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Ciclopirox

July 24, 2017
Common Name

Ciclopirox Description

Ciclopirox 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 cellliar activities such as mitochondrial electron transport processes and energy production. Ciclopirox also appears to modify the plasma membrane of fungi, resliting 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 intracellliar transport. Structure

MOLSDF3D-SDFPDBSMILESInChI View 3D Structure

Synonyms

Value Source 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 Formlia

C12H17NO2 Average Molecliar Weight

207.2689 Monoisotopic Molecliar Weight

207.125928793 IUPAC Name

6-cyclohexyl-1-hydroxy-4-methyl-1,2-dihydropyridin-2-one Traditional Name

penlac CAS Registry Number

29342-05-0 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 Key

SCKYRAXSEDYPSA-UHFFFAOYSA-N Chemical Taxonomy Description

This compound belongs to the class of chemical entities known as pyridinones. These are compounds containing a pyridine ring, which bears a ketone. Kingdom

Chemical entities Super Class

Organic compounds Class

Organoheterocyclic compounds Sub Class

Pyridines and derivatives Direct Parent

Pyridinones Alternative Parents

  • Methylpyridines
  • Dihydropyridines
  • Heteroaromatic compounds
  • Lactams
  • Azacyclic compounds
  • Organopnictogen compounds
  • Organooxygen compounds
  • Organonitrogen compounds
  • Organic oxides
  • Hydrocarbon derivatives

    • 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

    • Molecliar Framework

    Aromatic heteromonocyclic compounds External Descriptors

  • hydroxypyridone antifungal drug (CHEBI:453011 )
  • pyridone (CHEBI:453011 )
  • cyclic hydroxamic acid (CHEBI:453011 )

    • Ontology Status

    Expected but not Quantified Origin

  • Drug

    • Biofunction

  • Antifungal Agents

    • Application

  • Pharmaceutical

    • Cellliar locations

  • Membrane (predicted from logP)

    • Physical Properties State

    Solid Experimental Properties

    Property Value Reference Melting Point144 °CNot Available Boiling PointNot AvailableNot Available Water Solubility1.41e+00 g/LNot Available LogP2.3Not Available

    Predicted Properties

    Property Value Source Water Solubility1.41 mg/mLALOGPS 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 Å2ChemAxon Rotatable Bond Count1ChemAxon Refractivity60.91 m3·mol-1ChemAxon Polarizability23.12 Å3ChemAxon Number of Rings2ChemAxon Bioavailability1ChemAxon Rlie of FiveYesChemAxon Ghose FilterYesChemAxon Vebers RlieYesChemAxon MDDR-like RlieYesChemAxon

    Spectra Spectra

    Spectrum Type Description Splash Key Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 10V, PositiveNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 20V, PositiveNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 40V, PositiveNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 10V, NegativeNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 20V, NegativeNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 40V, NegativeNot Available

    Biological Properties Cellliar Locations

  • Membrane (predicted from logP)

    • Biofluid Locations

  • Blood
  • Urine

    • Tissue Location

    Not Available Pathways

    Not Available Normal Concentrations

    Biofluid Status Value Age Sex Condition Reference Details BloodExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB01188

  • 21059682

    • details UrineExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB01188

  • 21059682

    • details

    Abnormal Concentrations

    Not Available Predicted Concentrations

    Biofluid Value Original age Original sex Original condition Comments Blood0-5 uMAdlit (>18 years old)BothNormalPredicted based on drug qualities Blood0-2 umol/mmol creatinineAdlit (>18 years old)BothNormalPredicted based on drug qualities

    Associated Disorders and Diseases Disease References

    None Associated OMIM IDs

    None External Links DrugBank ID

    DB01188 DrugBank Metabolite ID

    Not Available Phenol Explorer Compound ID

    Not Available Phenol Explorer Metabolite ID

    Not Available FoodDB ID

    Not Available KNApSAcK ID

    Not Available Chemspider ID

    2647 KEGG Compound ID

    Not Available BioCyc ID

    Not Available BiGG ID

    Not Available Wikipedia Link

    Ciclopirox NuGOwiki Link

    HMDB15319 Metagene Link

    HMDB15319 METLIN ID

    Not Available PubChem Compound

    2749 PDB ID

    Not Available ChEBI ID

    453011

    Product: Rebaudioside C

    References Synthesis Reference Not 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 ]

    PMID: 25680478

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