DrugBank: Cephapirin (DB01139)

targets (1)

Identification

Name

Cephapirin

Accession Number

DB01139 (APRD00860)

Type

small molecule

Groups

approved

Description

Cephalosporin antibiotic, partly plasma-bound, that is effective against gram-negative and gram-positive organisms. [PubChem]

Structure

Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure

Synonyms

Cefapirin
Cefapirina [INN-Spanish]
Cefapirine [INN-French]
Cefapirinum [INN-Latin]
Cefaprin
Cefaprin sodium
Cephapirin Sodium
Cephapirine

Salts

Not Available

Brand names

Name	Company
Ambrocef
Cefa
Cefadyl
Cefatrex
Cefatrexyl

Brand mixtures

Not Available

Categories

Anti-Bacterial Agents
Cephalosporins

CAS number

21593-23-7

Weight

Average: 423.463
Monoisotopic: 423.055876671

Chemical Formula

C₁₇H₁₇N₃O₆S₂

InChI Key

InChIKey=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

Plain Text

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

Plain Text

Mass Spec

Not Available

Taxonomy

Kingdom

Organic

Classes

Carboxylic Acids and Derivatives
Pyridines and Derivatives
Cephalosporins

Substructures

Carboxylic Acids and Derivatives
Ethers
Hydroxy Compounds
Acetates
Amino Ketones
Pyridines and Derivatives
Aliphatic and Aryl Amines
Beta Lactams
Enamines
Heterocyclic compounds
Aromatic compounds
Carboxamides and Derivatives
Cephalosporins
Lactams
Azetidines

Pharmacology

Indication

For treatment of infections caused by susceptible bacteria.

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).

Absorption

Not Available

Volume of distribution

Not Available

Protein binding

Not Available

Metabolism

Major metabolite detected is desacetylcephapirin.

Route of elimination

Not Available

Half life

Not Available

Clearance

Not Available

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.

Affected organisms

Enteric bacteria and other eubacteria

Pathways

Not Available

Pharmacoeconomics

Manufacturers

Apothecon inc div bristol myers squibb
Abraxis pharmaceutical products
Baxter healthcare corp anesthesia and critical care

Packagers

Bristol-Myers Squibb Co.

Dosage forms

Not Available

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	1.51e-01 g/l	ALOGPS
logP	0.18	ALOGPS
logP	-2	ChemAxon
logS	-3.5	ALOGPS
pKa (strongest acidic)	3.54	ChemAxon
pKa (strongest basic)	5	ChemAxon
physiological charge	-1	ChemAxon
hydrogen acceptor count	6	ChemAxon
hydrogen donor count	2	ChemAxon
polar surface area	125.9	ChemAxon
rotatable bond count	8	ChemAxon
refractivity	102.43	ChemAxon
polarizability	40.63	ChemAxon

References

Synthesis Reference

Not Available

General Reference

Not Available

External Links

Resource	Link
KEGG Compound	C06896
PubChem Compound	30699
PubChem Substance	46505227
ChemSpider	28486
ChEBI	554446
ChEMBL	554446
Therapeutic Targets Database	DAP001160
PharmGKB	PA164749340
Drug Product Database	2173255

ATC Codes

Not Available

AHFS Codes

Not Available

PDB Entries

Not Available

FDA label

Not Available

MSDS

show (31.4 KB)

Interactions

Drug Interactions

Drug	Interaction
Amikacin	Increased risk of nephrotoxicity
Gentamicin	Increased risk of nephrotoxicity
Netilmicin	Increased risk of nephrotoxicity
Tobramycin	Increased risk of nephrotoxicity

Food Interactions

Not Available

Targets
1. Penicillin-binding proteins 1A/1B Pharmacological action: yes Actions: inhibitor Organism class: bacterial UniProt ID: Q8XJ01 Gene: pbpA Protein Sequence: FASTA Gene Sequence: FASTA SNPs: SNPJam Report References: Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed 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. Pubmed Hamilton TE, Lawrence PJ: The formation of functional penicillin-binding proteins. J Biol Chem. 1975 Aug 25;250(16):6578-85. Pubmed

Targets

1. Penicillin-binding proteins 1A/1B

Pharmacological action: yes
Actions: inhibitor
Organism class: bacterial
UniProt ID: Q8XJ01 Link_out

Gene: pbpA
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:

Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed
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. Pubmed
Hamilton TE, Lawrence PJ: The formation of functional penicillin-binding proteins. J Biol Chem. 1975 Aug 25;250(16):6578-85. Pubmed

Comments

Drug created on June 13, 2005 07:24 / Updated on February 08, 2013 16:19