Identification
- Summary
Cefapirin is a first generation cephalosporin indicated in the treatment of susceptible bacterial infections.
- Generic Name
- Cefapirin
- DrugBank Accession Number
- DB01139
- Background
Cefapirin (INN, also spelled cephapirin), commonly marketed under the trade name Cefadyl, is a first-generation cephalosporin antibiotic that is available in injectable formulations. Production for use in humans has been discontinued in the United States. Cefapirin is partly plasma-bound and is effective against gram-negative and gram-positive organisms.
- Type
- Small Molecule
- Groups
- Approved, Vet approved
- Structure
Structure for Cefapirin (DB01139)
- Weight
- Average: 423.463
Monoisotopic: 423.055876671 - Chemical Formula
- C17H17N3O6S2
- Synonyms
- (6R,7R)-3-(acetoxymethyl)-8-oxo-7-{[(pyridin-4-ylsulfanyl)acetyl]amino}-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
- Cefapirin
- Cefapirina
- Cefapirine
- Cefapirinum
- Cefaprin
- Cephapirin
- Cephapirine
- CEPR
Pharmacology
- Indication
For treatment of infections caused by susceptible bacteria.
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.- Associated Conditions
- Contraindications & Blackbox Warnings
Prevent Adverse Drug Events TodayTap into our Clinical API for life-saving information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events with our Clinical API- Pharmacodynamics
Cephapirin is a first-generation cephalosporin that has a wide spectrum of activity against gram-positive and gram-negative organisms. Cephapirin is more resistant to beta-lactamases than are the penicillins and so is effective against staphylococci, with the exception of methicillin-resistant staphylococci.
- Mechanism of action
The bactericidal activity of cephapirin results from the inhibition of cell wall synthesis via affinity for penicillin-binding proteins (PBPs).
Target Actions Organism APenicillin-binding protein 1A inhibitorClostridium perfringens (strain 13 / Type A) - Absorption
Not Available
- Volume of distribution
Not Available
- Protein binding
Not Available
- Metabolism
Major metabolite detected is desacetylcephapirin.
Hover over products below to view reaction partners
- Route of elimination
Not Available
- Half-life
Not Available
- Clearance
Not Available
- Adverse Effects
Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.- Toxicity
Rats exposed via the oral route to cephapirin displayed low acute toxicity (LD50 = 14000 mg/kg). The most common adverse reactions are hypersensitivity reactions and alterations to liver function. Evidence of white blood cell disorders and anaemia were noted in some subjects.
- 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 Cefapirin 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 Cefapirin. Aceclofenac The risk or severity of nephrotoxicity can be increased when Cefapirin is combined with Aceclofenac. Acemetacin The risk or severity of nephrotoxicity can be increased when Cefapirin is combined with Acemetacin. Acenocoumarol The risk or severity of bleeding can be increased when Cefapirin is combined with Acenocoumarol. Acetaminophen Cefapirin 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 Acetylsalicylic acid is combined with Cefapirin. Aclidinium Cefapirin may decrease the excretion rate of Aclidinium which could result in a higher serum level. Acrivastine Cefapirin 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 Acyclovir is combined with Cefapirin. 
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 Cefapirin benzathine 90G868409O 97468-37-6 JAHKOXGROZNHHG-RACYMRPCSA-N Cefapirin sodium 431LFF7I7J 24356-60-3 VGEOUKPOQQEQSX-OALZAMAHSA-M - International/Other Brands
- Cefadyl
Categories
- ATC Codes
- J01DB08 — Cefapirin
- Drug Categories
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as n-acyl-alpha amino acids and derivatives. These are compounds containing an alpha amino acid (or a derivative thereof) which bears an acyl group at its terminal nitrogen atom.
- Kingdom
- Organic compounds
- Super Class
- Organic acids and derivatives
- Class
- Carboxylic acids and derivatives
- Sub Class
- Amino acids, peptides, and analogues
- Direct Parent
- N-acyl-alpha amino acids and derivatives
- Alternative Parents
- Cephems / Alkylarylthioethers / 1,3-thiazines / Pyridines and derivatives / Dicarboxylic acids and derivatives / Tertiary carboxylic acid amides / Heteroaromatic compounds / Azetidines / Carboxylic acid esters / Thiohemiaminal derivatives show 11 more
- Substituents
- Alkylarylthioether / Aromatic heteropolycyclic compound / Aryl thioether / Azacycle / Azetidine / Beta-lactam / Carbonyl group / Carboxamide group / Carboximidic acid / Carboximidic acid derivative show 25 more
- Molecular Framework
- Aromatic heteropolycyclic compounds
- External Descriptors
- cephalosporin (CHEBI:554446)
- Affected organisms
- Enteric bacteria and other eubacteria
Chemical Identifiers
- UNII
- 89B59H32VN
- CAS number
- 21593-23-7
- InChI Key
- UQLLWWBDSUHNEB-CZUORRHYSA-N
- InChI
- InChI=1S/C17H17N3O6S2/c1-9(21)26-6-10-7-28-16-13(15(23)20(16)14(10)17(24)25)19-12(22)8-27-11-2-4-18-5-3-11/h2-5,13,16H,6-8H2,1H3,(H,19,22)(H,24,25)/t13-,16-/m1/s1
- IUPAC Name
- (6R,7R)-3-[(acetyloxy)methyl]-8-oxo-7-[2-(pyridin-4-ylsulfanyl)acetamido]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
- SMILES
- [H][C@]12SCC(COC(C)=O)=C(N1C(=O)[C@H]2NC(=O)CSC1=CC=NC=C1)C(O)=O
References
- Synthesis Reference
Crast, L.B. Jr.; U.S. Patent 3,422,100; January 14, 1969; assigned to Bristol-Myers Company Silvestri, H.H.and Johnson, D.A.; US. Patent 3,503,967; March 31,1970; assigned to Bristol-Myers Company. Havranek, R.E. and Crast, L.B. Jr.; U.S. Patent 3,578,661; May 11, 1971; assigned to Bristol- Myers Company.
- General References
- Not Available
- External Links
- Human Metabolome Database
- HMDB0015270
- KEGG Compound
- C06896
- PubChem Compound
- 30699
- PubChem Substance
- 46505227
- ChemSpider
- 28486
- BindingDB
- 50370592
- 2238
- ChEBI
- 554446
- ChEMBL
- CHEMBL1599
- ZINC
- ZINC000003830511
- Therapeutic Targets Database
- DAP001160
- PharmGKB
- PA164749340
- Wikipedia
- Cefapirin
- MSDS
- Download (31.4 KB)
Clinical Trials
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Bristol-Myers Squibb Co.
- Dosage Forms
Form Route Strength Injection, powder, for solution Intramuscular Suspension Oral 5 g - Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source water solubility 1030 mg/L Not Available logP -1.15 SANGSTER (1994) pKa 2.15 Not Available - Predicted Properties
Property Value Source Water Solubility 0.151 mg/mL ALOGPS logP 0.18 ALOGPS logP -2.1 Chemaxon logS -3.4 ALOGPS pKa (Strongest Acidic) 3.35 Chemaxon pKa (Strongest Basic) 4.99 Chemaxon Physiological Charge -1 Chemaxon Hydrogen Acceptor Count 6 Chemaxon Hydrogen Donor Count 2 Chemaxon Polar Surface Area 125.9 Å2 Chemaxon Rotatable Bond Count 8 Chemaxon Refractivity 102.43 m3·mol-1 Chemaxon Polarizability 40.63 Å3 Chemaxon Number of Rings 3 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter No Chemaxon Veber's Rule No Chemaxon MDDR-like Rule Yes Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption - 0.959 Blood Brain Barrier - 0.9971 Caco-2 permeable - 0.7523 P-glycoprotein substrate Substrate 0.8491 P-glycoprotein inhibitor I Non-inhibitor 0.6578 P-glycoprotein inhibitor II Non-inhibitor 0.8382 Renal organic cation transporter Non-inhibitor 0.8236 CYP450 2C9 substrate Non-substrate 0.7333 CYP450 2D6 substrate Non-substrate 0.8159 CYP450 3A4 substrate Substrate 0.5132 CYP450 1A2 substrate Non-inhibitor 0.7695 CYP450 2C9 inhibitor Non-inhibitor 0.7348 CYP450 2D6 inhibitor Non-inhibitor 0.8753 CYP450 2C19 inhibitor Non-inhibitor 0.7075 CYP450 3A4 inhibitor Non-inhibitor 0.8003 CYP450 inhibitory promiscuity High CYP Inhibitory Promiscuity 0.5917 Ames test Non AMES toxic 0.6996 Carcinogenicity Non-carcinogens 0.901 Biodegradation Not ready biodegradable 0.9955 Rat acute toxicity 1.4439 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9946 hERG inhibition (predictor II) Non-inhibitor 0.7588
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
- Clostridium perfringens (strain 13 / Type A)
- 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
- pbpA
- Uniprot ID
- Q8XJ01
- Uniprot Name
- Penicillin-binding protein 1A
- Molecular Weight
- 75176.35 Da
References
- Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
- Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [Article]
- Hamilton TE, Lawrence PJ: The formation of functional penicillin-binding proteins. J Biol Chem. 1975 Aug 25;250(16):6578-85. [Article]
Drug created at June 13, 2005 13:24 / Updated at October 02, 2023 22:13