CAS 56271-94-4

(6R,7R)-7-[[(2Z)-2-(2-Furanyl)-2-(methoxyimino)acetyl]amino]-3-(hydroxymethyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

Description:

The chemical substance with the name "(6R,7R)-7-[[(2Z)-2-(2-Furanyl)-2-(methoxyimino)acetyl]amino]-3-(hydroxymethyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid" and CAS number "56271-94-4" is a complex bicyclic compound that belongs to the class of antibiotics known as cephalosporins. It features a thiazolidine ring and a bicyclic structure, which contributes to its biological activity. The presence of a methoxyimino group enhances its stability against certain beta-lactamases, making it effective against a range of bacterial infections. The furan ring in its structure may also play a role in its pharmacological properties. This compound exhibits characteristics typical of beta-lactam antibiotics, including the ability to inhibit bacterial cell wall synthesis, which is crucial for its antimicrobial efficacy. Its stereochemistry, indicated by the (6R,7R) configuration, is essential for its biological activity, influencing how it interacts with bacterial enzymes. Overall, this compound represents a significant advancement in antibiotic development, targeting resistant bacterial strains.

Formula: C₁₅H₁₅N₃O₇S

InChI: InChI=1S/C15H15N3O7S/c1-24-17-9(8-3-2-4-25-8)12(20)16-10-13(21)18-11(15(22)23)7(5-19)6-26-14(10)18/h2-4,10,14,19H,5-6H2,1H3,(H,16,20)(H,22,23)/b17-9-/t10-,14-/m1/s1

InChI key: InChIKey=OUSLHGWWWMRAIG-FBCAJUAOSA-N

SMILES: C(O)(=O)C=1N2[C@@]([C@H](NC(/C(=N\OC)/C3=CC=CO3)=O)C2=O)(SCC1CO)[H]

Synonyms:

• (6R,7R)-7-[[(2Z)-2-(2-Furanyl)-2-(methoxyimino)acetyl]amino]-3-(hydroxymethyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
• (6R-(6alpha,7beta(Z)))-7-(2-Furyl(methoxyimino)acetamido)-3-(hydroxymethyl)-8-oxo-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acid
• 5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid, 7-[[(2Z)-2-(2-furanyl)-2-(methoxyimino)acetyl]amino]-3-(hydroxymethyl)-8-oxo-, (6R,7R)-
• 5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid, 7-[[(2Z)-2-furanyl(methoxyimino)acetyl]amino]-3-(hydroxymethyl)-8-oxo-, (6R,7R)-
• 5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid, 7-[[2-furanyl(methoxyimino)acetyl]amino]-3-(hydroxymethyl)-8-oxo-, [6R-[6α,7β(Z)]]-
• 7-{[(2E)-2-(furan-2-yl)-2-(methoxyimino)acetyl]amino}-3-(hydroxymethyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

(6R,7R)-7-((Z)-2-(Furan-2-yl)-2-(methoxyimino)acetamido)-3-(hydroxymethyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

CAS: 56271-94-4

Formula: C₁₅H₁₅N₃O₇S

Color and Shape: Solid

Molecular weight: 381.3605

Ref: IN-DA00DF5Z

Cefuroxime EP Impurity A (Descarbamoyl Cefuroxime)

CAS: 56271-94-4

Formula: C₁₅H₁₅N₃O₇S

Molecular weight: 381.36

Ref: 4Z-C-445006

Cefuroxime EP Impurity A

CAS: 56271-94-4

Formula: C₁₅H₁₅N₃O₇S

Molecular weight: 381.36

Ref: ST-EA-CP-C265001

Descarbamoyl Cefuroxime

Controlled Product

CAS: 56271-94-4

Impurity Cefuroxime Sodium EP Impurity A
Stability Hygroscopic
Applications Descarbamoyl Cefuroxime (Cefuroxime Sodium EP Impurity A) is a degradation product of Cefuroxime, and an intermediate for the synthesis of Cephalosporin antibiotics
References Nomura, H., et al.: J. Med. Chem., 17, 12 (1974), Takaya, T., et al.: J. Antibiotics, 34, 1300 (1981), Wang, D., et al.: J. Pharm. Sci., 83, 577 (1994), Okamoto, Y., et al.: J. Pharm. Sci., 85, 985 (1996),

Formula: C₁₅H₁₅N₃O₇S

Color and Shape: Neat

Molecular weight: 381.36

Ref: TR-D288830

Descarbamoyl cefuroxime

CAS: 56271-94-4

Descarbamoyl cefuroxime is also an intermediate in the synthesis of cephalosporin antibiotics. Decarbamyl cefuroxime is a degradation product of cefuroxime.

Formula: C₁₅H₁₅N₃O₇S

Purity: 98%

Color and Shape: Solid

Molecular weight: 381.36

Ref: TM-T11000

Descarbamoyl Cefuroxime-d3

Controlled Product

CAS: 56271-94-4

Applications A degradation product of labelled Cefuroxime, and an intermediate for the synthesis of labelled Cephalosporin antibiotics
References Nomura, H., et al.: J. Med. Chem., 17, 12 (1974), Takaya, T., et al.: J. Antibiotics, 34, 1300 (1981), Wang, D., et al.: J. Pharm. Sci., 83, 577 (1994), Okamoto, Y., et al.: J. Pharm. Sci., 85, 985 (1996),

Formula: C₁₅D₃H₁₂N₃O₇S

Color and Shape: Neat

Molecular weight: 384.379

Ref: TR-D288832

Descarbamoyl cefuroxime

CAS: 56271-94-4

Descarbamoyl cefuroxime is a prodrug that is hydrolyzed in vivo to cefuroxime, its active form. It can be prepared by acylation of cefuroxime with an organic acid chloride, such as acetyl chloride or propionyl chloride. The reaction is catalyzed by a strong base, such as sodium hydride or potassium tert-butoxide. Descarbamoyl cefuroxime has been shown to be effective against Staphylococcus aureus and Clostridium perfringens, although is not active against acid-fast bacteria such as Mycobacterium tuberculosis or Mycobacterium avium complex. This drug has shown anti-inflammatory properties, which may be due to its inhibition of prostaglandin synthesis.

Formula: C₁₅H₁₅N₃O₇S

Purity: Min. 95%

Molecular weight: 381.36 g/mol

Ref: 3D-FD21151