7-[(2R)-2-amino-2-phenylacetamido]-3-chloro-8-oxo-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid hydrate

• ChemBase编号: 330
• 分子式: C16H18ClN3O5
• 平均质量: 367.78422
• 单一同位素质量: 367.09349837
• SMILES: N12C(C(C1=O)NC(=O)[C@@H](c1ccccc1)N)CCC(=C2C(=O)O)Cl.O
• Canonical SMILES: N[C@H](c1ccccc1)C(=O)NC1C2CCC(=C(N2C1=O)C(=O)O)Cl.O
• InChI: InChI=1S/C16H16ClN3O4.H2O/c17-9-6-7-10-12(15(22)20(10)13(9)16(23)24)19-14(21)11(18)8-4-2-1-3-5-8;/h1-5,10-12H,6-7,18H2,(H,19,21)(H,23,24);1H2/t10?,11-,12?;/m1./s1
• InChIKey: GPYKKBAAPVOCIW-HZKXUOCSSA-N

名称和登记号

名称

• IUPAC标准名: 7-[(2R)-2-amino-2-phenylacetamido]-3-chloro-8-oxo-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid hydrate
• IUPAC传统名: 7-[(2R)-2-amino-2-phenylacetamido]-3-chloro-8-oxo-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid hydrate
• 商标名: Lorabid; Loribid
• 别名: Loracarbefum [INN-Latin]; Loracarbef

登记号

• CAS号: 76470-66-1
• PubChem SID: 160963793
• PubChem CID: 60746

理论计算性质

• Acid pKa: 3.1261737
• 质子受体: 5
• 质子供体: 3
• LogD (pH = 5.5): -2.3995888
• LogD (pH = 7.4): -2.6549032
• Log P: -2.3996444
• 摩尔折射率: 86.6375 cm^3
• 极化性: 33.446136 Å^3
• 极化表面积: 112.73 Å^2
• 可自由旋转的化学键: 4
• 里宾斯基五规则: true

分子性质

理化性质

• 疏水性(logP): 0.5

详细说明

DrugBank - DB00447

• Drug Groups: approved
• Description: Loracarbef is a carbacephem antibiotic sometimes grouped together with the second-generation cephalosporin antibiotics. It is marketed under the trade name Lorabid.
• Indication: Used to treat upper respiratory tract bacterial infections, chronic bronchitis, pneumonia, sinusitis, pharyntitis and tonsillitis, skin absceses, urinary tract infections and pyelonephritis caused by E. coli, S. pyogenes, S. aureus, S. saprphyticus, S. penumoniae, H. influenzae and M. catarrhalis.
• Pharmacology: Loracarbef is considered a second generation cephalosporin antibiotic. The advantages of cephalosporin antibiotics include a broad range of activity, a safe record in children with almost no dose-related toxicity, and the lack of need to monitor levels. Adverse reactions are rare and consist primarily of hypersensitivity reactions with urticaria, nonspecific rash, and pruritus. Loracarbef can be used to treat a large number of bacterial infections caused by gram-negative and gram-positive bacteria, including upper respiratory tract bacterial infections, chronic bronchitis, pneumonia, sinusitis, pharyntitis and tonsillitis, skin absceses, urinary tract infections and pyelonephritis caused by E. coli, S. pyogenes, S. aureus, S. saprphyticus, S. penumoniae, H. influenzae and M. catarrhalis.
• Toxicity: Adverse effects include diarrhea, nausea, stomach upset, vomiting, headache, dizziness, rash, bone marrow depression.
• Affected Organisms: Various gram-negative and gram-positive eubacteria
• Biotransformation: There is no evidence of metabolism in humans.
• Absorption: Well absorbed with approximately 90% absorbed from the gastrointestinal tract after oral ingestion.
• Half Life: 1 hour. In subjects with moderate impairment of renal function the plasma half-life was prolonged to approximately 5.6 hours.
• Protein Binding: 25%
• References: Dantzig AH, Duckworth DC, Tabas LB: Transport mechanisms responsible for the absorption of loracarbef, cefixime, and cefuroxime axetil into human intestinal Caco-2 cells. Biochim Biophys Acta. 1994 Apr 20;1191(1):7-13. [Pubmed] ; Brogden RN, McTavish D: Loracarbef. A review of its antimicrobial activity, pharmacokinetic properties and therapeutic efficacy. Drugs. 1993 May;45(5):716-36. [Pubmed] ; Force RW, Nahata MC: Loracarbef: a new orally administered carbacephem antibiotic. Ann Pharmacother. 1993 Mar;27(3):321-9. [Pubmed] ; Copper RD: The carbacephems: a new beta-lactam antibiotic class. Am J Med. 1992 Jun 22;92(6A):2S-6S. [Pubmed]
• External Links: Wikipedia; RxList; PDRhealth; Drugs.com

参考文献

• Copper RD: The carbacephems: a new beta-lactam antibiotic class. Am J Med. 1992 Jun 22;92(6A):2S-6S. Pubmed
• Dantzig AH, Duckworth DC, Tabas LB: Transport mechanisms responsible for the absorption of loracarbef, cefixime, and cefuroxime axetil into human intestinal Caco-2 cells. Biochim Biophys Acta. 1994 Apr 20;1191(1):7-13. Pubmed
• Brogden RN, McTavish D: Loracarbef. A review of its antimicrobial activity, pharmacokinetic properties and therapeutic efficacy. Drugs. 1993 May;45(5):716-36. Pubmed
• Force RW, Nahata MC: Loracarbef: a new orally administered carbacephem antibiotic. Ann Pharmacother. 1993 Mar;27(3):321-9. Pubmed