NAV

Candicidin

Identification

Generic Name
Candicidin
DrugBank Accession Number
DB01152
Background

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Approved, Withdrawn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
Similar Structures
Weight
Average: 1109.317
Monoisotopic: 1108.571913873
Chemical Formula
C59H84N2O18
Synonyms
  • Candicidin
  • Candicidina
  • Candicidine
  • Candicidinum
  • Candizidin
  • Levorin
  • Levorina
  • Levorine
  • Levorinum
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Pharmacology

Indication

Used in the topical treatment of vulvovaginal candidiasis.

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Contraindications & Blackbox Warnings
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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
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Toxicity

Not Available

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
Integrate drug-drug
interactions in your software
AbemaciclibThe serum concentration of Abemaciclib can be increased when it is combined with Candicidin.
AcalabrutinibThe serum concentration of Acalabrutinib can be increased when it is 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.
Food Interactions
Not Available

Products

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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)
Affected organisms
  • Various Fungus Species

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[C@H](C)[C@@H](O)[C@H](N)[C@@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
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-00dl-9400000001-b5eec76ee532d2f85c1f
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0a4r-3900000000-9273ece41feee6029c71
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-00di-6900000003-6bf7c6265c02e389e3d0
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-007c-9600000016-acdd09a22054b246fd17
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-05c6-4900000005-516c519211f99cd6dc46
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-000f-7500000039-35d62dd2c5f084df7c4b
Chromatographic Properties
Collision Cross Sections (CCS)
Not Available

Targets

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Details1. 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. [Article]
  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. [Article]
  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. [Article]

Enzymes

Details1. Cytochrome P450 3A4
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. [Article]

Drug created at June 13, 2005 13:24 / Updated at May 07, 2021 21:25