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Identification
Name Ticarcillin
Accession Number DB01607
Type small molecule
Groups approved
Description

An antibiotic derived from penicillin similar to carbenicillin in action.
Structure Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  • Ticarcilina [inn-spanish]
  • Ticarcillin supplement
  • Ticarcilline [inn-french]
  • Ticarcillinum [inn-latin]
Brand names Not Available
Brand name mixtures
  • Timentin (Ticarcillin + Clavulanate)
Categories
  • Anti-Bacterial Agents
  • Penicillins
CAS number 34787-01-4
Weight Average: 384.427
Monoisotopic: 384.044977634
Chemical Formula C15H16N2O6S2
InChI Key InChIKey=OHKOGUYZJXTSFX-KZFFXBSXSA-N
InChI
InChI=1S/C15H16N2O6S2/c1-15(2)9(14(22)23)17-11(19)8(12(17)25-15)16-10(18)7(13(20)21)6-3-4-24-5-6/h3-5,7-9,12H,1-2H3,(H,16,18)(H,20,21)(H,22,23)/t7-,8-,9+,12-/m1/s1
Plain Text
IUPAC Name
(2S,5R,6R)-6-[(2R)-2-carboxy-2-(thiophen-3-yl)acetamido]-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]2NC(=O)[C@H](C(O)=O)C1=CSC=C1)C(O)=O
Plain Text
Mass Spec Not Available
Taxonomy
Kingdom Organic
Classes
  • Keto-Acids
  • Penicillins
Substructures
  • Hydroxy Compounds
  • Acetates
  • Keto-Acids
  • Amino Ketones
  • Carboxylic Acids and Derivatives
  • Aliphatic and Aryl Amines
  • Beta Lactams
  • Penicillins
  • Thiazoles
  • Heterocyclic compounds
  • Aromatic compounds
  • Carboxamides and Derivatives
  • Lactams
  • Azetidines
  • Thiophenes
  • Thiazolidines
Pharmacology
Indication For the treatment of bacterial infections.
Pharmacodynamics Ticarcillin is a semisynthetic antibiotic with a broad spectrum of bactericidal activity against many gram-positive and gram-negative aerobic and anaerobic bacteria. Ticarcillin is, however, susceptible to degradation by ß-lactamases, and therefore, the spectrum of activity does not normally include organisms which produce these enzymes.
Mechanism of action Ticarcillin's antibiotic properties arise from its ability to prevent cross-linking of peptidoglycan during cell wall synthesis when the bacteria tries to divide, causing death.
Absorption Not Available
Volume of distribution Not Available
Protein binding 45%
Metabolism
Route of elimination Not Available
Half life 1.1 hours
Clearance Not Available
Toxicity As with other penicillins, neurotoxic reactions may arise when very high doses of ticarcillin are administered, especially in patients with impaired renal function.
Affected organisms
  • Enteric bacteria and other eubacteria
Pathways Not Available
Pharmacoeconomics
Manufacturers
  • Glaxosmithkline
Packagers
Dosage forms Not Available
Prices Not Available
Patents Not Available
Properties
State solid
Melting point Not Available
Experimental Properties Not Available
Predicted Properties
Property Value Source
water solubility 7.16e-02 g/l ALOGPS
logP 0.99 ALOGPS
logP 0.60 ChemAxon Molconvert
logS -3.73 ALOGPS
pKa 4.12 ChemAxon Molconvert
hydrogen acceptor count 6 ChemAxon Molconvert
hydrogen donor count 3 ChemAxon Molconvert
polar surface area 124.01 ChemAxon Molconvert
rotatable bond count 5 ChemAxon Molconvert
refractivity 87.93 ChemAxon Molconvert
polarizability 36.14 ChemAxon Molconvert
References
Synthesis Reference Not Available
General Reference Not Available
External Links
Resource Link
KEGG Compound C07139 Link_out
PubChem Compound 36921 Link_out
PubChem Substance 46505959 Link_out
ChemSpider 33876 Link_out
ChEBI 9587 Link_out
ChEMBL 9587 Link_out
Therapeutic Targets Database DAP000458 Link_out
PharmGKB PA451684 Link_out
Drug Product Database 0 Link_out
RxList http://www.rxlist.com/cgi/generic/timentin.htm Link_out
Drugs.com http://www.drugs.com/cdi/ticarcillin.html Link_out
Wikipedia http://en.wikipedia.org/wiki/Ticarcillin 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 protein 2a

Pharmacological action: yes
Actions: inhibitor
Organism class: bacterial
UniProt ID: C1KC03 Link_out
Gene: mecA Link_out
Protein Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Chambers HF, Sachdeva M, Kennedy S: Binding affinity for penicillin-binding protein 2a correlates with in vivo activity of beta-lactam antibiotics against methicillin-resistant Staphylococcus aureus. J Infect Dis. 1990 Sep;162(3):705-10. Pubmed
Comments
Drug created on August 29, 2007 12:51 / 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.