L-(+)-threo-Chloramphenicol

• CAT Number: R050569
• CAS Number: 134-90-7
• Molecular Formula: C11H12Cl2N2O5
• Molecular Weight: 323.126
• Purity: ≥95%
• Synonyms: 2,2-Dichloro-N-[(1S,2S)-2-hydroxy-1-(hydroxymethyl)-2-(4-nitrophenyl)ethyl]acetamide; (+)-Chloramphenicol; (1S,2S)-2-(2,2-Dichloroacetamido)-1-(4-nitrophenyl)?-1,3-propanediol; Dextramycin; Dextromycetin; L-threo-Chloramphenicol; L-threo-Chloroamphe
• Target: Antibiotic
• Storage: -20°C
• IUPAC Name: 2,2-dichloro-N-[(1S,2S)-1,3-dihydroxy-1-(4-nitrophenyl)propan-2-yl]acetamide
• InChI: 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-/m0/s1
• InChIKey: WIIZWVCIJKGZOK-IUCAKERBSA-N
• SMILES: C1=CC(=CC=C1C(C(CO)NC(=O)C(Cl)Cl)O)[N+](=O)[O-]

L-(+)-threo-Chloramphenicol is an antibiotic that belongs to the amphenicol class and is known for its broad-spectrum antibacterial activity. It is primarily used to treat serious bacterial infections, including meningitis, typhoid fever, and infections caused by Haemophilus influenzae. Chloramphenicol works by inhibiting bacterial protein synthesis through binding to the 50S ribosomal subunit, thus preventing peptide bond formation. The L-(+)-threo configuration refers to the specific stereochemistry of the molecule, which is crucial for its biological activity. While effective, its use is limited due to potential side effects, such as bone marrow suppression, leading to conditions like aplastic anemia.