6-(2-azido-2-phenylacetamido)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid

• ChemBase ID: 6396
• Molecular Formular: C16H17N5O4S
• Molecular Mass: 375.40228
• Monoisotopic Mass: 375.10012505
• SMILES: S1C2N(C(C1(C)C)C(=O)O)C(=O)C2NC(=O)C(N=[N+]=[N-])c1ccccc1
• Canonical SMILES: O=C(C(c1ccccc1)N=[N+]=[N-])NC1C(=O)N2C1SC(C2C(=O)O)(C)C
• InChI: InChI=1S/C16H17N5O4S/c1-16(2)11(15(24)25)21-13(23)10(14(21)26-16)18-12(22)9(19-20-17)8-6-4-3-5-7-8/h3-7,9-11,14H,1-2H3,(H,18,22)(H,24,25)
• InChIKey: ODFHGIPNGIAMDK-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 6-(2-azido-2-phenylacetamido)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
• IUPAC Traditional name: 6-(2-azido-2-phenylacetamido)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
• Synonyms: Azidocillin

Database IDs

• CAS Number: 17243-38-8
• PubChem SID: 160969703
• PubChem CID: 71886

CALCULATED PROPERTIES

JChem

• Polarizability: 35.687977 Å^3
• Polar Surface Area: 116.14 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true
• Acid pKa: 3.2919872
• H Acceptors: 6
• H Donor: 2
• LogD (pH = 5.5): -1.0835792
• LogD (pH = 7.4): -2.3511596
• Log P: 1.185864
• Molar Refractivity: 92.1585 cm^3

ALOGPS 2.1

• Solubility (Water): 6.11e-01 g/l
• Log P: 2.32
• LOG S: -2.79

DETAILS

DrugBank - DB08795

• Drug Groups: approved
• Description: Azidocillin is a penicillin antibiotic similir to ampicillin.
• Indication: For treatment of infection (Respiratory, GI, UTI and meningitis) due to E. coli, P. mirabilis, enterococci, Shigella, S. typhosa and other Salmonella, nonpenicillinase-producing N. gononhoeae, H. influenzae, staphylococci, streptococci including streptoc
• External Links: Wikipedia