C0857

Chloramphenicol

meets USP testing specifications

• Synonym(e): D(−)-threo-2,2-Dichlor-N-[β-hydroxy-α-(hydroxymethyl)-β-(4-nitrophenyl)-ethyl]-acetamid, D-(−)-threo-2-Dichloracetamido-1-(4-nitrophenyl)-1,3-propandiol, D-threo-2,2-Dichlor-N-[β-hydroxy-α-(hydroxymethyl)-4-nitrophenethyl]-acetamid, Chloromycetin
• Lineare Formel: Cl₂CHCONHCH(CH₂OH)CH(OH)C₆H₄NO₂
• CAS-Nummer: 56-75-7
• Molekulargewicht: 323.13
• UNSPSC Code: 51102831
• NACRES: NA.21
• PubChem Substance ID: 24892278
• EC Number: 200-287-4
• Beilstein/REAXYS Number: 2225532
• MDL number: MFCD00078159

Eigenschaften

• Quality Segment: 200
• agency: USP/NF, meets USP testing specifications
• assay: 97.0-103.0%
• form: crystalline
• mp: 149-153 °C (lit.)
• solubility: H₂O: insoluble 100% (practically)
• antibiotic activity spectrum: viruses
• application(s): pharmaceutical (small molecule)
• mode of action: protein synthesis | interferes
• storage temp.: 2-8°C
• 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
• InChI key: WIIZWVCIJKGZOK-RKDXNWHRSA-N
• Gene Information: human ... CYP1A2(1544)

Beschreibung

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 10-20 μg/mL and as a selection agent for transformed cells containing chloramphenicol reistance genes.

Biochem/physiol Actions

Wirkungsweise: Chloramphenicol hemmt die bakterielle Proteinsynthese durch Blockierung des Peptidyltransferaseschrittes, indem es an die ribosomale 50S-Untereinheit bindet und die Bindung der Aminoacyl-tRNA an das Ribosom verhindert. Es hemmt auch die mitochondriale und chloroplastische Proteinsynthese und die ribosomale Bildung von (p)ppGpp, wodurch die rRNA-Transkription unterdrückt wird.

Resistenzmechanismus: Die Verwendung von Chloramphenicol-Acetyltransferase führt zur Acetylierung und Inaktivierung des Produkts.

Antimikrobielles Spektrum: Es handelt sich um ein Breitbandantibiotikum gegen grampositive und gramnegative Bakterien, das vor allem in der Augenheilkunde und in der Tiermedizin eingesetzt wird.

Preparation Note

Stock solutions can be prepared directly in the vial at any recommended concentration. A solution at 50 mg/mL in ethanol yields a clear, very faint, yellow solution. 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.

Disclaimer

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.

Sicherheitshinweise

• 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
• Lagerklasse: 11 - Combustible Solids
• ppe: Eyeshields, Gloves, type P3 (EN 143) respirator cartridges