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Merck

C0857

Chloramphenicol

meets USP testing specifications

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

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Fórmula lineal:
Cl2CHCONHCH(CH2OH)CH(OH)C6H4NO2
Número CAS:
56-75-7
Peso molecular:
323.13
UNSPSC Code:
51102831
NACRES:
NA.21
PubChem Substance ID:
24892278
EC Number:
200-287-4
Beilstein/REAXYS Number:
2225532
MDL number:
MFCD00078159

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InChI key

WIIZWVCIJKGZOK-RKDXNWHRSA-N

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

SMILES string

OC[C@@H](NC(=O)C(Cl)Cl)[C@H](O)c1ccc(cc1)[N+]([O-])=O

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

Quality Level

200

Gene Information

human ... CYP1A2(1544)

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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

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).

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.

pictograms

Health hazardCorrosion
GHS08,GHS05

signalword

Danger

Hazard Classifications

Carc. 2 - Eye Dam. 1 - Repr. 2

Clase de almacenamiento

11 - Combustible Solids

ppe

Eyeshields, Gloves, type P3 (EN 143) respirator cartridges

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Certificados de análisis (COA)

Lot/Batch Number
0000480926
0000480927
0000480926
0000480927
0000472368

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Chloramphenicol eye drops: a dangerous drug?
J Diamond et al.
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