DrugBank: Pivampicillin (DB01604)

targets (1)

Identification

Name

Pivampicillin

Accession Number

DB01604

Type

small molecule

Groups

approved

Description

Pivalate ester analog of ampicillin.

Structure

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

Synonyms

Ampicillin pivaloyloxymethyl ester
Pivaloylampicillin
Pivaloyloxymethyl ampicillinate
Pivampicilina [inn-spanish]
Pivampicilline [inn-french]
Pivampicillinum [inn-latin]

Brand names

Pondocillin

Brand name mixtures

Not Available

Categories

Anti-Bacterial Agents
Penicillins

CAS number

33817-20-8

Weight

Average: 463.547
Monoisotopic: 463.177706365

Chemical Formula

C₂₂H₂₉N₃O₆S

InChI Key

InChIKey=ZEMIJUDPLILVNQ-ZXFNITATSA-N

InChI

InChI=1S/C22H29N3O6S/c1-21(2,3)20(29)31-11-30-19(28)15-22(4,5)32-18-14(17(27)25(15)18)24-16(26)13(23)12-9-7-6-8-10-12/h6-10,13-15,18H,11,23H2,1-5H3,(H,24,26)/t13-,14-,15+,18-/m1/s1

Plain Text

IUPAC Name

{[(2S,5R,6R)-6-[(2R)-2-amino-2-phenylacetamido]-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@@H](N1C(=O)[C@H]2NC(=O)[C@H](N)C1=CC=CC=C1)C(=O)OCOC(=O)C(C)(C)C

Plain Text

Mass Spec

Not Available

Taxonomy

Kingdom

Organic

Classes

Penicillins
Phenethylamines

Substructures

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

Pharmacology

Indication

or the treatment of respiratory tract infections (including acute bronchitis, acute exacerbations of chronic bronchitis and pneumonia); ear, nose and throat infections; gynecological infections; urinary tract infections (including acute uncomplicated gonococcal urethritis) when caused by non penicillinase-producing susceptible strains of the following organisms: gram-positive organisms, e.g., streptococci, pneumococci and staphylococci; gram-negative organisms, e.g., H. influenzae, N. gonorrhoeae, E. coli, P. mirabilis.

Pharmacodynamics

Pivampicillin is the pivaloyloxymethyl ester of (the semi-synthetic penicillin) ampicillin. It is an inactive pro-drug, which is converted during its absorption from the gastrointestinal tract to the microbiologically active ampicillin, together with formaldehyde and pivalic acid, by non-specific esterases present in most body tissues. Amounts in excess of 99% of the pivampicillin absorbed are converted to ampicillin within 15 minutes of absorption.

Mechanism of action

Ampicillin (the active metabolite of pivampicillin) has a bactericidal action resulting from inhibition of cell wall mucopeptide biosynthesis.

Absorption

Absorbed following oral administration.

Volume of distribution

Not Available

Protein binding

Not Available

Metabolism

Route of elimination

Not Available

Half life

Approximately 1 hour.

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

Form	Route	Strength
Tablet	Oral

Prices

Not Available

Patents

Not Available

Properties

State

solid

Melting point

Not Available

Experimental Properties

Not Available

Predicted Properties

Property	Value	Source
water solubility	3.54e-02 g/l	ALOGPS
logP	1.43	ALOGPS
logP	2.07	ChemAxon Molconvert
logS	-4.12	ALOGPS
pKa	14.35	ChemAxon Molconvert
hydrogen acceptor count	5	ChemAxon Molconvert
hydrogen donor count	2	ChemAxon Molconvert
polar surface area	128.03	ChemAxon Molconvert
rotatable bond count	9	ChemAxon Molconvert
refractivity	116.25	ChemAxon Molconvert
polarizability	47.54	ChemAxon Molconvert

References

Synthesis Reference

Not Available

General Reference

Albertson TE, Louie S, Chan AL: The diagnosis and treatment of elderly patients with acute exacerbation of chronic obstructive pulmonary disease and chronic bronchitis. J Am Geriatr Soc. 2010 Mar;58(3):570-9. Pubmed
Chanteux H, Van Bambeke F, Mingeot-Leclercq MP, Tulkens PM: Accumulation and oriented transport of ampicillin in Caco-2 cells from its pivaloyloxymethylester prodrug, pivampicillin. Antimicrob Agents Chemother. 2005 Apr;49(4):1279-88. Pubmed

External Links

Resource	Link
KEGG Compound	C11750
PubChem Compound	33478
PubChem Substance	46505340
ChemSpider	30899
ChEBI	8255
ChEMBL	8255
Therapeutic Targets Database	DAP001171
PharmGKB	PA10900
Drug Product Database	582247
Wikipedia	http://en.wikipedia.org/wiki/Pivampicillin

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 Okamoto T, Yoshiyama H, Nakazawa T, Park ID, Chang MW, Yanai H, Okita K, Shirai M: A change in PBP1 is involved in amoxicillin resistance of clinical isolates of Helicobacter pylori. J Antimicrob Chemother. 2002 Dec;50(6):849-56. 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
Okamoto T, Yoshiyama H, Nakazawa T, Park ID, Chang MW, Yanai H, Okita K, Shirai M: A change in PBP1 is involved in amoxicillin resistance of clinical isolates of Helicobacter pylori. J Antimicrob Chemother. 2002 Dec;50(6):849-56. 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.