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Showing drug card for Amdinocillin (DB01163)

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Version 2.5
Creation Date 2005-06-13 13:24:05
Update Date 2009-02-19 16:04:04
Primary Accession Number DB01163
Secondary Accession Number
  • APRD00789
Name Amdinocillin
Drug Type
  • Approved
  • Small Molecule
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]
Synonyms
  1. Amdinocillin mecillinam
Brand Names
  1. Coactin
Brand Mixtures Not Available
Chemical IUPAC Name (2S,5R,6R)-6-(azepan-1-ylmethylideneamino)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
Chemical Formula C15H23N3O3S
Chemical Structure Structure
CAS Registry Number 32887-01-7
InChI Identifier InChI=1/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/f/h20H
InChI Key BWWVAEOLVKTZFQ-QZPBSIJIDZ
KEGG Drug D02888 Link Image
KEGG Compound Not Available
PubChem Compound 36273 Link Image
PubChem Substance 10823391 Link Image
ChEBI ID Not Available
PharmGKB ID Not Available
HET ID Not Available
GenBank ID Not Available
Drug ID Number [DIN] Not Available
RxList Link Not Available
PDRhealth Link Not Available
Wikipedia Link Not Available
FDA Label Not Available
Material Safety Data Sheet (MSDS)
Synthesis Reference Not Available
Average Molecular Weight 325.4260
Monoisotopic Molecular Weight 325.1460
State Solid
Melting Point 156 oC
Experimental Water Solubility 0.0103 mg/mL at 25 oC [MEYLAN,WM et al. (1996)] Source: PhysProp
Predicted Water Solubility 9.79e-01 mg/mL Calculated using ALOGPS
Experimental LogP/Hydrophobicity 1.3 Source: PhysProp
Predicted LogP 1.42 Calculated using ALOGPS
Experimental LogS Not Available
Predicted LogS -2.52 Calculated using ALOGPS
Experimental Caco2 Permeability Not Available
pKa/Isoelectric Point Not Available
Mass Spectrum Not Available
MOL File Show Link Image | Download Link Image
SDF File Show Link Image | Download Link Image
PDB File Show Link Image | Download Link Image
2D Structure
3D Structure
Experimental PDB ID Not Available
Isomeric SMILES CC1(C)S[C@@H]2[C@H](\N=C\N3CCCCCC3)C(=O)N2[C@H]1C(O)=O
Canonical SMILES CC1(C)SC2C(N=CN3CCCCCC3)C(=O)N2C1C(O)=O
Drug Category
  • Anti-Bacterial Agents
  • Anti-Infective Agents, Urinary
  • Penicillins
ATC Codes Not Available
AHFS Codes Not Available
Indication Used in the treatment of urinary tract infections caused by some strains of E. coli and klebsiella and enterobacter species.
Pharmacology 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).
Absorption Poorly absorbed if given orally.
Toxicity Not Available
Protein Binding Not Available
Biotransformation Not Available
Half Life Approximately 1 hour in patients with normal renal function. Increases to 3 to 6 hours in anephric patients.
Dosage Forms Not Available
Patient Information Not Available
Contraindications Not Available
Interactions Not Available
Drug Interactions Not Available
Food Interactions Not Available
Pathways Not Available
General References Not Available
Organisms Affected
  • Gram-negative Bacteria
Targets
  1. Penicillin-binding protein 2B
Drug Target 1 [top]
Target 1 ID 159
Target 1 Name Penicillin-binding protein 2B
Target 1 Synonyms Not Available
Target 1 Gene Name penA
Target 1 Protein Sequence >Penicillin-binding protein 2B 
MRKFNSHSIPIRLNLLFSIVILLFMTIIGRLLYMQVLNKDFYEKKLASASQTKITSSSAR
GEIYDASGKPLVENTLKQVVSFTRSNKMTATDLKETAKKLLTYVSISSPNLTERQLADYY
LADPEIYKKIVEALPSEKRLDSDGNRLSESELYNNAVDSVQTSQLNYTEDEKKEIYLFSQ
LNAVGNFATGTIATDPLNDSQVAVIASISKEMPGISISTSWDRKVLETSLSSIVGSVSSE
KAGLPAEEAEAYLKKGYSLNDRVGTSYLEKQYEETLQGKRSVKEIHLDKYGNMESVDTIE
EGSKGNNIKLTIDLAFQDSVDALLKSYFNSELENGGAKYSEGVYAVALNPKTGAVLSMSG
IKHDLKTGELTPDSLGTVTNVFVPGSVVKAATISSGWENGVLSGNQTLTDQSIVFQGSAP
INSWYTQAYGSFPITAVQALEYSSNTYMVQTALGLMGQTYQPNMFVGTSNLESAMEKLRS
TFGEYGLGTATGIDLPDESTGFVPKEYSFANYITNAFGQFDNYTPMQLAQYVATIANNGV
RVAPRIVEGIYGNNDKGGLGDLIQQLQPTEMNKVNISDSDMSILHQGFYQVAHGTSGLTT
GRAFSNGALVSISGKTGTAESYVADGQQATNTNAVAYAPSDNPQIAVAVVFPHNTNLTNG
VGPSIARDIINLYQKYHPMN
Target 1 Number of Residues 691
Target 1 Molecular Weight 73874
Target 1 Theoretical pI 4.85
Target 1 GO Classification
Function
binding
drug binding
penicillin binding
Process
physiological process
cellular physiological process
cell organization and biogenesis
external encapsulating structure organization and biogenesis
cell wall organization and biogenesis
cell wall organization and biogenesis (sensu Bacteria)
cell wall biosynthesis (sensu Bacteria)
Component
Not Available
Target 1 General Function Cell wall/membrane/envelope biogenesis
Target 1 Specific Function Not Available
Target 1 Pathways Not Available
Target 1 Reactions Not Available
Target 1 Pfam Domain Function
Target 1 Signals
  • None
Target 1 Transmembrane Regions
  • 13-32
Target 1 Essentiality Essential
Target 1 GenBank ID Protein 14973165 Link Image
Target 1 UniProtKB/Swiss-Prot ID P0A3M5 Link Image
Target 1 UniProtKB/Swiss-Prot Entry Name PBP2_STRPN Link Image
Target 1 PDB ID Not Available
Target 1 Cellular Location Not Available
Target 1 Gene Sequence >2043 bp 
CTAATTCATTGGATGGTATTTTTGATACAGATTGATAATGTCACGCGCAATGGAAGGTCC
TACACCATTTGTTAGATTGGTATTATGAGGAAAGACCACTGCGACAGCGATTTGGGGATT
ATCAGATGGGGCATAGGCCACCGCATTGGTATTGGTTGCTTGCTGACCATCTGCCACATA
GCTTTCGGCTGTACCTGTTTTTCCGCTAATGGATACCAAGGCACCATTTGAAAAGGCACG
TCCAGTTGTCAATCCACTAGTACCATGGGCAACCTGATAAAAACCTTGGTGCAAGATGCT
CATATCGGAGTCGGATATATTGACCTTATTCATCTCTGTCGGTTGCAGTTGCTGAATCAA
GTCACCCAGTCCTCCCTTATCATTATTACCATAAATGCCTTCAACAATACGAGGAGCCAC
ACGAACACCATTATTTGCAATAGTTGCTACATACTGAGCCAACTGCATCGGCGTATAGTT
ATCAAACTGCCCAAAGGCATTAGTAATGTAATTAGCAAAGCTATACTCTTTGGGAACAAA
TCCAGTAGATTCATCTGGTAGGTCAATTCCTGTCGCAGTACCCAAGCCATATTCGCCAAA
GGTTGAACGCAGTTTCTCCATAGCAGACTCTAGATTGCTGGTGCCGACAAACATATTGGG
TTGATAGGTTTGCCCCATAAGACCTAAGGCTGTTTGGACCATATAGGTATTTGATGAATA
CTCCAGAGCTTGGACCGCTGTGATAGGGAATGAACCGTAAGCCTGAGTATACCAAGAATT
GATGGGAGCTGAACCTTGGAAGACAATGGACTGGTCTGTCAAGGTCTGGTTTCCTGACAA
GACTCCATTTTCCCAACCTGAGCTGATGGTCGCCGCCTTGACAACCGAACCTGGAACAAA
GACATTGGTTACCGTTCCCAAGGAATCAGGCGTCAACTCTCCCGTTTTCAAGTCATGTTT
AATCCCTGACATAGACAAAACCGCACCTGTTTTTGGGTTAAGGGCGACTGCATAGACACC
TTCAGAATACTTGGCTCCACCATTTTCTAGCTCAGAATTGAAATAACTTTTCAGTAAAGC
ATCCACGCTATCTTGGAAAGCCAAATCAATGGTCAGTTTGATATTGTTTCCCTTACTACC
TTCCTCAATTGTATCCACGCTTTCCATATTGCCATATTTATCCAGATGGATTTCTTTTAC
CGAGCGTTTTCCTTGTAAGGTCTCTTCATATTGCTTTTCCAAATAGGAGGTTCCTACACG
GTCATTTAGAGAATAGCCTTTTTTAAGATAGGCTTCTGCTTCTTCCGCTGGGAGACCAGC
TTTTTCACTGGATACACTCCCAACTATAGAAGAAAGGGAAGTTTCCAAAACCTTTCTATC
CCAAGAAGTAGAAATACTAATGCCAGGCATCTCCTTTGAAATAGAGGCAATAACAGCCAC
CTGAGAATCATTTAGAGGATCTGTCGCAATGGTTCCTGTCGCAAAGTTTCCAACAGCATT
TAACTGACTAAAAAGATAGATTTCTTTCTTTTCATCCTCTGTATAGTTTAGTTGACTCGT
TTGTACACTATCGACCGCATTGTTATACAGTTCTGATTCGGATAGACGATTGCCATCTGA
ATCCAAGCGTTTCTCACTTGGGAGAGCTTCCACTATTTTTTTATAGATTTCAGGATCAGC
CAAATAGTAATCCGCCAGCTGGCGTTCTGTCAAATTTGGAGAACTGATGCTCACATAAGT
CAGTAACTTTTTAGCTGTTTCTTTTAAGTCTGTAGCCGTCATTTTATTGCTACGCGTAAA
GGAAACAACCTGCTTTAACGTATTTTCTACCAAAGGTTTTCCACTAGCATCATAAATTTC
CCCACGGGCTGAACTGCTTGTAATCTTGGTCTGACTAGCTGAAGCTAGCTTTTTTTCGTA
AAAATCCTTGTTCAAAACCTGCATATACAACAAACGACCAATAATGGTCATAAAGAGTAA
AATGACGATTGAAAACAATAAATTAAGCCGAATCGGAATCGAATGGCTGTTAAATTTTCT
CAT
Target 1 GenBank Gene ID
Target 1 GeneCard ID Not Available
Target 1 GenAtlas ID Not Available
Target 1 HGNC ID Not Available
Target 1 Chromosome Location Not Available
Target 1 Locus Not Available
Target 1 SNPs SNPJam Report Link Image
Target 1 General References
  1. Tettelin H, Nelson KE, Paulsen IT, Eisen JA, Read TD, Peterson S, Heidelberg J, DeBoy RT, Haft DH, Dodson RJ, Durkin AS, Gwinn M, Kolonay JF, Nelson WC, Peterson JD, Umayam LA, White O, Salzberg SL, Lewis MR, Radune D, Holtzapple E, Khouri H, Wolf AM, Utterback TR, Hansen CL, McDonald LA, Feldblyum TV, Angiuoli S, Dickinson T, Hickey EK, Holt IE, Loftus BJ, Yang F, Smith HO, Venter JC, Dougherty BA, Morrison DA, Hollingshead SK, Fraser CM: Complete genome sequence of a virulent isolate of Streptococcus pneumoniae. Science. 2001 Jul 20;293(5529):498-506. [PubMed Link Image]
  2. Dowson CG, Hutchison A, Spratt BG: Extensive re-modelling of the transpeptidase domain of penicillin-binding protein 2B of a penicillin-resistant South African isolate of Streptococcus pneumoniae. Mol Microbiol. 1989 Jan;3(1):95-102. [PubMed Link Image]
Target 1 Drug References
  1. 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 Link Image]
  2. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed Link Image]

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.