clotrimazole
diphenyl-(2-chlorophenyl)-1-imidazolylmethane
 
Notes:
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 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. [HMDB]
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1-[(2-chlorophenyl)-diphenylmethyl]imidazole (Click)
CAS Number: 23593-75-1Picture of molecule
Other: 117829-71-7
FDA UNII: G07GZ97H65
Nikkaji Web: J3.156I
Beilstein Number: 0622318
MDL: MFCD00057220
XlogP3-AA: 5.00 (est)
Molecular Weight: 344.84349000
Formula: C22 H17 Cl N2
NMR Predictor: Predict (works with chrome or firefox)
Category: antidandruff, antimicrobial agents
 
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Physical Properties:
Assay: 95.00 to 100.00 % 
Food Chemicals Codex Listed: No
Melting Point: 148.00 °C. @ 760.00 mm Hg
Soluble in:
 water, 0.02984 mg/L @ 25 °C (est)
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Organoleptic Properties:
  
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Cosmetic Information:
CosIng: cosmetic data
Cosmetic Uses: antidandruff agents
antimicrobial agents
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Suppliers:
Sigma-Aldrich: Sigma
For experimental / research use only.
Clotrimazole
Universal Preserv-A-Chem Inc.
CLOTRIMAZOLE
Odor: characteristic
Use: Clotrimazole is an imidazole antifungal that is active against a wide variety of fungal forms and is effective in many types of fungal infections.
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Safety Information:
Preferred SDS: View
 
Hazards identification
 
Classification of the substance or mixture
GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)
None found.
GHS Label elements, including precautionary statements
 
Pictogram
 
Hazard statement(s)
None found.
Precautionary statement(s)
None found.
Oral/Parenteral Toxicity:
oral-cat LD50  > 1000 mg/kg
GASTROINTESTINAL: NAUSEA OR VOMITING
Arzneimittel-Forschung. Drug Research. Vol. 22, Pg. 1272, 1972.

oral-dog LD50  > 2000 mg/kg
GASTROINTESTINAL: NAUSEA OR VOMITING
Arzneimittel-Forschung. Drug Research. Vol. 22, Pg. 1272, 1972.

oral-mammal (species unspecified) LD50  750 mg/kg
Antimicrobial Agents and Chemotherapy Vol. -, Pg. 271, 1969.

intraperitoneal-mouse LD50  108 mg/kg
Drug and Chemical Toxicology. Vol. 13, Pg. 195, 1990.

intravenous-mouse LD50  198 mg/kg
Gekkan Yakuji. Pharmaceuticals Monthly. Vol. 9, Pg. 759, 1967.

oral-mouse LD50  761 mg/kg
Arzneimittel-Forschung. Drug Research. Vol. 22, Pg. 1272, 1972.

oral-rabbit LD50  > 1000 mg/kg
BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD BEHAVIORAL: MUSCLE WEAKNESS
Arzneimittel-Forschung. Drug Research. Vol. 22, Pg. 1272, 1972.

intraperitoneal-rat LD50  445 mg/kg
Kiso to Rinsho. Clinical Report. Vol. 7, Pg. 1333, 1973.

oral-rat LD50  708 mg/kg
Arzneimittel-Forschung. Drug Research. Vol. 22, Pg. 1272, 1972.

Dermal Toxicity:
subcutaneous-mouse LDLo 10000 mg/kg
Kiso to Rinsho. Clinical Report. Vol. 7, Pg. 1333, 1973.

subcutaneous-rat LDLo 10000 mg/kg
Kiso to Rinsho. Clinical Report. Vol. 7, Pg. 1333, 1973.

Inhalation Toxicity:
Not determined
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Safety in Use Information:
Category: antidandruff, antimicrobial agents
Recommendation for clotrimazole usage levels up to:
 not for fragrance use.
 
Recommendation for clotrimazole flavor usage levels up to:
 not for flavor use.
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Safety References:
EPI System: View
ClinicalTrials.gov: search
Daily Med: search
NLM Hazardous Substances Data Bank: Search
Chemical Carcinogenesis Research Information System: Search
AIDS Citations: Search
Cancer Citations: Search
Toxicology Citations: Search
Env. Mutagen Info. Center: Search
EPA ACToR: Toxicology Data
EPA Substance Registry Services (SRS): Registry
Laboratory Chemical Safety Summary : 2812
National Institute of Allergy and Infectious Diseases: Data
SCCNFP: opinion
WGK Germany: 3
 1-[(2-chlorophenyl)-diphenylmethyl]imidazole
Chemidplus: 0023593751
RTECS: NI4377000 for cas# 23593-75-1
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References:
 1-[(2-chlorophenyl)-diphenylmethyl]imidazole
NIST Chemistry WebBook: Search Inchi
Canada Domestic Sub. List: 23593-75-1
Pubchem (cid): 2812
Pubchem (sid): 134995329
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Other Information:
(IUPAC): Atomic Weights of the Elements 2009
(IUPAC): Atomic Weights of the Elements 2009 (pdf)
Videos: The Periodic Table of Videos
tgsc: Atomic Weights use for this web site
(IUPAC): Periodic Table of the Elements
CHEBI: View
CHEMBL: View
Golm Metabolome Database: Search
KEGG (GenomeNet): C06922
HMDB (The Human Metabolome Database): HMDB01922
FooDB: FDB022740
MedlinePlusSupp: View
ChemSpider: View
Wikipedia: View
RSC Learn Chemistry: View
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Potential Blenders and core components note
 
None Found
 
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Potential Uses:
None Found
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Occurrence (nature, food, other): note
 not found in nature
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Synonyms:
 bay 5097
 bay-B 5097
 canesten
 canestene
 canifug
1-(o-chloro-alpha,alpha-diphenylbenzyl)imidazole
1-((o-chloro-phenyl)diphenylmethyl)imidazole
1-[(2-chlorophenyl)-diphenylmethyl]imidazole
1-(alpha-(2-chlorophenyl)benzhydryl)imidazole
(2-chlorophenyl)diphenyl-1-imidazolylmethane
1-((2-chlorophenyl)diphenylmethyl)-1H-imidazole
1-((2-chlorophenyl)diphenylmethyl)-1H-imidazole (9CI)
1-(o-chlorophenyldiphenylmethyl)imidazole
(chlorotrityl)imidazole
1-(o-chlorotrityl)imidazole
 clomatin
 clotrimazolum
 cutistad
 desamix F
 diphenyl-(2-chlorophenyl)-1-imidazolylmethane
 diphenyl(2-chlorophenyl)(1-imidazolyl)methane
 empecid
bis-fenil-(2-clorofenil)-1-imidazolil-metano
 gino-lotremine
 gyne lotrimin
 gyne-lotrimin
 gyne-lotrimin 3
 gyne-lotrimin 3 combination pack
 gyne-lotrimin combination pack
 gynix
1H-imidazole, 1-((2-chlorophenyl)diphenylmethyl)-
 imidazole, 1-(o-chloro-alpha,alpha-diphenylbenzyl)-
 jidesheng
 lotrimax
 lotrimin AF
 lotrisone
 methane, bis-phenyl-(2-chlorophenyl)-1-imidazolyl-
 mono-baycuten
 monobaycuten
 mycelex 7
 mycelex G
 mycelex OTC
 mycelex troches
 mycelex-7
 mycelex-7 combination pack
 mycelex-G
 mycofug
 mycosporin
 mykosporin
 nalbix
 pan-fungex
 pedisafe
bis-phenyl-(2-chlorophenyl)(1-imidazoyl)methane
bisphenyl-(2-chlorphenyl)-1-imidazolyl-methan
bisphenyl-(2-chlorphenyl)-1-imidazolyl-methan [German]
 rimazole
 stiemazol
 tibatin
 trimysten
 trivagizole 3
 veltrim
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Articles:
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J-Stage: A Correlation between Antioxidant Activity and Metabolite Release during the Blanching of Chrysanthemum coronarium L.
PubMed: Disarming the jasmonate-dependent plant defense makes nonhost Arabidopsis plants accessible to the American serpentine leafminer.
PubMed: Preference of a polyphagous mirid bug, Apolygus lucorum (Meyer-Dür) for flowering host plants.
PubMed: Xanthine oxidase inhibitory activity of the methanolic extracts of selected Jordanian medicinal plants.
PubMed: Mediterranean wild plants reduce postprandial platelet aggregation in patients with metabolic syndrome.
PubMed: Characterization and risk assessment of polychlorinated biphenyls in soils and vegetations near an electronic waste recycling site, South China.
PubMed: A correlation between antioxidant activity and metabolite release during the blanching of Chrysanthemum coronarium L.
PubMed: Toll-like receptor-dependent IL-12 production by dendritic cells is required for activation of natural killer cell-mediated Type-1 immunity induced by Chrysanthemum coronarium L.
PubMed: Larvicidal activity of selected plant hydrodistillate extracts against the house mosquito, Culex pipiens, a West Nile virus vector.
PubMed: Volatile oil profiles of the aerial parts of Jordanian garland, Chrysanthemum coronarium.
PubMed: Isolation of a gibberellin-producing fungus (Penicillium sp. MH7) and growth promotion of Crown daisy (Chrysanthemum coronarium).
PubMed: Reducing plant uptake of PAHs by cationic surfactant-enhanced soil retention.
PubMed: Chemical and biological comparisons on supercritical extracts of Tanacetum cinerariifolium (Trevir) Sch. Bip. with three related species of chrysanthemums of Sardinia (Italy).
PubMed: In planta dynamic analysis of onion yellows phytoplasma using localized inoculation by insect transmission.
PubMed: Isolation and Characterization of Derivative Lines of the Onion Yellows Phytoplasma that Do Not Cause Stunting or Phloem Hyperplasia.
PubMed: Heterocyclic compounds from Chrysanthemum coronarium L. and their inhibitory activity on hACAT-1, hACAT-2, and LDL-oxidation.
PubMed: Metabolic fate of nicotinamide in higher plants.
PubMed: Copper accumulation and tolerance in Chrysanthemum coronarium L. and Sorghum sudanense L.
PubMed: Identification of campesterol from Chrysanthemum coronarium L. and its antiangiogenic activities.
PubMed: [Relationships between host preference of Liriomyza huidobrensis (Blanchard) and nutrient and chlorophyll contents in host foliage].
PubMed: Biodegradable chelating agent ethylenediaminedisuccinic acid reduces uptake of copper through alleviation of copper toxicity in hydroponically grown Chrysanthemum coronarium L.
PubMed: Identification and characterization of major flavonoids and caffeoylquinic acids in three Compositae plants by LC/DAD-APCI/MS.
PubMed: EDDS and EDTA-enhanced phytoextraction of metals from artificially contaminated soil and residual effects of chelant compounds.
PubMed: Milk and cheese fatty acid composition in sheep fed Mediterranean forages with reference to conjugated linoleic acid cis-9,trans-11.
PubMed: Anti-inflammatory effects of extracts from some traditional Mediterranean diet plants.
PubMed: Germination requirements and dispersal timing in two heterocarpic weedy asteraceae.
PubMed: Accumulation of pathogenesis-related type-5 like proteins in phytoplasma-infected garland chrysanthemum Chrysanthemum coronarium.
PubMed: Multiresidue method for the determination of pesticides in Korean domestic crops by gas chromatography/mass selective detection.
PubMed: Purification and characterization of polyphenol oxidase from garland chrysanthemum (Chrysanthemum coronarium L.).
PubMed: Differences in the fragrances of pollen, leaves, and floral parts of garland (Chrysanthemum coronarium) and composition of the essential oils from flowerheads and leaves.
PubMed: Isolation and identification of dihydrochrysanolide and its 1-epimer from Chrysanthemum coronarium L.
PubMed: Purification of chrysancorin, a novel antifungal protein with mitogenic activity from garland chrysanthemum seeds.
PubMed: Antifungal activity of the essential oil of flowerheads of garland chrysanthemum (Chrysanthemum coronarium) against agricultural pathogens.
PubMed: Stability and bioavailability of antioxidants in garland (Chrysanthemum coronarium L.).
PubMed: Chromatographic separation of a small subunit (PsbW/PsaY) and its assignment to Photosystem I reaction center.
PubMed: [Oxyanthraquinones and flavonoids from garland chrysanthenum].
PubMed: Pattern of cross-sensitivity between 4 Compositae plants, Parthenium hysterophorus, Xanthium strumarium, Helianthus annuus and Chrysanthemum coronarium, in Indian patients.
PubMed: Rhizosphere fungi of five plants in Egypt.
PubMed: Fluorescent petal constituents of Chrysanthemum coronarium L.
PubMed: Influence of moisture on the availability and persistence of clotrimazole and fluconazole in sludge-amended soil.
PubMed: Fate of the antifungal drug clotrimazole in agricultural soil.
PubMed: Effects of food limitation and pharmaceutical compounds on the larval development and morphology of Palaemon serratus.
PubMed: Typical azole biocides in biosolid-amended soils and plants following biosolid applications.
PubMed: Determination of clotrimazole in mice plasma by capillary electrophoresis.
PubMed: Clotrimazole/betamethasone diproprionate: a review of costs and complications in the treatment of common cutaneous fungal infections.
PubMed: Influence of gender, feeding regimen, and exposure duration on gene expression associated with xenobiotic metabolism in fathead minnows (Pimephales promelas).
PubMed: Presence of pharmaceuticals in benthic fauna living in a small stream affected by effluent from a municipal sewage treatment plant.
PubMed: QSAR model for human pregnane X receptor (PXR) binding: screening of environmental chemicals and correlations with genotoxicity, endocrine disruption and teratogenicity.
PubMed: Synthesis and synergistic, additive inhibitory effects of novel spiro derivatives against ringworm infections.
PubMed: From the Food and Drug Administration.
PubMed: Topical antifungal drug products for over-the-counter human use; amendment of final monograph. Final rule.
PubMed: Candidiasis (oropharyngeal).
PubMed: Arachidonic acid increases antifungal susceptibility of Candida albicans and Candida dubliniensis.
PubMed: Comparative efficacy of two regimens in syndromic management of lower genital infections.
PubMed: Stabilization of hot-melt extrusion formulations containing solid solutions using polymer blends.
PubMed: Candidiasis (oropharyngeal).
PubMed: Development of stably transfected human and rat hepatoma cell lines for the species-specific assessment of xenobiotic response enhancer module (XREM)-dependent induction of drug metabolism.
PubMed: Solid-state stability and characterization of hot-melt extruded poly(ethylene oxide) films.
PubMed: Management of oropharyngeal candidiasis with localized oral miconazole therapy: efficacy, safety, and patient acceptability.
PubMed: Influence of redox-active compounds and PXR-activators on human MRP1 and MRP2 gene expression.
PubMed: Athlete's foot.
PubMed: Is there a role for fluconazole in the treatment of vulvovaginal candidiasis?
PubMed: Safety assessment of dairy microorganisms: Geotrichum candidum.
PubMed: Antimycotic activity of 5'-prenylisoflavanones of the plant Geoffroea decorticans, against Aspergillus species.
PubMed: Comparative ability of various prescription and over-the-counter topical antifungal drug products to inhibit the growth of C. albicans.
PubMed: Targeting of cancer energy metabolism.
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