Cefpiramide

Title: Cefpiramide
CAS Registry Number: 70797-11-4
CAS Name: (6R,7R)-7-[[(2R)-[[(4-Hydroxy-6-methyl-3-pyridinyl)carbonyl]amino](4-hydroxyphenyl)acetyl]amino]-3-[[(1-methyl-1H-tetrazol-5-yl)thio]methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
Additional Names: 7-[(R)-2-(4-hydroxy-6-methylnicotinamido)-2-(p-hydroxyphenyl)acetamido]-3-[[(1-methyl-1H-tetrazol-5-yl)thio]methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid; D-7-[(4-hydroxy-6-methylnicotinamido)-4-hydroxyphenylacetamido]-3-(1-methyltetrazol-5-yl)thiomethylcephem-4-carboxylic acid
Molecular Formula: C25H24N8O7S2
Molecular Weight: 612.64
Percent Composition: C 49.01%, H 3.95%, N 18.29%, O 18.28%, S 10.47%
Literature References: Broad spectrum semi-synthetic cephalosporin antibiotic. Prepn: H. Yamada et al., BE 833063; eidem, US 4156724; US 4160087 (1975, 1979, 1979 all to Sumitomo); eidem, JP Kokai 79 119497 (1979 to Sumitomo), C.A. 92, 11042j (1980); I. Isaka et al., JP Kokai 79 30197 (1979 to Yamanouchi), C.A. 91, 57037a (1979); JP Kokai 84 65094 (1984 to Sumitomo), C.A. 101, 110641w (1984). Prepn, NMR data, antibacterial activity: H. Yamada et al., J. Antibiot. 36, 522, 543 (1983). Pharmacokinetics: H. Matsui et al., Antimicrob. Agents Chemother. 22, 213 (1982); K. Sata et al., ibid. 26, 578 (1984). Metabolism: H. Imasaki et al., ibid. 24, 42 (1983). In vitro activity: H. Wexler et al., ibid. 25, 162 (1984); M. A. Pfaller et al., ibid. 368. Comparison with other cephalosporins: N. J. Khan et al., ibid. 26, 585 (1984). Series of articles on in vitro, in vivo activity, determn in body fluids, pharmacokinetics, clinical studies: Chemotherapy (Tokyo) 31, Suppl. 1, 1-842 (1983).
Properties: Yellow crystals, mp 213-215° (dec).
Melting point: mp 213-215° (dec)
Derivative Type: Sodium salt
CAS Registry Number: 74849-93-7
Manufacturers' Codes: SM-1652; Wy-44635
Trademarks: Cefpiran (Sumitomo); Suncefal (Yamanouchi); Sepatren (Sumitomo)
Molecular Formula: C25H23N8NaO7S2
Molecular Weight: 634.62
Percent Composition: C 47.31%, H 3.65%, N 17.66%, Na 3.62%, O 17.65%, S 10.11%
Therap-Cat: Antibacterial.
Keywords: Antibacterial (Antibiotics); ?Lactams; Cephalosporins.
Cefpirome Cefpodoxime Proxetil Cefprozil Cefquinome Cefroxadine

Cefpiramide
Cefpiramide.svg
Systematic (IUPAC) name
(6R)-7-{[(2R)-2-(4-hydroxyphenyl)-2-[(6-methyl-
4-oxo-1H-pyridine-3-carbonyl)amino]acetyl]amino}-
3-[(1-methyltetrazol-5-yl)sulfanylmethyl]-8-oxo-
5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
Clinical data
AHFS/Drugs.com International Drug Names
Legal status  ?
Routes Intravenous, intramuscular
Pharmacokinetic data
Protein binding 93% to 99.3%
Half-life 4.44 hours
Excretion Renal and fecal
Identifiers
CAS number 70797-11-4 YesY
ATC code J01DD11
PubChem CID 636405
DrugBank DB00430
ChemSpider 552192 YesY
UNII P936YA152N YesY
KEGG D03428 YesY
ChEBI CHEBI:59213 YesY
ChEMBL CHEMBL1201204 N
Chemical data
Formula C25H24N8O7S2 
Mol. mass 612.64 g/mol
 N (what is this?)  (verify)

Cefpiramide is a third-generation cephalosporin antibiotic.