(6R,7R)-7-(2-amino-2-phenylacetamido)-3-chloro-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

• ChemBase ID: 712
• Molecular Formular: C15H14ClN3O4S
• Molecular Mass: 367.80736
• Monoisotopic Mass: 367.03935462
• SMILES: ClC1=C(N2[C@H](SC1)[C@H](NC(=O)C(N)c1ccccc1)C2=O)C(=O)O
• Canonical SMILES: NC(c1ccccc1)C(=O)N[C@@H]1C(=O)N2[C@@H]1SCC(=C2C(=O)O)Cl
• InChI: InChI=1S/C15H14ClN3O4S/c16-8-6-24-14-10(13(21)19(14)11(8)15(22)23)18-12(20)9(17)7-4-2-1-3-5-7/h1-5,9-10,14H,6,17H2,(H,18,20)(H,22,23)/t9?,10-,14-/m1/s1
• InChIKey: QYIYFLOTGYLRGG-WUMONGPASA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (6R,7R)-7-(2-amino-2-phenylacetamido)-3-chloro-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
• IUPAC Traditional name: cefaclor
• Brand Name: Alenfral; Alfacet; Alfatil; Ceclor; Ceclor CD; Distaclor; Kefral; Panacef; Panoral; Raniclor
• Synonyms: CCL; Cefaclor anhydrous; Cefaclorum [INN-Latin]; Cephaclor; Cefaclor

Database IDs

• CAS Number: 53994-73-3
• PubChem SID: 160964175
• PubChem CID: 40958

CALCULATED PROPERTIES

JChem

• Acid pKa: 3.0266292
• H Acceptors: 5
• H Donor: 3
• LogD (pH = 5.5): -2.3069453
• LogD (pH = 7.4): -2.5625703
• Log P: -2.3063354
• Molar Refractivity: 89.5618 cm^3
• Polarizability: 34.69509 Å^3
• Polar Surface Area: 112.73 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 0.85
• LOG S: -3.24
• Solubility (Water): 2.10e-01 g/l

PROPERTIES

Physical Property

• Solubility: 8.6 mg/mL
• Hydrophobicity(logP): 0.4

DETAILS

DrugBank - DB00833

• Drug Groups: approved
• Description: Semisynthetic, broad-spectrum antibiotic derivative of cephalexin. [PubChem]
• Indication: For the treatment of certain infections caused by bacteria such as pneumonia and ear, lung, skin, throat, and urinary tract infections.
• Pharmacology: Cefaclor is a second generation cephalosporin antibiotic with a spectrum resembling first-generation cephalosporins. In vitro tests demonstrate that the bactericidal action of the cephalosporins results from inhibition of cell-wall synthesis. Cefaclor has been shown to be active against most strains of the following microorganisms, both in vitro and in clinical infections: Gram positive aerobes - Staphylococci (including coagulase-positive, coagulase-negative, and penicillinase-producing strains), Streptococcus pneumoniae, and Streptococcus pyogenes (group A ß-hemolytic streptococci). Gram-negative aerobes - Escherichia coli, Haemophilus influenzae (including ß-lactamase-producing ampicillin-resistant strains), Klebsiella sp, and Proteus mirabilis.
• Toxicity: Symptoms of overdose include diarrhea, nausea, stomach upset, and vomiting.
• Affected Organisms: Enteric bacteria and other eubacteria
• Biotransformation: No appreciable biotransformation in liver (approximately 60% to 85% of the drug is excreted unchanged in the urine within 8 hours).
• Absorption: Well absorbed after oral administration, independent of food intake.
• Half Life: 0.6-0.9 hour
• Protein Binding: 23.5%
• Elimination: Approximately 60% to 85% of the drug is excreted unchanged in the urine within 8 hours, the greater portion being excreted within the first 2 hours.
• References: Hebert AA, Sigman ES, Levy ML: Serum sickness-like reactions from cefaclor in children. J Am Acad Dermatol. 1991 Nov;25(5 Pt 1):805-8. [Pubmed] ; Parra FM, Igea JM, Martin JA, Alonso MD, Lezaun A, Sainz T: Serum sickness-like syndrome associated with cefaclor therapy. Allergy. 1992 Aug;47(4 Pt 2):439-40. [Pubmed]
• External Links: Wikipedia; RxList; Drugs.com

REFERENCES

• Hebert AA, Sigman ES, Levy ML: Serum sickness-like reactions from cefaclor in children. J Am Acad Dermatol. 1991 Nov;25(5 Pt 1):805-8. Pubmed
• Parra FM, Igea JM, Martin JA, Alonso MD, Lezaun A, Sainz T: Serum sickness-like syndrome associated with cefaclor therapy. Allergy. 1992 Aug;47(4 Pt 2):439-40. Pubmed