기본 정보
- CAS
92665-29-7- 표준 SMILES
CC=CC1=C(C(=O)O)N2C(=O)[C@@H](NC(=O)[C@H](N)c3ccc(O)cc3)[C@H]2SC1- InChIKey
WDLWHQDACQUCJR-PBFPGSCMSA-N- 분자식
- C18H19N3O5S
- 평균 분자량
- 389.4 g/mol
- 단동위원소 질량
- 389.10454189
개요
Cefprozil is a cephalosporin antibiotic that is commonly employed to treat a variety of bacterial infections, including those of the ear and skin, bronchitis, and others.
이름 및 식별자
- 우선 이름
- Cefprozil
- IUPAC
- (6R,7R)-7-[[(2R)-2-amino-2-(4-hydroxyphenyl)acetyl]amino]-8-oxo-3-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
cefprozilCefzil92665-29-7Sulfate, CefprozilMonohydrate, CefprozilDTXSID6022767BMY 2810028100, BMYBMY-28100CHEBI:35061M698F4H4ENSC-759099
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(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
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
LogP0.6
Solubility1.49e-01 g/L
Human Drugs
Breast Feeding; Lactation; Milk, Human; Anti-Infective Agents; Antibacterial Agents; Cephalosporins
FDA approved drugs -> Active ingredient
FDA approved drugs -> Active ingredient
Melting Point
218-225 °C
218 - 225 °C
Physical DescriptionSolid
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
안전 및 규제
안전 정보는 참고용이며, 공급업체의 물질안전보건자료(SDS), 관련 법규 및 전문가 평가를 대체하지 않습니다.
유해성 정보
Regulatory Information5-Thia-1-azabicyclo4.2.0oct-2-ene-2-carboxylic acid, 7-(2R)-amino(4-hydroxyphenyl)acetylamino-8-oxo-3-(1-propenyl)-, (6R,7R)-: Does not have an individual approval but may be used under an appropriate group standard
독성 정보
Drug Induced Liver Injury
Drug Induced Liver Injury Rank (DILIrank 2.0)
Cefprozil
vLess-DILI-concern
4
Adverse reactions
DOI:10.1016/j.drudis.2016.02.015
Effects During Pregnancy and Lactation◉ Summary of Use during Lactation
EPA Human Health Benchmarks for Pharmaceuticals
Cefprozil
11.7
49.3
Administered orally at 500 mg/day or 250 mg b.i.d.
Data used to generate the benchmarks include the following: Lowest Daily Dose (LDD): 500 mg/day, Lowest Therapeutic Dose (LTD): 6.3 mg/kg-day, and Screening Dose: 0.002 mg/kg-day.
12-May-16
화학 및 산업
약리 정보
ATC Code
J - Antiinfectives for systemic use
QJ - Antiinfectives for systemic use
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
FDA Pharmacological Classification
4W0459ZA4V
CEFPROZIL
Established Pharmacologic Class [EPC] - Cephalosporin Antibacterial
Chemical Structure [CS] - Cephalosporins
Cefprozil is a Cephalosporin Antibacterial.
MeSH Pharmacological ClassificationBactericidal agents that contain a beta-lactam ring in their chemical structure. They inhibit bacterial cell wall synthesis by binding to PENICILLIN-BINDING PROTEINS, preventing the synthesis of peptidoglycan in bacterial cell walls.
Absorption, Distribution and Excretion
Oral bioavailability is approximately 95%.
0.23 L/kg
3 mL/min/kg [fasting subjects]
Cellular Locations
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