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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 Thumb
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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 Link_out
PubChem Compound 441397 Link_out
PubChem Substance 46507859 Link_out
ChemSpider 390135 Link_out
ChEBI 2968 Link_out
ChEMBL 2968 Link_out
Therapeutic Targets Database DAP001162 Link_out
PharmGKB PA448526 Link_out
Drug Product Database 0 Link_out
Drugs.com http://www.drugs.com/mtm/bacampicillin.html Link_out
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 Link_out
Gene: pbpA
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed
  2. 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.