7-[2-amino-2-(4-hydroxyphenyl)acetamido]-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

• ChemBase ID: 1011
• Molecular Formular: C16H17N3O5S
• Molecular Mass: 363.38828
• Monoisotopic Mass: 363.08889166
• SMILES: S1C2N(C(=O)C2NC(=O)C(N)c2ccc(O)cc2)C(=C(C1)C)C(=O)O
• Canonical SMILES: O=C(C(c1ccc(cc1)O)N)NC1C(=O)N2C1SCC(=C2C(=O)O)C
• InChI: InChI=1S/C16H17N3O5S/c1-7-6-25-15-11(14(22)19(15)12(7)16(23)24)18-13(21)10(17)8-2-4-9(20)5-3-8/h2-5,10-11,15,20H,6,17H2,1H3,(H,18,21)(H,23,24)
• InChIKey: BOEGTKLJZSQCCD-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 7-[2-amino-2-(4-hydroxyphenyl)acetamido]-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
• IUPAC Traditional name: cefadroxil
• Brand Name: Baxan; Bidocef; Cefa-Drops; Cefamox; Cephos; Duracef; Kefroxil; Oracefal; Sedral; Sumacef; Ultracef
• Synonyms: Cefadroxil Monohydrate; Cefradroxil; CDX; Cefadroxil

Database IDs

• CAS Number: 66592-87-8
• PubChem SID: 160964474
• PubChem CID: 2610

CALCULATED PROPERTIES

JChem

• Acid pKa: 3.4454033
• H Acceptors: 6
• H Donor: 4
• LogD (pH = 5.5): -2.4450464
• LogD (pH = 7.4): -2.7044444
• Log P: -2.4485235
• Molar Refractivity: 90.9545 cm^3
• Polarizability: 35.27431 Å^3
• Polar Surface Area: 132.96 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 0.51
• LOG S: -2.96
• Solubility (Water): 3.99e-01 g/l

PROPERTIES

Physical Property

• Solubility: 1110 mg/L
• Hydrophobicity(logP): -0.4

DETAILS

DrugBank - DB01140

• Drug Groups: approved
• Description: Long-acting, broad-spectrum, water-soluble, cephalexin derivative. [PubChem]
• Indication: For the treatment of the following infections (skin, UTI, ENT) caused by; S. pneumoniae, H. influenzae, staphylococci, S. pyogenes (group A beta-hemolytic streptococci), E. coli, P. mirabilis, Klebsiella sp, coagulase-negative staphylococci and Streptococcus pyogenes
• Pharmacology: Cefadroxil, a first-generation cephalosporin antibiotic, is used to treat urinary tract infections, skin and skin structure infections, pharyngitis, and tonsillitis.
• Toxicity: Nausea, vomiting, diarrhoea, allergic rashes may occur
• Affected Organisms: Enteric bacteria and other eubacteria
• Absorption: Cefadroxil is well absorbed on oral administration; food does not interfere with its absorption.
• Half Life: 1.5 hours
• Protein Binding: Binding rates of cefadroxil were 28.1% by U.F. method
• Elimination: Over 90% of the drug is excreted unchanged in the urine within 24 hours. It crosses the placenta and appears in breast milk.
• External Links: Wikipedia; RxList; Drugs.com