Cefotaxime sodium

Base Information

• Chemical Name: Cefotaxime sodium
• CAS No.: 64485-93-4
• Molecular Formula: C16H16N5NaO7S2
• Molecular Weight: 477.454
• Hs Code.: 29419000
• European Community (EC) Number: 264-299-1,264-915-9
• UNII: 258J72S7TZ
• DSSTox Substance ID: DTXSID4046991
• Wikipedia: Cefotaxime
• NCI Thesaurus Code: C2328
• RXCUI: 203117
• ChEMBL ID: CHEMBL1010
• Mol file: 64485-93-4.mol

Synonyms:Benaxima;Biosint;Cefotaxim;Cefotaxime;Cefotaxime Sodium;Cefradil;Cephotaxim;Claforan;Fotexina;HR 756;HR-756;HR756;Kendrick;Klaforan;Primafen;Ru 24756;Ru-24756;Ru24756;Sodium, Cefotaxime;Taporin

Chemical Property of Cefotaxime sodium

Chemical Property:

• Appearance/Colour: White to pale yellow crystalline powder
• Melting Point: 162-163 °C
• Refractive Index: 61 ° (C=1, H2O)
• PSA: 229.88000
• Density: 1.8 g/cm³
• LogP: -1.04720
• Storage Temp.: 2-8°C
• Solubility.: H2O: aqueous solutions of pH 4.3-6.2 are stable up to 3 weeks at
• Water Solubility.: Soluble in water.
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 12
• Rotatable Bond Count: 8
• Exact Mass: 477.03888450
• Heavy Atom Count: 31
• Complexity: 839

Purity/Quality:

99% ^*data from raw suppliers

Cefotaxime sodium ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn, Xi
• Hazard Codes: Xn,Xi
• Statements: 42/43
• Safety Statements: 22-36/37-60-45-37-24

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)OCC1=C(N2C(C(C2=O)NC(=O)C(=NOC)C3=CSC(=N3)N)SC1)C(=O)[O-].[Na+]
• Isomeric SMILES: CC(=O)OCC1=C(N2[C@@H]([C@@H](C2=O)NC(=O)/C(=N\OC)/C3=CSC(=N3)N)SC1)C(=O)[O-].[Na+]
• Recent ClinicalTrials: LiveSpo Navax? Supports the Treatment of Acute Rhinosinusitis and Otitis Media
• Recent EU Clinical Trials: Short course antibiotic treatment of Gram-negative bacteremia: A multicenter, randomized, non-blinded, non-inferiority interventional study
• Uses: Broad spectrum third generation cephalosporin antibiotic. The name Cefotaxime applies to the isomer having a syn-methoxy imino group Cephalosporin antibacterial Cefotaxime sodium salt acts as a beta-lactamase resistant antibiotic. It is used as an effective antibacterial against gram-negative bacteria, with the notable exception of pseudomonas and penicillin-resistant strains of streptococcus pneumoniae. It is used to treat infections of the bones, joints, skin, respiratory tract and blood stream.
• Therapeutic Function: Antibiotic
• Clinical Use: Cefotaxime (Claforan) was the first third-generationcephalosporin to be introduced. It possesses excellentbroad-spectrum activity against Gram-positive and Gramnegativeaerobic and anaerobic bacteria. It is more activethan moxalactam against Gram-positive organisms. Manyβ-lactamase–producing bacterial strains are sensitive to cefotaxime,including N. gonorrhoeae, Klebsiella spp., H. influenzae,S. aureus, and E. cloacae. Some, but not all,Pseudomonas strains are sensitive. Enterococci and Listeriamonocytogenes are resistant.The syn-isomer of cefotaxime is significantly more activethan the anti-isomer against β-lactamase–producing bacteria.This potency difference is, in part, because of greaterresistance of the syn-isomer to the action of β-lactamases.The higher affinity of the syn-isomer for PBPs, however,may also be a factor.Cefotaxime is metabolized in part to the less active desacetylmetabolite. Approximately 20% of the metaboliteand 25% of the parent drug are excreted in the urine. Theparent drug reaches the cerebrospinal fluid in sufficient concentrationto be effective in the treatment of meningitis.Solutions of cefotaxime sodium should be used within 24hours. If stored, they should be refrigerated. Refrigerated solutionsmaintain potency up to 10 days.

Technology Process of Cefotaxime sodium

There total 7 articles about Cefotaxime sodium which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 95.4%

cefotaxime (63527-52-6,152186-43-1) → cefotaxime sodium salt (64485-93-4)

Guidance literature:

With sodium hydrogencarbonate; In ethanol;

DOI:10.1016/S0014-827X(00)00058-6

Reference yield:

7-Aminocephalosporanic acid (957-68-6) → cefotaxime sodium salt (64485-93-4)

Guidance literature:

7-Aminocephalosporanic acid; In water; acetone; at 10 ℃; for 10h; Large scale;

With sodium hydroxide; In water; acetone; at 10 - 15 ℃; pH=9.5; Temperature; pH-value; Large scale;

Reference yield:

2-(2-amino-1,3-thiazol-4-yl)-2-(methoxyimino)acetic acid (91868-79-0) + (6R,7R)-7-amino-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid (36923-17-8) → cefotaxime sodium salt (64485-93-4)

Guidance literature:

2-(2-amino-1,3-thiazol-4-yl)-2-(methoxyimino)acetic acid; With dmap; dicyclohexyl-carbodiimide; In ethanol; at 20 ℃; for 0.5h;

With 1-hydroxy-pyrrolidine-2,5-dione; In ethanol; at 20 ℃; for 0.5h;

(6R,7R)-7-amino-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid; Further stages;

upstream raw materials:

(6R)-3-acetoxymethyl-7t-[2-(2-amino-thiazol-4-yl)-2-(Z)-methoxyimino-acetylamino]-8-oxo-(6rH)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid

cefotaxime

cefotaxime

7-Aminocephalosporanic acid

Downstream raw materials:

ceftiofur

Refernces

• 1、 -. "Cefotaxime sodium preparation method". Paragraph 0071-0073; 0078-0080; 0085-0087. . Retrieved 2019/04/17.
• 2、 -. "Cefotaxime sodium compound prepared by fluid mechanics principle and preparation of cefotaxime sodium compound". Paragraph 0030; 0031; 0038; 0039; 0040; 0041. . Retrieved 2017/04/28.