(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

• ChemBase ID: 1021
• Molecular Formular: C18H19N3O5S
• Molecular Mass: 389.42556
• Monoisotopic Mass: 389.10454172
• SMILES: S1[C@H]2N(C(=O)[C@H]2NC(=O)[C@H](N)c2ccc(O)cc2)C(=C(C1)/C=C/C)C(=O)O
• Canonical SMILES: C/C=C/C1=C(C(=O)O)N2[C@H](SC1)[C@@H](C2=O)NC(=O)[C@@H](c1ccc(cc1)O)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
• InChIKey: WDLWHQDACQUCJR-ZAMMOSSLSA-N

NAMES AND DATABASE IDS

Names

• 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
• IUPAC Traditional name: cefprozil
• Brand Name: Arzimol; Brisoral; Cronocef; Procef; Serozil
• Synonyms: Cefprozilo [INN-Spanish]; Cefprozil anhydrous; Cefprozilum [INN-Latin]; Cefprozil; (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; BMY 28100; Cefprozile; Cefzil; Cephprozyl; Procef; Prozef

Database IDs

• CAS Number: 92665-29-7
• PubChem SID: 160964484
• PubChem CID: 5281006

CALCULATED PROPERTIES

JChem

• Acid pKa: 3.5293207
• H Acceptors: 6
• H Donor: 4
• LogD (pH = 5.5): -1.9168022
• LogD (pH = 7.4): -2.175604
• Log P: -1.9216894
• Molar Refractivity: 101.2731 cm^3
• Polarizability: 38.68424 Å^3
• Polar Surface Area: 132.96 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 0.94
• LOG S: -3.42
• Solubility (Water): 1.49e-01 g/l

PROPERTIES

Physical Property

• Solubility: 55 mg/L; DMSO; Methanol
• Apperance: Pale Yellow Solid
• Melting Point: 215-217°C (dec.)
• Hydrophobicity(logP): 0.6

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

DrugBank - DB01150

• Drug Groups: approved
• Description: Cefprozil is a cephalosporin antibiotic. It can be used to treat bronchitis, ear infections, skin infections, and other bacterial infections.
• 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
• Pharmacology: Cefprozil, a semisynthetic, second-generation cephalosporin, is used to treat otitis media, soft-tissue infections, and respiratory tract infections.
• 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
• Biotransformation: Cefprozil is eliminated primarily by the kidneys
• Absorption: Oral bioavailability is approximately 95%.
• Half Life: 1.3 hours
• Protein Binding: 36%
• Distribution: * 0.23 L/kg
• Clearance: * 3 mL/min/kg [fasting subjects]
• External Links: Wikipedia; RxList; PDRhealth; Drugs.com

Toronto Research Chemicals - C243910

Semisynthetic oral cephalosporin consisting of approx. 90:10 Z/E isomeric mixture. Antibacterial.

REFERENCES

• Jones, R.N., et al.: Diagn. Microb. Infect. Dis., 9, 11 (1988)
• Barbhaiya, R.H., et al.: Antimicrob. Agents Chemother., 34, 1204 (1990)