DrugBank: Pivmecillinam (DB01605)

targets (1)

Identification

Name

Pivmecillinam

Accession Number

DB01605

Type

small molecule

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]

Structure

Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure

Synonyms

Amdinocillin pivoxil
Pivmecilinamo [inn-spanish]
Pivmecillinamum [inn-latin]

Brand names

Coactabs
Selexid

Brand name mixtures

Not Available

Categories

Anti-Bacterial Agents
Penicillins
Anti-Infective Agents, Urinary

CAS number

32886-97-8

Weight

Average: 439.569
Monoisotopic: 439.214091871

Chemical Formula

C₂₁H₃₃N₃O₅S

InChI Key

InChIKey=NPGNOVNWUSPMDP-LRKSUFLFSA-N

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

Plain Text

IUPAC Name

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

SMILES

[H][C@]12SC(C)(C)C(N1C(=O)[C@H]2\N=C\N1CCCCCC1)C(=O)OCOC(=O)C(C)(C)C

Plain Text

Mass Spec

Not Available

Taxonomy

Kingdom

Organic

Classes

Not Available

Substructures

Carbonyl Compounds
Carboxylic Acids and Derivatives
Acetates
Amino Ketones
Ethers
Aliphatic and Aryl Amines
Beta Lactams
Thiazoles
Heterocyclic compounds
Carboxamides and Derivatives
Lactams
Azetidines
Thiazolidines
Penicillins

Pharmacology

Indication

Used to treat infections due to mecillinam-sensitive organisms such as urinary tract infections, salmonellosis and typhoid fever.

Pharmacodynamics

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.

Mechanism of action

Pivmecillinam interferes with the biosynthesis of the bacterial cell wall however its activity is slightly different from that of other penicillins and cephalosporins

Absorption

Well absorbed following oral administration.

Volume of distribution

Not Available

Protein binding

Not Available

Metabolism

Route of elimination

Not Available

Half life

Not Available

Clearance

Not Available

Toxicity

Not Available

Affected organisms

Enteric bacteria and other eubacteria

Pathways

Not Available

Pharmacoeconomics

Manufacturers

Not Available

Packagers

Not Available

Dosage forms

Not Available

Prices

Not Available

Patents

Not Available

Properties

State

solid

Melting point

119 oC

Experimental Properties

Not Available

Predicted Properties

Property	Value	Source
water solubility	5.26e-02 g/l	ALOGPS
logP	3.23	ALOGPS
logP	2.91	ChemAxon Molconvert
logS	-3.92	ALOGPS
pKa		ChemAxon Molconvert
hydrogen acceptor count	5	ChemAxon Molconvert
hydrogen donor count	0	ChemAxon Molconvert
polar surface area	88.51	ChemAxon Molconvert
rotatable bond count	7	ChemAxon Molconvert
refractivity	113.03	ChemAxon Molconvert
polarizability	47.15	ChemAxon Molconvert

References

Synthesis Reference

Not Available

General Reference

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

External Links

Resource	Link
KEGG Drug	D02889
PubChem Compound	36272
PubChem Substance	46506880
ChemSpider	33356
ChEBI	51210
ChEMBL	51210
Therapeutic Targets Database	DAP001174
PharmGKB	PA10160
Drug Product Database	657212

ATC Codes

Not Available

AHFS Codes

Not Available

PDB Entries

Not Available

FDA label

Not Available

MSDS

Not Available

Interactions

Drug Interactions

Not Available

Food Interactions

Take without regard to meals.

Targets
1. Penicillin-binding proteins 1A/1B Pharmacological action: yes Actions: inhibitor Organism class: bacterial UniProt ID: Q8XJ01 Gene: pbpA Protein Sequence: FASTA Gene Sequence: FASTA SNPs: SNPJam Report References: Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. Pubmed Graninger W: Pivmecillinam—therapy of choice for lower urinary tract infection. Int J Antimicrob Agents. 2003 Oct;22 Suppl 2:73-8. Pubmed

Targets

1. Penicillin-binding proteins 1A/1B

Pharmacological action: yes
Actions: inhibitor
Organism class: bacterial
UniProt ID: Q8XJ01 Link_out

Gene: pbpA
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:

Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed
Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. Pubmed
Graninger W: Pivmecillinam—therapy of choice for lower urinary tract infection. Int J Antimicrob Agents. 2003 Oct;22 Suppl 2:73-8. Pubmed

Comments

Drug created on August 29, 2007 12:48 / Updated on April 19, 2011 15:10

This project is supported by Genome Alberta & Genome Canada, a not-for-profit organization that is leading Canada's national genomics strategy with $600 million in funding from the federal government. This project is also supported in part by GenomeQuest, Inc., an enterprise genomic information company serving the life science community.