email protected]](C)[[email protected]@H](O)[[email protected]](N)[[email protected]@H]2O)\C=C\C=C\C=C\C=C\C=C\C=C\C=C\C1C)C(O)=O)C(O)CC(=O)C1=CC=C(N)C=C1

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 References
Not Available
Human Metabolome Database
HMDB15283
KEGG Drug
D03347
KEGG Compound
C06690
PubChem Substance
46504812
ChemSpider
8255412
ChEBI
3349
ChEMBL
CHEMBL1200647
Therapeutic Targets Database
DAP001325
PharmGKB
PA164754911
Wikipedia
Candicidin

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
logP1.7Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.00714 mg/mLALOGPS
logP-0.76ALOGPS
logP-0.028ChemAxon
logS-5.2ALOGPS
pKa (Strongest Acidic)3.68ChemAxon
pKa (Strongest Basic)9.07ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count19ChemAxon
Hydrogen Donor Count11ChemAxon
Polar Surface Area364.22 Å2ChemAxon
Rotatable Bond Count10ChemAxon
Refractivity302.12 m3·mol-1ChemAxon
Polarizability118.61 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
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)

Spectra

Mass Spec (NIST)
Not Available
Spectra
Not Available

Targets

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]

Enzymes

Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
Inhibitor
General Function
Vitamin d3 25-hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation react...
Gene Name
CYP3A4
Uniprot ID
P08684
Uniprot Name
Cytochrome P450 3A4
Molecular Weight
57342.67 Da
References
  1. Kuper JI, D'Aprile M: Drug-Drug interactions of clinical significance in the treatment of patients with Mycobacterium avium complex disease. Clin Pharmacokinet. 2000 Sep;39(3):203-14. doi: 10.2165/00003088-200039030-00003. [PubMed:11020135]

Drug created on June 13, 2005 07:24 / Updated on June 12, 2020 10:51

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