Clotrimazole CAS#23593-75-1
Clotrimazole is an imidazole antifungal that exhibits activity against various fungal forms and is effective in treating a wide range of fungal infections. It binds tightly to the sterol 14-α demethylase isoform B in A. fumigatus, with a reported KD of 103 nM. Like other imidazole antifungals, clotrimazole disrupts Fungal Cell Membranes function. In mammalian cells, it also potently inhibits the calcium-dependent potassium channels Kv1.3 and IK-1, with IC50 values of 6.0 μM and 0.07 μM, respectively.
Chemical Properties
| Melting point | 147-149°C |
| Boiling point | 501.14°C (rough estimate) |
| density | 1.1095 (rough estimate) |
| refractive index | 1.5940 (estimate) |
| storage temp. | 2-8°C |
| solubility | Soluble in chloroform, DMSO, DMF and alcohols |
| pka | pKa 4.7(EtOH 50%aq ) (Uncertain) |
| form | Solid |
| color | White to Almost white |
| Water Solubility | <10mg/L(25 ºC) |
| λmax | 556nm(Phosphate buffer sol.)(lit.) |
| Merck | 142417 |
| Major Application | pharmaceutical |
| pharmaceutical small molecule | |
| Cosmetics Ingredients Functions | ANTIMICROBIAL |
| ANTI-SEBORRHEIC | |
| 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 |
| SMILES | C1N(C(C2=CC=CC=C2Cl)(C2=CC=CC=C2)C2=CC=CC=C2)C=CN=1 |
| NIST Chemistry Reference | Clotrimazole(23593-75-1) |
| Hazard Codes | Xn |
| Risk Statements | 22-36/38 |
| Safety Statements | 26-36 |
| WGK Germany | 3 |
| RTECS | NI4377000 |
| HS Code | 29332900 |
| Storage Class | 11 - Combustible Solids |
| Hazard Classifications | Acute Tox. 4 Oral |
| Aquatic Acute 1 | |
| Aquatic Chronic 1 | |
| Eye Irrit. 2 | |
| Skin Irrit. 2 | |
| Hazardous Substances Data | 23593-75-1(Hazardous Substances Data) |
| Toxicity | LD50 in male mice, rats (mg/kg): 923, 708 orally (Tettenborn) |
Product Application
Clotrimazole is clinically used topical applications, formulated as a 1% cream or solution, to treat candidiasis, ringworm, tinea versicolor, athlete's foot, nail fungal infections, and other skin infections. Clotrimazole vaginal tablets (100 mg) are used to treat candidal and trichomoniasis vaginal infections. Side effects may include local irritation and a burning sensation. Oral administration is used for deep fungal infections but may cause serious side effects, including gastrointestinal irritation, neutropenia, and abnormalities in liver function.
Oral administration:
(1) Clotrimazole can be used to treat oropharyngeal candidiasis.
(2) It can be used during chemotherapy and for the prevention of oropharyngeal candidiasis in immunocompromised or immunodeficient patients.
Topical administration:
(1) Skin candidiasis.
(2) Tinea (including jock itch and ringworm) caused by Trichophyton, Epidermophyton, and Microsporum species, as well as tinea versicolor caused by Pityrosporum.
Vaginal administration:
(1) Vaginitis caused by Candida or other fungi.
(2) Vaginal infections caused by yeast.
(3) Vaginal superinfection caused by drug-susceptible strains.
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