117929-10-9

Basic information

• Product Name: cefazolin delta-3-methyl ester
• Synonyms: cefazolin delta-3-methyl ester
• CAS NO: 117929-10-9
• Molecular Formula: C₁₅H₁₆N₈O₄S₃
• Molecular Weight: 468.53374
• Mol File: 117929-10-9.mol

Chemical Properties

• Boiling Point: °Cat760mmHg
• Flash Point: °C
• Appearance: /
• Density: 1.87g/cm³
• Refractive Index: 1.883
• CAS DataBase Reference: cefazolin delta-3-methyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: cefazolin delta-3-methyl ester(117929-10-9)
• EPA Substance Registry System: cefazolin delta-3-methyl ester(117929-10-9)

Safety Data

• Hazardous Substances Data: 117929-10-9(Hazardous Substances Data)

Usage

InChI:InChI=1/C15H16N8O4S3/c1-7-18-19-15(30-7)29-5-8-4-28-13-10(12(25)23(13)11(8)14(26)27-2)17-9(24)3-22-6-16-20-21-22/h4,6,10-11,13H,3,5H2,1-2H3,(H,17,24)/t10-,11?,13-/m1/s1

Upstream product

• 186581-53-3 diazomethane 
• 55390-53-9 delta-2 free acid of cefazolin 
• 684-93-5 1-methyl-1-nitrosourea 
• 79239-19-3 delta-3 methyl ester of cefazolin 

Downstream Products

• 79239-19-3 delta-3 methyl ester of cefazolin 

Relevant articles and documents

Kinetics and mechanism of decomposition of cefazolin ester in phosphate buffer solution

We evaluated the rate and mechanism of decomposition of cefazolin methyl ester (Λ3 ester) in phosphate buffer (pH 8.4). The decomposition of Λ3 ester proceeded simultaneously via 3 pathways. The first pathway is production of Λ2 ester (rate k12) by isomerization and production of Λ2 acid (k23) by hydrolysis of the Λ2 ester. The second pathway is the cleavage reaction of the β-lactam ring and simultaneous elimination of the substituent at position 3 (k14). The third pathway is production of Λ3 acid (k15) by hydrolysis of the carboxylic ester at position 4. Kinetic analysis of each pathway was performed. The reaction rate constant from Λ2 ester to Λ2 acid (k23) was the highest, and the reaction rate constant for the production of Λ2 ester by isomerization (k12) was similar to that for the elimination of the position 3 substituent by cleavage of the β- lactam ring (k14). The rate of production of Λ3 acid by hydrolysis of the position 4 carboxylic ester was the lowest. These results show that Λ3 ester decomposition under a basic condition predominantly occurs through cleavage reaction of the β-lactam ring and Λ2 ester production by isomerization. Since the production of Λ2 acid markedly depended on the production of Λ2 ester by isomerization, Λ2 ester production is the rate- limiting step of this pathway.

Synthesis and mechanisms of decomposition of some cephalosporin prodrugs

The delta-3 and delta-2 methyl esters of cefazolin were synthesized. The kinetics and mechanisms of degradation of the methyl esters and the delta-3 and delta-2 isomers of pivaloxymethyl prodrug esters of the new cephalosporin ceftetrame (Ro 19-5247) were investigated in buffer systems and in human plasma in vitro. The major hydrolytic products of all the delta-3 and delta-2 esters were the inactive delta-2 cephalosporin free acids. In addition, there was evidence of opening of the β-lactam ring to form cephalosporoic acid when the methyl ester of cefazolin was studied in human plasma and in the presence of penicillinase. For the methyl esters, the processes represented by k12, k21, and k20 were operative in buffers; in human plasma, the processes represented by k12, k21, and k20 were operative in addition to cephalosporoic acid formation. For the isomers of the cephalosporin prodrug ester Ro 19-5248 only k12 and k20 were operative in buffers; in human plasma all pathways were operative and there was no evidence of cephalosporoic acid formation. In all cases, the processes represented by k12, k21, and k20 were subject to general and/or specific base catalysis.