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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2006-05-18 08:31:29 UTC
Update Date2022-09-22 18:34:16 UTC
HMDB IDHMDB0001922
Secondary Accession Numbers
  • HMDB01922
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
Data?1582752217
Synonyms
ValueSource
1-((2-Chlorophenyl)diphenylmethyl)-1H-imidazoleChEBI
1-(alpha-(2-Chlorophenyl)benzhydryl)imidazoleChEBI
1-(O-Chloro-alpha,alpha-diphenylbenzyl)imidazoleChEBI
1-(O-Chlorotrityl)imidazoleChEBI
LotriminChEBI
MycelexChEBI
1-(a-(2-Chlorophenyl)benzhydryl)imidazoleGenerator
1-(Α-(2-chlorophenyl)benzhydryl)imidazoleGenerator
1-(O-Chloro-a,a-diphenylbenzyl)imidazoleGenerator
1-(O-Chloro-α,α-diphenylbenzyl)imidazoleGenerator
(Chlorotrityl)imidazoleHMDB
CanestenHMDB
Canesten 1-day cream combi-pakHMDB
Canesten 1-day therapyHMDB
Canesten 3-day therapyHMDB
Canesten 6-day therapyHMDB
Canesten combi-pak 1-day therapyHMDB
Canesten combi-pak 3-day therapyHMDB
Canesten creamHMDB
Canesten solutionHMDB
CanestineHMDB
ChlotrimazoleHMDB
ClotrimadermHMDB
Clotrimaderm creamHMDB
ClotrimazolHMDB
ClotrimazolumHMDB
Desamix FHMDB
EmpecidHMDB
Fem careHMDB
FemCareHMDB
Gyne lotriminHMDB
Gyne-lotriminHMDB
Gyne-lotrimin 3HMDB
Gyne-lotrimin 3 combination packHMDB
Gyne-lotrimin combination packHMDB
Gyne-lotrimin3HMDB
Gyne-lotrimin3 combination packHMDB
GynixHMDB
Lopac-C-6019HMDB
LotrimaxHMDB
Lotrimin afHMDB
Lotrimin af creamHMDB
Lotrimin af jock-itch creamHMDB
Lotrimin af lotionHMDB
Lotrimin af solutionHMDB
Lotrimin creamHMDB
Lotrimin lotionHMDB
Lotrimin solutionHMDB
LotrisoneHMDB
mono-BaycutenHMDB
MonobaycutenHMDB
MycelaxHMDB
Mycelex 7HMDB
Mycelex creamHMDB
Mycelex gHMDB
Mycelex otcHMDB
Mycelex solutionHMDB
Mycelex trochesHMDB
Mycelex twin packHMDB
Mycelex-7HMDB
Mycelex-7 combination packHMDB
Mycelex-gHMDB
Mycelex: mycosporinrimazoleHMDB
Myclo creamHMDB
Myclo solutionHMDB
Myclo spray solutionHMDB
Myclo-gyneHMDB
MycosporinHMDB
MykosporinHMDB
Neo-zol creamHMDB
OtomaxHMDB
PedisafeHMDB
Prestwick_120HMDB
RimazoleHMDB
TibatinHMDB
TrimystenHMDB
Trivagizole 3HMDB
VeltrimHMDB
KlotrimazoleHMDB
Schering brand OF clotrimazoleHMDB
Bayer brand 1 OF clotrimazoleHMDB
Bayer brand 2 OF clotrimazoleHMDB
FB b 5097HMDB
Bay b 5097HMDB
Clotrimazole schering brandHMDB
KanestenHMDB
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
Description Belongs to the class of organic compounds known as triphenyl compounds. These are aromatic compounds containing a triphenyl moiety.
KingdomOrganic compounds
Super ClassBenzenoids
ClassTriphenyl compounds
Sub ClassNot Available
Direct ParentTriphenyl compounds
Alternative Parents
Substituents
  • Triphenyl compound
  • Chlorobenzene
  • Halobenzene
  • Aryl chloride
  • Aryl halide
  • Monocyclic benzene moiety
  • N-substituted imidazole
  • Azole
  • Heteroaromatic compound
  • Imidazole
  • Azacycle
  • Organoheterocyclic compound
  • Organonitrogen compound
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Organopnictogen compound
  • Organochloride
  • Organohalogen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Ontology
Disposition

Biological location

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point148 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular 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 Area17.82 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity103.76 m³·mol⁻¹ChemAxon
Polarizability36.25 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
AllCCS[M+H]+180.75832859911
AllCCS[M-H]-179.90832859911
DeepCCS[M+H]+178.54530932474
DeepCCS[M-H]-176.18730932474
DeepCCS[M-2H]-210.21630932474
DeepCCS[M+Na]+185.62530932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
ClotrimazoleClC1=CC=CC=C1C(N1C=CN=C1)(C1=CC=CC=C1)C1=CC=CC=C13911.2Standard polar33892256
ClotrimazoleClC1=CC=CC=C1C(N1C=CN=C1)(C1=CC=CC=C1)C1=CC=CC=C12261.5Standard non polar33892256
ClotrimazoleClC1=CC=CC=C1C(N1C=CN=C1)(C1=CC=CC=C1)C1=CC=CC=C12690.4Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Clotrimazole GC-MS (Non-derivatized) - 70eV, Positivesplash10-0059-6090000000-3cccc4c11a7c5a63573d2017-08-28Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Clotrimazole GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
MSMass Spectrum (Electron Ionization)splash10-004i-1490000000-442fa75d6a2d80321e362014-09-20Not AvailableView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Clotrimazole Quattro_QQQ 10V, N/A-QTOF (Annotated)splash10-004i-0090000000-9ac001e37a55e61bc9162012-07-25HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Clotrimazole Quattro_QQQ 25V, N/A-QTOF (Annotated)splash10-004i-0290000000-6285150b307e50af52c72012-07-25HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Clotrimazole Quattro_QQQ 40V, N/A-QTOF (Annotated)splash10-016u-0690000000-5814802384fae84ca3df2012-07-25HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Clotrimazole LC-ESI-ITFT , positive-QTOFsplash10-004i-0090000000-23b69c41217f6b1483072017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Clotrimazole LC-ESI-ITFT , positive-QTOFsplash10-016r-0960000000-5b3632c056ca1c0fa6012017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Clotrimazole LC-ESI-ITFT , positive-QTOFsplash10-016r-0950000000-bcb189995c8cdcd623042017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Clotrimazole LC-ESI-ITFT , positive-QTOFsplash10-004i-0090000000-f1d5f44ac74388f9bf4f2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Clotrimazole , positive-QTOFsplash10-004i-1490000000-1ed188e9911ad62a7fc72017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Clotrimazole , positive-QTOFsplash10-004i-0390000000-c2f0490842646cf25d562017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Clotrimazole , positive-QTOFsplash10-014l-3970000000-0cf80068015e539b67c92017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Clotrimazole LC-ESI-QFT , positive-QTOFsplash10-00or-0391000000-e8d9d4c77703a87fdcd82017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Clotrimazole 20V, Positive-QTOFsplash10-004i-0090000000-0df2bee4ed15192bc0b62021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Clotrimazole 10V, Positive-QTOFsplash10-004i-0090000000-f0198e4e7eaad2f341472021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Clotrimazole 30V, Positive-QTOFsplash10-00or-0490000000-53d8902c6f7211fc3c502021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Clotrimazole 40V, Positive-QTOFsplash10-014i-0950000000-168bf9867190bc3708b32021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Clotrimazole 50V, Positive-QTOFsplash10-014i-0950000000-c0c372245eb2fe021e2e2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Clotrimazole 35V, Positive-QTOFsplash10-004i-0090000000-23b69c41217f6b1483072021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Clotrimazole 35V, Positive-QTOFsplash10-004i-0090000000-f1d5f44ac74388f9bf4f2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Clotrimazole 45V, Positive-QTOFsplash10-016r-0960000000-5b3632c056ca1c0fa6012021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Clotrimazole 10V, Positive-QTOFsplash10-0002-0019000000-a5e5b5c85ea879e2f63b2017-07-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Clotrimazole 20V, Positive-QTOFsplash10-00kb-1039000000-cf9a51f1cb5d717c41692017-07-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Clotrimazole 40V, Positive-QTOFsplash10-014i-9280000000-7b57b00ebea4c6a2f8642017-07-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Clotrimazole 10V, Negative-QTOFsplash10-0006-0009000000-416f1aa58c794269d0382017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Clotrimazole 20V, Negative-QTOFsplash10-0006-1009000000-25f48116b270c282f4772017-07-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Clotrimazole 40V, Negative-QTOFsplash10-014i-8192000000-fb089a74161c7e17e5da2017-07-26Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Experimental 2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, CD3OD, experimental)2012-12-05Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
Biospecimen Locations
  • Blood
  • Urine
Tissue Locations
  • Epidermis
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedCancer patients undergoing total body irradiation details
UrineDetected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedCancer patients undergoing total body irradiation details
Predicted Concentrations
BiospecimenValueOriginal ageOriginal sexOriginal conditionComments
Blood0.000 uMAdult (>18 years old)BothNormalPredicted based on drug qualities
Blood0.000 umol/mmol creatinineAdult (>18 years old)BothNormalPredicted based on drug qualities
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00257
Phenol Explorer Compound IDNot Available
FooDB IDFDB022740
KNApSAcK IDNot Available
Chemspider ID2710
KEGG Compound IDC06922
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkClotrimazole
METLIN ID1897
PubChem Compound2812
PDB IDNot Available
ChEBI ID3764
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
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