CAS 14365-52-7

Sulfamethoxazole N1-glucuronide

Description:

Sulfamethoxazole N1-glucuronide is a metabolite of the antibiotic sulfamethoxazole, which is commonly used in combination with trimethoprim to treat bacterial infections. This compound is characterized by the presence of a glucuronic acid moiety conjugated to the N1 position of the sulfamethoxazole molecule, which enhances its solubility and facilitates excretion from the body. The glucuronidation process is a phase II metabolic reaction that typically occurs in the liver, aiding in the detoxification and elimination of drugs. Sulfamethoxazole N1-glucuronide is generally considered to be less pharmacologically active than its parent compound, sulfamethoxazole. Its presence in biological samples can be indicative of sulfamethoxazole metabolism and is often monitored in pharmacokinetic studies. The compound's CAS number, 14365-52-7, allows for its identification in chemical databases and literature. Overall, sulfamethoxazole N1-glucuronide plays a significant role in understanding the metabolic pathways of sulfonamide antibiotics and their elimination from the body.

Formula: C₁₆H₁₉N₃O₉S

InChI: InChI=1S/C16H19N3O9S/c1-7-6-10(18-28-7)19(29(25,26)9-4-2-8(17)3-5-9)15-13(22)11(20)12(21)14(27-15)16(23)24/h2-6,11-15,20-22H,17H2,1H3,(H,23,24)/t11-,12-,13+,14-,15+/m0/s1

InChI key: InChIKey=BLFOMTRQSZIMKK-SBJFKYEJSA-N

SMILES: N(S(=O)(=O)C1=CC=C(N)C=C1)([C@@H]2O[C@H](C(O)=O)[C@@H](O)[C@H](O)[C@H]2O)C=3C=C(C)ON3

Synonyms:

• β-D-Glucopyranuronic acid, 1-[[(4-aminophenyl)sulfonyl](5-methyl-3-isoxazolyl)amino]-1-deoxy-
• Sulfisomezole N1-glucuronide
• Sulfamethoxazole N1-glucuronide
• 1-[[(4-Aminophenyl)sulfonyl](5-methyl-3-isoxazolyl)amino]-1-deoxy-β-D-glucopyranuronic acid

Sulfamethoxazole b-D-glucuronide

CAS: 14365-52-7

Ref: 7W-GC0561

Sulfamethoxazole β-D-Glucuronide

CAS: 14365-52-7

Applications The main metabolite of Sulfamethoxazole.
References Altenburger, R., et al.: Environ. Toxicol. Chem., 19, 2341 (2000), Pascoe, R., et al.: Anal. Chem., 73, 6014 (2001), Zhaohua, H., et al.: Eur. J. Med. Chem., 36, 863 (2001),

Formula: C₁₆H₁₉N₃O₉S

Color and Shape: Neat

Molecular weight: 429.40

Ref: TR-S699135

Sulfamethoxazole-d4 β-D-Glucuronide

Controlled Product

CAS: 14365-52-7

Applications The main labelled metabolite of Sulfamethoxazole.
References Altenburger, R., et al.: Environ. Toxicol. Chem., 19, 2341 (2000), Pascoe, R., et al.: Anal. Chem., 73, 6014 (2001), Zhaohua, H., et al.: Eur. J. Med. Chem., 36, 863 (2001),

Formula: C₁₆H₁₅D₄N₃O₉S

Color and Shape: Neat

Molecular weight: 433.43

Ref: TR-S699137

Sulfamethoxazole b-D-glucuronide

CAS: 14365-52-7

Sulfamethoxazole b-D-glucuronide is a microbial conjugate that is used to treat bacterial infections. It binds to microbial cell surfaces through covalent bonds, which prevents the synthesis of proteins and DNA, leading to cell death. Sulfamethoxazole b-D-glucuronide has been shown to be activated by the enzyme acetyltransferase in bacteria and may be used as an indicator for the presence of sulfonamide resistance. This antibiotic also has a high affinity for thyroxine and analytes such as acetaminophen and sulfate.

Formula: C₁₆H₁₉N₃O₉S

Purity: Min. 95%

Molecular weight: 429.41 g/mol

Ref: 3D-MS09648