Cephaloridine

Title: Cephaloridine
CAS Registry Number: 50-59-9
CAS Name: 1-[[(6R,7R)-2-Carboxy-8-oxo-7-[(2-thienylacetyl)amino]-5-thia-1-azabicyclo[4.2.0]oct-2-en-3-yl]methyl]pyridinium inner salt
Additional Names: 1-[(7¢-b-[2-(2-thienyl)acetamido]-8¢-oxo-1¢-aza-5¢-thiabicyclo[4.2.0]oct-2¢-en-3¢-yl)methyl]pyridinium-2¢-carboxylate; N-[7-[(2-thienyl)acetamido]ceph-3-em-3-ylmethyl]pyridinium-4-carboxylate; N-[7-(2¢-thienylacetamidoceph-3-ylmethyl)]pyridinium-2-carboxylate; cefaloridin
Trademarks: Ceflorin (Glaxo); Cepaloridin (Glaxo); Cer (Nippon Glaxo); Faredina (Lafare); Ceporan (Glaxo); Ceporin (Glaxo); Cilifor (C.E.P.A.); Intrasporin (Torlan); Keflodin (Lilly); Keflordin (obsolete) (Lilly); Lloncefal (Castillon); Sefacin (Schering); Cepalorin; Deflorin (Glaxo); Kefspor (Lilly); Loridine (Lilly); Ampligram (Hermes); Floridin (Coli)
Molecular Formula: C19H17N3O4S2
Molecular Weight: 415.49
Percent Composition: C 54.92%, H 4.12%, N 10.11%, O 15.40%, S 15.43%
Literature References: Semi-synthetic cephalosporin antibiotic. Prepn: FR 1384197 (1965 to Glaxo), C.A. 63, 11591c (1965); E. H. Flynn, US 3449338 (1969 to Lilly). Toxicity studies: Atkinson et al., Toxicol. Appl. Pharmacol. 8, 398 (1966).
Properties: Crystals. Soluble in water. Aq solns are slightly acid (pH 4.5-5); [a]D +47.7° (c = 1.25 in water). uv max: 239, 252 nm (e 15160, 13950). pKa 3.2. Aq solns (20% w/v) are stable for four weeks at 4° in the dark. Exposure to sunlight causes discoloration. LD50 mice, rats (g/kg): >15, 2.5-4 orally; in monkeys (g/kg): >0.2 i.m. (Atkinson).
pKa: pKa 3.2
Optical Rotation: [a]D +47.7° (c = 1.25 in water)
Absorption maximum: uv max: 239, 252 nm (e 15160, 13950)
Toxicity data: LD50 mice, rats (g/kg): >15, 2.5-4 orally; in monkeys (g/kg): >0.2 i.m. (Atkinson)
Therap-Cat: Antibacterial.
Therap-Cat-Vet: Antibacterial.
Keywords: Antibacterial (Antibiotics); ?Lactams; Cephalosporins.
Cephalosporin C Cephalosporin P1 Cephamycins Cephapirin Sodium Cepharanthine

Cephaloridine
Cefaloridine.svg
Systematic (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
Clinical data
AHFS/Drugs.com International Drug Names
Legal status  ?
Pharmacokinetic data
Excretion Renal
Identifiers
CAS number 50-59-9
ATC code J01DB02
PubChem CID 5773
ChemSpider 5569 YesY
UNII LVZ1VC61HB YesY
KEGG D01075 YesY
ChEMBL CHEMBL316157 YesY
Chemical data
Formula C19H17N3O4S2 
Mol. mass 415.486 g/mol
 YesY (what is this?)  (verify)

Cephaloridine (or cefaloridine) is a first generation semisynthetic derivative of cephalosporin C. It is unique among cephalosporins in that it exists as a zwitterion.