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Identification
Name Cefprozil
Accession Number DB01150 (APRD00461)
Type small molecule
Groups approved
Description

Cefprozil is a cephalosporin antibiotic. It can be used to treat bronchitis, ear infections, skin infections, and other bacterial infections.
Structure Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  • Cefprozil anhydrous
  • Cefprozilo [INN-Spanish]
  • Cefprozilum [INN-Latin]
Brand names
  • Arzimol
  • Brisoral
  • Cronocef
  • Procef
  • Serozil
Brand name mixtures Not Available
Categories
  • Anti-Bacterial Agents
  • Cephalosporins
CAS number 92665-29-7
Weight Average: 389.426
Monoisotopic: 389.104541423
Chemical Formula C18H19N3O5S
InChI Key InChIKey=WDLWHQDACQUCJR-ZAMMOSSLSA-N
InChI
InChI=1S/C18H19N3O5S/c1-2-3-10-8-27-17-13(16(24)21(17)14(10)18(25)26)20-15(23)12(19)9-4-6-11(22)7-5-9/h2-7,12-13,17,22H,8,19H2,1H3,(H,20,23)(H,25,26)/b3-2+/t12-,13-,17-/m1/s1
Plain Text
IUPAC Name
(6R,7R)-7-[(2R)-2-amino-2-(4-hydroxyphenyl)acetamido]-8-oxo-3-[(1E)-prop-1-en-1-yl]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
SMILES
[H][C@]12SCC(\C=C\C)=C(N1C(=O)[C@H]2NC(=O)[C@H](N)C1=CC=C(O)C=C1)C(O)=O
Plain Text
Mass Spec Not Available
Taxonomy
Kingdom Organic
Classes
  • Phenols and Derivatives
  • Phenethylamines
  • Cephalosporins
Substructures
  • Hydroxy Compounds
  • Alkanes and Alkenes
  • Acetates
  • Phenols and Derivatives
  • Amino Ketones
  • Carboxylic Acids and Derivatives
  • Aliphatic and Aryl Amines
  • Benzene and Derivatives
  • Beta Lactams
  • Enamines
  • Isoprenes
  • Phenethylamines
  • Heterocyclic compounds
  • Aromatic compounds
  • Carboxamides and Derivatives
  • Cephalosporins
  • Lactams
  • Azetidines
  • Phenyl Esters
Pharmacology
Indication For the treatment of the following infections (respiratory, skin, soft tissue, UTI, ENT) caused by; S. pneumoniae, H. influenzae, staphylococci, S. pyogenes (group A beta-hemolytic streptococci), E. coli, P. mirabilis, Klebsiella sp, coagulase-negative staph
Pharmacodynamics Cefprozil, a semisynthetic, second-generation cephalosporin, is used to treat otitis media, soft-tissue infections, and respiratory tract infections.
Mechanism of action Cefprozil, like the penicillins, is a beta-lactam antibiotic. By binding to specific penicillin-binding proteins (PBPs) located inside the bacterial cell wall, it inhibits the third and last stage of bacterial cell wall synthesis. Cell lysis is then mediated by bacterial cell wall autolytic enzymes such as autolysins; it is possible that cefprozil interferes with an autolysin inhibitor.
Absorption Oral bioavailability is approximately 95%.
Volume of distribution
  • 0.23 L/kg
Protein binding 36%
Metabolism

Cefprozil is eliminated primarily by the kidneys
Route of elimination Not Available
Half life 1.3 hours
Clearance
  • 3 mL/min/kg [fasting subjects]
Toxicity Single 5000 mg/kg oral doses of cefprozil caused no mortality or signs of toxicity in adult, weaning or neonatal rats, or adult mice. A single oral dose of 3000 mg/kg caused diarrhea and loss of appetite in cynomolgus monkeys, but no mortality.
Affected organisms
  • Enteric bacteria and other eubacteria
Pathways Not Available
Pharmacoeconomics
Manufacturers
  • Aurobindo pharma ltd
  • Lupin ltd
  • Orchid healthcare
  • Ranbaxy laboratories ltd
  • Sandoz inc
  • Teva pharmaceuticals usa
  • Bristol myers squibb co pharmaceutical research institute
  • Apotex inc
  • Aurobindo pharma ltd inc
  • Teva pharmaceuticals usa inc
  • Wockhardt ltd
Packagers
Dosage forms
Form Route Strength
Powder, for solution Oral
Tablet Oral
Prices
Unit description Cost Unit
Cefprozil 250 mg/5ml Suspension 100ml Bottle 78.86 USD bottle
Cefzil 500 mg tablet 6.6 USD tablet
Cefprozil 500 mg tablet 5.46 USD tablet
Cefzil 250 mg tablet 3.24 USD tablet
Cefprozil 250 mg tablet 2.7 USD tablet
Apo-Cefprozil 500 mg Tablet 1.99 USD tablet
Ran-Cefprozil 500 mg Tablet 1.99 USD tablet
Sandoz Cefprozil 500 mg Tablet 1.99 USD tablet
Apo-Cefprozil 250 mg Tablet 1.02 USD tablet
Ran-Cefprozil 250 mg Tablet 1.02 USD tablet
Sandoz Cefprozil 250 mg Tablet 1.02 USD tablet
Cefzil 50 mg/ml Suspension 0.35 USD ml
Apo-Cefprozil 50 mg/ml Suspension 0.2 USD ml
Cefprozil 50 mg/ml Suspension 0.2 USD ml
Ran-Cefprozil 50 mg/ml Suspension 0.2 USD ml
Sandoz Cefprozil 50 mg/ml Suspension 0.2 USD ml
Cefzil 25 mg/ml Suspension 0.18 USD ml
Apo-Cefprozil 25 mg/ml Suspension 0.1 USD ml
Ran-Cefprozil 25 mg/ml Suspension 0.1 USD ml
Sandoz Cefprozil 25 mg/ml Suspension 0.1 USD ml
Patents Not Available
Properties
State solid
Melting point 218-225oC
Experimental Properties
Property Value Source
water solubility 55 mg/L PhysProp
logP 0.6 PhysProp
Predicted Properties
Property Value Source
water solubility 1.49e-01 g/l ALOGPS
logP 0.94 ALOGPS
logP -3.26 ChemAxon Molconvert
logS -3.42 ALOGPS
pKa 9.48 ChemAxon Molconvert
hydrogen acceptor count 6 ChemAxon Molconvert
hydrogen donor count 4 ChemAxon Molconvert
polar surface area 132.96 ChemAxon Molconvert
rotatable bond count 5 ChemAxon Molconvert
refractivity 101.27 ChemAxon Molconvert
polarizability 36.81 ChemAxon Molconvert
References
Synthesis Reference Not Available
General Reference Not Available
External Links
Resource Link
KEGG Compound C06888 Link_out
PubChem Compound 5281006 Link_out
PubChem Substance 46504903 Link_out
ChemSpider 4444481 Link_out
ChEBI 3506 Link_out
ChEMBL 3506 Link_out
Therapeutic Targets Database DAP000447 Link_out
PharmGKB PA448860 Link_out
Drug Product Database 2163667 Link_out
RxList http://www.rxlist.com/cgi/generic/cefprozi.htm Link_out
Drugs.com http://www.drugs.com/cdi/cefprozil.html Link_out
PDRhealth http://www.pdrhealth.com/drug_info/rxdrugprofiles/drugs/cef1077.shtml Link_out
Wikipedia http://en.wikipedia.org/wiki/Cefprozil Link_out
ATC Codes
  • J01DC10
AHFS Codes
  • 08:12.06.08
PDB Entries Not Available
FDA label show (202.6 KB)
MSDS show (44.9 KB)
Interactions
Drug Interactions Not Available
Food Interactions
  • Take without regard to meals.
Targets

1. Penicillin-binding protein 1A

Pharmacological action: yes
Actions: inhibitor

Cell wall formation

Organism class: bacterial
UniProt ID: Q04707 Link_out
Gene: ponA
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Nagai K, Davies TA, Jacobs MR, Appelbaum PC: Effects of amino acid alterations in penicillin-binding proteins (PBPs) 1a, 2b, and 2x on PBP affinities of penicillin, ampicillin, amoxicillin, cefditoren, cefuroxime, cefprozil, and cefaclor in 18 clinical isolates of penicillin-susceptible, -intermediate, and -resistant pneumococci. Antimicrob Agents Chemother. 2002 May;46(5):1273-80. Pubmed

2. Penicillin-binding protein 2x

Pharmacological action: yes
Actions: inhibitor

Penicillin-binding proteins (PBPs) function in the late steps of murein biosynthesis. Beta-lactams inactivate the PBPs by acylating an essential serine residue in the active site of these proteins

Organism class: bacterial
UniProt ID: P14677 Link_out
Gene: pbpX
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Nagai K, Davies TA, Jacobs MR, Appelbaum PC: Effects of amino acid alterations in penicillin-binding proteins (PBPs) 1a, 2b, and 2x on PBP affinities of penicillin, ampicillin, amoxicillin, cefditoren, cefuroxime, cefprozil, and cefaclor in 18 clinical isolates of penicillin-susceptible, -intermediate, and -resistant pneumococci. Antimicrob Agents Chemother. 2002 May;46(5):1273-80. Pubmed

3. Penicillin-binding protein 2B

Pharmacological action: yes
Actions: inhibitor
Organism class: bacterial
UniProt ID: P0A3M5 Link_out
Gene: penA
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Nagai K, Davies TA, Jacobs MR, Appelbaum PC: Effects of amino acid alterations in penicillin-binding proteins (PBPs) 1a, 2b, and 2x on PBP affinities of penicillin, ampicillin, amoxicillin, cefditoren, cefuroxime, cefprozil, and cefaclor in 18 clinical isolates of penicillin-susceptible, -intermediate, and -resistant pneumococci. Antimicrob Agents Chemother. 2002 May;46(5):1273-80. Pubmed
Comments
Drug created on June 13, 2005 07:24 / Updated on April 19, 2011 15:08

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.