Human Metabolome Database Version 3.5

Showing metabocard for Clotrimazole (HMDB01922)

Record Information
Version 3.5
Creation Date 2006-05-18 02:31:29 -0600
Update Date 2013-02-08 17:11:01 -0700
HMDB ID HMDB01922
Secondary Accession Numbers None
Metabolite Identification
Common Name Clotrimazole
Description Clotrimazole 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
Download: MOL | SDF | PDB | SMILES | InChI
Display: 2D Structure | 3D Structure
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 Formula C22H17ClN2
Average Molecular Weight 344.837
Monoisotopic Molecular Weight 344.108026261
IUPAC Name 1-[(2-chlorophenyl)diphenylmethyl]-1H-imidazole
Traditional IUPAC Name clotrimazole
CAS Registry Number 23593-75-1
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 Key VNFPBHJOKIVQEB-UHFFFAOYSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Aromatic Heteropolycyclic Compounds
Class Diphenylmethanes
Sub Class N/A
Other Descriptors
  • Aromatic Heteropolycyclic Compounds
  • a small molecule(Cyc)
  • imidazoles(ChEBI)
  • organochlorine compound(ChEBI)
Substituents
  • Aryl Chloride
  • Chlorobenzene
  • Imidazole
  • Organochloride
  • Phenylmethylamine
Direct Parent Diphenylmethanes
Ontology
Status Expected and Not Quantified
Origin
  • Drug
Biofunction Not Available
Application Not Available
Cellular locations
  • Membrane (predicted from logP)
Physical Properties
State Solid
Experimental Properties
Property Value Reference
Melting Point 148 °C Not Available
Boiling Point Not Available Not Available
Water Solubility Not Available Not Available
LogP Not Available Not Available
Predicted Properties
Property Value Source
LogP 5.48 ALOGPS
LogP 5.84 ChemAxon
LogS -5.37 ALOGPS
pKa (strongest basic) 6.62 ChemAxon
Hydrogen Acceptor Count 1 ChemAxon
Hydrogen Donor Count 0 ChemAxon
Polar Surface Area 17.82 A2 ChemAxon
Rotatable Bond Count 4 ChemAxon
Refractivity 103.76 ChemAxon
Polarizability 36.25 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge 0 ChemAxon
Spectra
1H NMR Spectrum
MS/MS Spectrum Quattro_QQQ 10
MS/MS Spectrum Quattro_QQQ 25
MS/MS Spectrum Quattro_QQQ 40
[1H,13C] 2D NMR Spectrum
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
Biofluid Locations Not Available
Tissue Location
  • Skin
Pathways Not Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease References None
Associated OMIM IDs None
DrugBank ID Not Available
DrugBank Metabolite ID Not Available
Phenol Explorer Compound ID Not Available
Phenol Explorer Metabolite ID Not Available
FoodDB ID FDB022740
KNApSAcK ID Not Available
Chemspider ID 2710 Link_out
KEGG Compound ID C06922 Link_out
BioCyc ID Not Available
BiGG ID Not Available
Wikipedia Link Clotrimazole Link_out
NuGOwiki Link HMDB01922 Link_out
Metagene Link HMDB01922 Link_out
METLIN ID 1897 Link_out
PubChem Compound 2812 Link_out
PDB ID CL6 Link_out
ChEBI ID 3764 Link_out
References
Synthesis Reference Not Available
Material Safety Data Sheet (MSDS) Download (PDF)
General References
  1. 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 Link_out
  2. 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 Link_out
  3. 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 Link_out

Enzymes
Name: Cholesterol side-chain cleavage enzyme, mitochondrial
Reactions: Not Available
Gene Name: CYP11A1
Uniprot ID: P05108 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Protein ATP1B4
Reactions: Not Available
Gene Name: ATP1B4
Uniprot ID: Q9UN42 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: ATP synthase subunit b, mitochondrial
Reactions: Not Available
Gene Name: ATP5F1
Uniprot ID: P24539 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Cytochrome P450 2D6
Reactions: Not Available
Gene Name: CYP2D6
Uniprot ID: P10635 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Cytochrome P450 1A2
Reactions: Not Available
Gene Name: CYP1A2
Uniprot ID: P05177 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Amyloid beta A4 protein
Reactions: Not Available
Gene Name: APP
Uniprot ID: P05067 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Disintegrin and metalloproteinase domain-containing protein 9
Reactions: Not Available
Gene Name: ADAM9
Uniprot ID: Q13443 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: ATP synthase subunit epsilon-like protein, mitochondrial
Reactions: Not Available
Gene Name: ATP5EP2
Uniprot ID: Q5VTU8 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA