You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version4.0
Creation Date2012-09-06 15:16:51 UTC
Update Date2017-09-27 08:27:54 UTC
HMDB IDHMDB0015319
Secondary Accession Numbers
  • HMDB15319
Metabolite Identification
Common NameCiclopirox
DescriptionCiclopirox is only found in individuals that have used or taken this drug. It is a synthetic antifungal agent for topical dermatologic use. [Wikipedia] Unlike antifungals such as itraconazole and terbinafine, which affect sterol synthesis, ciclopirox is thought to act through the chelation of polyvalent metal cations, such as Fe3+ and Al3+. These cations inhibit many enzymes, including cytochromes, thus disrupting cellular activities such as mitochondrial electron transport processes and energy production. Ciclopirox also appears to modify the plasma membrane of fungi, resulting in the disorganization of internal structures. The anti-inflammatory action of ciclopirox is most likely due to inhibition of 5-lipoxygenase and cyclooxygenase. Ciclopirox may exert its effect by disrupting DNA repair, cell division signals and structures (mitotic spindles) as well as some elements of intracellular transport.
Structure
Thumb
Synonyms
ValueSource
6-Cyclohexyl-1-hydroxy-4-methyl-2(1H)-pyridinoneChEBI
CiclopiroxumChEBI
Ciclopirox olaminHMDB
Ciclopirox-olaminHMDB
CiclopiroxolamineHMDB
HOE 296bHMDB
HOE-296bHMDB
HOE 296MeSH
CyclopiroxMeSH
CyclopyroxolamineMeSH
BatrafenMeSH
Dafnegin-CSCMeSH
Ciclopirox olamineMeSH
6-Cyclohexyl-1-hydroxy-4-methyl-2(1H)-pyridone ethanolamine saltMeSH
LoproxMeSH
HOE-296MeSH
PenlacMeSH
Chemical FormulaC12H17NO2
Average Molecular Weight207.2689
Monoisotopic Molecular Weight207.125928793
IUPAC Name6-cyclohexyl-1-hydroxy-4-methyl-1,2-dihydropyridin-2-one
Traditional Namepenlac
CAS Registry Number29342-05-0
SMILES
CC1=CC(=O)N(O)C(=C1)C1CCCCC1
InChI Identifier
InChI=1S/C12H17NO2/c1-9-7-11(13(15)12(14)8-9)10-5-3-2-4-6-10/h7-8,10,15H,2-6H2,1H3
InChI KeySCKYRAXSEDYPSA-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as pyridinones. These are compounds containing a pyridine ring, which bears a ketone.
KingdomChemical entities
Super ClassOrganic compounds
ClassOrganoheterocyclic compounds
Sub ClassPyridines and derivatives
Direct ParentPyridinones
Alternative Parents
Substituents
  • Methylpyridine
  • Pyridinone
  • Dihydropyridine
  • Heteroaromatic compound
  • Lactam
  • Azacycle
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Ontology
Disposition

Biological Location:

  Subcellular:

  Biofluid and excreta:

Route of exposure:

  Enteral:

Role

Industrial application:

  Pharmaceutical industry:

Indirect biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point144 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility1.41 g/LNot Available
LogP2.3Not Available
Predicted Properties
PropertyValueSource
Water Solubility1.41 g/LALOGPS
logP2.15ALOGPS
logP2.22ChemAxon
logS-2.2ALOGPS
pKa (Strongest Acidic)6.84ChemAxon
pKa (Strongest Basic)-6.2ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area40.54 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity60.91 m³·mol⁻¹ChemAxon
Polarizability23.12 ųChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0390000000-1d9227c74bcc86583df3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-2690000000-963d9e37afedc3b4a600View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-05mo-9600000000-de9b944829cc25a5681bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-3090000000-ac55f8f5496920dc9ca4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-0490000000-6cd8e595360c6bddf33aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a6r-5900000000-7869913422c2e64d2101View in MoNA
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
Biofluid Locations
  • Blood
  • Urine
Tissue LocationNot Available
PathwaysNot Available
NameSMPDB/PathwhizKEGG
No entries found
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB01188 details
UrineExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB01188 details
Abnormal Concentrations
Not Available
Predicted Concentrations
BiofluidValueOriginal ageOriginal sexOriginal conditionComments
Blood0-5 uMAdult (>18 years old)BothNormalPredicted based on drug qualities
Blood0-2 umol/mmol creatinineAdult (>18 years old)BothNormalPredicted based on drug qualities
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB01188
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID2647
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkCiclopirox
METLIN IDNot Available
PubChem Compound2749
PDB IDNot Available
ChEBI ID453011
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Niewerth M, Kunze D, Seibold M, Schaller M, Korting HC, Hube B: Ciclopirox olamine treatment affects the expression pattern of Candida albicans genes encoding virulence factors, iron metabolism proteins, and drug resistance factors. Antimicrob Agents Chemother. 2003 Jun;47(6):1805-17. [PubMed:12760852 ]
  2. Sigle HC, Thewes S, Niewerth M, Korting HC, Schafer-Korting M, Hube B: Oxygen accessibility and iron levels are critical factors for the antifungal action of ciclopirox against Candida albicans. J Antimicrob Chemother. 2005 May;55(5):663-73. Epub 2005 Mar 24. [PubMed:15790671 ]
  3. Qadripur SA: [Antimycotic therapy. 2. Antimycotic chemotherapeutic agents: imidazole derivatives, tolciclate, haloprogin, ciclopiroxolamin]. Fortschr Med. 1983 Mar 10;101(9):355-63. [PubMed:6303928 ]
  4. Beikert FC, Le MT, Koeninger A, Technau K, Clad A: Recurrent vulvovaginal candidosis: focus on the vulva. Mycoses. 2011 Nov;54(6):e807-10. doi: 10.1111/j.1439-0507.2011.02030.x. Epub 2011 May 25. [PubMed:21615545 ]