基本情報
- CAS
92665-29-7- 標準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- 分子式
- C18H19N3O5S
- 平均分子量
- 389.4 g/mol
- 単同位体質量
- 389.10454189
概要
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.
名称と識別子
- 優先名称
- 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
- 現地名
- セフプロジル
- 英語名
- Cefprozil
- 分子式
- C18H19N3O5S
- 分子量
- 389.43
名称と別名
cefprozilCefzil92665-29-7Sulfate, CefprozilMonohydrate, CefprozilDTXSID6022767BMY 2810028100, BMYBMY-28100CHEBI:35061M698F4H4ENSC-759099
名称をさらに表示
cis-セフプロジルセフプロジル(6R,7R)-7-[(R)-2-アミノ-2-(p-ヒドロキシフェニル)アセチルアミノ]-8-オキソ-3-(1-プロペニル)-5-チア-1-アザビシクロ[4.2.0]オクタ-2-エン-2-カルボン酸(6R,7R)-7-[(2R)-2-アミノ-2-(4-ヒドロキシフェニル)アセトアミド]-8-オキソ-3-(プロパ-1-エン-1-イル)-5-チア-1-アザビシクロ[4.2.0]オクタ-2-エン-2-カルボン酸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
物性
構造計算による物性
- XLogP
- -1.4
- 極性表面積
- 158 Ų
- 水素結合供与体数
- 4
- 水素結合受容体数
- 7
- 回転可能結合数
- 5
- 重原子数
- 27
- 形式電荷
- 0
- 複雑度
- 699
実験および物理化学的性質
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
物理化学的性質
- 融点
- 215 · 215-217°C (dec.)
- 沸点
- 803 ℃ · 803℃
- 比重(密度)
- 1.53 · 1.53±0.1 g/cm3(Predicted)
- 闪点
- 110 ° · >110°(230°F)
- 貯蔵温度
- -20 °C · Keep in dark place,Inert atmosphere,Store in freezer, under -20°C
- 溶解性
- 0.3 mg/ml; · DMF: 0.3 mg/ml; DMSO: 2.5 mg/ml; PBS (pH 7.2): 1.25 mg/ml
- 酸解離定数(Pka)
- 2.92 · 2.92±0.50(Predicted)
- 外見
- Powder
- 水溶解度
- 10 mg/mlでDMSOに可溶。水に不溶。 · 10mg/mlでDMSOに可溶。水に不溶。
安全と法規制
安全情報は参考情報です。供給元の安全データシート（SDS）、適用法令、専門家による評価に代わるものではありません。
危険有害性情報
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
毒性情報
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
化学と産業
薬理情報
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
関連反応
0 件
現在のフィルター条件では反応記録がありません。
化合物ノート
読み込み中…