C0378

Chloramphenicol

≥98% (HPLC)

• Sinónimos: D-(−)-threo-2,2-Dichloro-N-[β-hydroxy-α-(hydroxymethyl)-β-(4-nitrophenyl)ethyl]acetamide, D-(−)-threo-2-Dichloroacetamido-1-(4-nitrophenyl)-1,3-propanediol, D-threo-2,2-Dichloro-N-[β-hydroxy-α-(hydroxymethyl)-4-nitrophenethyl]acetamide, Chloromycetin
• Fórmula lineal: Cl₂CHCONHCH(CH₂OH)CH(OH)C₆H₄NO₂
• Número de CAS: 56-75-7
• Peso molecular: 323.13
• Beilstein/REAXYS Number: 2225532
• EC Number: 200-287-4
• MDL number: MFCD00078159
• UNSPSC Code: 51102831
• PubChem Substance ID: 24892250
• NACRES: NA.76

Propiedades

• Quality Level: 200
• assay: ≥98% (HPLC)
• form: powder or crystals
• pKa: 5.5
• mp: 149-153 °C (lit.)
• antibiotic activity spectrum: Gram-negative bacteria; Gram-positive bacteria; mycobacteria; mycoplasma
• mode of action: protein synthesis | interferes
• storage temp.: room temp
• SMILES string: OC[C@@H](NC(=O)C(Cl)Cl)[C@H](O)c1ccc(cc1)[N+]([O-])=O
• InChI: 1S/C11H12Cl2N2O5/c12-10(13)11(18)14-8(5-16)9(17)6-1-3-7(4-2-6)15(19)20/h1-4,8-10,16-17H,5H2,(H,14,18)/t8-,9-/m1/s1

Descripción

General description

Chemical structure: phenicole

Application

Chloramphenicol is a synthetic antibiotic, isolated from strains of Streptomyces venezuelae. It is often used for bacterial selection in molecular biology applications at 10-20μg/mL and as a selection agent for transformed cells containing chloramphenicol reistance genes.
Chloramphenicol has been used as a bacteriostatic non potent antibiotic. It has been used for the selection/growth of positive bacterial cells.

Biochem/physiol Actions

Modo de acción: Inhibe la traducción en las subunidades de ribosomas 50S en la peptidiltransferasa (inhibición de elongación). Bacteriostático.
Modo de resistencia: Acetilación por cloranfenicol-acetiltransferasa (gen cat).

Caution

Stock solutions should be stored at 2-8°C and are stable at 37°C for 5 days. Aqueous solutions are neutral and stable over a wide pH range, with 50% hydrolysis occurring after 290 days. Use of a borax buffered solution reduces this number to 14%. Solutions should be protected from light as photochemical decomposition results in a yellowing of the solution. Heating aqueous solutions at 115°C for 30 minutes results in a 10% loss of chloramphenicol.

Preparation Note

Degradation of chloramphenicol in aqueous solution is catalyzed by general acids and bases. This rate of degradation is independent of the ionic strength and pH.

Other Notes

Keep container tightly closed in a dry and well-ventilated place.

Información de seguridad

• pictograms: GHS08,GHS05
• signalword: Danger
• hcodes: H318,H351,H361fd
• pcodes: P202 - P280 - P305 + P351 + P338 - P308 + P313 - P405 - P501
• Hazard Classifications: Carc. 2 - Eye Dam. 1 - Repr. 2
• Storage Class: 11 - Combustible Solids
• wgk_germany: WGK 3
• ppe: Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges