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3-Desacetyl Cefotaxime

3-Desacetyl Cefotaxime is a desacetylated derivative of the cephalosporin antibiotic Cefotaxime, characterized by the absence of the acetyl group at the 3-position of the beta-lactam ring. Its structure retains the 7-aminocephalosporanic acid (7-ACA) core, featuring a thiazole ring fused to the beta-lactam, a sulfur-containing side chain, and a 2-aminothiazolyl group at position 3. The molecule contains multiple functional groups, including a free amino group, carboxylic acid, and sulfhydryl moiety, critical for its role as a synthetic intermediate. This impurity arises during Cefotaxime synthesis via partial deacetylation and serves as an HPLC reference standard for quantifying process-related impurities in parenteral formulations.

On Request
Molecular Formula C14H15N5O6S2
Molecular Weight 413.4000
CAS Number 66340-28-1 โœ“ Verified
PubChem CID 9576239 โ†—
Purity N/A
Product Type API Impurity
Parent Drug Cefotaxime
Lead Time On Request
IUPAC Name (6R,7R)-7-[[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-methoxyiminoacetyl]amino]-3-(hydroxymethyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

๐Ÿ“ Synonyms

Desacetylcefotaxime 66340-28-1 Deacetylcefotaxime 6E65O1Y1P8 DTXSID801315709 5-Thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acid, 7-(((2-amino-4-thiazolyl)(methoxyimino)acetyl)amino)-3-(hydroxymethyl)-8-oxo-, (6R-(6alpha,7beta(Z)))- 5-Thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acid, 7-(((2Z)-(2-amino-4-thiazolyl)(methoxyimino)acetyl)amino)-3-(hydroxymethyl)-8-oxo-, (6R,7R)- (6R,7R)-7-(((2Z)-1-hydroxy-2-(2-imino-2,3-dihydro-1,3-thiazol-4-yl)-2-(methoxyimino)ethylidene)amino)-3-(hydroxymethyl)-8-oxo-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acid (6R,7R)-7-{[(2Z)-1-hydroxy-2-(2-imino-2,3-dihydro-1,3-thiazol-4-yl)-2-(methoxyimino)ethylidene]amino}-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-[[(2-amino-4-thiazolyl)(methoxyimino)acetyl]amino]-3-(hydroxymethyl)-8-oxo-, [6R-[6alpha,7beta(Z)]]-

๐Ÿ”ฌ Chemical Identifiers

CO/N=C(/C1=CSC(=N1)N)\C(=O)N[C@H]2[C@@H]3N(C2=O)C(=C(CS3)CO)C(=O)O
InChI=1S/C14H15N5O6S2/c1-25-18-7(6-4-27-14(15)16-6)10(21)17-8-11(22)19-9(13(23)24)5(2-20)3-26-12(8)19/h4,8,12,20H,2-3H2,1H3,(H2,15,16)(H,17,21)(H,23,24)/b18-7-/t8-,12-/m1/s1
FHYWAOQGXIZAAF-GHXIOONMSA-N

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