ChemicalBook > CAS DataBase List > Cefprozil

Cefprozil

Product Name
Cefprozil
CAS No.
92665-29-7
Chemical Name
Cefprozil
Synonyms
Prozef;Procef;bmy28100;Cefrozil;Cefprozi;CEFPROZIL;Cephprozyl;Cefprozile;Cefprozil-d4;cis-Cefprozil
CBNumber
CB4739649
Molecular Formula
C18H19N3O5S
Formula Weight
389.43
MOL File
92665-29-7.mol
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Cefprozil Property

Melting point:
215-217°C (dec.)
Boiling point:
803℃
Density 
1.53±0.1 g/cm3(Predicted)
RTECS 
XI0339000
Flash point:
>110°(230°F)
storage temp. 
Keep in dark place,Inert atmosphere,Store in freezer, under -20°C
solubility 
DMF: 0.3 mg/ml; DMSO: 2.5 mg/ml; PBS (pH 7.2): 1.25 mg/ml
pka
2.92±0.50(Predicted)
form 
Powder
Water Solubility 
Soluble in DMSO at 10mg/ml. Insoluble in water.
BCS Class
3
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)/t12-,13-,17-/m1/s1
InChIKey
WDLWHQDACQUCJR-PBFPGSCMSA-N
SMILES
N12[C@@]([H])([C@H](NC([C@H](N)C3=CC=C(O)C=C3)=O)C1=O)SCC(C=CC)=C2C(O)=O
CAS DataBase Reference
92665-29-7(CAS DataBase Reference)
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Hazard and Precautionary Statements (GHS)

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N-Bromosuccinimide Price

Alfa Aesar
Product number
J66326
Product name
Cefprozil
Packaging
100mg
Price
$143
Updated
2024/03/01
Alfa Aesar
Product number
J66326
Product name
Cefprozil
Packaging
1g
Price
$407
Updated
2023/06/20
Cayman Chemical
Product number
23840
Product name
Cefprozil
Purity
≥95% (mixture of cis and trans)
Packaging
5mg
Price
$32
Updated
2024/03/01
Cayman Chemical
Product number
23840
Product name
Cefprozil
Purity
≥95% (mixture of cis and trans)
Packaging
10mg
Price
$57
Updated
2024/03/01
Cayman Chemical
Product number
23840
Product name
Cefprozil
Purity
≥95% (mixture of cis and trans)
Packaging
25mg
Price
$116
Updated
2024/03/01
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Cefprozil Chemical Properties,Usage,Production

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

Originator

Bristol-Myers Squibb (U.S.A.)

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

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

As for group 2 cephalosporins . It should not be used in infections in which H. influenzae is, or is likely to be, implicated. It should not be used as an alternative to penicillin in syphilis.

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.

Side effects

Nausea, vomiting and abdominal discomfort are relatively common. Pseudomembranous colitis has been described and overgrowth of Candida with vaginitis may be troublesome. Otherwise, mild hypersensitivity reactions and biochemical changes common to cephalosporins occur. Very rare neurological disturbances have been described, particularly in patients in whom very high plasma levels have been achieved. There are rare reports of Stevens–Johnson syndrome and toxic epidermal necrolysis.

Cefprozil Preparation Products And Raw materials

Raw materials

Preparation Products

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Cefprozil Suppliers

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View Lastest Price from Cefprozil manufacturers

WUHAN FORTUNA CHEMICAL CO., LTD
Product
Cefprozil 92665-29-7
Price
US $0.00/KG
Min. Order
1KG
Purity
98%min
Supply Ability
30tons/month
Release date
2023-01-30
Hebei Weibang Biotechnology Co., Ltd
Product
Cefprozil 92665-29-7
Price
US $10.00/KG
Min. Order
1KG
Purity
99%
Supply Ability
10 mt
Release date
2024-11-06
Shaanxi TNJONE Pharmaceutical Co., Ltd
Product
Cefprozil 92665-29-7
Price
US $0.00/Kg
Min. Order
1Kg
Purity
99%
Supply Ability
10kg
Release date
2024-04-09

92665-29-7, CefprozilRelated Search:

Betaine Acetylacetone EC 2.6.1.2 3,4'-DIAMINODIPHENYLMETHANE Acetaminophen Glycine Acetyl chloride Sulfamic acid ALTRENOGEST Glucosamine Phenylacetone TRIS EDTA ACETATE BUFFER, 10X, DNASE, RNASE AND PROTEASE FREE, PH 8.3, FOR MOLECULAR BIOLOGY E-Cefprozil Cefprozil intermediate CEFPROZIL HYDRATE,CEFPROZIL MONOHYDRATE Cefprozil USP CEFPROZIL (Z)-ISOMER (200 MG)H0E054927UG/MG(AI) Cefprozil

  • CEFPROZIL:(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
  • Cefprozile
  • Cephprozyl
  • Procef
  • Prozef
  • 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-[(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)-1-oxoethyl]amino]-8-oxo-3-[(Z)-prop-1-enyl]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
  • Cefprozil - mix of Z (92%), and E (7%) isomers
  • (6R-(6alpha,7beta(R*)))-7-((Amino(4-hydroxyphenyl)acetyl)amino)-8-oxo-3-(1-propenyl)-5-Thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acid
  • 8-[2-Amino-2-(4-hydroxyphenyl)-acetyl]amino-7-oxo-4-prop-1-enyl-2-thia-6-azabicyclo[4.2.0]oct-4-ene-5-carboxylic acid
  • (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
  • cis-Cefprozil
  • (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
  • Cefprozil-d4
  • (6r-(6-alpha,7beta(r*)))-l)acetyl)amino)-8-oxo-3-(1-propenyl)
  • bmy28100
  • (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
  • Cefrozil
  • (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
  • K690 Cefprozil
  • CEFPROZIL
  • 5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid, 7-[[(2R)-2-amino-2-(4-hydroxyphenyl)acetyl]amino]-8-oxo-3-(1-propen-1-yl)-, (6R,7R)-
  • Cefprozil USP/EP/BP
  • Cefprozil DISCONTINUED. Please see C243933.
  • Cefprozi
  • Cefprozil (Mixture of E,Z isomers)Q: What is Cefprozil (Mixture of E,Z isomers) Q: What is the CAS Number of Cefprozil (Mixture of E,Z isomers) Q: What is the storage condition of Cefprozil (Mixture of E,Z isomers) Q: What are the applications of Cefprozil (Mixture of E,Z isomers)
  • Cefazolin propylene
  • Cefprozil (BMY-28100)
  • 92665-29-7
  • 156-1-46
  • 99-0-2
  • C18H19N3SH2O
  • C18H19N3O5S
  • API
  • cephalosporins
  • Aromatics
  • Heterocycles
  • Sulfur & Selenium Compounds
  • Intermediates & Fine Chemicals
  • Pharmaceuticals