Cephapirin

Base Information

• Chemical Name: Cephapirin
• CAS No.: 21593-23-7
• Molecular Formula: C17H17N3O6S2
• Molecular Weight: 423.47
• European Community (EC) Number: 246-194-2,244-466-5
• UNII: 89B59H32VN
• DSSTox Substance ID: DTXSID9022784
• Nikkaji Number: J11.255K
• Wikipedia: Cefapirin
• Wikidata: Q549803
• NCI Thesaurus Code: C61670
• Metabolomics Workbench ID: 43361
• ChEMBL ID: CHEMBL1599
• Mol file: 21593-23-7.mol

Synonyms:BL P 1322;BL-P 1322;BLP 1322;Brisfirina;Céfaloject;Cefadyl;Cefapirin;Cephapirin;Cephapirin Monosodium Salt;Cephapirin Sodium;Cephapirin, Sodium;Monosodium Salt, Cephapirin;Salt, Cephapirin Monosodium;Sodium Cephapirin

Chemical Property of Cephapirin

Chemical Property:

• Appearance/Colour: Beige Solid
• Vapor Pressure: 6.98E-26mmHg at 25°C
• Melting Point: >135 °C (dec.)
• Refractive Index: 1.688
• Boiling Point: 783.902 °C at 760 mmHg
• PKA: 2.67±0.50(Predicted)
• Flash Point: 427.889 °C
• PSA: 179.99000
• Density: 1.573 g/cm³
• LogP: 1.25360
• Storage Temp.: -20?C Freezer, Under Inert Atmosphere
• Solubility.: ≤10mg/ml in DMSO;5mg/ml in dimethyl formamide
• XLogP3: -1.1
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 9
• Rotatable Bond Count: 8
• Exact Mass: 423.05587762
• Heavy Atom Count: 28
• Complexity: 707

Purity/Quality:

99.9% ^*data from raw suppliers

Cefapirin ≥95% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC(=O)OCC1=C(N2C(C(C2=O)NC(=O)CSC3=CC=NC=C3)SC1)C(=O)O
• Isomeric SMILES: CC(=O)OCC1=C(N2[C@@H]([C@@H](C2=O)NC(=O)CSC3=CC=NC=C3)SC1)C(=O)O
• Uses: An antimicrobial agent.
• Therapeutic Function: Antibacterial

Technology Process of Cephapirin

There total 6 articles about Cephapirin 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: 90.0%

Cephapirin benzhydryl ester (78754-13-9) → cephapirin (21593-23-7)

Guidance literature:

With formic acid; at 40 - 45 ℃; for 0.5h; Product distribution;

DOI:10.1248/cpb.30.4545

Reference yield:

pyridine-4-thiol (4556-23-4) + N-bromoacetyl-7-aminocephalosporanic acid (26973-80-8) → cephapirin (21593-23-7)

Guidance literature:

With triethylamine;

DOI:10.1021/jm00270a025

Reference yield:

7-Aminocephalosporanic acid (957-68-6) → cephapirin (21593-23-7)

Guidance literature:

Multi-step reaction with 2 steps

1: aq. NaHCO₃, H₄PO₄

2: Et₃N

With sodium hydrogencarbonate; triethylamine;

DOI:10.1021/jm00270a025

upstream raw materials:

pyridine-4-thiol

N-bromoacetyl-7-aminocephalosporanic acid

Cephapirin benzhydryl ester

7-Aminocephalosporanic acid

Downstream raw materials:

cephapirin Sodium

4-[((6R)-3-acetoxymethyl-2-carboxy-8-oxo-(6rH)-5-thia-1-aza-bicyclo[4.2.0]oct-2-en-7t-ylcarbamoyl)-methylsulfanyl]-1-methyl-pyridinium betaine

Refernces

• 1、 Kametani,Sekine,Honda. "The deblocking of cephalosporin benzhydryl esters with formic acid". . p. 4545 - 4547. Retrieved 2007/10/02.
• 2、 -. "Method for increasing antibacterial effectiveness of a β-lactam antibiotic". . . Retrieved 2008/06/13.