DrugBank: Bacampicillin (DB01602)

targets (1)

Identification

Name

Bacampicillin

Accession Number

DB01602

Type

small molecule

Groups

approved

Description

Bacampicillin is a prodrug of ampicillin and is microbiologically inactive. It is absorbed following oral administration. During absorption from the gastrointestinal tract, bacampicillin is hydrolyzed by esterases present in the intestinal wall. It is microbiologically active as ampicillin, and exerts a bactericidal action through the inhibition of the biosynthesis of cell wall mucopeptides. It is used to cure infection of upper and lower respiratory tract; skin and soft tissue; urinary tract and acute uncomplicated gonococcal urethritis etc.

Structure

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

Synonyms

Bacampicillin Hydrochloride

Brand names

Penglobe
Spectrobid

Brand name mixtures

Not Available

Categories

Anti-Bacterial Agents
Penicillins

CAS number

50972-17-3

Weight

Average: 465.52
Monoisotopic: 465.156970923

Chemical Formula

C₂₁H₂₇N₃O₇S

InChI Key

InChIKey=PFOLLRNADZZWEX-FFGRCDKISA-N

InChI

InChI=1S/C21H27N3O7S/c1-5-29-20(28)31-11(2)30-19(27)15-21(3,4)32-18-14(17(26)24(15)18)23-16(25)13(22)12-9-7-6-8-10-12/h6-11,13-15,18H,5,22H2,1-4H3,(H,23,25)/t11?,13-,14-,15+,18-/m1/s1

Plain Text

IUPAC Name

1-[(ethoxycarbonyl)oxy]ethyl (2S,5R,6R)-6-[(2R)-2-amino-2-phenylacetamido]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate

SMILES

[H][C@]12SC(C)(C)[C@@H](N1C(=O)[C@H]2NC(=O)[C@H](N)C1=CC=CC=C1)C(=O)OC(C)OC(=O)OCC

Plain Text

Mass Spec

Not Available

Taxonomy

Kingdom

Organic

Classes

Penicillins
Phenethylamines

Substructures

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
Carbonic Acids and Derivatives
Thiazolidines

Pharmacology

Indication

For infections at the following sites: upper and lower respiratory tract; skin and soft tissue; urinary tract and acute uncomplicated gonococcal urethritis, when due to sensitive strains of the following organisms: Gram-positive: streptococci (including S. faecalis and S. pneumoniae) and nonpenicillinase-producing staphylococci; Gram-negative: H. influenzae, N. gonorrhoeae, E. coli, P. mirabilis, Salmonellae and Shigellae.

Pharmacodynamics

Bacampicillin is a prodrug of ampicillin and is microbiologically inactive.

Mechanism of action

During absorption from the gastrointestinal tract, bacampicillin is hydrolyzed by esterases present in the intestinal wall. It is microbiologically active as ampicillin, and exerts a bactericidal action through the inhibition of the biosynthesis of cell wall mucopeptides.

Absorption

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

Pfizer laboratories div pfizer inc

Packagers

Pfizer Inc.
Pharmaceutical Utilization Management Program VA Inc.

Dosage forms

Form	Route	Strength
Suspension	Oral
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	1.23e-01 g/l	ALOGPS
logP	1.17	ALOGPS
logP	1.47	ChemAxon Molconvert
logS	-3.58	ALOGPS
pKa	14.35	ChemAxon Molconvert
hydrogen acceptor count	6	ChemAxon Molconvert
hydrogen donor count	2	ChemAxon Molconvert
polar surface area	137.26	ChemAxon Molconvert
rotatable bond count	10	ChemAxon Molconvert
refractivity	113.76	ChemAxon Molconvert
polarizability	46.80	ChemAxon Molconvert

References

Synthesis Reference

Not Available

General Reference

Not Available

External Links

Resource	Link
KEGG Compound	C08122
PubChem Compound	441397
PubChem Substance	46507859
ChemSpider	390135
ChEBI	2968
ChEMBL	2968
Therapeutic Targets Database	DAP001162
PharmGKB	PA448526
Drug Product Database	0
Drugs.com	http://www.drugs.com/mtm/bacampicillin.html

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

Not Available

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

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

Comments

Drug created on August 29, 2007 12:46 / 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.