92665-29-7 Usage
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.
Chemical Properties
Pale Yellow Solid
Uses
Semisynthetic oral cephalosporin consisting of approx. 90:10 Z/E isomeric mixture. Antibacterial
Definition
ChEBI: A semisynthetic, second-generation cephalosporin, with prop-1-enyl and (R)-2-amino-2-(4-hydroxyphenyl)acetamido groups at positions 3 and 7, respectively, of the cephem skeleton. It is used to treat bronchitis as well as ear, skin and other bacterial infec
ions.
Manufacturing Process
A mixture of 4-hydroxy-D-phenylglycine (10 g), ethylene glycol (15 ml) and
concentrated sulfuric acid (5 ml) was stirred for 18 hours at 55°C under
anhydrous conditions. The solution was cooled, and then ice (10 g) was added
to it, and the pH was adjusted to 1.0 with 10 N NH4OH (4.5 ml) giving 40 ml
of solution of hydroxyethyl ester of 4-hydroxy-D-phenylglycine.The enzyme mixture of 20 ml containing immobilized recombinant penicillin G
amidase as the enzyme, 10% hydroxyethyl ester of 4-hydroxy-D-phenylglycine, 4% cefprozil (amine source), and 8% enzyme (immobilized
recombinant penicillin G amidase, equivalent to 32 IU/ml of enzyme) was
made up without buffer. The above prepared ester solution (6.9 ml) was
mixed with water (2 ml) and adjusted to pH 7.5 with 10 N NH4OH. Then the
amine source (0.8 g) was added to it and the pH adjusted to 7.5 with 1 N
NH4OH and the volume to 18.4 ml. Then the mixture was cooled to 5-15°C
and solid enzyme (1.6 g; 640 IU) was added to it. The pH was not maintained
at 7.5 and fell about 0.6 units during the reaction. The reaction mixture was
analyzed by HPLC on a C18 Reverse Phase column. The mobile phase was
10% acetonitrile/0.3% H3PO4. The isomers of cefprozil appeared at 2.9
minutes (cis) and at 5.1 minutes (trans). The final product was obtained with
a maximum yield of 92-96%. The whole experiment was completed in 25-50
min.Synthesis of cefprozil may be carried out at 15°C using Boehringer penicillin G
amidase as the enzyme and hydroxyethyl ester of 4-hydroxy-D-phenylglycine.
A maximum yield of about 95%. The experiment was completed in 35
minutes.
Brand name
Cefzil (Bristol-Myers Squibb).
Therapeutic Function
Antibiotic
Antimicrobial activity
Activity against Gram-positive cocci and Gram-negative
bacilli is better than that of cefadroxil (which it structurally
resembles) but is not as good as that of group 5 agents
. It is moderately stable to hydrolysis
by the common plasmid-mediated β-lactamases, but is hydrolyzed
by the chromosomal enzymes of Gram-negative bacilli
.
Hazard
Moderately toxic by ingestion. Human sys-
temic effects.
Pharmacokinetics
Different sources of media describe the Pharmacokinetics of 92665-29-7 differently. You can refer to the following data:
1. Oral absorption: >90%
Cmax 250 mg oral: 5–7 mg/L after 1 h
500 mg oral: 10 mg/L after 1
Plasma half-life: 1–1.4 h
Volume of distribution: 15–201
Plasma protein binding: 35–45%
Absorption and distribution
It is almost completely absorbed and well distributed, penetrating
well into tonsillar and other tissues and inflammatory
exudate. Absorption is unaffected by food or
antacids and there is no accumulation on multiple dosing
regimens.
Metabolism and excretion
Most of the dose is excreted unchanged in urine, though
about 20% is found in feces. Urinary concentrations after a
500 mg oral dose usually exceed 1 g/L. The elimination halflife
is prolonged in patients with renal impairment, reaching
6 h in anuric patients. About half the drug is removed in 3 h
by hemodialysis.
2. Oral absorption: >90%
Cmax 250 mg oral: 5–7 mg/L after 1 h
500 mg oral: 10 mg/L after 1
Plasma half-life: 1–1.4 h
Volume of distribution: 15–201
Plasma protein binding: 35–45%
Absorption and distribution
It is almost completely absorbed and well distributed, penetrating
well into tonsillar and other tissues and inflammatory
exudate. Absorption is unaffected by food or
antacids and there is no accumulation on multiple dosing
regimens.
Metabolism and excretion
Most of the dose is excreted unchanged in urine, though
about 20% is found in feces. Urinary concentrations after a
500 mg oral dose usually exceed 1 g/L. The elimination halflife
is prolonged in patients with renal impairment, reaching
6 h in anuric patients. About half the drug is removed in 3 h
by hemodialysis.
Clinical Use
Different sources of media describe the Clinical Use of 92665-29-7 differently. You can refer to the following data:
1. 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.
2. It has been used for various infections for which oral cephalosporins
are appropriate.
Side effects
It is well tolerated. Diarrhea and gastrointestinal discomfort
may occur. There have been a few reports of pseudomembranous
colitis and serum sickness-like reactions.
Check Digit Verification of cas no
The CAS Registry Mumber 92665-29-7 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 9,2,6,6 and 5 respectively; the second part has 2 digits, 2 and 9 respectively.
Calculate Digit Verification of CAS Registry Number 92665-29:
(7*9)+(6*2)+(5*6)+(4*6)+(3*5)+(2*2)+(1*9)=157
157 % 10 = 7
So 92665-29-7 is a valid CAS Registry Number.
InChI:InChI=1/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-
92665-29-7Relevant articles and documents
Synthesis method of cefprozil
-
Paragraph 0011; 0042-0050, (2020/06/24)
The invention discloses a synthesis method of cefprozil. The method comprises the following steps: carrying out a reaction of a compound II and di-tert-butyl dicarbonate ester under the condition of 4-dimethylaminopyridine to prepare a compound III, after reaction between the compound III and oxalyl chloride, carrying out a reaction between the compound III and a compound IV to prepare a compoundV, and performing deprotection to prepare the final product, namely cefprozil (I). The raw materials for the reaction are easily available, the process route is simple, the total yield is high, the byproducts are few and the method is suitable for industrialized production.
Preparation method of cefprozil
-
Paragraph 0023; 0024; 0025; 0026; 0027-0031, (2019/02/04)
The invention relates to the technical field of preparation of antibiotics, and specifically discloses a preparation method of cefprozil. The preparation method is characterized by taking GCLE (7-phenylacetyl amino-3-chloromethyl-3-cephem-4-carboxylic acid p-methoxybenzyl ester) as a starting material, and carrying out hydroformylation, ethylation and dewatering, thus obtaining GPRE; then hydrolyzing, thus obtaining APRA; firstly protecting hydroxyl groups and amino groups of p-hydroxyl phenylglycine, then carrying out condensation reaction with the APRA, and then deprotecting, thus obtainingthe cefprozil. According to the preparation method disclosed by the invention, toxic triphenyl phosphine is not used for preparing phosphine salt, so that the method is more environment-friendly; a reaction route requires no wittig reaction, so that the cost is lower; the hydroxyl groups and the amino groups of the p-hydroxyl phenylglycine are protected by adopting chloromethyl methyl ether and then are in reacting with a compound as shown in a formula VI, the cost is low, a deprotection reaction system is neutral, and the yield and the purity of a product are favorably increased.