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

• ChemBase ID: 330
• Molecular Formular: C16H18ClN3O5
• Molecular Mass: 367.78422
• Monoisotopic Mass: 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

NAMES AND DATABASE IDS

Names

• IUPAC name: 7-[(2R)-2-amino-2-phenylacetamido]-3-chloro-8-oxo-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid hydrate
• IUPAC Traditional name: 7-[(2R)-2-amino-2-phenylacetamido]-3-chloro-8-oxo-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid hydrate
• Brand Name: Lorabid; Loribid
• Synonyms: Loracarbefum [INN-Latin]; Loracarbef

Database IDs

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

CALCULATED PROPERTIES

• Acid pKa: 3.1261737
• H Acceptors: 5
• H Donor: 3
• LogD (pH = 5.5): -2.3995888
• LogD (pH = 7.4): -2.6549032
• Log P: -2.3996444
• Molar Refractivity: 86.6375 cm^3
• Polarizability: 33.446136 Å^3
• Polar Surface Area: 112.73 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Hydrophobicity(logP): 0.5

DETAILS

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

REFERENCES

• 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