Clotrimazole
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| Category | Bioactive by-products |
| Catalog number | BBF-04005 |
| CAS | 23593-75-1 |
| Molecular Weight | 344.84 |
| Molecular Formula | C22H17ClN2 |
| Purity | >98% |
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Description
Clotrimazole is a synthetic, antifungal and broad-spectrum derivate of imidazole. It is an antifungal medication commonly used in the treatment of fungal infections.
Specification
| Related CAS | 117829-71-7 (Deleted CAS) |
| Synonyms | Lotrimin; Canesten; Mycelex; Clotrimazol; Mycosporin; Empecid; 1H-Imidazole, 1-[(2-chlorophenyl)diphenylmethyl]-; 1-[(2-Chlorophenyl)diphenylmethyl]-1H-imidazole; Imidazole, 1-(o-chloro-α,α-diphenylbenzyl)-; 1-(o-Chlorophenyldiphenylmethyl)imidazole; 1-(o-Chlorotrityl)imidazole; Agisten; Canifug; Femcare; Locasten; Monobaycuten; NSC 257473; Pedisafe; Plimycol; Rimazole; Tibatin; Trimysten; Veltrim |
| Storage | Store at 2-8°C |
| 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 |
| 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 |
| Source | Synthetic |
Properties
| Appearance | White Solid |
| Antibiotic Activity Spectrum | fungi |
| Boiling Point | 482.3±40.0°C at 760 mmHg |
| Melting Point | 147-149°C |
| Flash Point | 245.5ºC |
| Density | 1.13 g/cm3 |
| Solubility | Soluble in Chloroform, DMSO (Slightly), Ethyl Acetate (Slightly) |
| LogP | 6.1 |
Toxicity
| Carcinogenicity | No indication of carcinogenicity to humans (not listed by IARC). |
| Mechanism Of Toxicity | Clotrimazole interacts with yeast 14-α 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. |
Reference Reading
1.Deficiency of sex hormones does not affect 17-ß-estradiol-induced coronary vasodilation in the isolated rat heart.
Santos RL1, Lima JT1, Rouver WN1, Moysés MR1. Braz J Med Biol Res. 2016;49(5):e5058. doi: 10.1590/1414-431X20165058. Epub 2016 Apr 12.
The relaxation of coronary arteries by estrogens in the coronary vascular beds of naive and hypertensive rats has been well described. However, little is known about this action in gonadectomized rats. We investigated the effect of 17-ß-estradiol (E2) in coronary arteries from gonadectomized rats, as well as the contributions of endothelium-derived factors and potassium channels. Eight-week-old female and male Wistar rats weighing 220-300 g were divided into sham-operated and gonadectomized groups (n=9-12 animals per group). The baseline coronary perfusion pressure (CPP) was determined, and the vasoactive effects of 10 μM E2 were assessed by bolus administration before and after endothelium denudation or by perfusion with NG-nitro-L-arginine methyl ester (L-NAME), indomethacin, clotrimazole, L-NAME plus indomethacin, L-NAME plus clotrimazole or tetraethylammonium (TEA). The CPP differed significantly between the female and sham-operated male animals.
2.ABC transporters and xenobiotic defense systems in early life stages of rainbow trout (Oncorhynchus mykiss).
Kropf C1, Segner H2, Fent K3. Comp Biochem Physiol C Toxicol Pharmacol. 2016 Mar 2;185-186:45-56. doi: 10.1016/j.cbpc.2016.02.006. [Epub ahead of print]
Embryos of oviparous fish, in contrast to (ovo) viviparous species, develop in the aquatic environment, and therefore need solute transport systems at their body surfaces for maintaining internal homeostasis and defending against potentially harmful substances. We hypothesized that solute transporters undergo changes in tissue distribution from the embryo to the larval stage. We therefore studied the mRNA profiles of eight ABC transporters (abcb1a, abcb1b, abcc1, abcc2, abcc3, abcc4, abcc5, abcg2) and three solute carriers (oatp1d, putative oatp2 putative, mate1) in different body regions (head, yolk sac epithelium, abdominal viscera, skin/muscles) of developing rainbow trout. Additionally, we investigated mRNA levels of phase I (cyp1a, cyp3a) and phase II (gstp, putative ugt1, putative ugt2) biotransformation enzymes. The study covered the developmental period from the eleuthero-embryo stage to the first-feeding larval stage (1-20days post-hatch, dph).
3.Mucoadhesive in situ gel formulation for vaginal delivery of clotrimazole: formulation, preparation, and in vitro/in vivo evaluation.
Rençber S1, Karavana SY1, Şenyiğit ZA1, Eraç B2, Limoncu MH2, Baloğlu E1. Pharm Dev Technol. 2016 Apr 7:1-11. [Epub ahead of print]
The purpose of this study was to develop a suitable mucoadhesive in situ gel formulation of clotrimazole (CLO) for the treatment of vaginal candidiasis. For this aim, the mixture of poloxamer (PLX) 407 and 188 were used to prepare in situ gels. Hydroxypropyl methylcellulose (HPMC) K100M or E50 was added to in situ gels in 0.5% ratio to improve the mucoadhesive and mechanical properties of formulations and to prolong the residence time in vaginal cavity. After the preparation of mucoadhesive in situ gels; gelation temperature/time, viscosity, mechanical, mucoadhesive, syringeability, spreadibility and rheological properties, in vitro release behavior, and anticandidal activities were determined. Moreover vaginal retention of mucoadhesive in situ gels was investigated with in vivo distribution studies in rats. Based on the obtained results, it was found that gels prepared with 20% PLX 407, 10% PLX 188 and 0.5% HPMC K100M/E50 might be suitable for vaginal administration of CLO.
4.Comparative antibiogram of coagulase-negative Staphylococci (CNS) associated with subclinical and clinical mastitis in dairy cows.
Bansal BK1, Gupta DK1, Shafi TA1, Sharma S1. Vet World. 2015 Mar;8(3):421-6. doi: 10.14202/vetworld.2015.421-426. Epub 2015 Mar 28.
AIM: The present study was planned to determine the in vitro antibiotic susceptibility of coagulase-negative Staphylococci (CNS) strains isolated from clinical and subclinical cases of mastitis in dairy cows. Antibiotic sensitivity profile will be helpful to recommend early therapy at the field level prior to availability of CST results.
Spectrum
Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive
Experimental Conditions
Ionization Mode: Positive
Ionization Energy: 70 eV
Chromatography Type: Gas Chromatography Column (GC)
Instrument Type: Single quadrupole, spectrum predicted by CFM-ID(EI)
Mass Resolution: 0.0001 Da
Molecular Formula: C22H17ClN2
Molecular Weight (Monoisotopic Mass): 344.108 Da
Molecular Weight (Avergae Mass): 344.837 Da
Ionization Energy: 70 eV
Chromatography Type: Gas Chromatography Column (GC)
Instrument Type: Single quadrupole, spectrum predicted by CFM-ID(EI)
Mass Resolution: 0.0001 Da
Molecular Formula: C22H17ClN2
Molecular Weight (Monoisotopic Mass): 344.108 Da
Molecular Weight (Avergae Mass): 344.837 Da
LC-MS/MS Spectrum - Quattro_QQQ 10V, N/A (Annotated)
Experimental Conditions
Sample Assessment: Excellent
Spectrum Assessment: Excellent
Instrument Type: Quattro_QQQ
Collision Energy Level: low
Collision Energy Voltage: 10
Ionization Mode: N/A
Spectrum Assessment: Excellent
Instrument Type: Quattro_QQQ
Collision Energy Level: low
Collision Energy Voltage: 10
Ionization Mode: N/A
Predicted LC-MS/MS Spectrum - 10V, Positive
Experimental Conditions
Ionization Mode: Positive
Collision Energy: 10 eV
Instrument Type: QTOF (generic), spectrum predicted by CFM-ID
Mass Resolution: 0.0001 Da
Molecular Formula: C22H17ClN2
Molecular Weight (Monoisotopic Mass): 344.108 Da
Molecular Weight (Avergae Mass): 344.837 Da
Collision Energy: 10 eV
Instrument Type: QTOF (generic), spectrum predicted by CFM-ID
Mass Resolution: 0.0001 Da
Molecular Formula: C22H17ClN2
Molecular Weight (Monoisotopic Mass): 344.108 Da
Molecular Weight (Avergae Mass): 344.837 Da
Mass Spectrum (Electron Ionization)
1H NMR Spectrum
Experimental Conditions
Sample Concentration: 25.0 mM
Solvent: CD3OD
Sample Mass: 8.6 mg
Sample Assessment: Excellent
Spectrum Assessment: Excellent
Instrument Type: Bruker
Nucleus: 1H
Frequency: 600 MHz
Sample pH: 7.00
Sample Temperature: 25.0 Celsius
Chemical Shift Reference: TMS
Solvent: CD3OD
Sample Mass: 8.6 mg
Sample Assessment: Excellent
Spectrum Assessment: Excellent
Instrument Type: Bruker
Nucleus: 1H
Frequency: 600 MHz
Sample pH: 7.00
Sample Temperature: 25.0 Celsius
Chemical Shift Reference: TMS
[1H,13C] 2D NMR Spectrum
Experimental Conditions
Sample Concentration: 25.0 mM
Solvent: CD3OD
Sample Mass: 8.6 mg
Sample Assessment: Excellent
Spectrum Assessment: Excellent
Instrument Type: Bruker
Nucleus X: 1H
Nucleus Y: 13C
Frequency: 600 MHz
Sample pH: 7.00
Sample Temperature: 25.0 Celsius
Chemical Shift Reference: TMS
Solvent: CD3OD
Sample Mass: 8.6 mg
Sample Assessment: Excellent
Spectrum Assessment: Excellent
Instrument Type: Bruker
Nucleus X: 1H
Nucleus Y: 13C
Frequency: 600 MHz
Sample pH: 7.00
Sample Temperature: 25.0 Celsius
Chemical Shift Reference: TMS
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Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
