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

• ChemBase ID: 1382
• Molecular Formular: C21H33N3O5S
• Molecular Mass: 439.56882
• Monoisotopic Mass: 439.21409217
• SMILES: S1[C@H]2N(C(C1(C)C)C(=O)OCOC(=O)C(C)(C)C)C(=O)[C@H]2/N=C/N1CCCCCC1
• Canonical SMILES: O=C(C1N2C(=O)[C@H]([C@H]2SC1(C)C)/N=C/N1CCCCCC1)OCOC(=O)C(C)(C)C
• InChI: InChI=1S/C21H33N3O5S/c1-20(2,3)19(27)29-13-28-18(26)15-21(4,5)30-17-14(16(25)24(15)17)22-12-23-10-8-6-7-9-11-23/h12,14-15,17H,6-11,13H2,1-5H3/b22-12+/t14-,15?,17-/m1/s1
• InChIKey: NPGNOVNWUSPMDP-LRKSUFLFSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: [(5R,6R)-6-[(E)-(azepan-1-ylmethylidene)amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carbonyloxy]methyl 2,2-dimethylpropanoate
• IUPAC Traditional name: [(5R,6R)-6-[(E)-(azepan-1-ylmethylidene)amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carbonyloxy]methyl 2,2-dimethylpropanoate
• Brand Name: Coactabs; Selexid
• Synonyms: Amdinocillin pivoxil; Pivmecilinamo [inn-spanish]; Pivmecillinamum [inn-latin]; Pivmecillinam

Database IDs

• CAS Number: 32886-97-8
• PubChem SID: 160964842
• PubChem CID: 36272

CALCULATED PROPERTIES

JChem

• Acid pKa: 13.660257
• H Acceptors: 5
• H Donor: 0
• LogD (pH = 5.5): 0.7931336
• LogD (pH = 7.4): 2.2838886
• Log P: 2.9085426
• Molar Refractivity: 113.0317 cm^3
• Polarizability: 44.969994 Å^3
• Polar Surface Area: 88.51 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 3.23
• LOG S: -3.92
• Solubility (Water): 5.26e-02 g/l

DETAILS

DrugBank - DB01605

• Drug Groups: approved
• Description: Pivmecillinam is a mecillinam prodrug, a pivaloyloxymethyl ester of amdinocillin that is well absorbed orally, but broken down to amdinocillin in the intestinal mucosa. It is active against gram-negative organisms and used as for amdinocillin. [PubChem]
• Indication: Used to treat infections due to mecillinam-sensitive organisms such as urinary tract infections, salmonellosis and typhoid fever.
• Pharmacology: Pivmecillinam is a pivaloyloxymethyl ester of amdinocillin that is well absorbed orally, but broken down to amdinocillin in the intestinal mucosa. It is active against gram-negative organisms and used as for amdinocillin.
• Affected Organisms: Enteric bacteria and other eubacteria
• Absorption: Well absorbed following oral administration.
• References: Sjovall J, Huitfeldt B, Magni L, Nord CE: Effect of beta-lactam prodrugs on human intestinal microflora. Scand J Infect Dis Suppl. 1986;49:73-84. [Pubmed] ; Graninger W: Pivmecillinam--therapy of choice for lower urinary tract infection. Int J Antimicrob Agents. 2003 Oct;22 Suppl 2:73-8. [Pubmed] ; Pivmecillinam (selexid). Drug Ther Bull. 1978 Dec 22;16(26):103-4. [Pubmed]

REFERENCES

• Graninger W: Pivmecillinam--therapy of choice for lower urinary tract infection. Int J Antimicrob Agents. 2003 Oct;22 Suppl 2:73-8. Pubmed
• Sjovall J, Huitfeldt B, Magni L, Nord CE: Effect of beta-lactam prodrugs on human intestinal microflora. Scand J Infect Dis Suppl. 1986;49:73-84. Pubmed
• Pivmecillinam (selexid). Drug Ther Bull. 1978 Dec 22;16(26):103-4. Pubmed