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23593-75-1 molecular structure
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1-[(2-chlorophenyl)diphenylmethyl]-1H-imidazole

ChemBase ID: 142
Molecular Formular: C22H17ClN2
Molecular Mass: 344.83678
Monoisotopic Mass: 344.10802623
SMILES and InChIs

SMILES:
Clc1c(C(n2ccnc2)(c2ccccc2)c2ccccc2)cccc1
Canonical SMILES:
Clc1ccccc1C(n1cncc1)(c1ccccc1)c1ccccc1
InChI:
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
InChIKey:
VNFPBHJOKIVQEB-UHFFFAOYSA-N

Cite this record

CBID:142 http://www.chembase.cn/molecule-142.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
1-[(2-chlorophenyl)diphenylmethyl]-1H-imidazole
IUPAC Traditional name
lotrimin
1-[(2-chlorophenyl)diphenylmethyl]-1H-imidazole
clotrimazole
Brand Name
Canesten
Canesten 1-Day Cream Combi-Pak
Canesten 1-Day Therapy
Canesten 3-Day Therapy
Canesten 6-Day Therapy
Canesten Combi-Pak 1-Day Therapy
Canesten Combi-Pak 3-Day Therapy
Canesten Cream
Canesten Solution
Canestine
Canifug
Cimitidine
Clotrimaderm
Empecid
FemCare
Gyne lotrimin
Gyne-Lotrimin 3
Gyne-Lotrimin 3 Combination Pack
Gyne-Lotrimin Combination Pack
Gyne-lotrimin
Gynix
Lotrimin
Lotrimin AF Cream
Lotrimin AF Jock-Itch Cream
Lotrimin AF Lotion
Lotrimin AF Solution
Lotrimin Af
Lotrimin Cream
Lotrimin Lotion
Lotrimin Solution
Mono-baycuten
Mycelax
Mycelex
Mycelex 7
Mycelex Cream
Mycelex G
Mycelex Solution
Mycelex Troches
Mycelex Twin Pack
Mycelex-7
Mycelex-7 Combination Pack
Mycelex-G
Myclo Cream
Myclo Solution
Myclo Spray Solution
Myclo-Gyne
Mycosporin
Mykosporin
Neo-Zol Cream
Trimysten
Trivagizole 3
Veltrim
Lotrimin AF, Mycelex
Synonyms
Clotrimazol
Chlotrimazole
Clotrimazole
Lotrimin
Mycelex
Canesten
1-(o-Chlorotrityl)imidazole
1-(o-Chloro-α,α-diphenylbenzyl)imidazole
Clotrimazole
1-[(2-Chlorophenyl)-diphenyl-methyl]-1H-imidazole
FB-5097
Bay b 5097
Canifug
Empecid
Mycofung
Desamix F
Diphenyl(2-chlorophenyl)(1-imidazolyl)methane
Femcare
Gyne-Lotrimin
Gyne-Lotrimin 7
Locasten
Clotrimazole(Canesten)
1-((2-chlorophenyl)diphenylmethyl)-1h-imidazole
1-[(2-Chlorophenyl)diphenylmethyl]-1H-imidazole
1-[(2-氯苯基)二苯甲基]-1H-咪唑
三苯氯甲咪唑
氯苯甲咪唑
克霉唑
CAS Number
23593-75-1
EC Number
245-764-8
MDL Number
MFCD00057220
PubChem SID
24860592
46507927
24278327
160963605
PubChem CID
2812
CHEBI ID
3764
ATC CODE
QJ02AB90
A01AB18
G01AF02
D01AC01
CHEMBL
104
Chemspider ID
2710
DrugBank ID
DB00257
KEGG ID
D00282
Unique Ingredient Identifier
G07GZ97H65
Wikipedia Title
Clotrimazole
Medline Plus
a682753

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem ALOGPS 2.1
H Acceptors H Donor
LogD (pH = 5.5) 5.3291874  LogD (pH = 7.4) 5.7905 
Log P 5.839452  Molar Refractivity 103.7645 cm3
Polarizability 39.57285 Å3 Polar Surface Area 17.82 Å2
Rotatable Bonds Lipinski's Rule of Five false 
Log P 5.48  LOG S -5.37 
Solubility (Water) 1.47e-03 g/l 

PROPERTIES

PROPERTIES

Physical Property Safety Information Pharmacology Properties Product Information Bioassay(PubChem)
Solubility
29.84 mg/mL expand Show data source
Chloroform expand Show data source
DMSO expand Show data source
Ethyl Acetate expand Show data source
Apperance
White Solid expand Show data source
Melting Point
142-144°C expand Show data source
Hydrophobicity(logP)
6.1 expand Show data source
Storage Condition
-20°C expand Show data source
Refrigerator expand Show data source
Room Temperature (15-30°C) expand Show data source
RTECS
NI4377000 expand Show data source
European Hazard Symbols
Harmful Harmful (Xn) expand Show data source
MSDS Link
Download expand Show data source
Download expand Show data source
Download expand Show data source
Download expand Show data source
German water hazard class
3 expand Show data source
Risk Statements
22-36/38 expand Show data source
R:22 expand Show data source
Safety Statements
26-36 expand Show data source
S:36/37/39 expand Show data source
GHS Pictograms
GHS07 expand Show data source
GHS Signal Word
Warning expand Show data source
GHS Hazard statements
H302-H315-H319 expand Show data source
GHS Precautionary statements
P305 + P351 + P338 expand Show data source
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Gloves expand Show data source
Admin Routes
topical expand Show data source
Bioavailability
Poorly and erratically absorbed orally expand Show data source
Half Life
2 hours expand Show data source
Metabolism
hepatic expand Show data source
Protein Bound
90% expand Show data source
Legal Status
P (UK) expand Show data source
Pregnancy Category
A (Australia) expand Show data source
C (oral) and B (topical) (US) expand Show data source
Gene Information
human ... ABCB1(5243), CYP17A1(1586), CYP3A4(1576)mouse ... Abcb1a(18671), Abcb1b(18669) expand Show data source
Mechanism of Action
Appears to increase permeability of fungal-cell-membrane causing leakage of intracellular components. expand Show data source
Functions as Lanosterol C-14 demethylation inhibitor expand Show data source
Induces K+ release from Trichophyton mentagrophytes mycelium expand Show data source
Induces membrane disruption expand Show data source
Potent cytochrome P-450b and P-450c inhibitor expand Show data source
Purity
98% expand Show data source
Grade
VETRANAL™, analytical standard expand Show data source
Salt Data
Free Base expand Show data source
Certificate of Analysis
Download expand Show data source
Download expand Show data source
Application(s)
Antifungal agent expand Show data source
Pharmacopeia Traceability
traceable to BP 379 expand Show data source
traceable to PhEur C2430000 expand Show data source
traceable to USP 1141002 expand Show data source
Empirical Formula (Hill Notation)
C22H17ClN2 expand Show data source

DETAILS

DETAILS

DrugBank DrugBank Sigma Aldrich Sigma Aldrich Selleck Chemicals Selleck Chemicals MP Biomedicals MP Biomedicals Wikipedia Wikipedia TRC TRC
DrugBank - DB00257 external link
Item Information
Drug Groups approved
Description 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]
Indication For the local treatment of oropharyngeal candidiasis and vaginal yeast infections, also used in fungal infections of the skin such as ringworm, athlete's foot, and jock itch.
Pharmacology Clotrimazole, an imidazole derivative with a broad spectrum of antimycotic activity, 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. Betamethasone and clotrimazole are used together to treat cutaneous tinea infections. In studies in fungal cultures, the minimum fungicidal concentration of clotrimazole caused leakage of intracellular phosphorous compounds into the ambient medium with concomitant breakdown of cellular nucleic acids, and accelerated potassium etflux. Both of these events began rapidly and extensively after addition of the drug to the cultures. The primary action of clotrimazole is against dividing and growing organisms.
Toxicity Symptoms of overdose include erythema, stinging, blistering, peeling, edema, pruritus, urticaria, burning, and general irritation of the skin, and cramps.
Affected Organisms
Yeast and other fungi
Biotransformation Hepatic (metabolized to inactive metabolites)
Absorption Poorly and erratically absorbed orally, minimal vaginal or topical absorption.
Half Life 2 hours
Protein Binding 90%
External Links
Wikipedia
RxList
Drugs.com
Sigma Aldrich - C6019 external link
Biochem/physiol Actions
Specific inhibitor of Ca2+-activated K+ channels. Antifungal azole. Antifungal mode of action: Inhibits cytochrome P450-dependent 14α-demethylase, which is critical to ergosterol biosynthesis. The accumulated 14α-methylated sterols change the membrane structure of sensitive fungi, altering cell membrane permeability.
Sigma Aldrich - 33894 external link
Legal Information
VETRANAL is a trademark of Sigma-Aldrich Co. LLC
Selleck Chemicals - S1606 external link
Research Area: Infection
Biological Activity:
Clotrimazole(Canesten) is a synthetic, antifungal and broad-spectrum derivate of imidazole. Clotrimazole inhibits biosynthesis of sterols, particularly inhibiting ergosterol, which is an essential component of the fungal cell membrane, thereby damaging and affecting the permeability of the cell membrane. This results in the  leakage and the loss of essential intracellular compounds, and eventually causes the lysis of cell.  [1, 2]
MP Biomedicals - 02198944 external link
Specific inhibitor of Ca2+ activated K+ channels.
Toronto Research Chemicals - C587400 external link
Clotrimazole is an antifungal agent.

REFERENCES

REFERENCES

From Suppliers Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • • Buechel, K.H. et al., Arzneim.-Forsch., 1972, 22, 1260, (synth, pharmacol)
  • • Kracmar, J. et al., Cesk. Farm., 1977, 26, 345, (uv)
  • • Raab, W., Curr. Ther. Res., Clin. Exp., 1977, 22, 65, (pharmacol)
  • • Ruppert, J.F., Diss. Abstr. Int., B, 1977, 38, 2681, (synth)
  • • Hoogerheide, J.G. et al., Anal. Profiles Drug Subst., 1982, 11, 225, (rev)
  • • Lewis, D.F.V. et al., J. Biochem. Toxicol., 1989, 4, 231, (pharmacol)
  • • Martindale, The Extra Pharmacopoeia, 30th edn., Pharmaceutical Press, 1993, 320
  • • Negwer, M., Organic-Chemical Drugs and their Synonyms, 7th edn., Akademie-Verlag, 1994, 8792
  • • Song, H. et al., Acta Cryst. C, 1998, 54, 1675-1677, (cryst struct)
  • • Lewis, R.J., Sax's Dangerous Properties of Industrial Materials, 8th edn., Van Nostrand Reinhold, 1992, MRX500
  • •  http://en.wikipedia.org/wiki/Clotrimazole
  • • Podust, L., et al.: J. Biol. Chem., 284, 25211 (2009)
  • • Hollender, J., et al.: Environ. Sci. Technol., 43, 7862 (2009)
  • • Marciniec, B., et al.: J. Pharm. Biomed. Anal., 50, 675 (2009)
  • • McGinnity, D., et al.: Drug Metab. Disposition, 37, 1259 (2009)
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PATENTS

PATENTS

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