92665-29-7 Usage
Description
Cefprozil is a semisynthetic oral cephalosporin antibiotic, consisting of approximately a 90:10 Z/E isomeric mixture. It is structurally similar to cefadroxil but has a broader spectrum of antibacterial activity, comparable to cefaclor, with greater activity against various bacteria such as Staphylococcus aureus, Staphylococcus epidermidis, Listeria monocytogenes, Streptococci, Haemophilus influenzae, Propionibacterium acnes, Clostridium perfringens, and Clostridium difficile.
Used in Pharmaceutical Industry:
Cefprozil is used as an antibiotic for the treatment of various infections, including otitis media, uncomplicated skin and skin structure infections, and upper/lower respiratory tract infections. Its broad-spectrum activity and effectiveness against a range of bacteria make it a valuable treatment option in this industry.
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.
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
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.
Pharmacokinetics
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
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.
Clinical Use
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 0024-0031; 0036-0041, (2019/04/14)
The invention relates to a preparation method of cefprozil. A synthesis method comprises the following steps: taking 7-ACA (7-aminocephalosporanic acid) as a starting raw material; after carrying outsilylation protection, carrying out a series of reactions including iodination and the like to generate a compound 2; taking the compound 2 to react with methyl D-(-)-4-hydroxy-phenylglycinate under the catalysis of immobilized penicillin acylase to generate a compound 1, so as to obtain a target product cefprozil. The preparation method provided by the invention has the advantages of moderate reaction conditions, environmental friendliness, high conversion ratio, simple technology and high cis-isomer content.
