Cefzil

Base Information

• Chemical Name: Cefzil
• CAS No.: 92665-29-7
• Molecular Formula: C18H19N3O5S
• Molecular Weight: 389.432
• Hs Code.: 2941905990
• European Community (EC) Number: 618-870-0,685-390-6
• UNII: 3ADV90MJVU
• Wikipedia: Cefprozil
• Wikidata: Q27256965
• NCI Thesaurus Code: C28917,C77189
• RXCUI: 19552
• Mol file: 92665-29-7.mol

Synonyms:7-(2-amino-2-(4-hydroxyphenyl)acetamido)-3-(propenyl)-3-cephem-4-carboxylic acid monohydrate;7-(2-amino-2-(p-hydroxyphenyl)acetamido)-8-oxo-3-(1-propenyl)-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acid;Arzimol;BMY 28100;BMY-28100;Brisoral;cefprozil;cefprozil monohydrate;Cefzil;Procef

Chemical Property of Cefzil

Chemical Property:

• Appearance/Colour: white powder
• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 76°C
• Refractive Index: 1.718
• Boiling Point: 803.1 °C at 760 mmHg
• PKA: 2.92±0.50(Predicted)
• Flash Point: 439.5 °C
• PSA: 158.26000
• Density: 1.53 g/cm³
• LogP: 1.73580
• Storage Temp.: -20°C Freezer
• Water Solubility.: Soluble in DMSO at 10mg/ml. Insoluble in water.
• Hydrogen Bond Donor Count: 5
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 5
• Exact Mass: 407.11510657
• Heavy Atom Count: 28
• Complexity: 699

Purity/Quality:

99% ^*data from raw suppliers

Cefprozil United States Pharmacopeia (USP) Reference Standard ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC=CC1=C(N2C(C(C2=O)NC(=O)C(C3=CC=C(C=C3)O)N)SC1)C(=O)O.O
• Isomeric SMILES: C/C=C/C1=C(N2[C@@H]([C@@H](C2=O)NC(=O)[C@@H](C3=CC=C(C=C3)O)N)SC1)C(=O)O.O
• Recent ClinicalTrials: To Demonstrate the Relative Bioavailability of Cefzil 500 mg Cefprozil Tablets Under Fasting Conditions
• Description: Cefprozil is a new orally active cephalosporin useful in the treatment of otitis media, uncomplicated skin and skin structure infections plus upper/lower respiratory tract infections. Although structurally similar to cefadroxil, its spectrum of antibacterial activity is comparable to cefaclor, but exhibits greater activity against S.aureus, S. epidermidis, Listeria monocytogenes, Streptococci, H. influenzae, Propionibacterium acnes. Clostridium perfringens and difficile.
• Uses: Semisynthetic oral cephalosporin consisting of approx. 90:10 Z/E isomeric mixture. Antibacterial
• Therapeutic Function: Antibiotic
• Clinical Use: Cefprozil (Cefzil) is an orally active second-generationcephalosporin that is similar in structure and antibacterialspectrum to cefadroxil. Oral absorption is excellent (oralbioavailability is about 95%) and is not affected by antacidsor histamine H2-antagonists. Cefprozil exhibits greater invitro activity against streptococci, Neisseria spp., and S. aureusthan does cefadroxil. It is also more active than thefirst-generation cephalosporins against members of theEnterobacteriaceae family, such as E. coli, Klebsiella spp., P. mirabilis, and Citrobacter spp. The plasma half-life of1.2 to 1.4 hours permits twice-a-day dosing for the treatmentof most community-acquired respiratory and urinary tractinfections caused by susceptible organisms. It has been used for various infections for which oral cephalosporins are appropriate.

Technology Process of Cefzil

There total 5 articles about Cefzil which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 97.74%

(7R,8R)-7-amino-3-[propen-1-yl]-3-cephem-4-carboxylic acid (120709-09-3) + D-2-p-hydroxyphenylglycine methyl ester (37763-23-8) → 7-[2-amino-2-(4-hydroxyphenyl)acetamido]-3-(propen-1-yl)-3-cephem-4-carboxylic acid (92665-29-7)

Guidance literature:

(7R,8R)-7-amino-3-[propen-1-yl]-3-cephem-4-carboxylic acid; With penicillin acylase; at 30 - 35 ℃; for 0.5h; pH=7; Enzymatic reaction;

D-2-p-hydroxyphenylglycine methyl ester; With sodium lauryl sulfate; In 1,4-dioxane; at 30 - 35 ℃; for 2h; Reagent/catalyst;

Reference yield: 97.0%

C31H35N3O8S → 7-[2-amino-2-(4-hydroxyphenyl)acetamido]-3-(propen-1-yl)-3-cephem-4-carboxylic acid (92665-29-7)

Guidance literature:

With trifluoroacetic acid; In dichloromethane; at 25 - 30 ℃; for 10h;

Reference yield:

C22H27N3O7S → 7-[2-amino-2-(4-hydroxyphenyl)acetamido]-3-(propen-1-yl)-3-cephem-4-carboxylic acid (92665-29-7)

Guidance literature:

With pyridinium p-toluenesulfonate; In tert-butyl alcohol; for 2h; Reflux;

upstream raw materials:

D-4-hydroxyphenylglycine

(7R,8R)-7-amino-3-[propen-1-yl]-3-cephem-4-carboxylic acid

D-2-p-hydroxyphenylglycine methyl ester

p-hydroxyphenylglycine

Refernces

• 1、 -. "Preparation method of cefprozil". . . Retrieved 2019/02/04.
• 2、 -. "Cefprozil refining method". . . Retrieved 2019/12/02.