CL6

1-[(2-CHLOROPHENYL)(DIPHENYL)METHYL]-1H-IMIDAZOLE

Created: 2006-10-26
Last modified:  2021-03-01

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Chemical Details

Formal Charge0
Atom Count42
Chiral Atom Count0
Bond Count45
Aromatic Bond Count23
2D diagram of CL6

Chemical Component Summary

Name1-[(2-CHLOROPHENYL)(DIPHENYL)METHYL]-1H-IMIDAZOLE
SynonymsCLOTRIMAZOLE
Systematic Name (OpenEye OEToolkits)1-[(2-chlorophenyl)-diphenyl-methyl]imidazole
FormulaC22 H17 Cl N2
Molecular Weight344.837
TypeNON-POLYMER

Chemical Descriptors

TypeProgram Version Descriptor
SMILESACDLabs10.04Clc1ccccc1C(c2ccccc2)(c3ccccc3)n4ccnc4
SMILESCACTVS3.341Clc1ccccc1C(n2ccnc2)(c3ccccc3)c4ccccc4
SMILESOpenEye OEToolkits1.5.0c1ccc(cc1)C(c2ccccc2)(c3ccccc3Cl)n4ccnc4
Canonical SMILESCACTVS3.341 Clc1ccccc1C(n2ccnc2)(c3ccccc3)c4ccccc4
Canonical SMILESOpenEye OEToolkits1.5.0 c1ccc(cc1)C(c2ccccc2)(c3ccccc3Cl)n4ccnc4
InChIInChI1.03 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
InChIKeyInChI1.03 VNFPBHJOKIVQEB-UHFFFAOYSA-N

Drug Info: DrugBank

DrugBank IDDB00257 
NameClotrimazole
Groups
  • approved
  • vet_approved
DescriptionThis drug is a broad spectrum antimycotic or antifungal agent. Clotrimazole's antimycotic properties were discovered in the late 1960s [A174094]. Clotrimazole falls under the _imidazole_ category of _azole_ antifungals, possessing broad-spectrum antimycotic activity [A174094]. It is available in various preparations, including creams, pessaries, and troche formulations (slowly dissolving tablets). As well as its antifungal activity, clotrimazole has become a drug of interest in treating several other diseases such as sickle cell disease, malaria and some cancers [A174094]. The minimal side effect profile of this drug and its uncomplicated metabolic profile have led it to gain widespread acceptance for the treatment of mycotic outbreaks such as vaginal yeast infections as well as athlete's foot [A174097].
Synonyms
  • 1-((2-Chlorophenyl)diphenylmethyl)-1H-imidazole
  • 1-(o-Chlorotrityl)imidazole
  • 1-(o-Chloro-α,α-diphenylbenzyl)imidazole
  • Clotrimazol
  • Clotrimazole
Brand Names
  • Canesten External Cream
  • MakeSense
  • TopCare Clotrimazole 3
  • Akin Anti-fungal
  • Canesten 1 Day Internal Cream
Indication**Topical preparations** Clotrimazole topical cream is indicated for the topical treatment of the following dermal infections [F3088], [F3121]: Tinea pedis, tinea cruris, and tinea corporis due to _Trichophyton rubrum_, _Trichophyton mentagrophytes_, _Epidermophyton floccosum_ Candidiasis due to _Candida albicans_ Tinea versicolor due to _Malassezia furfur_ Diaper rash infected by _Candida albicans_ In some preparations, clotrimazole may be combined with betamethasone dipropionate, a corticosteroid [F3121]. **Oral preparations** The oral troche preparation is indicated for the local treatment of oropharyngeal candidiasis [FDA label]. It is also indicated as a prophylactic drug to reduce the incidence of oropharyngeal candidiasis in patients immunocompromised by conditions such as chemotherapy, radiotherapy, or steroid therapy utilized in the treatment of leukemia, solid tumors, or renal transplantation [FDA label]. Troche preparations are not indicated for the treatment of any systemic mycoses [FDA label].
Categories
  • Anti-Infective Agents
  • Anti-Infective Agents, Local
  • Antifungal Agents
  • Antifungal Agents (Vaginal)
  • Antifungals for Dermatological Use
ATC-Code
  • D01AC01
  • A01AB18
  • G01AF02
  • G01AF20
CAS number23593-75-1

Drug Targets

NameTarget SequencePharmacological ActionActions
Cytochrome P450 51MAIVETVIDGINYFLSLSVTQQISILLGVPFVYNLVWQYLYSLRKDRAPL...unknownantagonist,inhibitor
Intermediate conductance calcium-activated potassium channel protein 4MGGDLVLGLGALRRRKRLLEQEKSLAGWALVLAGTGIGLMVLHAEMLWFG...unknowninhibitor
Ergosterol-unknowninhibitor
Nuclear receptor subfamily 1 group I member 2MEVRPKESWNHADFVHCEDTESVPGKPSVNADEEVGGPQICRVCGDKATG...unknownactivator
Hydroxycarboxylic acid receptor 2MNRHHLQDHFLEIDKKNCCVFRDDFIVKVLPPVLGLEFIFGLLGNGLALW...unknownpartial agonist
View More
Drug Info/Drug Targets: DrugBank 3.0: a comprehensive resource for 'omics' research on drugs. Knox C, Law V, Jewison T, Liu P, Ly S, Frolkis A, Pon A, Banco K, Mak C, Neveu V, Djoumbou Y, Eisner R, Guo AC, Wishart DS. Nucleic Acids Res. 2011 Jan; 39 (Database issue):D1035-41. | PMID:21059682

Related Resource References

Resource NameReference
Pharos CHEMBL104
PubChem 2812
ChEMBL CHEMBL104
ChEBI CHEBI:3764
CCDC/CSD PUVRIH, PUVRIH01, DUJXUD, UCAYUW, UCAYIK, UCAYEG
COD 2007778