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Record Information
Version3.6
Creation Date2006-05-18 08:31:29 UTC
Update Date2014-09-23 05:26:00 UTC
HMDB IDHMDB01922
Secondary Accession NumbersNone
Metabolite Identification
Common NameClotrimazole
DescriptionClotrimazole is an imidazole derivative with a broad spectrum of antimycotic activity. It inhibits biosynthesis of the sterol ergostol, an important component of fungal cell membranes. Its action leads to increased membrane permeability and apparent disruption of enzyme systems bound to the membrane. -- Pubchem; There is the potential for drug interactions with Clotrimazole if taken orally, as it is a potent, specific inhibitor of cytochrome P450 oxidase enzymes and so may alter the metabolism of other drugs. Clotrimazole is an antifungal medication commonly used in the treatment of fungal infections of both humans and animals such as vaginal yeast infections and ringworm. -- Wikipedia; An imidazole derivative with a broad spectrum of antimycotic activity. It inhibits biosynthesis of the sterol ergostol, an important component of fungal cell membranes. Its action leads to increased membrane permeability and apparent disruption of enzyme systems bound to the membrane. Clotrimazole is a potent, specific inhibitor of cytochrome P450 oxidase enzymes. Hence, it may alter the metabolism of other drugs particularly if taken orally. -- Wikipedia; Clotrimazole is an antifungal medication commonly used in the treatment of fungal infections of both humans and animals such as vaginal yeast infections and ringworm. It also used to treat athlete's foot and jock itch.
Structure
Thumb
Synonyms
  1. (Chlorotrityl)imidazole
  2. 1-(O-Chlorotrityl)imidazole
  3. Canesten
  4. Canesten 1-Day Cream Combi-Pak
  5. Canesten 1-Day Therapy
  6. Canesten 3-Day Therapy
  7. Canesten 6-Day Therapy
  8. Canesten Combi-Pak 1-Day Therapy
  9. Canesten Combi-Pak 3-Day Therapy
  10. Canesten Cream
  11. Canesten Solution
  12. Canestine
  13. Chlotrimazole
  14. Clotrimaderm
  15. Clotrimaderm Cream
  16. Clotrimazol
  17. Clotrimazole
  18. Clotrimazolum
  19. Desamix F
  20. Empecid
  21. Fem Care
  22. FemCare
  23. Gyne lotrimin
  24. Gyne-lotrimin
  25. Gyne-Lotrimin 3
  26. Gyne-Lotrimin 3 Combination Pack
  27. Gyne-Lotrimin Combination Pack
  28. Gyne-Lotrimin3
  29. Gyne-Lotrimin3 Combination Pack
  30. Gynix
  31. Lopac-C-6019
  32. Lotrimax
  33. Lotrimin
  34. Lotrimin AF
  35. Lotrimin AF Cream
  36. Lotrimin AF Jock-Itch Cream
  37. Lotrimin AF Lotion
  38. Lotrimin AF Solution
  39. Lotrimin Cream
  40. Lotrimin Lotion
  41. Lotrimin Solution
  42. Lotrisone
  43. Mono-baycuten
  44. Monobaycuten
  45. Mycelax
  46. Mycelex
  47. Mycelex 7
  48. Mycelex Cream
  49. Mycelex G
  50. Mycelex OTC
  51. Mycelex Solution
  52. Mycelex Troches
  53. Mycelex Twin Pack
  54. Mycelex-7
  55. Mycelex-7 Combination Pack
  56. Mycelex-G
  57. Mycelex: MycosporinRimazole
  58. Myclo Cream
  59. Myclo Solution
  60. Myclo Spray Solution
  61. Myclo-Gyne
  62. Mycosporin
  63. Mykosporin
  64. Neo-Zol Cream
  65. Otomax
  66. Pedisafe
  67. Prestwick_120
  68. Rimazole
  69. Tibatin
  70. Trimysten
  71. Trivagizole 3
  72. Veltrim
Chemical FormulaC22H17ClN2
Average Molecular Weight344.837
Monoisotopic Molecular Weight344.108026261
IUPAC Name1-[(2-chlorophenyl)diphenylmethyl]-1H-imidazole
Traditional Nameclotrimazole
CAS Registry Number23593-75-1
SMILES
ClC1=CC=CC=C1C(N1C=CN=C1)(C1=CC=CC=C1)C1=CC=CC=C1
InChI Identifier
InChI=1S/C22H17ClN2/c23-21-14-8-7-13-20(21)22(25-16-15-24-17-25,18-9-3-1-4-10-18)19-11-5-2-6-12-19/h1-17H
InChI KeyVNFPBHJOKIVQEB-UHFFFAOYSA-N
Chemical Taxonomy
KingdomOrganic Compounds
Super ClassAromatic Heteropolycyclic Compounds
ClassDiphenylmethanes
Sub ClassN/A
Other Descriptors
  • Aromatic Heteropolycyclic Compounds
  • a small molecule(Cyc)
  • imidazoles(ChEBI)
  • organochlorine compound(ChEBI)
Substituents
  • Aryl Chloride
  • Chlorobenzene
  • Imidazole
  • Organochloride
  • Phenylmethylamine
Direct ParentDiphenylmethanes
Ontology
StatusExpected and Not Quantified
Origin
  • Drug
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Membrane (predicted from logP)
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point148 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.0015ALOGPS
logP5.48ALOGPS
logP5.84ChemAxon
logS-5.4ALOGPS
pKa (Strongest Basic)6.62ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area17.82 Å2ChemAxon
Rotatable Bond Count4ChemAxon
Refractivity103.76 m3·mol-1ChemAxon
Polarizability36.25 Å3ChemAxon
Spectra
SpectraMS/MSMS1D NMR2D NMR
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
Biofluid LocationsNot Available
Tissue Location
  • Skin
PathwaysNot Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Predicted Concentrations
BiofluidValueOriginal ageOriginal sexOriginal conditionComments
Blood0-3 uMAdult (>18 years old)BothNormalPredicted based on drug qualities
Blood0-1 umol/mmol creatinineAdult (>18 years old)BothNormalPredicted based on drug qualities
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB022740
KNApSAcK IDNot Available
Chemspider ID2710
KEGG Compound IDC06922
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkClotrimazole
NuGOwiki LinkHMDB01922
Metagene LinkHMDB01922
METLIN ID1897
PubChem Compound2812
PDB IDCL6
ChEBI ID3764
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Schmook FP, Meingassner JG, Billich A: Comparison of human skin or epidermis models with human and animal skin in in-vitro percutaneous absorption. Int J Pharm. 2001 Mar 14;215(1-2):51-6. Pubmed: 11250091
  2. Lucker PW, Beubler E, Kukovetz WR, Ritter W: Retention time and concentration in human skin of bifonazole and clotrimazole. Dermatologica. 1984;169 Suppl 1:51-5. Pubmed: 6526092
  3. Schmidt A, Ruhl-Horster B: In vitro susceptibility of Malassezia furfur against azole compounds. Mycoses. 1996 Jul-Aug;39(7-8):309-12. Pubmed: 9009652

Enzymes

General function:
Involved in monooxygenase activity
Specific function:
Catalyzes the side-chain cleavage reaction of cholesterol to pregnenolone.
Gene Name:
CYP11A1
Uniprot ID:
P05108
Molecular weight:
60101.87
General function:
Involved in sodium:potassium-exchanging ATPase activity
Specific function:
May act as a transcriptional coregulator during muscle development through its interaction with SNW1. Has lost its ancestral function as a Na,K-ATPase beta-subunit
Gene Name:
ATP1B4
Uniprot ID:
Q9UN42
Molecular weight:
41597.4
General function:
Involved in hydrogen ion transmembrane transporter activity
Specific function:
Mitochondrial membrane ATP synthase (F(1)F(0) ATP synthase or Complex V) produces ATP from ADP in the presence of a proton gradient across the membrane which is generated by electron transport complexes of the respiratory chain. F-type ATPases consist of two structural domains, F(1) - containing the extramembraneous catalytic core, and F(0) - containing the membrane proton channel, linked together by a central stalk and a peripheral stalk. During catalysis, ATP synthesis in the catalytic domain of F(1) is coupled via a rotary mechanism of the central stalk subunits to proton translocation. Part of the complex F(0) domain and the peripheric stalk, which acts as a stator to hold the catalytic alpha(3)beta(3) subcomplex and subunit a/ATP6 static relative to the rotary elements
Gene Name:
ATP5F1
Uniprot ID:
P24539
Molecular weight:
28908.5
General function:
Involved in monooxygenase activity
Specific function:
Responsible for the metabolism of many drugs and environmental chemicals that it oxidizes. It is involved in the metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic antidepressants.
Gene Name:
CYP2D6
Uniprot ID:
P10635
Molecular weight:
55768.94
General function:
Involved in monooxygenase 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 oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Most active in catalyzing 2-hydroxylation. Caffeine is metabolized primarily by cytochrome CYP1A2 in the liver through an initial N3-demethylation. Also acts in the metabolism of aflatoxin B1 and acetaminophen. Participates in the bioactivation of carcinogenic aromatic and heterocyclic amines. Catalizes the N-hydroxylation of heterocyclic amines and the O-deethylation of phenacetin.
Gene Name:
CYP1A2
Uniprot ID:
P05177
Molecular weight:
58406.915
General function:
Involved in binding
Specific function:
N-APP binds TNFRSF21 triggering caspase activation and degeneration of both neuronal cell bodies (via caspase-3) and axons (via caspase-6)
Gene Name:
APP
Uniprot ID:
P05067
Molecular weight:
86942.7
General function:
Involved in metalloendopeptidase activity
Specific function:
Probable zinc protease. May mediate cell-cell or cell- matrix interactions. Isoform 2 displays alpha-secretase activity for APP
Gene Name:
ADAM9
Uniprot ID:
Q13443
Molecular weight:
90555.3
General function:
Involved in hydrogen ion transporting ATP synthase activity, rotational mechanism
Specific function:
Mitochondrial membrane ATP synthase (F(1)F(0) ATP synthase or Complex V) produces ATP from ADP in the presence of a proton gradient across the membrane which is generated by electron transport complexes of the respiratory chain. F-type ATPases consist of two structural domains, F(1) - containing the extramembraneous catalytic core, and F(0) - containing the membrane proton channel, linked together by a central stalk and a peripheral stalk. During catalysis, ATP synthesis in the catalytic domain of F(1) is coupled via a rotary mechanism of the central stalk subunits to proton translocation. Part of the complex F(1) domain and of the central stalk which is part of the complex rotary element. Rotation of the central stalk against the surrounding alpha(3)beta(3) subunits leads to hydrolysis of ATP in three separate catalytic sites on the beta subunits
Gene Name:
ATP5EP2
Uniprot ID:
Q5VTU8
Molecular weight:
5806.8