Clotrimazole
White crystalline powder.
Others
Clotrimazole is a synthetic, imidazole derivate with broad-spectrum, antifungal activity. Clotrimazole inhibits biosynthesis of sterols, particularly ergosterol, an essential component of the fungal cell membrane, thereby damaging and affecting the permeability of the cell membrane. This results in leakage and loss of essential intracellular compounds, and eventually causes cell lysis.
Clotrimazole is an imidazole antifungal agent used primarily in the treatment of skin, oral and vaginal candida infections. Clotrimazole is typically given topically or as oral or vaginal troches and has only modest systemic absorption. Nevertheless, clotrimazole given orally or as troches has been associated with transient and asymptomatic serum aminotransferase elevations during therapy, but it has not been linked to instances of clinically apparent acute liver injury.
Clotrimazole, also known as lotrimin or mycelex, belongs to the class of organic compounds known as triphenyl compounds. These are aromatic compounds containing a triphenyl moiety. Clotrimazole is a drug which is used 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. Clotrimazole exists as a solid and is considered to be practically insoluble (in water) and relatively neutral. Clotrimazole has been found in human skin tissue. Within the cell, clotrimazole is primarily located in the membrane (predicted from logP). Clotrimazole is a potentially toxic compound. 344.8 g/mol
Clotrimazole is an imidazole antifungal agent used primarily in the treatment of skin, oral and vaginal candida infections. Clotrimazole is typically given topically or as oral or vaginal troches and has only modest systemic absorption. Nevertheless, clotrimazole given orally or as troches has been associated with transient and asymptomatic serum aminotransferase elevations during therapy, but it has not been linked to instances of clinically apparent acute liver injury.
Clotrimazole, also known as lotrimin or mycelex, belongs to the class of organic compounds known as triphenyl compounds. These are aromatic compounds containing a triphenyl moiety. Clotrimazole is a drug which is used 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. Clotrimazole exists as a solid and is considered to be practically insoluble (in water) and relatively neutral. Clotrimazole has been found in human skin tissue. Within the cell, clotrimazole is primarily located in the membrane (predicted from logP). Clotrimazole is a potentially toxic compound. 344.8 g/mol
Formulation:
344.8 g/mol
Source:
Usage:
Clotrimazole
The product is for non-human research only. Not for therapeutic or veterinary use.
Catalog Number: BT-263932
CAS Number: 23593-75-1
Molecular Formula: C22H17ClN2
Molecular Weight: 344.8 g/mol
| CAS Number | 23593-75-1 |
|---|---|
| Product Name | Clotrimazole |
| Molecular Formula | C22H17ClN2 |
| Molecular Weight | 344.8 g/mol |
| Appearance | White crystalline powder. |
| Colorform | Crystals White to pale yellow crystalline powde |
| 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 |
| InChI Key | VNFPBHJOKIVQEB-UHFFFAOYSA-N |
| IUPAC Name | 1-[(2-chlorophenyl)-diphenylmethyl]imidazole |
| Canonical SMILES | C1=CC=C(C=C1)C(C2=CC=CC=C2)(C3=CC=CC=C3Cl)N4C=CN=C4 |
| Description | Clotrimazole is a synthetic, imidazole derivate with broad-spectrum, antifungal activity. Clotrimazole inhibits biosynthesis of sterols, particularly ergosterol, an essential component of the fungal cell membrane, thereby damaging and affecting the permeability of the cell membrane. This results in leakage and loss of essential intracellular compounds, and eventually causes cell lysis. Clotrimazole is an imidazole antifungal agent used primarily in the treatment of skin, oral and vaginal candida infections. Clotrimazole is typically given topically or as oral or vaginal troches and has only modest systemic absorption. Nevertheless, clotrimazole given orally or as troches has been associated with transient and asymptomatic serum aminotransferase elevations during therapy, but it has not been linked to instances of clinically apparent acute liver injury. Clotrimazole, also known as lotrimin or mycelex, belongs to the class of organic compounds known as triphenyl compounds. These are aromatic compounds containing a triphenyl moiety. Clotrimazole is a drug which is used 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. Clotrimazole exists as a solid and is considered to be practically insoluble (in water) and relatively neutral. Clotrimazole has been found in human skin tissue. Within the cell, clotrimazole is primarily located in the membrane (predicted from logP). Clotrimazole is a potentially toxic compound. |
| Melting Point | 148 148.0 °C 147-149 °C 148°C |
| Other CAS Number | 23593-75-1 |
| Physical Description | Solid |
| Pictograms | Acute Toxic;Irritant;Health Hazard;Environmental Hazard |
| Shelf Life | >2 years if stored properly |
| SMILES | C1=CC=C(C=C1)C(C2=CC=CC=C2)(C3=CC=CC=C3Cl)N4C=CN=C4 |
| Solubility | 0.49 mg/L SOL IN ACETONE, CHLOROFORM, ETHYL ACETATE; SLIGHTLY SOL IN WATER, BENZENE, TOLUENE Freely soluble in alcohol; soluble in polyethylene glycol 400 Slightly soluble in ether 3.7 [ug/mL] |
| Storage | Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years). |
| Synonyms | Bay b 5097 Canesten Clotrimazole FB b 5097 Kanesten Klotrimazole Lotrimin Mycelex |
| Reference | 1: El-Asmar J, Gonzalez R, Bookout R, Mishra A, Kharfan-Dabaja MA. Clotrimazole troches induce supratherapeutic blood levels of sirolimus and tacrolimus in an allogeneic hematopoietic cell-transplant recipient resulting in acute kidney injury. Hematol Oncol Stem Cell Ther. 2015 Nov 27. pii: S1658-3876(15)00103-X. doi: 10.1016/j.hemonc.2015.11.001. [Epub ahead of print] PubMed PMID: 26684920. 2: Herasym K, Bonaparte JP, Kilty S. A comparison of Locacorten-Vioform and clotrimazole in otomycosis: A systematic review and one-way meta-analysis. Laryngoscope. 2015 Nov 24. doi: 10.1002/lary.25761. [Epub ahead of print] PubMed PMID: 26600419. 3: Behmanesh F, Pasha H, Sefidgar AA, Taghizadeh M, Moghadamnia AA, Adib Rad H, Shirkhani L. Antifungal Effect of Lavender Essential Oil (Lavandula angustifolia) and Clotrimazole on Candida albicans: An In Vitro Study. Scientifica (Cairo). 2015;2015:261397. doi: 10.1155/2015/261397. Epub 2015 Oct 13. PubMed PMID: 26550521; PubMed Central PMCID: PMC4621348. 4: Pais P, Costa C, Pires C, Shimizu K, Chibana H, Teixeira MC. Membrane proteome-wide response to the antifungal drug clotrimazole in Candida glabrata: role of the transcription factor CgPdr1 and the Drug:H+ Antiporters CgTpo1_1 and CgTpo1_2. Mol Cell Proteomics. 2015 Oct 28. pii: mcp.M114.045344. [Epub ahead of print] PubMed PMID: 26512119. 5: Kalhapure RS, Sonawane SJ, Sikwal DR, Jadhav M, Rambharose S, Mocktar C, Govender T. Solid lipid nanoparticles of clotrimazole silver complex: An efficient nano antibacterial against Staphylococcus aureus and MRSA. Colloids Surf B Biointerfaces. 2015 Oct 8;136:651-658. doi: 10.1016/j.colsurfb.2015.10.003. [Epub ahead of print] PubMed PMID: 26492156. 6: Sehati N, Dalali N, Soltanpour S, Seyed Dorraji MS. Application of hollow fiber membrane mediated with titanium dioxide nanowire/reduced graphene oxide nanocomposite in preconcentration of clotrimazole and tylosin. J Chromatogr A. 2015 Nov 13;1420:46-53. doi: 10.1016/j.chroma.2015.09.063. Epub 2015 Sep 25. PubMed PMID: 26477522. 7: Montemiglio LC, Parisi G, Scaglione A, Sciara G, Savino C, Vallone B. Functional analysis and crystallographic structure of clotrimazole bound OleP, a cytochrome P450 epoxidase from Streptomyces antibioticus involved in oleandomycin biosynthesis. Biochim Biophys Acta. 2015 Oct 15. pii: S0304-4165(15)00273-1. doi: 10.1016/j.bbagen.2015.10.009. [Epub ahead of print] PubMed PMID: 26475642. 8: Brogi S, Brindisi M, Joshi BP, Sanna Coccone S, Parapini S, Basilico N, Novellino E, Campiani G, Gemma S, Butini S. Exploring clotrimazole-based pharmacophore: 3D-QSAR studies and synthesis of novel antiplasmodial agents. Bioorg Med Chem Lett. 2015 Nov 15;25(22):5412-8. doi: 10.1016/j.bmcl.2015.09.007. Epub 2015 Sep 5. PubMed PMID: 26428874. 9: Lexmond WS, Rufo PA, Fiebiger E, Lencer WI. Electrophysiological Studies into the Safety of the Anti-diarrheal Drug Clotrimazole during Oral Rehydration Therapy. PLoS Negl Trop Dis. 2015 Sep 25;9(9):e0004098. doi: 10.1371/journal.pntd.0004098. eCollection 2015 Sep. PubMed PMID: 26405813; PubMed Central PMCID: PMC4583490. 10: Nezhad ZK, Nagai N, Yamamoto K, Kaji H, Nishizawa M, Saya H, Nakazawa T, Abe T. Application of clotrimazole via a novel controlled release device provides potent retinal protection. J Mater Sci Mater Med. 2015 Sep;26(9):230. doi: 10.1007/s10856-015-5561-9. Epub 2015 Sep 3. PubMed PMID: 26335210; PubMed Central PMCID: PMC4559097. |
| PubChem Compound | Clotrimazole |
| Last Modified | Mar 14 2022 |