Identification

Name
Cefpiramide
Accession Number
DB00430  (APRD00856)
Type
Small Molecule
Groups
Approved
Description

Cefpiramide is a third-generation cephalosporin antibiotic.

Structure
Thumb
Synonyms
  • Cefpiramide
  • Cefpiramido
  • Cefpiramidum
External IDs
SM-1652
Product Ingredients
IngredientUNIICASInChI Key
Cefpiramide Sodium137KB7GYKB74849-93-7RIWWMGQFMUUYIY-UHFFFAOYSA-M
Categories
UNII
P936YA152N
CAS number
70797-11-4
Weight
Average: 612.637
Monoisotopic: 612.120936542
Chemical Formula
C25H24N8O7S2
InChI Key
PWAUCHMQEXVFJR-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][[email protected]]12SCC(CSC3=NN=NN3C)=C(N1C(=O)[[email protected]@]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

Indication

For treatment of severe infections caused by susceptible bacteria such as P. aeruginosa.

Structured Indications
Not Available
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).

TargetActionsOrganism
APeptidoglycan synthase FtsI
inhibitor
Escherichia coli (strain K12)
APenicillin-binding protein 1B
inhibitor
Escherichia coli (strain K12)
APenicillin-binding protein 1A
inhibitor
Pseudomonas aeruginosa (strain ATCC 15692 / PAO1 / 1C / PRS 101 / LMG 12228)
APenicillin-binding protein 1B
inhibitor
Pseudomonas aeruginosa
AD-alanyl-D-alanine carboxypeptidase DacC
inhibitor
Escherichia coli (strain K12)
APenicillin-binding protein 1A
inhibitor
Escherichia coli (strain K12)
NPenicillin binding protein 2a
inhibitor
Staphylococcus aureus
Absorption

Rapidly absorbed following intramuscular injection.

Volume of distribution
Not Available
Protein binding
Not Available
Metabolism
Not Available
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
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteractionDrug group
BCG vaccineThe therapeutic efficacy of BCG vaccine 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 Interactions
Not Available

References

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
Human Metabolome Database
HMDB14574
KEGG Drug
D01904
KEGG Compound
C13376
PubChem Compound
636405
PubChem Substance
46505548
ChemSpider
552192
ChEBI
59213
ChEMBL
CHEMBL1201204
Therapeutic Targets Database
DAP001157
PharmGKB
PA164748136
Wikipedia
Cefpiramide
ATC Codes
J01DD11 — Cefpiramide

Clinical Trials

Clinical Trials
Not Available

Pharmacoeconomics

Manufacturers
  • Wyeth ayerst laboratories
Packagers
Not Available
Dosage forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
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 FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
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)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Taxonomy

Description
This compound belongs to the class of organic compounds known as peptides. These are compounds containing an amide derived from two or more amino carboxylic acid molecules (the same or different) by formation of a covalent bond from the carbonyl carbon of one to the nitrogen atom of another.
Kingdom
Organic compounds
Super Class
Organic acids and derivatives
Class
Carboxylic acids and derivatives
Sub Class
Amino acids, peptides, and analogues
Direct Parent
Peptides
Alternative Parents
Cephalosporins / N-acyl-alpha amino acids and derivatives / Alpha amino acid amides / Phenylacetamides / Nicotinamides / 1-hydroxy-2-unsubstituted benzenoids / Alkylarylthioethers / Dihydropyridines / Methylpyridines / 1,3-thiazines
show 17 more
Substituents
Alpha peptide / Cephalosporin / N-acyl-alpha amino acid or derivatives / Alpha-amino acid amide / N-substituted-alpha-amino acid / Alpha-amino acid or derivatives / Phenylacetamide / Cephem / Nicotinamide / Pyridine carboxylic acid or derivatives
show 40 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
cephalosporin, carboxylic acid (CHEBI:59213)

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 fr...
Gene Name
ftsI
Uniprot ID
P0AD68
Uniprot Name
Peptidoglycan synthase FtsI
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 str...
Gene Name
mrcB
Uniprot ID
P02919
Uniprot Name
Penicillin-binding protein 1B
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 str...
Gene Name
mrcA
Uniprot ID
Q07806
Uniprot Name
Penicillin-binding protein 1A
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 str...
Gene Name
ponB
Uniprot ID
Q9X6W0
Uniprot Name
Penicillin-binding protein 1B
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
Uniprot Name
D-alanyl-D-alanine carboxypeptidase DacC
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 str...
Gene Name
mrcA
Uniprot ID
P02918
Uniprot Name
Penicillin-binding protein 1A
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
Uniprot Name
Penicillin binding protein 2a
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 colloid...
Gene Name
ALB
Uniprot ID
P02768
Uniprot Name
Serum albumin
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]

Drug created on June 13, 2005 07:24 / Updated on November 07, 2017 01:37