CAS 39751-33-2

Chloramphenicol 3-glucuronide

Description:

Chloramphenicol 3-glucuronide is a metabolite of the antibiotic chloramphenicol, which is known for its broad-spectrum antibacterial properties. This compound is formed through the glucuronidation process, where a glucuronic acid moiety is conjugated to chloramphenicol, enhancing its solubility and facilitating excretion from the body. The chemical structure of chloramphenicol 3-glucuronide includes a glucuronic acid unit linked to the chloramphenicol molecule, which alters its pharmacokinetic properties compared to the parent compound. It is typically found in biological samples, such as urine, following chloramphenicol administration, and is used as a biomarker for exposure to chloramphenicol. The compound is characterized by its relatively high polarity, which affects its interaction with biological systems and its elimination pathways. While chloramphenicol itself is associated with potential side effects, including bone marrow suppression, chloramphenicol 3-glucuronide is generally considered to be less toxic. Its study is important in pharmacology and toxicology, particularly in understanding drug metabolism and the safety profiles of chloramphenicol.

Formula: C₁₇H₂₀Cl₂N₂O₁₁

InChI: InChI=1S/C17H20Cl2N2O11/c18-14(19)15(26)20-8(9(22)6-1-3-7(4-2-6)21(29)30)5-31-17-12(25)10(23)11(24)13(32-17)16(27)28/h1-4,8-14,17,22-25H,5H2,(H,20,26)(H,27,28)/t8-,9-,10+,11+,12-,13+,17-/m1/s1

InChI key: InChIKey=UARPTSDFEIFMJP-PEXHWNMISA-N

SMILES: O(C[C@H]([C@H](O)C1=CC=C(N(=O)=O)C=C1)NC(C(Cl)Cl)=O)[C@@H]2O[C@H](C(O)=O)[C@@H](O)[C@H](O)[C@H]2O

Synonyms:

• β-D-Glucopyranosiduronic acid, (2R,3R)-2-[(dichloroacetyl)amino]-3-hydroxy-3-(4-nitrophenyl)propyl
• (2R,3R)-2-[(2,2-Dichloroacetyl)amino]-3-hydroxy-3-(4-nitrophenyl)propyl β-D-glucopyranosiduronic acid
• β-D-Glucopyranosiduronic acid, (2R,3R)-2-[(2,2-dichloroacetyl)amino]-3-hydroxy-3-(4-nitrophenyl)propyl
• β-D-Glucopyranosiduronic acid, 2-[(dichloroacetyl)amino]-3-hydroxy-3-(4-nitrophenyl)propyl, [R-(R*,R*)]-
• Glucopyranosiduronic acid, 2-(2,2-dichloroacetamido)-3-hydroxy-3-(p-nitrophenyl)propyl, β-D-

Chloramphenicol 3-O-β-D-Glucuronide

CAS: 39751-33-2

Applications The major glucuronide metabolite of Chloramphenicol (C325030).
References Simons, P., et al.: Xenobiotica, 22, 1267 (1992), Kaji, H., et al.: Drug Metab. Dispos., 33, 60 (2005),

Formula: C₁₇H₂₀Cl₂N₂O₁₁

Color and Shape: Off-White

Molecular weight: 499.25

Ref: TR-C325045

Chloramphenicol glucuronide

CAS: 39751-33-2

Chloramphenicol glucuronide is an active metabolite of chloramphenicol. It can be detected in human serum and urine, as well as rat liver microsomes. Chloramphenicol glucuronide binds to the cytosolic protein, cytochrome b5 reductase, which inhibits protein synthesis and cell growth. This compound has been shown to be effective for treating infectious diseases such as typhoid fever, pelvic inflammatory disease, and pneumonia. The chloramphenicol glucuronide group also includes a number of other metabolites that are formed from chloramphenicol by conjugation with glucuronic acid.

Formula: C₁₇H₂₀Cl₂N₂O₁₁

Purity: Min. 95 Area-%

Color and Shape: Powder

Molecular weight: 499.26 g/mol

Ref: 3D-MC09459

Chloramphenicol 3-O-b-D-Glucuronide Sodium Salt

Controlled Product

CAS: 39751-33-2

Applications Chloramphenicol 3-O-β-D-Glucuronide is the major glucuronide metabolite of Chloramphenicol (C325030).
References Simons, P., et al.: Xenobiotica, 22, 1267 (1992); Kaji, H., et al.: Drug Metab. Dispos., 33, 60 (2005)

Formula: C₁₇H₁₉Cl₂N₂NaO₁₁

Color and Shape: Neat

Molecular weight: 521.24

Ref: TR-C325095

Chloramphenicol 3-O-β-D-Glucuronide

CAS: 39751-33-2

Formula: C₁₇H₂₀Cl₂N₂O₁₁

Molecular weight: 499.25

Ref: ST-EA-CP-C161013