Banner
targets (6)
for drugs
Identification
Name Amdinocillin
Accession Number DB01163 (APRD00789)
Type small molecule
Groups approved
Description

Amidinopenicillanic acid derivative with broad spectrum antibacterial action. It is poorly absorbed if given orally and is used in urinary infections and typhus. [PubChem]
Structure Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  • Amdinocillin mecillinam
  • Mecillinam
Brand names
  • Coactin
Brand name mixtures Not Available
Categories
  • Anti-Bacterial Agents
  • Penicillins
  • Anti-Infective Agents, Urinary
CAS number 32887-01-7
Weight Average: 325.426
Monoisotopic: 325.146012307
Chemical Formula C15H23N3O3S
InChI Key InChIKey=BWWVAEOLVKTZFQ-ISVUSNJMSA-N
InChI
InChI=1S/C15H23N3O3S/c1-15(2)11(14(20)21)18-12(19)10(13(18)22-15)16-9-17-7-5-3-4-6-8-17/h9-11,13H,3-8H2,1-2H3,(H,20,21)/b16-9+/t10-,11+,13-/m1/s1
Plain Text
IUPAC Name
(2S,5R,6R)-6-[(E)-(azepan-1-ylmethylidene)amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
SMILES
[H][C@]12SC(C)(C)[C@@H](N1C(=O)[C@H]2\N=C\N1CCCCCC1)C(O)=O
Plain Text
Mass Spec Not Available
Taxonomy
Kingdom Organic
Classes
  • Beta Lactams
  • Penicillins
Substructures
  • Hydroxy Compounds
  • Carboxylic Acids and Derivatives
  • Acetates
  • Amino Ketones
  • Aliphatic and Aryl Amines
  • Beta Lactams
  • Thiazoles
  • Heterocyclic compounds
  • Carboxamides and Derivatives
  • Lactams
  • Azetidines
  • Thiazolidines
  • Penicillins
Pharmacology
Indication Used in the treatment of urinary tract infections caused by some strains of E. coli and klebsiella and enterobacter species. Used mainly against Gram negative organisms.
Pharmacodynamics Amdinocillin is a novel, semisynthetic penicillin effective against many gram-negative bacteria. The antibacterial activity of amdinocillin is derived from its ability to bind specifically and avidly to Penicillin Binding Protein-2 (PBP 2). Amdinocillin is active alone against many gram-negative organisms. Pseudomonas and non-fermenting gram-negative bacteria, however, are usually resistant. Amdinocillin, in combination with many beta-lactams, exhibits marked synergy against many enterobacteriaceae. No such synergy can be demonstrated for gram-positive organisms or pseudomonas species. Amdinocillin is not beta-lactamase stable. Organisms which produce high levels of plasma-mediated beta-lactamase are resistant to the drug. Co-administration of probenecid results in markedly elevated plasma levels of amdinocillin and delays its excretion.
Mechanism of action Amdinocillin is a stong and specific antagonist of Penicillin Binding Protein-2 (PBP 2). It is active against gram negative bacteria, preventing cell wall synthesis by inhibiting the activity of PBP2. PBP2 is a peptidoglycan elongation initiating enzyme. Peptidoglycan is a polymer of sugars and amino acids that is the main component of bacterial cell walls.
Absorption Poorly absorbed if given orally.
Volume of distribution Not Available
Protein binding Not Available
Metabolism
Route of elimination Not Available
Half life Approximately 1 hour in patients with normal renal function. Increases to 3 to 6 hours in anephric patients.
Clearance Not Available
Toxicity Not Available
Affected organisms
  • Gram-negative Bacteria
Pathways Not Available
Pharmacoeconomics
Manufacturers
  • Hoffmann la roche inc
Packagers Not Available
Dosage forms Not Available
Prices Not Available
Patents Not Available
Properties
State solid
Melting point 156 oC
Experimental Properties
Property Value Source
water solubility 0.0103 mg/mL at 25 oC [MEYLAN,WM et al. (1996)] PhysProp
logP 1.3 PhysProp
Predicted Properties
Property Value Source
water solubility 9.79e-01 g/l ALOGPS
logP 1.41 ALOGPS
logP -0.99 ChemAxon Molconvert
logS -2.52 ALOGPS
pKa 13.78 ChemAxon Molconvert
hydrogen acceptor count 5 ChemAxon Molconvert
hydrogen donor count 1 ChemAxon Molconvert
polar surface area 73.21 ChemAxon Molconvert
rotatable bond count 2 ChemAxon Molconvert
refractivity 84.31 ChemAxon Molconvert
polarizability 34.05 ChemAxon Molconvert
References
Synthesis Reference Not Available
General Reference
  1. Neu HC: Penicillin-binding proteins and role of amdinocillin in causing bacterial cell death. Am J Med. 1983 Aug 29;75(2A):9-20. Pubmed
External Links
Resource Link
KEGG Drug D02888 Link_out
PubChem Compound 36273 Link_out
PubChem Substance 46508450 Link_out
ChemSpider 33357 Link_out
ChEBI 51208 Link_out
ChEMBL 51208 Link_out
Therapeutic Targets Database DAP001176 Link_out
Drug Product Database 0 Link_out
ATC Codes Not Available
AHFS Codes Not Available
PDB Entries Not Available
FDA label Not Available
MSDS show (42.1 KB)
Interactions
Drug Interactions
Drug Interaction
Food Interactions Not Available
Targets

1. Penicillin-binding protein 2a

Pharmacological action: yes
Actions: inhibitor
UniProt ID: Q8DNB6 Link_out
Gene: pbp2a
SNPs: SNPJam Report Link_out

References:
  1. Williamson R, Hakenbeck R, Tomasz A: In vivo interaction of beta-lactam antibiotics with the penicillin-binding proteins of Streptococcus pneumoniae. Antimicrob Agents Chemother. 1980 Oct;18(4):629-37. Pubmed

2. Penicillin-binding protein 2

Pharmacological action: yes
Actions: inhibitor
UniProt ID: P74872 Link_out
Gene: mrdA
SNPs: SNPJam Report Link_out

References:
  1. Neu HC: Penicillin-binding proteins and role of amdinocillin in causing bacterial cell death. Am J Med. 1983 Aug 29;75(2A):9-20. Pubmed
  2. Licht J, Gally D, Henderson T, Young K, Cooper S: Effect of mecillinam on peptidoglycan synthesis during the division cycle of Salmonella typhimurium 2616. Res Microbiol. 1993 Jul-Aug;144(6):423-33. Pubmed

3. Penicillin-binding protein 3

Pharmacological action: yes
Actions: inhibitor
UniProt ID: Q75Y35 Link_out
Gene: pbp3
SNPs: SNPJam Report Link_out

References:
  1. Williamson R, Hakenbeck R, Tomasz A: In vivo interaction of beta-lactam antibiotics with the penicillin-binding proteins of Streptococcus pneumoniae. Antimicrob Agents Chemother. 1980 Oct;18(4):629-37. Pubmed

4. Penicillin-binding protein 1A

Pharmacological action: yes
Actions: inhibitor

Cell wall formation

Organism class: bacterial
UniProt ID: Q8DR59 Link_out
Gene: pbpA Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Williamson R, Hakenbeck R, Tomasz A: In vivo interaction of beta-lactam antibiotics with the penicillin-binding proteins of Streptococcus pneumoniae. Antimicrob Agents Chemother. 1980 Oct;18(4):629-37. Pubmed

5. Penicillin-binding protein 2B

Pharmacological action: yes
Actions: inhibitor
Organism class: bacterial
UniProt ID: P0A3M6 Link_out
Gene: penA Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Williamson R, Hakenbeck R, Tomasz A: In vivo interaction of beta-lactam antibiotics with the penicillin-binding proteins of Streptococcus pneumoniae. Antimicrob Agents Chemother. 1980 Oct;18(4):629-37. Pubmed

6. Penicillin-binding protein 1b

Pharmacological action: yes
Actions: inhibitor
Organism class: bacterial
UniProt ID: Q7CRA4 Link_out
Gene: pbp1b Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Williamson R, Hakenbeck R, Tomasz A: In vivo interaction of beta-lactam antibiotics with the penicillin-binding proteins of Streptococcus pneumoniae. Antimicrob Agents Chemother. 1980 Oct;18(4):629-37. Pubmed
Comments
Drug created on June 13, 2005 07:24 / Updated on April 19, 2011 15:08

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.