Cefprozil
Basic information
- CAS
92665-29-7- Standard SMILES
CC=CC1=C(C(=O)O)N2C(=O)[C@@H](NC(=O)[C@H](N)c3ccc(O)cc3)[C@H]2SC1- InChIKey
WDLWHQDACQUCJR-PBFPGSCMSA-N- Molecular formula
- C18H19N3O5S
- Average molar mass
- 389.4 g/mol
- Monoisotopic mass
- 389.10454189
Overview
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.
Names & identifiers
- Preferred name
- Cefprozil
- IUPAC
- (6R,7R)-7-[[(2R)-2-amino-2-(4-hydroxyphenyl)acetyl]amino]-8-oxo-3-prop-1-enyl-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
- English name
- Cefprozil
- Molecular formula
- C18H19N3O5S
- Molecular weight
- 389.43
Names & synonyms
cefprozilCefzil92665-29-7Sulfate, CefprozilMonohydrate, CefprozilDTXSID6022767BMY 2810028100, BMYBMY-28100CHEBI:35061M698F4H4ENSC-759099
Show more names
5-Thia-1-azabicyclo4.2.0oct-2-ene-2-carboxylic acid, 7-(2R)-amino(4-hydroxyphenyl)acetylamino-8-oxo-3-(1-propenyl)-, (6R,7R)-(6R,7R)-7-[(R)-2-Amino-2-(p-hydroxyphenyl)acetylamino]-8-oxo-3-(1-propenyl)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid(6R,7R)-7-[(2R)-2-AMINO-2-(4-HYDROXYPHENYL)ACETYLAMINO]-8-OXO-3-(1-PRO-PENYL)-5-THIA-1-AZABICYCLO[4.2.0]OCT-2-ENE-2-CARBOXYLIC ACID(6R,7R)-7-[(2R)-2-Amino-2-(4-hydroxyphenyl) acetylamino]-8-oxo-3-(1-pro-penyl)-5-thia-1-azabicylo [4.2.0]oct-2-ene-2-carboxylic acid(6R,7R)-7-[[(2R)-2-Amino-2-(4-hydroxyphenyl)acetyl]amino]-8-oxo-3-(1-propen-1-yl)-5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid(6S,7R)-7-((R)-2-Amino-2-(4-hydroxyphenyl)acetamido)-8-oxo-3-((E)-prop-1-en-1-yl)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
Properties
Computed structural properties
- XLogP
- -1.4
- Topological polar surface area
- 158 Ų
- Hydrogen bond donors
- 4
- Hydrogen bond acceptors
- 7
- Rotatable bonds
- 5
- Heavy atoms
- 27
- Formal charge
- 0
- Complexity
- 699
Experimental & physicochemical properties
LogP0.6
Solubility1.49e-01 g/L
Human Drugs
Breast Feeding; Lactation; Milk, Human; Anti-Infective Agents; Antibacterial Agents; Cephalosporins
FDA approved drugs -> Active ingredient
FDA approved drugs -> Active ingredient
Melting Point
218-225 °C
218 - 225 °C
Physical DescriptionSolid
Physicochemical properties
- Melting point
- 215 · 215-217°C (dec.)
- Boiling point
- 803 ℃ · 803℃
- Density
- 1.53 · 1.53±0.1 g/cm3(Predicted)
- RTECS
- 339000 · XI0339000
- Flash point
- 110 ° · >110°(230°F)
- storage temp.
- -20 °C · Keep in dark place,Inert atmosphere,Store in freezer, under -20°C
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
Hazard information
Regulatory Information5-Thia-1-azabicyclo4.2.0oct-2-ene-2-carboxylic acid, 7-(2R)-amino(4-hydroxyphenyl)acetylamino-8-oxo-3-(1-propenyl)-, (6R,7R)-: Does not have an individual approval but may be used under an appropriate group standard
Toxicology
Drug Induced Liver Injury
Drug Induced Liver Injury Rank (DILIrank 2.0)
Cefprozil
vLess-DILI-concern
4
Adverse reactions
DOI:10.1016/j.drudis.2016.02.015
Effects During Pregnancy and Lactation◉ Summary of Use during Lactation
EPA Human Health Benchmarks for Pharmaceuticals
Cefprozil
11.7
49.3
Administered orally at 500 mg/day or 250 mg b.i.d.
Data used to generate the benchmarks include the following: Lowest Daily Dose (LDD): 500 mg/day, Lowest Therapeutic Dose (LTD): 6.3 mg/kg-day, and Screening Dose: 0.002 mg/kg-day.
12-May-16
Chemistry & industry
Pharmacology
ATC Code
J - Antiinfectives for systemic use
QJ - Antiinfectives for systemic use
Protein Binding36%
PharmacodynamicsCefprozil, 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.
Biological Half-Life1.3 hours
Metabolism/MetabolitesCefprozil is eliminated primarily by the kidneys
FDA Pharmacological Classification
4W0459ZA4V
CEFPROZIL
Established Pharmacologic Class [EPC] - Cephalosporin Antibacterial
Chemical Structure [CS] - Cephalosporins
Cefprozil is a Cephalosporin Antibacterial.
MeSH Pharmacological ClassificationBactericidal agents that contain a beta-lactam ring in their chemical structure. They inhibit bacterial cell wall synthesis by binding to PENICILLIN-BINDING PROTEINS, preventing the synthesis of peptidoglycan in bacterial cell walls.
Absorption, Distribution and Excretion
Oral bioavailability is approximately 95%.
0.23 L/kg
3 mL/min/kg [fasting subjects]
Related reactions
0 records
No reaction records under the current filter.
Compound notes
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