Product Name

Clotrimazole

CAS Number

23593-75-1

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Product Name:
Clotrimazole
CAS Number:
23593-75-1
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.
Mode of Action:

Clotrimazole interacts with yeast 14-_ demethylase, a cytochrome P-450 enzyme that converts lanosterol to ergosterol, an essential component of the membrane. In this way, clotrimazole inhibits ergosterol synthesis, resulting in increased cellular permeability. Clotrimazole may also inhibit endogenous respiration, interact with membrane phospholipids, inhibit the transformation of yeasts to mycelial forms and the uptake of purine, impair triglyceride and/or phospholipid biosynthesis, and inhibit the movement of calcium and potassium ions across the cell membrane by blocking the ion transport pathway known as the Gardos channel.

Pharmacodynamics:

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.

Metabolism:

Hepatic (metabolized to inactive metabolites)

Toxicity:

Symptoms of overdose include erythema, stinging, blistering, peeling, edema, pruritus, urticaria, burning, and general irritation of the skin, and cramps.

IUPAC:
1-[(2-chlorophenyl)diphenylmethyl]-1H-imidazole
ATC:
A01AB18 D01AC01 G01AF02
DrugBank:
DB00257 (APRD00244)
Formula:
C19H27N5
Molecular Mass:
344.837
Synonyms:
Chlotrimazole Clotrimazol
SMILES:
ClC1=CC=CC=C1C(N1C=CN=C1)(C1=CC=CC=C1)C1=CC=CC=C1
AHFS Code:
84:04.08.08
InChi:
VNFPBHJOKIVQEB-UHFFFAOYSA-N

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