(2S,5R,6R)-3,3-dimethyl-7-oxo-6-{2-[(2-oxoimidazolidine-1-carbonyl)amino]-2-phenylacetamido}-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid

• ChemBase ID: 932
• Molecular Formular: C20H23N5O6S
• Molecular Mass: 461.49152
• Monoisotopic Mass: 461.13690448
• SMILES: S1[C@H]2N([C@H](C1(C)C)C(=O)O)C(=O)[C@H]2NC(=O)C(NC(=O)N1CCNC1=O)c1ccccc1
• Canonical SMILES: O=C(C(c1ccccc1)NC(=O)N1CCNC1=O)N[C@@H]1C(=O)N2[C@@H]1SC([C@@H]2C(=O)O)(C)C
• InChI: InChI=1S/C20H23N5O6S/c1-20(2)13(17(28)29)25-15(27)12(16(25)32-20)22-14(26)11(10-6-4-3-5-7-10)23-19(31)24-9-8-21-18(24)30/h3-7,11-13,16H,8-9H2,1-2H3,(H,21,30)(H,22,26)(H,23,31)(H,28,29)/t11?,12-,13+,16-/m1/s1
• InChIKey: JTWOMNBEOCYFNV-XQERAMJGSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,5R,6R)-3,3-dimethyl-7-oxo-6-{2-[(2-oxoimidazolidine-1-carbonyl)amino]-2-phenylacetamido}-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
• IUPAC Traditional name: (2S,5R,6R)-3,3-dimethyl-7-oxo-6-[2-(2-oxoimidazolidine-1-carbonylamino)-2-phenylacetamido]-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid; azlocillin
• Brand Name: Azlin; Bayer Brand of Azlocillin; Securopen
• Synonyms: Azlocilina [INN-Spanish]; Azlocillin sodium salt; Azlocilline [INN-French]; Azlocillinum [INN-Latin]; Azlocillin

Database IDs

• CAS Number: 37091-66-0
• PubChem SID: 160964395
• PubChem CID: 37625

CALCULATED PROPERTIES

JChem

• Acid pKa: 3.4850655
• H Acceptors: 6
• H Donor: 4
• LogD (pH = 5.5): -2.3311994
• LogD (pH = 7.4): -3.7049859
• Log P: -0.32517126
• Molar Refractivity: 111.711 cm^3
• Polarizability: 43.685253 Å^3
• Polar Surface Area: 148.15 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 0.2
• LOG S: -3.3
• Solubility (Water): 2.33e-01 g/l

PROPERTIES

Physical Property

• Solubility: Sodium salt is soluble in water (50 mg/ml)
• Hydrophobicity(logP): 0.2

Product Information

• Classification: Derivatives & analogs of Natural Compounds

DETAILS

DrugBank - DB01061

• Drug Groups: approved
• Description: A semisynthetic ampicillin-derived acylureido penicillin. [PubChem]
• Indication: For the treatment of infections caused by Pseudomonas aeruginosa, Escherichia coli, and Haemophilus influenzae.
• Pharmacology: Azlocillin, similar to mezlocillin and piperacillin, is an acylampicillin with an extended spectrum of activity and greater in vitro potency than the carboxy penicillins. Azlocillin demonstrates antibacterial activity against a broad spectrum of bacteria, including Pseudomonas aeruginosa, and, in contrast to most cephalosporins, exhibits activity against enterococci.
• Affected Organisms: Enteric bacteria and other eubacteria
• Biotransformation: Eliminated predominantly by renal mechanisms, but also undergoes biotransformation within body tissues and intraintestinal degradation by bowel bacteria, with high concentrations found in bile.
• Absorption: Not significantly absorbed from the gastrointestinal tract.
• Half Life: Mean elimination half-life is 1.3 to 1.5 hours. Longer in neonates, and 2 to 6 hours in patients with renal impairment.
• Protein Binding: 20 to 46% bound to plasma proteins
• References: Wright AJ: The penicillins. Mayo Clin Proc. 1999 Mar;74(3):290-307. [Pubmed]
• External Links: Wikipedia

REFERENCES

• Wright AJ: The penicillins. Mayo Clin Proc. 1999 Mar;74(3):290-307. Pubmed