Cephaloridine

Base Information

• Chemical Name: Cephaloridine
• CAS No.: 50-59-9
• Molecular Formula: C19H17 N3 O4 S2
• Molecular Weight: 415.494
• European Community (EC) Number: 200-052-6
• UNII: LVZ1VC61HB
• DSSTox Substance ID: DTXSID9022782
• Wikipedia: Cephaloridine
• Wikidata: Q5063323
• NCI Thesaurus Code: C76594
• Pharos Ligand ID: 6XX8T3F4UTX3
• Metabolomics Workbench ID: 49984
• ChEMBL ID: CHEMBL316157
• Mol file: 50-59-9.mol

Synonyms:Cefaloridine;Cephalomycine;Cephaloridin;Cephaloridine;Ceporin

Chemical Property of Cephaloridine

Chemical Property:

• Melting Point: 184°C
• Refractive Index: 1.6390 (estimate)
• PKA: 3.2(at 25℃)
• PSA: 146.96000
• Density: 1.3230 (rough estimate)
• LogP: 0.01100
• Storage Temp.: 2-8°C
• Water Solubility.: >20g/L(21 oC)
• XLogP3: 1.9
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 5
• Exact Mass: 415.06604838
• Heavy Atom Count: 28
• Complexity: 687

Purity/Quality:

99% ^*data from raw suppliers

Cephaloridine ^*data from reagent suppliers

Safty Information:

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

MSDS Files:

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1C(=C(N2C(S1)C(C2=O)NC(=O)CC3=CC=CS3)C(=O)[O-])C[N+]4=CC=CC=C4
• Isomeric SMILES: C1C(=C(N2[C@H](S1)[C@@H](C2=O)NC(=O)CC3=CC=CS3)C(=O)[O-])C[N+]4=CC=CC=C4
• Description: This was derived by adding two side chains to the nucleus of cephalothin, and has the formula 7-(2-thienyl acetamido)-3-(1-pyridylmethyl)-3-cephem-4-carboxylic acid betaine (Muggleton et al., 1964). Cephaloridine was initially widely used, but it had two main disadvantages. It was an unreliable antistaphylococcal drug, as it was relatively easily hydrolyzed by Staphylococcus aureus beta-lactamase (Laverdiere et al., 1978; Sabath, 1989). Second, cephaloridine was nephrotoxic (Foord, 1975; Appel and Neu, 1977). Marketing of the drug was discontinued in the USA in December 1980. Nowadays, this drug is used very rarely, if at all.
• Uses: Antibacterial agent.
• Therapeutic Function: Antibacterial

Technology Process of Cephaloridine

There total 13 articles about Cephaloridine 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:

pyridine (110-86-1) + 5-Methylene-2-[propylcarbamoyl-(2-thiophen-2-yl-acetylamino)-methyl]-5,6-dihydro-2H-[1,3]thiazine-4-carboxylic acid → propylamine (107-10-8,42939-71-9) + cefaloridine (50-59-9)

Guidance literature:

With potassium chloride; In water; at 30 ℃; Equilibrium constant;

DOI:10.1021/ja00325a019

Reference yield:

2,2,2-trichloroethyl (1S,6R,7R)-3-bromomethyl-7-formamidoceph-3-em-4-carboxylate 1-oxide (33465-56-4) → cefaloridine (50-59-9)

Guidance literature:

Multi-step reaction with 4 steps

1: 1.) phosphorus oxychloride; 2.) dimethylacetamide / 1.) MeOH, 45-55 deg C; 2.) CH₂Cl₂, 0-5 deg C, 45 min

2: 67.3 percent / 1.5 h / 20 °C

3: 72.6 percent / phosphorus trichloride / CH₂Cl₂; dimethylformamide / 1.5 h / 21 °C

4: 1.) Zn, ZnCl₂; 2.) Deacidite FF ion-exchange resin / 1.) formic acid, 22 deg C, 2 h

With ISOPROPYLAMIDE; Deacidite FF ion-exchange resin; zinc(II) chloride; zinc; trichlorophosphate; phosphorus trichloride; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4020(01)88547-1

Reference yield:

pyridine (110-86-1) → cefaloridine (50-59-9)

Guidance literature:

Multi-step reaction with 3 steps

1: 67.3 percent / 1.5 h / 20 °C

2: 72.6 percent / phosphorus trichloride / CH₂Cl₂; dimethylformamide / 1.5 h / 21 °C

3: 1.) Zn, ZnCl₂; 2.) Deacidite FF ion-exchange resin / 1.) formic acid, 22 deg C, 2 h

With Deacidite FF ion-exchange resin; zinc(II) chloride; zinc; phosphorus trichloride; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4020(01)88547-1

upstream raw materials:

pyridine

2,2,2-trichloroethyl (6R,7R)-N-<7-(thien-2-ylacetamido)ceph-3-em-3-ylmethyl>pyridinium chloride 4-carboxylate

2-thienylacetic acid chloride

Thiophene-2-acetic acid

Downstream raw materials:

but-1-yne

2,3-dimethylbutene

3-methyl-but-1-yne

isoprene

Refernces

• 1、 Page,Proctor. "Mechanism of β-lactam ring opening in cephalosporins". . p. 3820 - 3825. Retrieved 2007/10/02.