1107004

Chloramphenicol

United States Pharmacopeia (USP) Reference Standard

• Synonym(s): 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
• Linear Formula: Cl₂CHCONHCH(CH₂OH)CH(OH)C₆H₄NO₂
• CAS Number: 56-75-7
• Molecular Weight: 323.13
• UNSPSC Code: 41116107
• NACRES: NA.24
• PubChem Substance ID: 329749306
• MDL number: MFCD00078159
• Beilstein/REAXYS Number: 2225532

Properties

• grade: pharmaceutical primary standard
• API family: chloramphenicol
• manufacturer/tradename: USP
• mp: 149-153 °C (lit.)
• application(s): pharmaceutical (small molecule)
• format: neat
• 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

Description

General description

This product is provided as delivered and specified by the issuing Pharmacopoeia. All information provided in support of this product, including SDS and any product information leaflets have been developed and issued under the Authority of the issuing Ph

Application

Chloramphenicol USP Reference standard, intended for use in specified quality tests and assays as specified in the USP compendia. Also, for use with USP monographs such as:

• Chloramphenicol
• Chloramphenicol Injection
• Chloramphenicol Capsules
• Chloramphenicol Tablets
• Chloramphenicol Sodium Succinate
• Chloramphenicol Ophthalmic Ointment
• Chloramphenicol Compounded Oral Suspension, Veterinary
• Chloramphenicol Sodium Succinate for Injection

Biochem/physiol Actions

Mode of Action: Chloramphenicol inhibits bacterial protein synthesis by blocking the peptidyl transferase step by binding to the 50S ribosomal subunit and preventing attachment of aminoacyl tRNA to the ribosome. It also inhibits mitochondrial and chloroplast protein synthesis and ribosomal formation of (p)ppGpp, de-pressing rRNA transcription.

Mode of Resistance: Use of chloramphenicol acetyltransferase will acetylate the product and inactivate it.

Antimicrobial Spectrum: This is a broad spectrum antibiotic against gram-positive and gram-negative bacteria, and is used mainly for ophthalmic and veterinary purposes.

Analysis Note

These products are for test and assay use only. They are not meant for administration to humans or animals and cannot be used to diagnose, treat, or cure diseases of any kind.  ​

Other Notes

Sales restrictions may apply.

Safety Information

• 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: WGK 3