You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on DrugBank.
Identification
NameCefprozil
Accession NumberDB01150  (APRD00461)
TypeSmall Molecule
GroupsApproved
Description

Cefprozil is a cephalosporin antibiotic. It can be used to treat bronchitis, ear infections, skin infections, and other bacterial infections.

Structure
Thumb
Synonyms
Cefprozil anhydrous
Cefprozilo
Cefprozilum
Cefzil
External Identifiers Not Available
Approved Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Auro-cefproziltablet500 mgoralAuro Pharma Inc2012-01-13Not applicableCanada
Auro-cefprozilpowder for suspension250 mgoralAuro Pharma Inc2012-01-13Not applicableCanada
Auro-cefproziltablet250 mgoralAuro Pharma Inc2012-01-13Not applicableCanada
Auro-cefprozilpowder for suspension125 mgoralAuro Pharma Inc2012-01-13Not applicableCanada
Ava-cefprozilpowder for suspension125 mgoralAvanstra Inc2011-10-112014-08-21Canada
Ava-cefproziltablet500 mgoralAvanstra Inc2011-10-112014-08-21Canada
Ava-cefproziltablet250 mgoralAvanstra Inc2011-10-112014-08-21Canada
Ava-cefprozilpowder for suspension250 mgoralAvanstra Inc2011-10-112014-08-21Canada
Cefproziltablet500 mgoralPro Doc Limitee2009-06-102014-07-24Canada
Cefprozil Powder for Oral Suspensionpowder for suspension250 mgoralRanbaxy Pharmaceuticals Canada Inc.Not applicableNot applicableCanada
Cefprozil Tabletstablet500 mgoralRanbaxy Pharmaceuticals Canada Inc.Not applicableNot applicableCanada
Cefprozil Tabletstablet250 mgoralRanbaxy Pharmaceuticals Canada Inc.Not applicableNot applicableCanada
Cefzil Powder for Oral Suspension-125mg/5mlpowder for solution125 mgoralBristol Myers Squibb Canada1995-12-31Not applicableCanada
Cefzil Powder for Oral Suspension-250mg/5mlpowder for solution250 mgoralBristol Myers Squibb Canada1995-12-31Not applicableCanada
Cefzil Tablets - 250mgtablet250 mgoralBristol Myers Squibb Canada1995-12-31Not applicableCanada
Cefzil Tablets - 500mgtablet500 mgoralBristol Myers Squibb Canada1995-12-31Not applicableCanada
Mint-cefproziltablet500 mgoralMint Pharmaceuticals Inc2008-10-292012-08-02Canada
Mint-cefproziltablet250 mgoralMint Pharmaceuticals Inc2008-10-292012-08-02Canada
Nu-cefprozilpowder for suspension125 mgoralNu Pharm IncNot applicableNot applicableCanada
Nu-cefproziltablet500 mgoralNu Pharm IncNot applicableNot applicableCanada
Nu-cefproziltablet250 mgoralNu Pharm IncNot applicableNot applicableCanada
Nu-cefprozilpowder for suspension250 mgoralNu Pharm IncNot applicableNot applicableCanada
Ran-cefprozilpowder for suspension250 mgoralRanbaxy Pharmaceuticals Canada Inc.2007-04-17Not applicableCanada
Ran-cefproziltablet500 mgoralRanbaxy Pharmaceuticals Canada Inc.2007-04-17Not applicableCanada
Ran-cefprozilpowder for suspension125 mgoralRanbaxy Pharmaceuticals Canada Inc.2010-01-12Not applicableCanada
Ran-cefproziltablet250 mgoralRanbaxy Pharmaceuticals Canada Inc.2007-04-17Not applicableCanada
Sandoz Cefprozilpowder for suspension250 mgoralSandoz Canada Incorporated2007-12-19Not applicableCanada
Sandoz Cefprozilpowder for suspension125 mgoralSandoz Canada Incorporated2007-12-19Not applicableCanada
Sandoz Cefproziltablet500 mgoralSandoz Canada Incorporated2008-01-24Not applicableCanada
Sandoz Cefproziltablet250 mgoralSandoz Canada Incorporated2008-01-24Not applicableCanada
Approved Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Apo-cefproziltablet500 mgoralApotex Inc2007-03-12Not applicableCanada
Apo-cefprozilpowder for suspension250 mgoralApotex Inc2007-04-20Not applicableCanada
Apo-cefproziltablet250 mgoralApotex Inc2007-03-12Not applicableCanada
Apo-cefprozilpowder for suspension125 mgoralApotex Inc2007-04-20Not applicableCanada
Cefproziltablet, film coated500 mg/1oralWockhardt USA LLC.2007-06-15Not applicableUs
Cefprozilpowder, for suspension250 mg/5mLoralOrchid Pharma Inc2015-08-19Not applicableUs
Cefprozilpowder, for suspension125 mg/5mLoralTeva Pharmaceuticals USA Inc2006-03-04Not applicableUs
Cefproziltablet, film coated500 mg/1oralAurobindo Pharma Limited2007-05-24Not applicableUs
Cefproziltablet500 mg/1oralH. J. Harkins Company, Inc.2005-12-08Not applicableUs
Cefprozilpowder, for suspension125 mg/5mLoralCitron Pharma LLC2007-01-30Not applicableUs
Cefprozilpowder, for suspension125 mg/5mLoralSandoz Inc2005-12-05Not applicableUs
Cefprozilpowder, for suspension250 mg/5mLoralDAVA Pharmaceuticals Inc2014-08-01Not applicableUs
Cefprozilpowder, for suspension125 mg/5mLoralOrchid Pharma Inc2015-08-19Not applicableUs
Cefproziltablet, film coated250 mg/1oralWockhardt USA LLC.2007-06-15Not applicableUs
Cefproziltablet, film coated500 mg/1oralWockhardt Limited2007-06-15Not applicableUs
Cefproziltablet, film coated500 mg/1oralSandoz Inc2005-11-14Not applicableUs
Cefprozilpowder, for suspension125 mg/5mLoralDAVA Pharmaceuticals Inc2014-08-01Not applicableUs
Cefproziltablet, film coated500 mg/1oralNorth Star Rx Llc2007-05-24Not applicableUs
Cefproziltablet500 mg/1oralLupin Pharmaceuticals, Inc.2005-12-01Not applicableUs
Cefproziltablet, film coated500 mg/1oralApotex Corp2008-05-09Not applicableUs
Cefproziltablet, film coated250 mg/1oralSandoz Inc2005-11-14Not applicableUs
Cefproziltablet, film coated500 mg/1oralDAVA Pharmaceuticals Inc2014-08-01Not applicableUs
Cefproziltablet, film coated250 mg/1oralWockhardt Limited2007-06-15Not applicableUs
Cefproziltablet, film coated250 mg/1oralNorth Star Rx Llc2007-05-24Not applicableUs
Cefproziltablet250 mg/1oralLupin Pharmaceuticals, Inc.2005-12-01Not applicableUs
Cefproziltablet, film coated250 mg/1oralApotex Corp2008-05-09Not applicableUs
Cefproziltablet, film coated500 mg/1oralTeva Pharmaceuticals USA Inc2005-12-23Not applicableUs
Cefproziltablet, film coated250 mg/1oralDAVA Pharmaceuticals Inc2014-08-01Not applicableUs
Cefprozilpowder, for suspension250 mg/5mLoralPhysicians Total Care, Inc.2007-02-05Not applicableUs
Cefprozilpowder, for suspension250 mg/5mLoralNorth Star Rx Llc2007-01-30Not applicableUs
Cefprozilpowder, for suspension250 mg/5mLoralLUPIN PHARMACEUTICALS INC2005-12-01Not applicableUs
Cefproziltablet, film coated500 mg/1oralCitron Pharma LLC2007-05-24Not applicableUs
Cefproziltablet, film coated250 mg/1oralTeva Pharmaceuticals USA Inc2005-12-23Not applicableUs
Cefprozilpowder, for suspension250 mg/5mLoralAurobindo Pharma Limited2007-01-30Not applicableUs
Cefproziltablet500 mg/1oralPhysicians Total Care, Inc.2007-02-05Not applicableUs
Cefprozilpowder, for suspension125 mg/5mLoralNorth Star Rx Llc2007-01-30Not applicableUs
Cefprozilpowder, for suspension125 mg/5mLoralLUPIN PHARMACEUTICALS INC2005-12-01Not applicableUs
Cefproziltablet, film coated250 mg/1oralCitron Pharma LLC2007-05-24Not applicableUs
Cefproziltablet, film coated250 mg/1oralAurobindo Pharma Limited2007-05-24Not applicableUs
Cefproziltablet, film coated500 mg/1oralMedsource Pharmaceuticals2007-05-24Not applicableUs
Cefprozilpowder, for suspension250 mg/5mLoralTeva Pharmaceuticals USA Inc2005-12-23Not applicableUs
Cefprozilpowder, for suspension125 mg/5mLoralAurobindo Pharma Limited2007-01-30Not applicableUs
Cefprozilpowder, for suspension250 mg/5mLoralA S Medication Solutions Llc2005-12-01Not applicableUs
Cefprozilpowder, for suspension250 mg/5mLoralSandoz Inc2005-12-05Not applicableUs
Cefproziltablet500 mg/1oralRed Pharm Drug Inc.2005-12-08Not applicableUs
Cefprozilpowder, for suspension250 mg/5mLoralCitron Pharma LLC2007-01-30Not applicableUs
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International Brands
NameCompany
BrisoralNot Available
CronocefNot Available
SerozilNot Available
Brand mixturesNot Available
Salts
Name/CASStructureProperties
Cefprozil monohydrate
121123-17-9
Thumb
  • InChI Key: ALYUMNAHLSSTOU-CIRGZYLNSA-N
  • Monoisotopic Mass: 407.115106582
  • Average Mass: 407.44
DBSALT001051
Categories
UNII1M698F4H4E
CAS number92665-29-7
WeightAverage: 389.426
Monoisotopic: 389.104541423
Chemical FormulaC18H19N3O5S
InChI KeyInChIKey=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
IUPAC Name
(6R,7R)-7-[(2R)-2-amino-2-(4-hydroxyphenyl)acetamido]-8-oxo-3-(prop-1-en-1-yl)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
SMILES
[H][C@]12SCC(C=CC)=C(N1C(=O)[C@@]2([H])NC(=O)[[email protected]](N)C1=CC=C(O)C=C1)C(O)=O
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as cephalosporins. These are compounds containing a 1,2-thiazine fused to a 2-azetidinone to for a oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid moiety or a derivative thereof.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassLactams
Sub ClassBeta lactams
Direct ParentCephalosporins
Alternative Parents
Substituents
  • Cephalosporin
  • N-acyl-alpha amino acid or derivatives
  • Alpha-amino acid amide
  • Phenylacetamide
  • Alpha-amino acid or derivatives
  • Aralkylamine
  • Phenol
  • Benzenoid
  • Monocyclic benzene moiety
  • Meta-thiazine
  • Tertiary carboxylic acid amide
  • Tertiary amine
  • Secondary carboxylic acid amide
  • Carboxamide group
  • Azetidine
  • Azacycle
  • Dialkylthioether
  • Hemithioaminal
  • Thioether
  • Monocarboxylic acid or derivatives
  • Enamine
  • Carboxylic acid
  • Carboxylic acid derivative
  • Carboxylic acid amide
  • Hydrocarbon derivative
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Primary aliphatic amine
  • Carbonyl group
  • Amine
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Pharmacology
IndicationFor 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
PharmacodynamicsCefprozil, a semisynthetic, second-generation cephalosporin, is used to treat otitis media, soft-tissue infections, and respiratory tract infections.
Mechanism of actionCefprozil, 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.
Related Articles
AbsorptionOral bioavailability is approximately 95%.
Volume of distribution
  • 0.23 L/kg
Protein binding36%
Metabolism

Cefprozil is eliminated primarily by the kidneys

Route of eliminationNot Available
Half life1.3 hours
Clearance
  • 3 mL/min/kg [fasting subjects]
ToxicitySingle 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
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption-0.8478
Blood Brain Barrier-0.9962
Caco-2 permeable-0.8353
P-glycoprotein substrateSubstrate0.7853
P-glycoprotein inhibitor INon-inhibitor0.9315
P-glycoprotein inhibitor IINon-inhibitor0.9889
Renal organic cation transporterNon-inhibitor0.9264
CYP450 2C9 substrateNon-substrate0.8214
CYP450 2D6 substrateNon-substrate0.8324
CYP450 3A4 substrateSubstrate0.5102
CYP450 1A2 substrateNon-inhibitor0.8866
CYP450 2C9 inhibitorNon-inhibitor0.8768
CYP450 2D6 inhibitorNon-inhibitor0.9196
CYP450 2C19 inhibitorNon-inhibitor0.8825
CYP450 3A4 inhibitorNon-inhibitor0.8724
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.8149
Ames testNon AMES toxic0.6562
CarcinogenicityNon-carcinogens0.8849
BiodegradationNot ready biodegradable0.9584
Rat acute toxicity1.6050 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9935
hERG inhibition (predictor II)Non-inhibitor0.7516
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Pharmacoeconomics
ManufacturersNot Available
Packagers
Dosage forms
FormRouteStrength
Powder for suspensionoral125 mg
Powder, for suspensionoral125 mg/5mL
Powder, for suspensionoral250 mg/5mL
Tabletoral250 mg/1
Tabletoral500 mg/1
Tablet, film coatedoral250 mg/1
Tablet, film coatedoral500 mg/1
Powder for solutionoral125 mg
Powder for solutionoral250 mg
Tabletoral250 mg
Tabletoral500 mg
Powder for suspensionoral250 mg
Prices
Unit descriptionCostUnit
Cefprozil 250 mg/5ml Suspension 100ml Bottle78.86USD bottle
Cefzil 500 mg tablet6.6USD tablet
Cefprozil 500 mg tablet5.46USD tablet
Cefzil 250 mg tablet3.24USD tablet
Cefprozil 250 mg tablet2.7USD tablet
Apo-Cefprozil 500 mg Tablet1.99USD tablet
Ran-Cefprozil 500 mg Tablet1.99USD tablet
Sandoz Cefprozil 500 mg Tablet1.99USD tablet
Apo-Cefprozil 250 mg Tablet1.02USD tablet
Ran-Cefprozil 250 mg Tablet1.02USD tablet
Sandoz Cefprozil 250 mg Tablet1.02USD tablet
Cefzil 50 mg/ml Suspension0.35USD ml
Apo-Cefprozil 50 mg/ml Suspension0.2USD ml
Cefprozil 50 mg/ml Suspension0.2USD ml
Ran-Cefprozil 50 mg/ml Suspension0.2USD ml
Sandoz Cefprozil 50 mg/ml Suspension0.2USD ml
Cefzil 25 mg/ml Suspension0.18USD ml
Apo-Cefprozil 25 mg/ml Suspension0.1USD ml
Ran-Cefprozil 25 mg/ml Suspension0.1USD ml
Sandoz Cefprozil 25 mg/ml Suspension0.1USD ml
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
PatentsNot Available
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point218-225 °CNot Available
water solubility55 mg/LNot Available
logP0.6Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.149 mg/mLALOGPS
logP0.94ALOGPS
logP-1.9ChemAxon
logS-3.4ALOGPS
pKa (Strongest Acidic)3.53ChemAxon
pKa (Strongest Basic)7.43ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area132.96 Å2ChemAxon
Rotatable Bond Count5ChemAxon
Refractivity101.27 m3·mol-1ChemAxon
Polarizability39.35 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
SpectraNot Available
References
Synthesis Reference

Julia Greil, Johannes Ludescher, Siegfried Wolf, “Intermediates in cefprozil production.” U.S. Patent US07355041, issued April 08, 2008.

US07355041
General ReferencesNot Available
External Links
ATC CodesJ01DC10
AHFS Codes
  • 08:12.06.08
PDB EntriesNot Available
FDA labelDownload (203 KB)
MSDSDownload (44.9 KB)
Interactions
Drug Interactions
Drug
AcenocoumarolCefprozil may increase the anticoagulant activities of Acenocoumarol.
AmikacinCefprozil may increase the nephrotoxic activities of Amikacin.
ArbekacinCefprozil may increase the nephrotoxic activities of Arbekacin.
DicoumarolCefprozil may increase the anticoagulant activities of Dicoumarol.
FramycetinCefprozil may increase the nephrotoxic activities of Framycetin.
GentamicinCefprozil may increase the nephrotoxic activities of Gentamicin.
KanamycinCefprozil may increase the nephrotoxic activities of Kanamycin.
NeomycinCefprozil may increase the nephrotoxic activities of Neomycin.
NetilmicinCefprozil may increase the nephrotoxic activities of Netilmicin.
Picosulfuric acidThe therapeutic efficacy of Sodium picosulfate can be decreased when used in combination with Cefprozil.
ProbenecidThe serum concentration of Cefprozil can be increased when it is combined with Probenecid.
RibostamycinCefprozil may increase the nephrotoxic activities of Ribostamycin.
SpectinomycinCefprozil may increase the nephrotoxic activities of Spectinomycin.
StreptomycinCefprozil may increase the nephrotoxic activities of Streptomycin.
TobramycinCefprozil may increase the nephrotoxic activities of Tobramycin.
WarfarinCefprozil may increase the anticoagulant activities of Warfarin.
Food Interactions
  • Take without regard to meals.

Targets

Kind
Protein
Organism
Streptococcus pneumoniae serotype 4 (strain ATCC BAA-334 / TIGR4)
Pharmacological action
yes
Actions
inhibitor
General Function:
Penicillin binding
Specific Function:
Cell wall formation.
Gene Name:
ponA
Uniprot ID:
Q04707
Molecular Weight:
79757.96 Da
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:11959556 ]
Kind
Protein
Organism
Streptococcus pneumoniae serotype 4 (strain ATCC BAA-334 / TIGR4)
Pharmacological action
yes
Actions
inhibitor
General Function:
Penicillin binding
Specific Function:
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.
Gene Name:
pbpX
Uniprot ID:
P14677
Molecular Weight:
82312.475 Da
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:11959556 ]
Kind
Protein
Organism
Streptococcus pneumoniae serotype 4 (strain ATCC BAA-334 / TIGR4)
Pharmacological action
yes
Actions
inhibitor
General Function:
Penicillin binding
Specific Function:
Not Available
Gene Name:
penA
Uniprot ID:
P0A3M5
Molecular Weight:
73872.305 Da
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:11959556 ]
Comments
comments powered by Disqus
Drug created on June 13, 2005 07:24 / Updated on August 17, 2016 12:23