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Cefpiramide

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Chemical compound

Pharmaceutical compound

Cefpiramide
Clinical data

AHFS/Drugs.com	International Drug Names
Routes of administration	Intravenous,intramuscular
ATC code	J01DD11 (WHO)
Pharmacokinetic data
Protein binding	93% to 99.3%
Eliminationhalf-life	4.44 hours
Excretion	Renal and fecal
Identifiers
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
CAS Number	70797-11-4^Y
PubChemCID	636405
DrugBank	DB00430^Y
ChemSpider	552192^Y
UNII	P936YA152N
KEGG	D03428^Y
ChEBI	CHEBI:59213^Y
ChEMBL	ChEMBL1201204^N
CompTox Dashboard(EPA)	DTXSID6046630
Chemical and physical data
Formula	C₂₅H₂₄N₈O₇S₂
Molar mass	612.64 g·mol⁻¹
3D model (JSmol)	Interactive image
Melting point	213 to 215 °C (415 to 419 °F) (dec.)
SMILES O=C2N1/C(=C(\CS[C@@H]1[C@@H]2NC(=O)[C@@H](c3ccc(O)cc3)NC(=O)C\4=C\N\C(=C/C/4=O)C)CSc5nnnn5C)C(=O)O
InChI InChI=1S/C25H24N8O7S2/c1-11-7-16(35)15(8-26-11)20(36)27-17(12-3-5-14(34)6-4-12)21(37)28-18-22(38)33-19(24(39)40)13(9-41-23(18)33)10-42-25-29-30-31-32(25)2/h3-8,17-18,23,34H,9-10H2,1-2H3,(H,26,35)(H,27,36)(H,28,37)(H,39,40)/t17-,18-,23-/m1/s1^Y Key:PWAUCHMQEXVFJR-PMAPCBKXSA-N^Y
^NY (what is this?) (verify)

Cefpiramide is a third-generationcephalosporin antibiotic.^{[citation needed]}

References

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External links

[edit]

Wang H, Yu Y, Xie X, Wang C, Zhang Y, Yuan Y, Zhang X, Liu J, Wang P, Chen M (2000). "In-vitro antibacterial activities of cefpiramide and other broad-spectrum antibiotics against 440 clinical isolates in China".J Infect Chemother.6 (2):81–85.doi:10.1007/PL00012156.PMID 11810540.S2CID 30532462.
Iakovlev V, Vishnevskiĭ V, Khlebnikov E, Khadin I, Plavlova M, Elagina L, Izotova G (1995). "[Cefpiramide (Tamicin) in the treatment of purulent complications of abdominal surgery]".Antibiot Khimioter.40 (9):30–4.PMID 8651827.
Sampi K, Hattori M (1992). "[Comparative study of cefpiramide + amikacin versus piperacillin + amikacin in granulocytopenic patients: a randomized, prospective study]".Gan to Kagaku Ryoho.19 (9):1315–20.PMID 1503486.

Antibacterials active on thecell wall andenvelope (J01C-J01D)

β-lactams
(inhibit synthesis
of peptidoglycan
layer of bacterial
cell wall by binding
to and inhibiting
PBPs, a group of
D-alanyl-D-alanine
transpeptidases)

Penicillins (Penams)

Narrow
spectrum

β-lactamase sensitive (1st generation)	Benzylpenicillin (G)^# Benzathine benzylpenicillin^# Procaine benzylpenicillin^# Phenoxymethylpenicillin (V)^# Propicillin^‡ Pheneticillin^‡ Azidocillin^‡ Clometocillin^‡ Penamecillin^‡
β-lactamase resistant (2nd generation)	Cloxacillin^# (Dicloxacillin Flucloxacillin) Oxacillin Nafcillin Methicillin^‡

Extended
spectrum

Aminopenicillins (3rd generation)	Amoxicillin^# Ampicillin^# (Pivampicillin Hetacillin^‡ Bacampicillin^‡ Lenampicillin Metampicillin^‡ Talampicillin^‡) Epicillin^‡
Carboxypenicillins (4th generation)	Ticarcillin Carbenicillin^‡ /Carindacillin^‡ Temocillin^‡
Ureidopenicillins (4th generation)	Piperacillin Azlocillin^‡ Mezlocillin^‡
Other	Mecillinam (Pivmecillinam) Sulbenicillin^‡

Carbapenems /Penems

Cephems
Cephalosporins
Cephamycins
Carbacephems

1st generation	Cefazolin^# Cefalexin^# Cefadroxil Cefapirin Cefazedone^‡ Cefazaflur^‡ Cefradine^‡ Cefroxadine^‡ Ceftezole^‡ Cefaloglycin^‡ Cefacetrile^‡ Cefalonium^‡ Cefaloridine^‡ Cefalotin Cefatrizine^‡
2nd generation	Cefaclor Cefprozil Cefuroxime Cefuroxime axetil Cefamandole^‡ Cefonicid^‡ Ceforanide^‡ Cefuzonam^‡ Cephamycin (Cefoxitin Cefotetan Cefminox^‡ Cefbuperazone^‡ Cefmetazole^‡) Carbacephem (Loracarbef^‡)
3rd generation	Cefixime^# Ceftriaxone^# Cefotaxime^# Antipseudomonal (Ceftazidime^# Cefoperazone) Cefdinir Cefcapene Cefdaloxime Ceftizoxime Cefmenoxime Cefpiramide Cefpodoxime Ceftibuten Cefditoren Cefotiam^‡ Cefetamet^‡ Cefodizime^‡ Cefpimizole^‡ Cefsulodin^‡ Cefteram^‡ Ceftiolene^‡ Oxacephem (Flomoxef Latamoxef^‡)
4th generation	Cefepime Cefozopran^‡ Cefpirome Cefquinome^‡
5th generation	Ceftaroline fosamil Ceftolozane Ceftobiprole
Siderophore	Cefiderocol^#
Veterinary	Ceftiofur Cefquinome Cefovecin

Monobactams

β-lactamase inhibitors

Combinations

Polypeptides

Lipopeptides	Insert into bacterial cell wall causing perforation and depolarization:Daptomycin Surfactin
Other	Inhibits PG elongation and crosslinking:Ramoplanin^§

Intracellular

InhibitPG subunit synthesis and transport:NAM synthesis inhibition
- Fosfomycin
DADAL/AR inhibitors
- Cycloserine
- Terizidone
bactoprenol inhibitors
- Bacitracin

Other

^#WHO-EM
^‡Withdrawn from market
Clinical trials:
- ^†Phase III
- ^§Never to phase III

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