기본 정보
- CAS
92665-29-7- 표준 SMILES
C/C=C/C1=C(C(=O)O)N2C(=O)[C@@H](NC(=O)[C@H](N)c3ccc(O)cc3)[C@H]2SC1- InChIKey
WDLWHQDACQUCJR-ZAMMOSSLSA-N- 분자식
- C18H19N3O5S
- 평균 분자량
- 389.4 g/mol
- 단동위원소 질량
- 389.10454171
개요
Cefprozil is 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 infections. It has a role as an antibacterial drug. It is a cephalosporin and a semisynthetic derivative.
이름 및 식별자
- 우선 이름
- Procef
- IUPAC
- (6R,7R)-7-[[(2R)-2-amino-2-(4-hydroxyphenyl)acetyl]amino]-8-oxo-3-[(E)-prop-1-enyl]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
- 현지명
- 세프프로질(cefprozil)
- 영어명
- Cefprozil
- 분자식
- C18H19N3O5S
- 분자량
- 389.43
이름 및 동의어
Procef92676-86-3Cefprozilum [INN-Latin]Cefprozilo [INN-Spanish]BrisoralCefprozil (E)-isomerCefprozil Impurity 8S1SDI2FJIYArzimolCronocefSerozilCefzil (TN)
이름 더 보기
세프프로질(cefprozil)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-[(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(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(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(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
물성
구조 계산 물성
- XLogP
- -1.4
- 극성 표면적
- 158 Ų
- 수소 결합 공여자 수
- 4
- 수소 결합 수용자 수
- 7
- 회전 가능 결합 수
- 5
- 무거운 원자 수
- 27
- 형식 전하
- 0
- 복잡도
- 699
실험 및 물리화학적 성질
Drugs
Pharmaceuticals -> Antibiotics
Pharmaceuticals -> Antibiotics
Pharmaceuticals -> Listed in ZINC15
Melting Point218-225 °C
Collision Cross Section195.07 Ų [M+Na]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
물리화학적 성질
- 녹는점
- 215 · 215-217°C (dec.)
- 끓는 점
- 803 ℃ · 803℃
- 밀도
- 1.53 · 1.53±0.1 g/cm3(Predicted)
- 인화점
- 110 ° · >110°(230°F)
- 저장 조건
- -20 °C · Keep in dark place,Inert atmosphere,Store in freezer, under -20°C
- 용해도
- 0.3 mg/ml; · DMF: 0.3 mg/ml; DMSO: 2.5 mg/ml; PBS (pH 7.2): 1.25 mg/ml
- 산도 계수 (pKa)
- 2.92 · 2.92±0.50(Predicted)
- 물리적 상태
- 가루
- 수용성
- 10 mg/ml의 · 10mg/ml의 DMSO에 용해됩니다. 물에 불용성.
- BCS Class
- 3 · 3
- InChIKey
- WDLWHQDACQUCJR-PBFPGSCMSA-N
화학 및 산업
약리 정보
Protein Binding36%
PharmacodynamicsCefprozil, a semisynthetic, second-generation cephalosporin, is used to treat otitis media, soft-tissue infections, and respiratory tract infections.
Mechanism of Action
Cefprozil, like the penicillins, is a beta-lactam antibiotic. By binding to specific penicillin-binding proteins (PBPs) located inside the bacterial cell wall, it inhibits the third and last stage of bacterial cell wall synthesis. Cell lysis is then mediated by bacterial cell wall autolytic enzymes such as autolysins; it is possible that cefprozil interferes with an autolysin inhibitor.
Biological Half-Life1.3 hours
Metabolism/MetabolitesCefprozil is eliminated primarily by the kidneys
Absorption, Distribution and Excretion
Oral bioavailability is approximately 95%.
0.23 L/kg
3 mL/min/kg [fasting subjects]
응용 분야
개요Cefprozil 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.
용도Semisynthetic oral cephalosporin consisting of approx. 90:10 Z/E isomeric mixture. Antibacterial
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