DrugBank: Cefpodoxime (DB01416)

targets (1)

Identification

Name

Cefpodoxime

Accession Number

DB01416

Type

small molecule

Groups

approved

Description

Cefpodoxime is an oral third generation cephalosporin antibiotic. It is active against most Gram positive and Gram negative bacteria. It is commonly used to treat acute otitis media, pharyngitis, and sinusitis. Cefpodoxime proxetil is a prodrug which is absorbed and de-esterified by the intestinal mucosa to Cefpodoxime.

Structure

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

Synonyms

Cefpodoxime proxetil
CPDX-PR
RU 51807

Brand names

Banan
Doxef
Vantin

Brand name mixtures

Not Available

Categories

Anti-Bacterial Agents
Antibacterial Agents
Cephalosporins

CAS number

82619-04-3

Weight

Average: 427.455
Monoisotopic: 427.062024681

Chemical Formula

C₁₅H₁₇N₅O₆S₂

InChI Key

InChIKey=WYUSVOMTXWRGEK-HBWVYFAYSA-N

InChI

InChI=1S/C15H17N5O6S2/c1-25-3-6-4-27-13-9(12(22)20(13)10(6)14(23)24)18-11(21)8(19-26-2)7-5-28-15(16)17-7/h5,9,13H,3-4H2,1-2H3,(H2,16,17)(H,18,21)(H,23,24)/b19-8-/t9-,13-/m1/s1

Plain Text

IUPAC Name

(6R,7R)-7-[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-(methoxyimino)acetamido]-3-(methoxymethyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

SMILES

[H][C@]12SCC(COC)=C(N1C(=O)[C@H]2NC(=O)C(=N/OC)\C1=CSC(N)=N1)C(O)=O

Plain Text

Mass Spec

Not Available

Taxonomy

Kingdom

Organic

Classes

Ethers
Cephalosporins

Substructures

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

Pharmacology

Indication

For the treatment of patients with mild to moderate infections caused by susceptible strains of the designated microorganisms.

Pharmacodynamics

Cefpodoxime is an oral third generation cephalosporin antibiotic. It is active against most Gram positive and Gram negative bacteria. Notable exceptions include Pseudomonas aeruginosa, Enterococcus, and Bacteroides fragilis.

Mechanism of action

Cefpodoxime is active against a wide spectrum of Gram-positive and Gram-negative bacteria. Cefpodoxime is stable in the presence of beta-lactamase enzymes. As a result, many organisms resistant to penicillins and cephalosporins, due to their production of beta-lactamase, may be susceptible to cefpodoxime. Cefpodoxime is inactivated by certain extended spectrum beta-lactamases. The bactericidal activity of cefpodoxime results from its inhibition of cell wall synthesis. The active metabolite of cefpodoxime binds preferentially to penicillin binding protein 3, which inhibits production of peptidoglycan, the primary constituent of bacterial cell walls.

Absorption

Cefpodoxime proxetil is a prodrug that is absorbed from the gastrointestinal tract and de-esterified to its active metabolite, cefpodoxime. Following oral administration of 100 mg of cefpodoxime proxetil to fasting subjects, approximately 50% of the administered cefpodoxime dose was absorbed systemically.

Volume of distribution

Not Available

Protein binding

22 to 33% in serum and from 21 to 29% in plasma.

Metabolism

Route of elimination

Over the recommended dosing range (100 to 400 mg), approximately 29 to 33% of the administered cefpodoxime dose was excreted unchanged in the urine in 12 hours.

Half life

2.09 to 2.84 hours

Clearance

Not Available

Toxicity

Not Available

Affected organisms

Enteric bacteria and other eubacteria

Pathways

Not Available

Pharmacoeconomics

Manufacturers

Sankyo usa corp
Aurobindo pharma ltd
Ranbaxy laboratories ltd
Sandoz inc
Pharmacia and upjohn co
Orchid healthcare

Packagers

Aurobindo Pharma Ltd.
Dispensing Solutions
Murfreesboro Pharmaceutical Nursing Supply
Northstar Rx LLC
Nucare Pharmaceuticals Inc.
Orchid Healthcare
PD-Rx Pharmaceuticals Inc.
Pfizer Inc.
Pharmaceutical Utilization Management Program VA Inc.
Pharmacia Inc.
Public Health Department Seattle and King County
Putney Inc.
Ranbaxy Laboratories
Redpharm Drug
Sandoz

Dosage forms

Form	Route	Strength
Granule, for suspension	Oral
Tablet, film coated	Oral

Prices

Unit description	Cost	Unit
Vantin 20 200 mg tablet Bottle	194.37 USD	bottle
Vantin 20 100 mg tablet Bottle	137.26 USD	bottle
Vantin 100 mg/5ml Suspension 100ml Bottle	133.84 USD	bottle
Vantin 50 mg/5ml Suspension 100ml Bottle	70.34 USD	bottle
Vantin 50 mg/5ml Suspension 50ml Bottle	36.95 USD	bottle
Vantin 200 mg tablet	9.67 USD	tablet
Cefpodoxime Proxetil 200 mg tablet	7.02 USD	tablet
Cefpodoxime 200 mg tablet	6.41 USD	tablet
Vantin 100 mg tablet	6.33 USD	tablet
Cefpodoxime 100 mg tablet	5.11 USD	tablet

Patents

Not Available

Properties

State

solid

Melting point

Not Available

Experimental Properties

Not Available

Predicted Properties

Property	Value	Source
water solubility	1.85e-01 g/l	ALOGPS
logP	0.05	ALOGPS
logP	-1.22	ChemAxon Molconvert
logS	-3.36	ALOGPS
pKa	11.09	ChemAxon Molconvert
hydrogen acceptor count	9	ChemAxon Molconvert
hydrogen donor count	3	ChemAxon Molconvert
polar surface area	156.44	ChemAxon Molconvert
rotatable bond count	7	ChemAxon Molconvert
refractivity	100.71	ChemAxon Molconvert
polarizability	39.90	ChemAxon Molconvert

References

Synthesis Reference

Not Available

General Reference

Not Available

External Links

Resource	Link
PubChem Compound	6335986
PubChem Substance	46504897
ChemSpider	4891496
Therapeutic Targets Database	DAP000457
PharmGKB	PA448858
Drug Product Database	0
RxList	http://www.rxlist.com/cgi/generic/vantin.htm
Drugs.com	http://www.drugs.com/cdi/cefpodoxime.html
Wikipedia	http://en.wikipedia.org/wiki/Cefpodoxime

ATC Codes

J01DD13

AHFS Codes

Not Available

PDB Entries

Not Available

FDA label

show (369.2 KB)

MSDS

Not Available

Interactions

Drug Interactions

Drug	Interaction

Food Interactions

Take on empty stomach: 1 hour before or 2 hours after meals.

Targets
1. Peptidoglycan synthetase ftsI Pharmacological action: yes Actions: inhibitor Cell wall formation. Essential for the formation of a septum of the murein sacculus. Synthesis of cross-linked peptidoglycan from the lipid intermediates Organism class: bacterial UniProt ID: P0AD68 Gene: ftsI Protein Sequence: FASTA Gene Sequence: FASTA SNPs: SNPJam Report References: Boaretti M, Lleo MM, Canepari P: In vitro activity, beta-lactamase stability and PBP affinity of RU 51,746-2, the active metabolite of the new orally absorbed cephalosporin ester, RU 51807. J Chemother. 1991 Jan;3 Suppl 1:57-61. Pubmed

Targets

1. Peptidoglycan synthetase ftsI

Pharmacological action: yes
Actions: inhibitor

Cell wall formation. Essential for the formation of a septum of the murein sacculus. Synthesis of cross-linked peptidoglycan from the lipid intermediates

Organism class: bacterial
UniProt ID: P0AD68 Link_out

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

References:

Boaretti M, Lleo MM, Canepari P: In vitro activity, beta-lactamase stability and PBP affinity of RU 51,746-2, the active metabolite of the new orally absorbed cephalosporin ester, RU 51807. J Chemother. 1991 Jan;3 Suppl 1:57-61. Pubmed

Comments

Drug created on July 23, 2007 07:09 / Updated on December 21, 2010 23:04

This project is supported by Genome Alberta & Genome Canada, a not-for-profit organization that is leading Canada's national genomics strategy with $600 million in funding from the federal government. This project is also supported in part by GenomeQuest, Inc., an enterprise genomic information company serving the life science community.