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Identification
NameCefpiramide
Accession NumberDB00430  (APRD00856)
TypeSmall Molecule
GroupsApproved
DescriptionCefpiramide is a third-generation cephalosporin antibiotic.
Structure
Thumb
Synonyms
Cefpiramide
Cefpiramido
Cefpiramidum
External Identifiers
  • SM-1652
Approved Prescription ProductsNot Available
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International BrandsNot Available
Brand mixturesNot Available
Salts
Name/CASStructureProperties
Cefpiramide Sodium
Thumb
  • InChI Key: RIWWMGQFMUUYIY-ALLHVENQSA-M
  • Monoisotopic Mass: 634.102881185
  • Average Mass: 634.619
DBSALT000624
Categories
UNIIP936YA152N
CAS number70797-11-4
WeightAverage: 612.637
Monoisotopic: 612.120936542
Chemical FormulaC25H24N8O7S2
InChI KeyPWAUCHMQEXVFJR-PMAPCBKXSA-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
IUPAC Name
(6R,7R)-7-[(2R)-2-[(4-hydroxy-6-methylpyridin-3-yl)formamido]-2-(4-hydroxyphenyl)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)[C@@]2([H])NC(=O)[[email protected]](NC(=O)C1=C(O)C=C(C)N=C1)C1=CC=C(O)C=C1)C(O)=O
Pharmacology
IndicationFor treatment of severe infections caused by susceptible bacteria such as P. aeruginosa.
Structured Indications Not Available
PharmacodynamicsCefpiramide 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 actionThe bactericidal activity of cefpiramide results from the inhibition of cell wall synthesis via affinity for penicillin-binding proteins (PBPs).
TargetKindPharmacological actionActionsOrganismUniProt ID
Peptidoglycan synthase FtsIProteinyes
inhibitor
Escherichia coli (strain K12)P0AD68 details
Penicillin-binding protein 1BProteinyes
inhibitor
Escherichia coli (strain K12)P02919 details
Penicillin-binding protein 1AProteinyes
inhibitor
Pseudomonas aeruginosa (strain ATCC 15692 / PAO1 / 1C / PRS 101 / LMG 12228)Q07806 details
Penicillin-binding protein 1BProteinyes
inhibitor
Pseudomonas aeruginosaQ9X6W0 details
D-alanyl-D-alanine carboxypeptidase DacCProteinyes
inhibitor
Escherichia coli (strain K12)P08506 details
Penicillin-binding protein 1AProteinyes
inhibitor
Escherichia coli (strain K12)P02918 details
Penicillin binding protein 2aProteinno
inhibitor
Staphylococcus aureusC1KC03 details
Related Articles
AbsorptionRapidly absorbed following intramuscular injection.
Volume of distributionNot Available
Protein bindingNot Available
MetabolismNot Available
Route of eliminationNot Available
Half life4.44 hours
ClearanceNot Available
ToxicityAdverse effects following overdosage include nausea, vomiting, epigastric distress, diarrhea, and convulsions.
Affected organisms
  • Enteric bacteria and other eubacteria
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
Interactions
Drug Interactions
DrugInteractionDrug group
BcgThe therapeutic efficacy of Bcg can be decreased when used in combination with Cefpiramide.Investigational
Picosulfuric acidThe therapeutic efficacy of Picosulfuric acid can be decreased when used in combination with Cefpiramide.Approved
Food InteractionsNot Available
References
Synthesis ReferenceNot Available
General References
  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:11810540 ]
  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:8651827 ]
  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:1503486 ]
External Links
ATC CodesJ01DD11
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSNot Available
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption-0.9183
Blood Brain Barrier-0.9936
Caco-2 permeable-0.7804
P-glycoprotein substrateSubstrate0.7714
P-glycoprotein inhibitor INon-inhibitor0.9068
P-glycoprotein inhibitor IINon-inhibitor0.8039
Renal organic cation transporterNon-inhibitor0.8634
CYP450 2C9 substrateNon-substrate0.7608
CYP450 2D6 substrateNon-substrate0.8257
CYP450 3A4 substrateSubstrate0.5139
CYP450 1A2 substrateNon-inhibitor0.8399
CYP450 2C9 inhibitorNon-inhibitor0.7766
CYP450 2D6 inhibitorNon-inhibitor0.8715
CYP450 2C19 inhibitorNon-inhibitor0.7565
CYP450 3A4 inhibitorNon-inhibitor0.7794
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.5
Ames testNon AMES toxic0.7018
CarcinogenicityNon-carcinogens0.9052
BiodegradationNot ready biodegradable0.7805
Rat acute toxicity2.2438 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9111
hERG inhibition (predictor II)Non-inhibitor0.5656
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Pharmacoeconomics
Manufacturers
  • Wyeth ayerst laboratories
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
StateSolid
Experimental Properties
PropertyValueSource
logP-0.9Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.0668 mg/mLALOGPS
logP0.53ALOGPS
logP0.22ChemAxon
logS-4ALOGPS
pKa (Strongest Acidic)3.47ChemAxon
pKa (Strongest Basic)2.66ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count11ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area212.76 Å2ChemAxon
Rotatable Bond Count9ChemAxon
Refractivity164.81 m3·mol-1ChemAxon
Polarizability58.79 Å3ChemAxon
Number of Rings5ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as cephalosporins. These are compounds containing a 1,2-thiazine fused to a 2-azetidinone to for a oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid moiety or a derivative thereof.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassLactams
Sub ClassBeta lactams
Direct ParentCephalosporins
Alternative Parents
Substituents
  • Cephalosporin
  • N-acyl-alpha amino acid or derivatives
  • Alpha-amino acid amide
  • Phenylacetamide
  • Alpha-amino acid or derivatives
  • N-substituted-alpha-amino acid
  • Pyridine carboxylic acid or derivatives
  • Nicotinamide
  • Methylpyridine
  • Hydroxypyridine
  • Alkylarylthioether
  • Phenol
  • Pyridine
  • Meta-thiazine
  • Heteroaromatic compound
  • Vinylogous acid
  • Tetrazole
  • Tertiary carboxylic acid amide
  • Azole
  • Tertiary amine
  • Secondary carboxylic acid amide
  • Carboxamide group
  • Azetidine
  • Azacycle
  • Dialkylthioether
  • Sulfenyl compound
  • Hemithioaminal
  • Thioether
  • Monocarboxylic acid or derivatives
  • Enamine
  • Carboxylic acid
  • Carboxylic acid derivative
  • Carboxylic acid amide
  • Hydrocarbon derivative
  • Organosulfur compound
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Amine
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors

Targets

Kind
Protein
Organism
Escherichia coli (strain K12)
Pharmacological action
yes
Actions
inhibitor
General Function:
Peptidoglycan glycosyltransferase activity
Specific Function:
Essential cell division protein that is required for the synthesis of peptidoglycan at the division septum (PubMed:1103132, PubMed:9614966). Catalyzes the synthesis of cross-linked peptidoglycan from the lipid-linked precursors (PubMed:7030331). Required for localization of FtsN (PubMed:9282742).
Gene Name:
ftsI
Uniprot ID:
P0AD68
Molecular Weight:
63876.925 Da
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:3943292 ]
  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:6448021 ]
Kind
Protein
Organism
Escherichia coli (strain K12)
Pharmacological action
yes
Actions
inhibitor
General Function:
Serine-type d-ala-d-ala carboxypeptidase activity
Specific Function:
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).
Gene Name:
mrcB
Uniprot ID:
P02919
Molecular Weight:
94291.875 Da
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:3943292 ]
  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:6448021 ]
Kind
Protein
Organism
Pseudomonas aeruginosa (strain ATCC 15692 / PAO1 / 1C / PRS 101 / LMG 12228)
Pharmacological action
yes
Actions
inhibitor
General Function:
Transferase activity, transferring glycosyl groups
Specific Function:
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).
Gene Name:
mrcA
Uniprot ID:
Q07806
Molecular Weight:
91198.715 Da
References
  1. Pfaller MA, Niles AC, Murray PR: In vitro antibacterial activity of cefpiramide. Antimicrob Agents Chemother. 1984 Mar;25(3):368-72. [PubMed:6426381 ]
  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:3943292 ]
  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:6448021 ]
Kind
Protein
Organism
Pseudomonas aeruginosa
Pharmacological action
yes
Actions
inhibitor
General Function:
Peptidoglycan glycosyltransferase activity
Specific Function:
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).
Gene Name:
ponB
Uniprot ID:
Q9X6W0
Molecular Weight:
85486.615 Da
References
  1. Pfaller MA, Niles AC, Murray PR: In vitro antibacterial activity of cefpiramide. Antimicrob Agents Chemother. 1984 Mar;25(3):368-72. [PubMed:6426381 ]
  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:3943292 ]
  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:6448021 ]
Kind
Protein
Organism
Escherichia coli (strain K12)
Pharmacological action
yes
Actions
inhibitor
General Function:
Serine-type d-ala-d-ala carboxypeptidase activity
Specific Function:
Removes C-terminal D-alanyl residues from sugar-peptide cell wall precursors.
Gene Name:
dacC
Uniprot ID:
P08506
Molecular Weight:
43608.595 Da
References
  1. Pfaller MA, Niles AC, Murray PR: In vitro antibacterial activity of cefpiramide. Antimicrob Agents Chemother. 1984 Mar;25(3):368-72. [PubMed:6426381 ]
  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:3943292 ]
  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:6448021 ]
Kind
Protein
Organism
Escherichia coli (strain K12)
Pharmacological action
yes
Actions
inhibitor
General Function:
Serine-type d-ala-d-ala carboxypeptidase activity
Specific Function:
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).
Gene Name:
mrcA
Uniprot ID:
P02918
Molecular Weight:
93635.545 Da
References
  1. Pfaller MA, Niles AC, Murray PR: In vitro antibacterial activity of cefpiramide. Antimicrob Agents Chemother. 1984 Mar;25(3):368-72. [PubMed:6426381 ]
  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:3943292 ]
  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:6448021 ]
Kind
Protein
Organism
Staphylococcus aureus
Pharmacological action
no
Actions
inhibitor
General Function:
Penicillin binding
Specific Function:
Not Available
Gene Name:
mecA
Uniprot ID:
C1KC03
Molecular Weight:
54918.915 Da
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:1864279 ]

Carriers

Kind
Protein
Organism
Human
Pharmacological action
unknown
General Function:
Toxic substance binding
Specific Function:
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. Major zinc transporter in plasma, typically binds about 80% of all plasma zinc.
Gene Name:
ALB
Uniprot ID:
P02768
Molecular Weight:
69365.94 Da
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:1686912 ]
Comments
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Drug created on June 13, 2005 07:24 / Updated on August 17, 2016 12:23