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Identification
Name Cefpiramide
Accession Number DB00430 (APRD00856)
Type small molecule
Groups approved
Description

Cefpiramide is a third-generation cephalosporin antibiotic.
Structure Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  • SM-1652
Brand names
  • Cefpiramide [USAN:INN]
  • Cefpiramide Sodium
  • Cefpiramido [INN-Spanish]
  • Cefpiramidum [INN-Latin]
Brand name mixtures Not Available
Categories
  • Anti-Bacterial Agents
  • Cephalosporins
CAS number 70797-11-4
Weight Average: 612.637
Monoisotopic: 612.120936542
Chemical Formula C25H24N8O7S2
InChI Key InChIKey=PWAUCHMQEXVFJR-JIUDAOPXSA-N
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
Plain Text
IUPAC Name
(6R)-7-[(2R)-2-(4-hydroxyphenyl)-2-[(6-methyl-4-oxo-1,4-dihydropyridin-3-yl)formamido]acetamido]-3-{[(1-methyl-1H-1,2,3,4-tetrazol-5-yl)sulfanyl]methyl}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
SMILES
[H][C@]12SCC(CSC3=NN=NN3C)=C(N1C(=O)C2NC(=O)[C@H](NC(=O)C1=CNC(C)=CC1=O)C1=CC=C(O)C=C1)C(O)=O
Plain Text
Mass Spec Not Available
Taxonomy
Kingdom Organic
Classes
  • Phenols and Derivatives
  • Phenethylamines
  • Polypeptides
  • Cephalosporins
Substructures
  • Ethers
  • Hydroxy Compounds
  • Acetates
  • Phenols and Derivatives
  • Amino Ketones
  • Carboxylic Acids and Derivatives
  • Pyridines and Derivatives
  • Benzene and Derivatives
  • Aliphatic and Aryl Amines
  • Beta Lactams
  • Enamines
  • Tetrazoles
  • Phenethylamines
  • Polypeptides
  • Heterocyclic compounds
  • Aromatic compounds
  • Carboxamides and Derivatives
  • Cephalosporins
  • Amino Acids
  • Lactams
  • Imines
  • Azetidines
  • Cyanamides
  • Phenyl Esters
Pharmacology
Indication For treatment of severe infections caused by susceptible bacteria such as P. aeruginosa.
Pharmacodynamics Cefpiramide is a cephalosporin active against Pseudomonas aeruginosa. It has a broad spectrum of antibacterial activity. Cefpiramide works by inhibiting bacterial cell wall biosynthesis. The plasma half-lives of cefpiramide in rabbits, dogs, and rhesus monkeys were much longer than those of cefoperazone and cefazolin.
Mechanism of action The bactericidal activity of cefpiramide results from the inhibition of cell wall synthesis via affinity for penicillin-binding proteins (PBPs).
Absorption Rapidly absorbed following intramuscular injection.
Volume of distribution Not Available
Protein binding Not Available
Metabolism
Route of elimination Not Available
Half life 4.44 hours
Clearance Not Available
Toxicity Adverse effects following overdosage include nausea, vomiting, epigastric distress, diarrhea, and convulsions.
Affected organisms
  • Enteric bacteria and other eubacteria
Pathways Not Available
Pharmacoeconomics
Manufacturers
  • Wyeth ayerst laboratories
Packagers Not Available
Dosage forms Not Available
Prices Not Available
Patents Not Available
Properties
State solid
Melting point Not Available
Experimental Properties
Property Value Source
logP -0.9 PhysProp
Predicted Properties
Property Value Source
water solubility 5.13e-02 g/l ALOGPS
logP 0.85 ALOGPS
logP -0.29 ChemAxon Molconvert
logS -4.08 ALOGPS
pKa 8.43 ChemAxon Molconvert
hydrogen acceptor count 11 ChemAxon Molconvert
hydrogen donor count 5 ChemAxon Molconvert
polar surface area 208.74 ChemAxon Molconvert
rotatable bond count 9 ChemAxon Molconvert
refractivity 166.59 ChemAxon Molconvert
polarizability 59.37 ChemAxon Molconvert
References
Synthesis Reference Not Available
General Reference
  1. Wang H, Yu Y, Xie X, Wang C, Zhang Y, Yuan Y, Zhang X, Liu J, Wang P, Chen M: In-vitro antibacterial activities of cefpiramide and other broad-spectrum antibiotics against 440 clinical isolates in China. J Infect Chemother. 2000 Jun;6(2):81-5. Pubmed
  2. Iakovlev VP, Vishnevskii VA, Khlebnikov EP, Khadin IM, Plavlova MV, Elagina LV, Izotova GN: [Cefpiramide (Tamicin) in the treatment of purulent complications of abdominal surgery] Antibiot Khimioter. 1995 Sep;40(9):30-4. Pubmed
  3. Sampi K, Hattori M: [Comparative study of cefpiramide + amikacin versus piperacillin + amikacin in granulocytopenic patients: a randomized, prospective study] Gan To Kagaku Ryoho. 1992 Aug;19(9):1315-20. Pubmed
External Links
Resource Link
KEGG Drug D01904 Link_out
KEGG Compound C13376 Link_out
PubChem Compound 107654 Link_out
PubChem Substance 46505548 Link_out
ChemSpider 96834 Link_out
ChEBI 59213 Link_out
ChEMBL 59213 Link_out
Therapeutic Targets Database DAP001157 Link_out
Drug Product Database 0 Link_out
Wikipedia http://en.wikipedia.org/wiki/Cefpiramide Link_out
ATC Codes
  • J01DD11
AHFS Codes Not Available
PDB Entries Not Available
FDA label Not Available
MSDS Not Available
Interactions
Drug Interactions
Drug Interaction
Food Interactions Not Available
Targets

1. Peptidoglycan synthetase ftsI

Pharmacological action: yes
Actions: inhibitor

Cell wall formation. Essential for the formation of a septum of the murein sacculus. Synthesis of cross-linked peptidoglycan from the lipid intermediates

Organism class: bacterial
UniProt ID: P0AD68 Link_out
Gene: ftsI
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Fass RJ, Helsel VL: In vitro activity of cefpiramide (SM-1652) against gram-negative bacilli. Diagn Microbiol Infect Dis. 1986 Jan;4(1):77-81. Pubmed
  2. Matsubara N, Minami S, Matsuhashi M, Takaoka M, Mitsuhashi S: Affinity of cefoperazone for penicillin-binding proteins. Antimicrob Agents Chemother. 1980 Jul;18(1):195-9. Pubmed

2. Penicillin-binding protein 1B

Pharmacological action: yes
Actions: inhibitor

Cell wall formation. Synthesis of cross-linked peptidoglycan from the lipid intermediates. The enzyme has a penicillin-insensitive transglycosylase N-terminal domain (formation of linear glycan strands) and a penicillin-sensitive transpeptidase C-terminal domain (cross-linking of the peptide subunits)

Organism class: bacterial
UniProt ID: P02919 Link_out
Gene: mrcB
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Fass RJ, Helsel VL: In vitro activity of cefpiramide (SM-1652) against gram-negative bacilli. Diagn Microbiol Infect Dis. 1986 Jan;4(1):77-81. Pubmed
  2. Matsubara N, Minami S, Matsuhashi M, Takaoka M, Mitsuhashi S: Affinity of cefoperazone for penicillin-binding proteins. Antimicrob Agents Chemother. 1980 Jul;18(1):195-9. Pubmed

3. Penicillin-binding protein 1A

Pharmacological action: yes
Actions: inhibitor

Cell wall formation. Synthesis of cross-linked peptidoglycan from the lipid intermediates. The enzyme has a penicillin-insensitive transglycosylase N-terminal domain (formation of linear glycan strands) and a penicillin-sensitive transpeptidase C-terminal domain (cross-linking of the peptide subunits) (By similarity)

Organism class: bacterial
UniProt ID: Q07806 Link_out
Gene: mrcA Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Pfaller MA, Niles AC, Murray PR: In vitro antibacterial activity of cefpiramide. Antimicrob Agents Chemother. 1984 Mar;25(3):368-72. Pubmed
  2. Fass RJ, Helsel VL: In vitro activity of cefpiramide (SM-1652) against gram-negative bacilli. Diagn Microbiol Infect Dis. 1986 Jan;4(1):77-81. Pubmed
  3. Matsubara N, Minami S, Matsuhashi M, Takaoka M, Mitsuhashi S: Affinity of cefoperazone for penicillin-binding proteins. Antimicrob Agents Chemother. 1980 Jul;18(1):195-9. Pubmed

4. Penicillin-binding protein 1B

Pharmacological action: yes
Actions: inhibitor
Organism class: bacterial
UniProt ID: Q9X6W0 Link_out
Gene: ponB Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Pfaller MA, Niles AC, Murray PR: In vitro antibacterial activity of cefpiramide. Antimicrob Agents Chemother. 1984 Mar;25(3):368-72. Pubmed
  2. Fass RJ, Helsel VL: In vitro activity of cefpiramide (SM-1652) against gram-negative bacilli. Diagn Microbiol Infect Dis. 1986 Jan;4(1):77-81. Pubmed
  3. Matsubara N, Minami S, Matsuhashi M, Takaoka M, Mitsuhashi S: Affinity of cefoperazone for penicillin-binding proteins. Antimicrob Agents Chemother. 1980 Jul;18(1):195-9. Pubmed

5. D-alanyl-D-alanine carboxypeptidase dacC

Pharmacological action: yes
Actions: inhibitor

Removes C-terminal D-alanyl residues from sugar-peptide cell wall precursors

Organism class: bacterial
UniProt ID: P08506 Link_out
Gene: dacC Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Pfaller MA, Niles AC, Murray PR: In vitro antibacterial activity of cefpiramide. Antimicrob Agents Chemother. 1984 Mar;25(3):368-72. Pubmed
  2. Fass RJ, Helsel VL: In vitro activity of cefpiramide (SM-1652) against gram-negative bacilli. Diagn Microbiol Infect Dis. 1986 Jan;4(1):77-81. Pubmed
  3. Matsubara N, Minami S, Matsuhashi M, Takaoka M, Mitsuhashi S: Affinity of cefoperazone for penicillin-binding proteins. Antimicrob Agents Chemother. 1980 Jul;18(1):195-9. Pubmed

6. Penicillin-binding protein 1A

Pharmacological action: yes
Actions: inhibitor

Cell wall formation. Synthesis of cross-linked peptidoglycan from the lipid intermediates. The enzyme has a penicillin-insensitive transglycosylase N-terminal domain (formation of linear glycan strands) and a penicillin-sensitive transpeptidase C-terminal domain (cross-linking of the peptide subunits)

Organism class: bacterial
UniProt ID: P02918 Link_out
Gene: mrcA
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Pfaller MA, Niles AC, Murray PR: In vitro antibacterial activity of cefpiramide. Antimicrob Agents Chemother. 1984 Mar;25(3):368-72. Pubmed
  2. Fass RJ, Helsel VL: In vitro activity of cefpiramide (SM-1652) against gram-negative bacilli. Diagn Microbiol Infect Dis. 1986 Jan;4(1):77-81. Pubmed
  3. Matsubara N, Minami S, Matsuhashi M, Takaoka M, Mitsuhashi S: Affinity of cefoperazone for penicillin-binding proteins. Antimicrob Agents Chemother. 1980 Jul;18(1):195-9. Pubmed

7. Penicillin binding protein 2a

Pharmacological action: no
Actions: inhibitor
Organism class: bacterial
UniProt ID: C1KC03 Link_out
Gene: mecA Link_out
Protein Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Sumita Y, Mitsuhashi S: In vitro synergistic activity between meropenem and other beta-lactams against methicillin-resistant Staphylococcus aureus. Eur J Clin Microbiol Infect Dis. 1991 Feb;10(2):77-84. Pubmed
Carriers

1. Serum albumin

Serum albumin, the main protein of plasma, has a good binding capacity for water, Ca(2+), Na(+), K(+), fatty acids, hormones, bilirubin and drugs. Its main function is the regulation of the colloidal osmotic pressure of blood

UniProt ID: P02768 Link_out
Gene: ALB Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Ohshima T, Hasegawa T, Johno I, Kitazawa S: Protein binding of cefpiramide in the plasma of various species. J Pharm Pharmacol. 1991 Nov;43(11):805-6. Pubmed
Comments
Drug created on June 13, 2005 07:24 / Updated on April 19, 2011 15:03

This project is supported by Genome Alberta & Genome Canada, a not-for-profit organization that is leading Canada's national genomics strategy with $600 million in funding from the federal government. This project is also supported in part by GenomeQuest, Inc., an enterprise genomic information company serving the life science community.