219380

Cefotaxime sodium salt

Potent β-lactamase-resistant antibiotic of cephalosporin class. Active against Gram-positive and Gram-negative organisms, including Gram-negative anaerobes. Inhibits cell wall synthesis.

• Synonym(s): 7-[2-(2-Amino-4-thiazolyl)glyoxylamido]-3-(hydroxymethyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate 7²-(Z)-(O-methyloxime) Acetate, Na, Cefotaxim sodium salt
• Empirical Formula (Hill Notation): C₁₆H₁₆N₅NaO₇S₂
• CAS Number: 64485-93-4
• Molecular Weight: 477.45
• UNSPSC Code: 12352200
• Beilstein/REAXYS Number: 5711411
• MDL number: MFCD00079073

Properties

• InChI: 1S/C16H17N5O7S2.Na/c1-6(22)28-3-7-4-29-14-10(13(24)21(14)11(7)15(25)26)19-12(23)9(20-27-2)8-5-30-16(17)18-8;/h5,10,14H,3-4H2,1-2H3,(H2,17,18)(H,19,23)(H,25,26);/q;+1/p-1/b20-9-;/t10-,14-;/m1./s1
• SMILES string: [Na+].[H][C@]12SCC(COC(C)=O)=C(N1C(=O)[C@H]2NC(=O)C(=N/OC)\c3csc(N)n3)C([O-])=O
• InChI key: AZZMGZXNTDTSME-JUZDKLSSSA-M
• assay: ≥91% dry basis (HPLC)
• form: crystalline solid
• optical activity: [α]/D +58 to +64°, c = 1 in H₂O
• manufacturer/tradename: Calbiochem^®
• storage condition: OK to freeze, desiccated (hygroscopic), protect from light
• color: white
• solubility: water: 250 mg/mL
• shipped in: ambient
• storage temp.: 15-25°C

Description

General description

Potent β-lactamase-resistant antibiotic of cephalosporin class. Active against gram-positive and gram-negative organisms, including gram-negative anaerobes. Inhibits cell wall synthesis. Has an optimal pH of 4.5-6.5.

Biochem/physiol Actions

Cefotaxim inhibits bacterial cell wall synthesis by binding to penicillin-binding proteins (PBPs) which inhibits the final transpeptidation step of peptidoglycan synthesis in bacterial cell walls. As a result, bacteria lyse due to cell wall autolytic enzymes.

Mode of Action: Inhibits bacterial cell wall synthesis.

Preparation Note

Following reconstitution, aliquot and freeze (-20°C) for long term storage or refrigerate (4°C) for short-term storage. Stock solutions are stable for up to 10 days at 4°C or for up to 13 weeks at -20°C.

Other Notes

Broad spectrum third generation cephalosporin antibiotic.

Molinari, G., et al. 1991. J. Chemotherap. 3, 6.
Vallee, F., and LeBel, M. 1991. Antimicrob. Agents Chemother. 35, 2057.

Legal Information

CALBIOCHEM is a registered trademark of Merck KGaA, Darmstadt, Germany

Disclaimer

Toxicity: Standard Handling (A)

Safety Information

• pictograms: GHS08
• signalword: Danger
• hcodes: H317,H334
• pcodes: P261 - P272 - P280 - P284 - P302 + P352 - P333 + P313
• Hazard Classifications: Resp. Sens. 1 - Skin Sens. 1
• Storage Class: 11 - Combustible Solids
• wgk: WGK 2
• flash_point_f: Not applicable
• flash_point_c: Not applicable