CAS 10318-16-8

chloramphenicol 3-acetate

Description:

Chloramphenicol 3-acetate is an ester derivative of chloramphenicol, a broad-spectrum antibiotic originally derived from the bacterium Streptomyces venezuelae. This compound is characterized by its ability to inhibit bacterial protein synthesis by binding to the 50S subunit of the bacterial ribosome. Chloramphenicol 3-acetate is typically a white to off-white crystalline powder, and it is soluble in organic solvents such as ethanol and acetone, but has limited solubility in water. The acetate group enhances its lipophilicity, which can influence its pharmacokinetic properties, including absorption and distribution in biological systems. It is important to note that while chloramphenicol has significant therapeutic applications, its use is often limited due to potential side effects, such as aplastic anemia and gray baby syndrome. As a chemical entity, chloramphenicol 3-acetate is primarily utilized in research and may serve as a prodrug, converting to the active form of chloramphenicol in vivo. Proper handling and safety measures are essential due to its biological activity and potential toxicity.

Formula: C₁₃H₁₄Cl₂N₂O₆

InChI: InChI=1/C13H14Cl2N2O6/c1-7(18)23-6-10(16-13(20)12(14)15)11(19)8-2-4-9(5-3-8)17(21)22/h2-5,10-12,19H,6H2,1H3,(H,16,20)/t10-,11-/m1/s1

InChI key: InChIKey=VVOIFRARHIZCJD-GHMZBOCLSA-N

SMILES: [C@@H]([C@H](O)C1=CC=C(N(=O)=O)C=C1)(NC(C(Cl)Cl)=O)COC(C)=O

Synonyms:

• (2R,3R)-2-[(dichloroacetyl)amino]-3-hydroxy-3-(4-nitrophenyl)propyl acetate
• 3-Acetoxychloramphenicol
• 3-Acetylchloramphenicol
• 3-O-Monoacetylchloramphenicol
• Acetamide, 2,2-dichloro-N-[β-hydroxy-α-(hydroxymethyl)-p-nitrophenethyl]-, α-acetate, <span class="text-smallcaps">D</span>-threo-(-)-
• Acetamide, N-(1-((acetyloxy)methyl)-2-hydroxy-2-(4-nitrophenyl)ethyl)-2,2-dichloro-, (R-(R*,R*))-
• Acetamide, N-[(1R,2R)-1-[(acetyloxy)methyl]-2-hydroxy-2-(4-nitrophenyl)ethyl]-2,2-dichloro-
• Chloramphenicol, acetate
• N-[(1R,2R)-1-[(Acetyloxy)methyl]-2-hydroxy-2-(4-nitrophenyl)ethyl]-2,2-dichloroacetamide
• Chloramphenicol 3-acetate
• Acetamide, 2,2-dichloro-N-[β-hydroxy-α-(hydroxymethyl)-p-nitrophenethyl]-, α-acetate, D-threo-(-)-
• Chloramphenicol Impurity 9

Chloramphenicol Acetate

CAS: 10318-16-8

Chloramphenicol acetate, an acetylated and inactive derivative of chloramphenicol, is synthesized in E. coli and S. aureus through the action of the inducible enzyme chloramphenicol acetyltransferase, utilizing acetyl coenzyme A (acetyl-CoA), to impart resistance to chloramphenicol. This compound exhibits no antibiotic activity against S. sonnei in turbidimetric assays.

Formula: C₁₃H₁₄Cl₂N₂O₆

Color and Shape: Solid

Molecular weight: 365.16

Ref: TM-TN7563

Chloramphenicol 3-Acetate

Controlled Product

CAS: 10318-16-8

Formula: C₁₃H₁₄Cl₂N₂O₆

Color and Shape: Off-White

Molecular weight: 365.17

Ref: TR-C325105

Chloramphenicol 3-Acetate

CAS: 10318-16-8

Formula: C₁₃H₁₄Cl₂N₂O₆

Molecular weight: 365.16

Ref: ST-EA-CP-C161007