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32886-97-8 molecular structure
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[(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 and InChIs

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

Cite this record

CBID:1382 http://www.chembase.cn/molecule-1382.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
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
CAS Number
32886-97-8
PubChem SID
160964842
PubChem CID
36272

DATA SOURCES

DATA SOURCES

All Sources Commercial Sources Non-commercial Sources
Data Source Data ID
DrugBank DB01605 external link
PubChem 36272 external link
Data Source Data ID Price

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem ALOGPS 2.1
Acid pKa 13.660257  H Acceptors
H Donor LogD (pH = 5.5) 0.7931336 
LogD (pH = 7.4) 2.2838886  Log P 2.9085426 
Molar Refractivity 113.0317 cm3 Polarizability 44.969994 Å3
Polar Surface Area 88.51 Å2 Rotatable Bonds
Lipinski's Rule of Five true 
Log P 3.23  LOG S -3.92 
Solubility (Water) 5.26e-02 g/l 

PROPERTIES

PROPERTIES

Bioassay(PubChem)

DETAILS

DETAILS

DrugBank DrugBank
DrugBank - DB01605 external link
Item Information
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

REFERENCES

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  • • 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
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PATENTS

PATENTS

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INTERNET

INTERNET

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