Cephalothin

Base Information

• Chemical Name: Cephalothin
• CAS No.: 153-61-7
• Deprecated CAS: 2073-29-2
• Molecular Formula: C16H16N2O6S2
• Molecular Weight: 396.445
• European Community (EC) Number: 205-815-7
• UNII: R72LW146E6
• DSSTox Substance ID: DTXSID4022783
• Nikkaji Number: J3.273E
• Wikipedia: Cefalotin
• Wikidata: Q2736126
• NCI Thesaurus Code: C62021
• Pharos Ligand ID: 6GZ28JVHSX6H
• Metabolomics Workbench ID: 42806
• ChEMBL ID: CHEMBL617
• Mol file: 153-61-7.mol

Synonyms:Cefalotin;Cefalotina Normon;Cefalotina Sodica Spaly;Ceftina;Cephalothin;Cephalothin Monosodium Salt;Cephalothin, Sodium;Keflin;Monosodium Salt, Cephalothin;Salt, Cephalothin Monosodium;Seffin;Sodium Cephalothin

Chemical Property of Cephalothin

Chemical Property:

• Appearance/Colour: white crystal powder
• Vapor Pressure: 4.25E-24mmHg at 25°C
• Melting Point: 160-161 °C
• Refractive Index: 1.675
• Boiling Point: 757.222 °C at 760 mmHg
• PKA: pKa 2.5 (Uncertain)
• Flash Point: 411.753 °C
• PSA: 166.55000
• Density: 1.569 g/cm³
• LogP: 0.92110
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• Solubility.: DMSO (Sparingly), Dioxane (Slightly), Methanol (Slightly)
• Water Solubility.: 158 MG/L
• XLogP3: -0.4
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 7
• Exact Mass: 396.04497858
• Heavy Atom Count: 26
• Complexity: 680

Purity/Quality:

99% ^*data from raw suppliers

Cephalothin ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC(=O)OCC1=C(N2C(C(C2=O)NC(=O)CC3=CC=CS3)SC1)C(=O)O
• Isomeric SMILES: CC(=O)OCC1=C(N2[C@@H]([C@@H](C2=O)NC(=O)CC3=CC=CS3)SC1)C(=O)O
• Description: Cephalothin is a semisynthetic, beta-lactam, first-generation cephalosporin antibiotic with bactericidal activity. Cephalothin binds to and inactivates penicillin-binding proteins (PBP) located on the inner membrane of the bacterial cell wall. PBPs participate in the terminal stages of assembling the bacterial cell wall, and in reshaping the cell wall during cell division. Inactivation of PBPs interferes with the cross-linkage of peptidoglycan chains necessary for bacterial cell wall strength and rigidity. This results in the weakening of the bacterial cell wall and causes cell lysis.
• Uses: A first generation cephalosporin antibiotic with a wide range antibacterial activity. It is effective against gram-positive and gram-negative bacteria, and has been tested in respiratory disease and neuromuscular junction studies.Cephalothin is most effective against Gram-positive cocci and is also effective against several Gram-negative organisms. First generation cephalosporins are used primarily to treat skin and soft tissue infections caused by Staphylococcus and Streptococcus species. Cephalothin is ineffective against enterococci and evidence of in vitro sensitivity should be discounted.
• Therapeutic Function: Antibacterial
• Clinical Use: Cephalothin is a relatively short acting first generation cephalosporin that is administered injectably. Although cephalothin is not approved for use in any animal species in the United States, the drug is used clinically in veterinary medicine. Cephalothin can cause nephrotoxicity.

Technology Process of Cephalothin

There total 31 articles about Cephalothin 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: 92.0%

2-thienylacetic acid chloride (39098-97-0) + 7-Aminocephalosporanic acid (957-68-6) → cephalothin (153-61-7)

Guidance literature:

7-Aminocephalosporanic acid; With N,O-bis-(trimethylsilyl)-acetamide; In dichloromethane; at 25 - 30 ℃; Inert atmosphere;

2-thienylacetic acid chloride; In dichloromethane; at 10 ℃; for 1h; Temperature; Solvent; Reagent/catalyst; Inert atmosphere;

Reference yield: 85.0%

Thiophene-2-acetic acid (1918-77-0) + 7-Aminocephalosporanic acid (957-68-6) → cephalothin (153-61-7)

Guidance literature:

With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; In dichloromethane; at 30 ℃; for 2h; Time; Reagent/catalyst; Green chemistry;

Reference yield: 70.0%

Thiophene-2-acetic acid (1918-77-0) + 1-methanesulfonyloxy-1,2,3-benzotriazole (54769-22-1) + 3-acetoxymethyl-7-aminoceph-3-em-4-carboxylic acid → cephalothin (153-61-7)

Guidance literature:

With sodium acetate; acetic acid; triethylamine; In dichloromethane;

upstream raw materials:

3-(trimethylsiloxy)-8-oxo-7-(2-(2-thienyl) acetamido)-5-thiazabicyclo [4.2.0]Carboxylic acid

2,2,2-trichloroethyl (6R,7R)-3-acetoxymethyl-7-(thien-2-ylacetamido)ceph-3-em-4-carboxylate

acetic acid

2-thienylacetic acid chloride

Downstream raw materials:

(6R)-3-acetoxymethyl-8-oxo-7t-(2-thiophen-2-yl-acetylamino)-(6rH)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzhydryl ester

acetic acid

p-nitrobenzyl 7β-(2-thienylacetamido)-3-(acetoxymethyl)-3-cephem-4-carboxylate

sodium cephalothin

Refernces

• 1、 -. "Preparation method of cefoxitin lactone". Paragraph 0011; 0044-0045; 0051-0052; 0055-0056. . Retrieved 2020/02/08.
• 2、 -. "Application of cefoxitin sodium pharmaceutical preparations in preoperative infection prevention for transvaginal hysterectomy, laparoscopic hysterectomy and cesarean section". Paragraph 0168-0169; 0174-0175; 0180-0181; 0202-0203. . Retrieved 2019/11/13.