Record Information
Version3.6
Creation Date2006-05-18 08:31:29 UTC
Update Date2013-02-09 00:11:01 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 IUPAC 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 solubility0.0015 g/LALOGPS
logP5.48ALOGPS
logP5.84ChemAxon
logS-5.4ALOGPS
pKa (strongest basic)6.62ChemAxon
physiological charge0ChemAxon
hydrogen acceptor count1ChemAxon
hydrogen donor count0ChemAxon
polar surface area17.82ChemAxon
rotatable bond count4ChemAxon
refractivity103.76ChemAxon
polarizability36.25ChemAxon
Spectra
Spectra
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
Biofluid LocationsNot Available
Tissue Location
  • Skin
PathwaysNot Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
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)Not Available
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

Gene Name:
ATP1B4
Uniprot ID:
Q9UN42
Gene Name:
ATP5F1
Uniprot ID:
P24539
Gene Name:
CYP2D6
Uniprot ID:
P10635
Gene Name:
CYP1A2
Uniprot ID:
P05177
Gene Name:
APP
Uniprot ID:
P05067