Thiamphenicol
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| Category | Antibiotics |
| Catalog number | BBF-03992 |
| CAS | 15318-45-3 |
| Molecular Weight | 356.22 |
| Molecular Formula | C12H15Cl2NO5S |
| Purity | >98% |
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Description
Thiamphenicol is an antimicrobial antibiotic and a methyl-sulfonyl analogue of chloramphenicol. Thiamphenicol is used to treat chicken intestinal infections caused by E. coli.
Specification
| Synonyms | Thiophenicol |
| Storage | Store at -20°C |
| IUPAC Name | 2,2-dichloro-N-[(1R,2R)-1,3-dihydroxy-1-(4-methylsulfonylphenyl)propan-2-yl]acetamide |
| Canonical SMILES | CS(=O)(=O)C1=CC=C(C=C1)C(C(CO)NC(=O)C(Cl)Cl)O |
| InChI | InChI=1S/C12H15Cl2NO5S/c1-21(19,20)8-4-2-7(3-5-8)10(17)9(6-16)15-12(18)11(13)14/h2-5,9-11,16-17H,6H2,1H3,(H,15,18)/t9-,10-/m1/s1 |
| InChI Key | OTVAEFIXJLOWRX-NXEZZACHSA-N |
| Source | Synthetic |
Properties
| Appearance | White to Off-white Solid |
| Application | Anti-Bacterial Agents |
| Antibiotic Activity Spectrum | Gram-positive bacteria; Gram-negative bacteria |
| Boiling Point | 695.9°C at 760 mmHg |
| Melting Point | 163-166°C |
| Density | 1.491 g/cm3 |
| Solubility | Soluble in ethanol, methanol, DMF, DMSO |
Reference Reading
1.Trace determination of antibacterial pharmaceuticals in fishes by microwave-assisted extraction and solid-phase purification combined with dispersive liquid-liquid microextraction followed by ultra-high performance liquid chromatography-tandem mass spectr
Huang P1, Zhao P2, Dai X2, Hou X1, Zhao L3, Liang N4. J Chromatogr B Analyt Technol Biomed Life Sci. 2016 Feb 1;1011:136-44. doi: 10.1016/j.jchromb.2015.12.059. Epub 2016 Jan 2.
A novel pretreatment method involving microwave-assisted extraction and solid-phase purification combined with dispersive liquid-liquid microextraction (MAE-SPP-DLLME) followed by ultra-high performance liquid chromatography-tandem mass spectrometry (UHPLC-MS/MS) was established for the simultaneous determination of six antibacterial pharmaceuticals including metronidazole, tinidazole, chloramphenicol, thiamphenicol, malachite green and crystal violet. The conditions of MAE were optimized using an orthogonal design and the optimal conditions were found to be 8mL for acetonitrile, 50°C for 5min. Then, neutral alumina column was employed in the solid-phase purification. Finally, the critical parameters affecting DLLME, including selection of extraction and dispersive solvent, adjustment of pH, salt concentration, extraction time, were investigated by single factor study. Under optimum conditions, good linearities (r>0.9991) and satisfied recoveries (Recoveries>87.
2.Impact of persulfate and ultraviolet light activated persulfate pre-oxidation on the formation of trihalomethanes, haloacetonitriles and halonitromethanes from the chlor(am)ination of three antibiotic chloramphenicols.
Chu W1, Chu T2, Bond T3, Du E4, Guo Y4, Gao N5. Water Res. 2016 Apr 15;93:48-55. doi: 10.1016/j.watres.2016.02.013. Epub 2016 Feb 11.
Persulfate oxidation processes, with and without activation using ultraviolet light (respectively UV/PS and PS) have the potential to degrade anthropogenic chemicals in water. However, little is known about the impact of PS or UV/PS pre-oxidation on downstream formation of disinfection by-products (DBPs). In this study the three antibiotic chloramphenicols (chloramphenicol and two of its analogues [thiamphenicol and florfenicol], referred to collectively as CAPs), which frequently occur in wastewater-impacted source waters used by drinking water treatment plants, were selected as model antibiotic compounds. The formation of carbonaceous and nitrogenous disinfection by-products, including halomethanes, haloacetonitriles and halonitromethanes, during chlorination and chloramination preceded by PS and UV/PS was investigated. No significant concentrations of haloacetonitriles and halonitromethanes were detected during chlorination. During chloramination chloramphenicol formed a considerable amount of dichloronitromethane (e.
3.Determination of chloramphenicol, thiamphenicol and florfenicol in milk and honey using modified QuEChERS extraction coupled with polymeric monolith-based capillary liquid chromatography tandem mass
Liu HY1, Lin SL1, Fuh MR2. Talanta. 2016 Apr 1;150:233-9. doi: 10.1016/j.talanta.2015.12.045. Epub 2015 Dec 18.
A poly(lauryl methacrylate-co-methacrylic acid-co-ethylene glycol dimethacrylate) [LMA-MAA-EDMA] monolithic column was used to simultaneously determine amphenicol antibiotics (chloramphenicol/CAP, thiamphenicol/TAP, and florfenicol/FF) in milk and honey samples by capillary liquid chromatography tandem mass spectrometry (LC-MS/MS). QuEChERS (quick, easy, cheap, effective, rugged, and safe) method was optimized for sample pretreatment. Good linearity (0.1-15ngg(-1)) and extraction recoveries (95.8-100.2% and 95.6-99.3% for milk and honey samples, respectively; n=3) with minor matrix effect (≦5% ion suppression) were obtained. Limits of detection were estimated at 0.02-0.045ngg(-1). Good intra-day/inter-day precision (0.2-9.1%/0.3-8.7%) and accuracy (90.5-110.0%/93.4-109.3%) were achieved. With more than 200 analyses of real samples, no noticeable carry-over and deterioration of separation efficiency were observed using the monolithic column.
4.Preparation, characterisation and antibacterial activity of a florfenicol-loaded solid lipid nanoparticle suspension.
Wang T1, Chen X1, Lu M1, Li X2, Zhou W3. IET Nanobiotechnol. 2015 Dec;9(6):355-61. doi: 10.1049/iet-nbt.2015.0012.
A florfenicol-loaded solid lipid nanoparticle (FFC-SLN) suspension was prepared by hot homogenisation and ultrasonic technique. The suspension was characterised for its release profile, stability, toxicity, and the physicochemical properties of the nanoparticles. Antibacterial activity of the suspension was evaluated in vitro and in vivo. The results showed that the mean diameter, polydispersity index and zeta potential of the nanoparticles were 253 ± 3 nm, 0.409 ± 0.022 and 47.5 ± 0.21 mV, respectively. In vitro release profile showed the FFC-SLN suspension had sustained release effect. The minimum inhibition concentration values of the FFC-SLN suspension were 6 and 3 µg/mL against Staphylococcus aureus and Escherichia coli respectively, compared with 3.5 and 2 µg/mL of native florfenicol. The suspension was relatively stable at 4°C and less stable at room temperature during 9 months storage. Although the nanoparticle carriers exhibited cytotoxicity in cell cultures, the LD50 of the lyophilised dry power of the suspension was higher than 5 g/kg body weight.
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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 ╳
