Identification
- Generic Name
- Cefpiramide
- DrugBank Accession Number
- DB00430
- Background
Cefpiramide is a third-generation cephalosporin antibiotic.
- Type
- Small Molecule
- Groups
- Approved
- Structure
Structure for Cefpiramide (DB00430)
- Weight
- Average: 612.637
Monoisotopic: 612.120936542 - Chemical Formula
- C25H24N8O7S2
- Synonyms
- Cefpiramide
- Cefpiramido
- Cefpiramidum
- External IDs
- SM-1652
Pharmacology
- Indication
For treatment of severe infections caused by susceptible bacteria such as P. aeruginosa.
Reduce drug development failure ratesBuild, train, & validate machine-learning modelswith evidence-based and structured datasets.Build, train, & validate predictive machine-learning models with structured datasets.- Contraindications & Blackbox Warnings
Avoid life-threatening adverse drug eventsImprove clinical decision support with information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events & improve clinical decision support.- 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).
Target Actions Organism APeptidoglycan synthase FtsI inhibitorEscherichia coli (strain K12) APenicillin-binding protein 1B inhibitorEscherichia coli (strain K12) APenicillin-binding protein 1A inhibitorPseudomonas aeruginosa (strain ATCC 15692 / PAO1 / 1C / PRS 101 / LMG 12228) APenicillin-binding protein 1B inhibitorPseudomonas aeruginosa AD-alanyl-D-alanine carboxypeptidase DacC inhibitorEscherichia coli (strain K12) APenicillin-binding protein 1A inhibitorEscherichia coli (strain K12) NPenicillin binding protein 2a inhibitorStaphylococcus 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
- Adverse Effects
Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates.Improve decision support & research outcomes with our structured adverse effects data.- Toxicity
Adverse effects following overdosage include nausea, vomiting, epigastric distress, diarrhea, and convulsions.
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs
- Not Available
Interactions
- Drug Interactions
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Drug Interaction Integrate drug-drug
interactions in your softwareAbacavir Cefpiramide may decrease the excretion rate of Abacavir which could result in a higher serum level. Abciximab The therapeutic efficacy of Abciximab can be decreased when used in combination with Cefpiramide. Aceclofenac The risk or severity of nephrotoxicity can be increased when Cefpiramide is combined with Aceclofenac. Acemetacin The risk or severity of nephrotoxicity can be increased when Cefpiramide is combined with Acemetacin. Acenocoumarol The risk or severity of bleeding can be increased when Cefpiramide is combined with Acenocoumarol. Acetaminophen Cefpiramide may decrease the excretion rate of Acetaminophen which could result in a higher serum level. Acetylsalicylic acid The risk or severity of nephrotoxicity can be increased when Cefpiramide is combined with Acetylsalicylic acid. Aclidinium Cefpiramide may decrease the excretion rate of Aclidinium which could result in a higher serum level. Acrivastine Cefpiramide may decrease the excretion rate of Acrivastine which could result in a higher serum level. Acyclovir The risk or severity of nephrotoxicity can be increased when Cefpiramide is combined with Acyclovir. 
Identify potential medication risksEasily compare up to 40 drugs with our drug interaction checker.Get severity rating, description, and management advice.Learn more - Food Interactions
- Not Available
Products
Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.- Product Ingredients
Ingredient UNII CAS InChI Key Cefpiramide sodium 137KB7GYKB 74849-93-7 RIWWMGQFMUUYIY-ALLHVENQSA-M
Categories
- ATC Codes
- J01DD11 — Cefpiramide
- Drug Categories
- Chemical TaxonomyProvided by Classyfire
- 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
- 1-hydroxy-2-unsubstituted benzenoid / Alkylarylthioether / Alpha peptide / Alpha-amino acid amide / Alpha-amino acid or derivatives / Aromatic heteropolycyclic compound / Aryl thioether / Azacycle / Azetidine / Azole show 40 more
- Molecular Framework
- Aromatic heteropolycyclic compounds
- External Descriptors
- cephalosporin, carboxylic acid (CHEBI:59213)
- Affected organisms
- Enteric bacteria and other eubacteria
Chemical Identifiers
- UNII
- P936YA152N
- CAS number
- 70797-11-4
- 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][C@]12SCC(CSC3=NN=NN3C)=C(N1C(=O)[C@@]2([H])NC(=O)[C@H](NC(=O)C1=C(O)C=C(C)N=C1)C1=CC=C(O)C=C1)C(O)=O
References
- General References
- 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. [Article]
- 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. [Article]
- 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. [Article]
- External Links
- Human Metabolome Database
- HMDB0014574
- KEGG Drug
- D01904
- KEGG Compound
- C13376
- PubChem Compound
- 636405
- PubChem Substance
- 46505548
- ChemSpider
- 552192
- ChEBI
- 59213
- ChEMBL
- CHEMBL1201204
- ZINC
- ZINC000004215257
- Therapeutic Targets Database
- DAP001157
- PharmGKB
- PA164748136
- Wikipedia
- Cefpiramide
Clinical Trials
Pharmacoeconomics
- Manufacturers
- Wyeth ayerst laboratories
- Packagers
- Not Available
- Dosage Forms
- Not Available
- Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source logP -0.9 Not Available - Predicted Properties
Property Value Source Water Solubility 0.0668 mg/mL ALOGPS logP 0.53 ALOGPS logP 0.15 Chemaxon logS -4 ALOGPS pKa (Strongest Acidic) 3.32 Chemaxon pKa (Strongest Basic) 2.61 Chemaxon Physiological Charge -1 Chemaxon Hydrogen Acceptor Count 11 Chemaxon Hydrogen Donor Count 5 Chemaxon Polar Surface Area 212.76 Å2 Chemaxon Rotatable Bond Count 9 Chemaxon Refractivity 164.81 m3·mol-1 Chemaxon Polarizability 58.79 Å3 Chemaxon Number of Rings 5 Chemaxon Bioavailability 0 Chemaxon Rule of Five No Chemaxon Ghose Filter No Chemaxon Veber's Rule No Chemaxon MDDR-like Rule Yes Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption - 0.9183 Blood Brain Barrier - 0.9936 Caco-2 permeable - 0.7804 P-glycoprotein substrate Substrate 0.7714 P-glycoprotein inhibitor I Non-inhibitor 0.9068 P-glycoprotein inhibitor II Non-inhibitor 0.8039 Renal organic cation transporter Non-inhibitor 0.8634 CYP450 2C9 substrate Non-substrate 0.7608 CYP450 2D6 substrate Non-substrate 0.8257 CYP450 3A4 substrate Substrate 0.5139 CYP450 1A2 substrate Non-inhibitor 0.8399 CYP450 2C9 inhibitor Non-inhibitor 0.7766 CYP450 2D6 inhibitor Non-inhibitor 0.8715 CYP450 2C19 inhibitor Non-inhibitor 0.7565 CYP450 3A4 inhibitor Non-inhibitor 0.7794 CYP450 inhibitory promiscuity High CYP Inhibitory Promiscuity 0.5 Ames test Non AMES toxic 0.7018 Carcinogenicity Non-carcinogens 0.9052 Biodegradation Not ready biodegradable 0.7805 Rat acute toxicity 2.2438 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9111 hERG inhibition (predictor II) Non-inhibitor 0.5656
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted GC-MS Spectrum - GC-MS Predicted GC-MS Not Available Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS Not Available
Targets
Build, predict & validate machine-learning models
Use our structured and evidence-based datasets to unlock newinsights and accelerate drug research.
Use our structured and evidence-based datasets to unlock new insights and accelerate drug research.
- 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
- 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. [Article]
- 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. [Article]
- 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
- 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. [Article]
- 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. [Article]
- 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
- Pfaller MA, Niles AC, Murray PR: In vitro antibacterial activity of cefpiramide. Antimicrob Agents Chemother. 1984 Mar;25(3):368-72. [Article]
- 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. [Article]
- 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. [Article]
- 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
- Pfaller MA, Niles AC, Murray PR: In vitro antibacterial activity of cefpiramide. Antimicrob Agents Chemother. 1984 Mar;25(3):368-72. [Article]
- 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. [Article]
- 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. [Article]
- 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
- Pfaller MA, Niles AC, Murray PR: In vitro antibacterial activity of cefpiramide. Antimicrob Agents Chemother. 1984 Mar;25(3):368-72. [Article]
- 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. [Article]
- 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. [Article]
- 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
- Pfaller MA, Niles AC, Murray PR: In vitro antibacterial activity of cefpiramide. Antimicrob Agents Chemother. 1984 Mar;25(3):368-72. [Article]
- 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. [Article]
- 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. [Article]
- 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
- 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. [Article]
Carriers
- Kind
- Protein
- Organism
- Humans
- 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
- 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. [Article]
Drug created at June 13, 2005 13:24 / Updated at February 03, 2023 08:16