(2S,5R,6R)-6-[(E)-(azepan-1-ylmethylidene)amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid

• ChemBase ID: 1034
• Molecular Formular: C15H23N3O3S
• Molecular Mass: 325.42642
• Monoisotopic Mass: 325.14601261
• SMILES: S1[C@H]2N([C@H](C1(C)C)C(=O)O)C(=O)[C@H]2/N=C/N1CCCCCC1
• Canonical SMILES: OC(=O)[C@@H]1N2C(=O)[C@H]([C@H]2SC1(C)C)/N=C/N1CCCCCC1
• InChI: InChI=1S/C15H23N3O3S/c1-15(2)11(14(20)21)18-12(19)10(13(18)22-15)16-9-17-7-5-3-4-6-8-17/h9-11,13H,3-8H2,1-2H3,(H,20,21)/b16-9+/t10-,11+,13-/m1/s1
• InChIKey: BWWVAEOLVKTZFQ-ISVUSNJMSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,5R,6R)-6-[(E)-(azepan-1-ylmethylidene)amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid; (2S,5R,6R)-6-[(azepan-1-ylmethylidene)amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
• IUPAC Traditional name: selexidin; mecillinam; amdinocillin
• Brand Name: Coactin
• Synonyms: Amdinocillin mecillinam; Mecillinam; Amdinocillin; Mecillinam; (2S,5R,6R)-6-[[(Hexahydro-1H-azepin-1-yl)methylene]amino]-3,3-dimethyl-7-oxo-4-Thia-1-azabicyclo[3.2.0]heptane-2-carboxylic Acid; FL-1060, Ro-9070, Mecillinam, 6-[[(Hexahydro-1H-azepin-1-yl)methylene]amino]penicillanic Acid; 美西林

Database IDs

• CAS Number: 32887-01-7
• EC Number: 251-277-1
• MDL Number: MFCD00056869
• PubChem SID: 160964497
• PubChem CID: 36273

CALCULATED PROPERTIES

JChem

• Acid pKa: 3.3024578
• H Acceptors: 5
• H Donor: 1
• LogD (pH = 5.5): -0.5463934
• LogD (pH = 7.4): -0.6564004
• Log P: -0.54836655
• Molar Refractivity: 84.3069 cm^3
• Polarizability: 32.891243 Å^3
• Polar Surface Area: 73.21 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 1.41
• LOG S: -2.52
• Solubility (Water): 9.79e-01 g/l

PROPERTIES

Physical Property

• Solubility: 0.0103 mg/mL at 25 oC [MEYLAN,WM et al. (1996)]; Methanol; Water
• Apperance: White Solid
• Melting Point: 149-151°C (dec.)
• Hydrophobicity(logP): 1.3

Safety Information

• Storage Condition: -20°C Freezer
• RTECS: XI0185000
• German water hazard class: 2
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: 2-8°C

Product Information

• Grade: VETRANAL™, analytical standard
• Empirical Formula (Hill Notation): C15H23N3O3S

DETAILS

DrugBank - DB01163

• Drug Groups: approved
• Description: Amidinopenicillanic acid derivative with broad spectrum antibacterial action. It is poorly absorbed if given orally and is used in urinary infections and typhus. [PubChem]
• Indication: Used in the treatment of urinary tract infections caused by some strains of E. coli and klebsiella and enterobacter species. Used mainly against Gram negative organisms.
• Pharmacology: Amdinocillin is a novel, semisynthetic penicillin effective against many gram-negative bacteria. The antibacterial activity of amdinocillin is derived from its ability to bind specifically and avidly to Penicillin Binding Protein-2 (PBP 2). Amdinocillin is active alone against many gram-negative organisms. Pseudomonas and non-fermenting gram-negative bacteria, however, are usually resistant. Amdinocillin, in combination with many beta-lactams, exhibits marked synergy against many enterobacteriaceae. No such synergy can be demonstrated for gram-positive organisms or pseudomonas species. Amdinocillin is not beta-lactamase stable. Organisms which produce high levels of plasma-mediated beta-lactamase are resistant to the drug. Co-administration of probenecid results in markedly elevated plasma levels of amdinocillin and delays its excretion.
• Affected Organisms: Gram-negative Bacteria
• Absorption: Poorly absorbed if given orally.
• Half Life: Approximately 1 hour in patients with normal renal function. Increases to 3 to 6 hours in anephric patients.
• References: Neu HC: Penicillin-binding proteins and role of amdinocillin in causing bacterial cell death. Am J Med. 1983 Aug 29;75(2A):9-20. [Pubmed]

Sigma Aldrich - 33447

Legal Information
VETRANAL is a trademark of Sigma-Aldrich Co. LLC

Toronto Research Chemicals - A576300

Active antibacterial against gram-negative bacteria.

REFERENCES

• Neu HC: Penicillin-binding proteins and role of amdinocillin in causing bacterial cell death. Am J Med. 1983 Aug 29;75(2A):9-20. Pubmed
• Cagnacci, S., et al.: J. Clin. Microbiol., 46, 2605 (2008)
• Obach, R., et al.: Drug Metab. Disposition, 36, 1385 (2008)
• Ma, C., et al.: J. Pharm. Biomed. Anal., 47, 677 (2008)