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Merck
CN

33894

Clotrimazole

VETRANAL®, analytical standard

Synonym(s):

1-(o-Chloro-α,α-diphenylbenzyl)imidazole, 1-(o-Chlorotrityl)imidazole, 1-[(2-Chlorophenyl)diphenylmethyl]-1H-imidazole

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About This Item

Empirical Formula (Hill Notation):
C22H17ClN2
CAS Number:
23593-75-1
Molecular Weight:
344.84
NACRES:
NA.24
PubChem Substance ID:
329754531
UNSPSC Code:
41116107
EC Number:
245-764-8
MDL number:
MFCD00057220

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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

SMILES string

Clc1ccccc1C(c2ccccc2)(c3ccccc3)n4ccnc4

grade

analytical standard

product line

VETRANAL®

shelf life

limited shelf life, expiry date on the label

technique(s)

HPLC: suitable, gas chromatography (GC): suitable

antibiotic activity spectrum

fungi

application(s)

agriculture
environmental

format

neat

mode of action

protein synthesis | interferes

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General description

Clotrimazole, a non-toxic, systemic, imidazole derivative with broad-spectrum antimycotic activity, is primarily used in the treatment of oropharyngeal candidiasis.
Its mode of action involves the inhibition of ergosterol synthesis, which leads to structural and functional damage of the cell membrane.

Application

Clotrimazole may be used as a reference standard for the determination of the analyte in topical creams and ear drops by reversed-phase high-performance liquid chromatographic (RP-HPLC) method.
Clotrimazole may be used as an analytical reference standard for the determination of the analyte in:
  • Milk samples using solid-phase extraction followed by high-performance liquid chromatography (SPE-HPLC).
  • Environmental water samples using dispersive liquid-liquid microextraction followed by high-performance liquid chromatography with tandem mass spectrometry (HPLC-MS/MS).

Refer to the product′s Certificate of Analysis for more information on a suitable instrument technique. Contact Technical Service for further support.

Legal Information

VETRANAL is a registered trademark of Merck KGaA, Darmstadt, Germany

pictograms

Exclamation markEnvironment
GHS07,GHS09

signalword

Warning

Hazard Classifications

Acute Tox. 4 Oral - Aquatic Acute 1 - Aquatic Chronic 1 - Eye Irrit. 2 - Skin Irrit. 2

Storage Class

11 - Combustible Solids

wgk

WGK 3

ppe

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
BCCG0234
BCBT4094

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Clotrimazole is effective for the regression of endometriotic implants in a Wistar rat experimental model of endometriosis.
Machado D, et al.
Molecular and Cellular Endocrinology, 476, 17-26 (2018)
Mode of action of clotrimazole.
Iwata K, et al.
Sabouraudia, 11(2), 158-166 (1973)
SPE-HPLC method for determination of ketoconazole and clotrimazole residues in cow's milk.
Beigi KAF, et al.
Journal of the Brazilian Chemical Society, 22(9), 1679-1685 (2011)
Clotrimazole treatment for prevention of oral candidiasis in patients with acute leukemia undergoing chemotherapy: Results of a double-blind study.
Cuttner J, et al.
The American Journal of Medicine, 81(5), 771-774 (1986)
Sandra Gemma et al.
Journal of medicinal chemistry, 52(2), 502-513 (2008-12-31)
Antimalarial agents structurally based on novel pharmacophores, synthesized by low-cost synthetic procedures and characterized by low potential for developing resistance are urgently needed. Recently, we developed an innovative class of antimalarials based on a polyaromatic pharmacophore. Hybridizing the 4-aminoquinoline or
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