Cephaloridine Properties, Molecular Formula, Applications - WorldOfChemicals

Cephaloridine Properties

Cephaloridine

Molecule Structure Image

Description

 

Cephaloridine is a cephalosporin compound with pyridinium-1-ylmethyl and 2-thienylacetamido side groups. Cephaloridine is a first generation semisynthetic derivative of cephalosporin C. Cephaloridine can be synthesised from Cephalotin and pyridine by deacetylation. Cephalosporins have a six membered sulfur containing ring adjoining a β lactam ring. Cephaloridine is very active against gram positive cocci and used in a large variety of bacterial infections, such as respiratory tract, skin and urinary tract infections. Antibiotics require constant drug level in body for therapeutic effect. Cephaloridine is, however, highly cytotoxic to the proximal renal tubule, the segment of the nephron responsible for the secretion of organic anions, including para-am-minohippurate (PAH), as well as the various penicillin and cephalosporin antibiotics. Cephaloridine was used to treat 136 bacterial infections in 122 hospitalized patients. Its antibacterial and clinical effectiveness against serious staphylococcal infections compared favorably with that of cephalothin sodium and of penicillinase-resistant penicillins in similar cases. Cephaloridine was highly effective clinically and in eradicating the causative organisms in infections due to pneumococci, streptococci, Escherichia coli, and Proteus mirabilis; but its effectiveness against klebsielleae was variable. Cephaloridine is excreted in the urine without undergoing metabolism. It inhibits organic ion transport in the kidney. This process is preceded by the lipid peroxidation.

Chemical Properties

CAS Number 50-59-9
IUPAC Name (6R,7R)-8-oxo-3-(pyridin-1-ium-1-ylmethyl)-7-[(2-thiophen-2-ylacetyl)amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate
InChI 1S/C19H17N3O4S2/c23-14(9-13-5-4-8-27-13)20-15-17(24)22-16(19(25)26)12(11-28-18(15)22)10-21-6-2-1-3-7-21/h1-8,15,18H,9-11H2,(H-,20,23,25,26)/t15-,18-/m1/s1
InChIKey CZTQZXZIADLWOZ-CRAIPNDOSA-N
Molar Mass 415.486 g/mol
Molecular Formula C19H17N3O4S2
Synonyms Cefaloridine;N-[7-(2'-Thienylacetamidoceph-3-ylmethyl)]pyridinium-2-carboxylate
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