Cefotaxima

Base Information

• Chemical Name: Cefotaxima
• CAS No.: 63527-52-6
• Molecular Formula: C16H17N5O7S2
• Molecular Weight: 455.472
• Hs Code.: 29419000
• European Community (EC) Number: 264-299-1
• DSSTox Substance ID: DTXSID80860785
• Wikipedia: Cefotaxime
• Wikidata: Q27166288
• ChEMBL ID: CHEMBL4595304
• Mol file: 63527-52-6.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 Cefotaxima

Chemical Property:

• Appearance/Colour: white power
• Refractive Index: 1.778
• PKA: pKa 2.1 (H2O t=20.0 I<0.005 ) (Uncertain);3.4(H2O t=20.0 I<0.005 ) (Uncertain);10.9(H2O t=20.0 I<0.005 ) (Uncertain)
• PSA: 227.05000
• Density: 1.8 g/cm³
• LogP: 0.28750
• Storage Temp.: Hygroscopic, -20°C Freezer, Under inert atmosphere
• Solubility.: DMSO (Slightly), Methanol (Slightly)
• XLogP3: -1.4
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 12
• Rotatable Bond Count: 8
• Exact Mass: 455.05694025
• Heavy Atom Count: 30
• Complexity: 833

Purity/Quality:

99% ^*data from raw suppliers

Cefotaxime ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

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
• Recent EU Clinical Trials: Accelerated treatment of infectious endocarditis
• Description: Like other third-generation cephalosporins, it has excellent anti-Gram-negative activity and is useful institutionally. It has a metabolically vulnerable acetoxy group attached to C-3 and loses approximately 90% of its activity when this is hydrolyzed. This metabolic feature also complicates the pharmacokinetic data, because both active forms are present and have different properties. Cefotaxime should be protected from heat and light and may color slightly without significant loss of potency. Like other third-generation cephalosporins, cefotaxime has less activity against staphylococci but has greater activity against Gram-negative organisms.
• Uses: Cefotaxime has a broad spectrum of antibicrobial use. It acts bactericidally. It is highly active with respect to Gram-negative microorganisms (E. coli, Citrobacter, Proteus mirabilis, P. indole, Providencia, Klebsiella, Serratia), and a few strains of Pseudomonas, H. influenzae that are resistant to other antibiotics. Cefotaxime is less active with respect to streptococci, pneumococci, meningococci, gonococci, and bacteroides. It is resistant to the majority of beta-lacatamases of Gram-positive and Gram-negative microorganisms. This drug is used for severe bacterial infections caused by microorganisms that are sensitive to the drug such as peritonitis, sepsis, abdominal infections, infections of the pelvis minor, infections of the lower respiratory tract, urinary tract, bones, joints, skin, soft tissues, and infected wounds and burns. Synonyms of this drug are claforan, zarivis, and others. Cefotaxime is an antibiotic with broad spectrum activity against Gram positive and Gram negative bacteria.
• Therapeutic Function: Antibiotic
• Clinical Use: Cefotaxime is widely used in neutropenic patients, respiratory infection, meningitis, intra-abdominal sepsis, osteomyelitis, typhoid fever, urinary tract infection, neonatal sepsis and gonorrhea.

Technology Process of Cefotaxima

There total 51 articles about Cefotaxima 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: 95.0%

(Z)-S-benzo[d]thiazol-2-yl 2-(2-aminothiazol-4-yl)-2-(methoxyimino)ethanethioate (80756-85-0) + 7-Aminocephalosporanic acid (957-68-6) → cefotaxime (63527-52-6,152186-43-1)

Guidance literature:

With TEA; In dichloromethane; at 20 ℃; for 1h;

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

Reference yield: 94.4%

diethylthiophosphoryl-(Z)-(2-aminothiazol-4-yl)methoxyimino acetate (162208-27-7) + 7-Aminocephalosporanic acid (957-68-6) → cefotaxime (63527-52-6,152186-43-1)

Guidance literature:

7-Aminocephalosporanic acid; With N,O-bis-(trimethylsilyl)-acetamide; In dichloromethane; at 20 ℃; for 1h;

diethylthiophosphoryl-(Z)-(2-aminothiazol-4-yl)methoxyimino acetate; In dichloromethane; at 20 ℃; for 8h;

With sodium hydroxide; In dichloromethane; water; at 15 - 20 ℃; pH=7.5 - 7.8;

Reference yield: 93.1%

C21H16N6O3S + 7-Aminocephalosporanic acid (957-68-6) → cefotaxime (63527-52-6,152186-43-1)

Guidance literature:

With N,O-bis-(trimethylsilyl)-acetamide; In acetonitrile; at -5 - 0 ℃; for 1h; Temperature;

upstream raw materials:

7-aminocephalosporanic acid

4-(diethylphosphoryl)-2-(2-amino-4-thiazolyl)-2-syn-(2-methoxyimino)acetate

cefotaxime

thiourea

Downstream raw materials:

cefpirome

cefatoxime sodium

ceftriaxone

cefotaxime sodium salt

Refernces

• 1、 -. "Cefotaxime sodium pharmaceutical preparation in the transabdominal or vaginal hysterectomy, gastrointestinal tract and genital tract such as the prevention of infection before the application (by machine translation)". Paragraph 0138-0140; 0143-0145; 0148-0150; 0171-0174. . Retrieved 2019/11/13.
• 2、 -. "Preparation method for cefotaxime acid". Paragraph 0011; 0016. . Retrieved 2017/02/09.