Identification
- Summary
Cefprozil is a cephalosporin antibiotic used in the treatment of various bacterial infections, such as pharyngitis, tonsillitis, otitis media, and uncomplicated skin infections.
- Generic Name
- Cefprozil
- DrugBank Accession Number
- DB01150
- Background
Cefprozil is a cephalosporin antibiotic that is commonly employed to treat a variety of bacterial infections, including those of the ear and skin, bronchitis, and others.
- Type
- Small Molecule
- Groups
- Approved
- Structure
Structure for Cefprozil (DB01150)
- Weight
- Average: 389.426
Monoisotopic: 389.104541423 - Chemical Formula
- C18H19N3O5S
- Synonyms
- Cefprozil
- Cefprozil anhydrous
- Cefprozilo
- Cefprozilum
- External IDs
- BBS-1067
- BMY-28167
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
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- Contraindications & Blackbox Warnings
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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.
Target Actions Organism APenicillin-binding protein 1A inhibitorStreptococcus pneumoniae serotype 4 (strain ATCC BAA-334 / TIGR4) APenicillin-binding protein 2x inhibitorStreptococcus pneumoniae serotype 4 (strain ATCC BAA-334 / TIGR4) APenicillin-binding protein 2B inhibitorStreptococcus pneumoniae serotype 4 (strain ATCC BAA-334 / TIGR4) - 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]
- Adverse Effects
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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.
- 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 Cefprozil 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 Cefprozil. Aceclofenac The risk or severity of nephrotoxicity can be increased when Cefprozil is combined with Aceclofenac. Acemetacin The risk or severity of nephrotoxicity can be increased when Cefprozil is combined with Acemetacin. Acenocoumarol The risk or severity of bleeding can be increased when Cefprozil is combined with Acenocoumarol. Acetaminophen Cefprozil 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 Cefprozil. Aclidinium Cefprozil may decrease the excretion rate of Aclidinium which could result in a higher serum level. Acrivastine Cefprozil 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 Cefprozil. 
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- Take with or without food. The absorption is unaffected by food.
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 Cefprozil monohydrate 3ADV90MJVU 121123-17-9 ALYUMNAHLSSTOU-CIRGZYLNSA-N - Product Images
- International/Other Brands
- Brisoral / Cronocef / Serozil
- Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Cefprozil Powder, for suspension 250 mg/5mL Oral Par Pharmaceutical Companies, Inc. 2007-02-21 2007-02-21 US 
Cefprozil Tablet 500 mg Oral Pro Doc Limitee 2009-06-10 2014-07-24 Canada 
Cefprozil Powder, for suspension 125 mg/5mL Oral Par Pharmaceutical Companies, Inc. 2007-02-21 2007-02-21 US Cefprozil Powder for Oral Suspension Powder, for suspension 250 mg / 5 mL Oral Ranbaxy Inc. Not applicable Not applicable Canada Cefprozil Tablets Tablet 500 mg Oral Ranbaxy Inc. Not applicable Not applicable Canada Cefprozil Tablets Tablet 250 mg Oral Ranbaxy Inc. Not applicable Not applicable Canada Cefzil Suspension 125 mg/5mL Oral Corden Pharma Latina S.p.A. 2016-12-06 2016-12-23 US Cefzil Powder, for suspension 250 mg/5mL Oral Bristol Myers Squibb 2009-06-01 2010-02-28 US Cefzil Tablet, film coated 250 mg/1 Oral Bristol Myers Squibb 2009-06-01 2010-02-28 US Cefzil Powder, for suspension 125 mg/5mL Oral Bristol Myers Squibb 2009-06-01 2010-02-28 US - Generic Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Apo-cefprozil Powder, for suspension 250 mg / 5 mL Oral Apotex Corporation 2007-04-20 Not applicable Canada Apo-cefprozil Tablet 250 mg Oral Apotex Corporation 2007-03-12 Not applicable Canada Apo-cefprozil Powder, for suspension 125 mg / 5 mL Oral Apotex Corporation 2007-04-20 Not applicable Canada Apo-cefprozil Tablet 500 mg Oral Apotex Corporation 2007-03-12 Not applicable Canada Auro-cefprozil Tablet 250 mg Oral Auro Pharma Inc 2012-01-13 Not applicable Canada Auro-cefprozil Powder, for suspension 250 mg / 5 mL Oral Auro Pharma Inc 2012-01-13 Not applicable Canada Auro-cefprozil Powder, for suspension 125 mg / 5 mL Oral Auro Pharma Inc 2012-01-13 Not applicable Canada Auro-cefprozil Tablet 500 mg Oral Auro Pharma Inc 2012-01-13 Not applicable Canada Ava-cefprozil Powder, for suspension 250 mg / 5 mL Oral Avanstra Inc 2011-10-11 2014-08-21 Canada Ava-cefprozil Tablet 500 mg Oral Avanstra Inc 2011-10-11 2014-08-21 Canada - Unapproved/Other Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image PREFIX 500 MG FILM TABLET, 10 ADET Cefprozil (500 mg) Tablet, film coated Oral NOBEL İLAÇ SAN. VE TİC. A.Ş. 2020-08-14 Not applicable Turkey 
PREFIX 500 MG FILM TABLET, 20 ADET Cefprozil (500 mg) Tablet, film coated Oral NOBEL İLAÇ SAN. VE TİC. A.Ş. 2020-08-14 Not applicable Turkey
Categories
- ATC Codes
- J01DC10 — Cefprozil
- Drug Categories
- Chemical TaxonomyProvided by Classyfire
- Description
- This 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.
- Kingdom
- Organic compounds
- Super Class
- Organoheterocyclic compounds
- Class
- Lactams
- Sub Class
- Beta lactams
- Direct Parent
- Cephalosporins
- Alternative Parents
- N-acyl-alpha amino acids and derivatives / Alpha amino acid amides / Phenylacetamides / 1-hydroxy-2-unsubstituted benzenoids / Aralkylamines / 1,3-thiazines / Tertiary carboxylic acid amides / Secondary carboxylic acid amides / Amino acids / Azetidines show 10 more
- Substituents
- 1-hydroxy-2-unsubstituted benzenoid / Alpha-amino acid amide / Alpha-amino acid or derivatives / Amine / Amino acid / Amino acid or derivatives / Aralkylamine / Aromatic heteropolycyclic compound / Azacycle / Azetidine show 26 more
- Molecular Framework
- Aromatic heteropolycyclic compounds
- External Descriptors
- cephalosporin, semisynthetic derivative (CHEBI:3506)
- Affected organisms
- Enteric bacteria and other eubacteria
Chemical Identifiers
- UNII
- 1M698F4H4E
- CAS number
- 92665-29-7
- InChI Key
- WDLWHQDACQUCJR-PBFPGSCMSA-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)/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)[C@H](N)C1=CC=C(O)C=C1)C(O)=O
References
- Synthesis Reference
Julia Greil, Johannes Ludescher, Siegfried Wolf, "Intermediates in cefprozil production." U.S. Patent US07355041, issued April 08, 2008.
US07355041- General References
- Not Available
- External Links
- Human Metabolome Database
- HMDB0015281
- KEGG Compound
- C06888
- PubChem Compound
- 5281006
- PubChem Substance
- 46504903
- ChemSpider
- 56685
- 1546020
- ChEBI
- 3506
- ChEMBL
- CHEMBL3301800
- ZINC
- ZINC000003776970
- Therapeutic Targets Database
- DAP000447
- PharmGKB
- PA164746342
- RxList
- RxList Drug Page
- Drugs.com
- Drugs.com Drug Page
- PDRhealth
- PDRhealth Drug Page
- Wikipedia
- Cefprozil
- FDA label
- Download (203 KB)
- MSDS
- Download (44.9 KB)
Clinical Trials
- Clinical Trials
Phase Status Purpose Conditions Count 1 Completed Not Available Healthy Subjects (HS) 4 1 Completed Treatment Healthy Subjects (HS) 5 0 Terminated Treatment Osteomyelitis 1 Not Available Completed Not Available Healthy Subjects (HS) 4
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Apotex Inc.
- A-S Medication Solutions LLC
- Aurobindo Pharma Ltd.
- Bristol-Myers Squibb Co.
- Dispensing Solutions
- Greenstone LLC
- Howard Beach Medical Equipment
- Lupin Pharmaceuticals Inc.
- Northstar Rx LLC
- Orchid Healthcare
- PD-Rx Pharmaceuticals Inc.
- Pharmaceutical Utilization Management Program VA Inc.
- Physicians Total Care Inc.
- Ranbaxy Laboratories
- Redpharm Drug
- Sandoz
- Southwood Pharmaceuticals
- Teva Pharmaceutical Industries Ltd.
- Wockhardt Ltd.
- Dosage Forms
Form Route Strength Powder, for suspension Oral 125 mg / 5 mL Powder, for suspension Oral 250 mg / 5 mL Tablet, effervescent Tablet Oral 500 mg/1 Powder, for suspension Oral 125 mg/5mL Powder, for suspension Oral 250 mg/5mL Suspension Oral 125 mg/5mL Suspension Oral 250 mg/5mL Tablet Oral 250 mg/1 Tablet, film coated Oral 250 mg/1 Tablet, film coated Oral 500 mg/1 Tablet Oral 250 MG Tablet Oral 500 MG Syrup Tablet, film coated Oral Powder, for suspension Oral Tablet Oral Tablet, film coated Oral 500 mg Tablet, effervescent 250 mg Tablet, film coated Oral 250 mg Tablet, effervescent 500 mg - Prices
Unit description Cost Unit Cefprozil 250 mg/5ml Suspension 100ml Bottle 78.86USD bottle Cefzil 500 mg tablet 6.6USD tablet Cefprozil 500 mg tablet 5.46USD tablet Cefzil 250 mg tablet 3.24USD tablet Cefprozil 250 mg tablet 2.7USD tablet Apo-Cefprozil 500 mg Tablet 1.99USD tablet Ran-Cefprozil 500 mg Tablet 1.99USD tablet Sandoz Cefprozil 500 mg Tablet 1.99USD tablet Apo-Cefprozil 250 mg Tablet 1.02USD tablet Ran-Cefprozil 250 mg Tablet 1.02USD tablet Sandoz Cefprozil 250 mg Tablet 1.02USD tablet Cefzil 50 mg/ml Suspension 0.35USD ml Apo-Cefprozil 50 mg/ml Suspension 0.2USD ml Cefprozil 50 mg/ml Suspension 0.2USD ml Ran-Cefprozil 50 mg/ml Suspension 0.2USD ml Sandoz Cefprozil 50 mg/ml Suspension 0.2USD ml Cefzil 25 mg/ml Suspension 0.18USD ml Apo-Cefprozil 25 mg/ml Suspension 0.1USD ml Ran-Cefprozil 25 mg/ml Suspension 0.1USD ml Sandoz Cefprozil 25 mg/ml Suspension 0.1USD ml DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 218-225 °C Not Available water solubility 55 mg/L Not Available logP 0.6 Not Available - Predicted Properties
Property Value Source Water Solubility 0.149 mg/mL ALOGPS logP 0.94 ALOGPS logP -1.9 Chemaxon logS -3.4 ALOGPS pKa (Strongest Acidic) 3.3 Chemaxon pKa (Strongest Basic) 7.22 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 6 Chemaxon Hydrogen Donor Count 4 Chemaxon Polar Surface Area 132.96 Å2 Chemaxon Rotatable Bond Count 5 Chemaxon Refractivity 101.27 m3·mol-1 Chemaxon Polarizability 39.35 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 No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption - 0.8478 Blood Brain Barrier - 0.9962 Caco-2 permeable - 0.8353 P-glycoprotein substrate Substrate 0.7853 P-glycoprotein inhibitor I Non-inhibitor 0.9315 P-glycoprotein inhibitor II Non-inhibitor 0.9889 Renal organic cation transporter Non-inhibitor 0.9264 CYP450 2C9 substrate Non-substrate 0.8214 CYP450 2D6 substrate Non-substrate 0.8324 CYP450 3A4 substrate Substrate 0.5102 CYP450 1A2 substrate Non-inhibitor 0.8866 CYP450 2C9 inhibitor Non-inhibitor 0.8768 CYP450 2D6 inhibitor Non-inhibitor 0.9196 CYP450 2C19 inhibitor Non-inhibitor 0.8825 CYP450 3A4 inhibitor Non-inhibitor 0.8724 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.8149 Ames test Non AMES toxic 0.6562 Carcinogenicity Non-carcinogens 0.8849 Biodegradation Not ready biodegradable 0.9584 Rat acute toxicity 1.6050 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9935 hERG inhibition (predictor II) Non-inhibitor 0.7516
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
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- 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
- Uniprot Name
- Penicillin-binding protein 1A
- Molecular Weight
- 79757.96 Da
References
- 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. [Article]
- 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
- Uniprot Name
- Penicillin-binding protein 2x
- Molecular Weight
- 82312.475 Da
References
- 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. [Article]
- 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
- Uniprot Name
- Penicillin-binding protein 2B
- Molecular Weight
- 73872.305 Da
References
- 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. [Article]
Drug created at June 13, 2005 13:24 / Updated at June 05, 2023 06:28