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QuickView for tigecycline (compound)

Name: tigecycline
PubChem Compound ID: 5282044
Molecular formula: C29H39N5O8
Molecular weight: 585.649 g/mol
Tygacil (TN); AIDS094224; D01079; Tigecycline[USAN]; GAR 936; Tigilcycline; AIDS-094224; C12012; 220620-09-7; (4S,12aS)-4,7-Bis(dimethylamino)-9-{2-[(tert-butyl)amino]acetylamino}-3,10,12,12a-tetrahydroxy-1,11-dioxo-4,5,6,12a,4a,5a-hexahydronaphthacene-2-carboxamide.
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Name: tigecycline
Name (isomeric): DB00560
Drug Type: small molecule
WAY-GAR-936; GAR-936; GAR-936,Tigecycline
Brand: Tygacil
Category: Anti-Bacterial Agents, Antibacterial Agents, Tetracyclines
CAS number: 220620-09-7
Indication: For the treatment of infections caused by susceptible strains of the designated microorganisms in the following conditions: Complicated skin and skin structure infections caused by <i>Escherichia coli</i>, <i>Enterococcus faecalis</i> (vancomycin-susceptible isolates only), <i>Staphylococcus aureus</i> (methicillin-susceptible and -resistant isolates), <i>Streptococcus agalactiae</i>, <i>Streptococcus anginosus</i> grp. (includes <i>S. anginosus</i>, <i>S. intermedius</i>, and <i>S. constellatus</i>), <i>Streptococcus pyogenes</i> and <i>Bacteroides fragilis</i>. Complicated intra-abdominal infections caused by <i>Citrobacter freundii</i>, <i>Enterobacter cloacae</i>, <i>Escherichia coli</i>, <i>Klebsiella oxytoca</i>, <i>Klebsiella pneumoniae</i>, <i>Enterococcus faecalis</i> (vancomycin-susceptible isolates only), <i>Staphylococcus aureus</i> (methicillin-susceptible isolates only), <i>Streptococcus anginosus</i> grp. (includes <i>S. anginosus</i>, <i>S. intermedius</i>, and <i>S. constellatus</i>), <i>Bacteroides fragilis</i>, <i>Bacteroides thetaiotaomicron</i>, <i>Bacteroides uniformis</i>, <i>Bacteroides vulgatus</i>, <i>Clostridium perfringens</i>, and <i>Peptostreptococcus micros</i>.
Tigecycline is the first clinically-available drug in a new class of antibiotics called the glycylcyclines. Glycylcyclines are a new class of antibiotics derived from tetracycline. These tetracycline analogues are specifically designed to overcome two common mechanisms of tetracycline resistance, namely resistance mediated by acquired efflux pumps ...
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Mechanism of Action:
Tigecycline, a glycylcycline, inhibits protein translation in bacteria by binding to the 30S ribosomal subunit and blocking entry of amino-acyl tRNA molecules into the A site of the ribosome. This prevents incorporation of amino acid residues into elongating peptide chains. Tigecycline carries a glycylamido moiety attached to the 9-position of mino...
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Protein binding: 71% to 89%
Biotransformation: Tigecycline is not extensively metabolized. In vitro studies with tigecycline using human liver microsomes, liver slices, and hepatocytes led to the formation of only trace amounts of metabolites. A glucuronide, an N-acetyl metabolite, and a tigecycline epimer (each at no more than 10% of the administered dose) are the primary metabolites.
Half Life: 27-43 hours
Toxicity: Since glycylcyclines are similar to tetracyclines, they share many of the same side effects and contraindications as tetracyclines. These side effects may include nausea/vomiting, headache, photosensitivity, discoloration of growing teeth, and fetal damage.
Affected organisms: Enteric bacteria and other eubacteria
Drug interaction:
AcenocoumarolTigecycline may increase the anticoagulant effect of acenocoumarol.
TretinoinDemeclocycline may increase the adverse effects of oral Tretinoin. Increase risk of pseudotumour cerebri. Concurrent therapy should be avoided.
AnisindioneTigecycline may increase the anticoagulant effect of anisindione.
DicumarolTigecycline may increase the anticoagulant effect of dicumarol.
BexaroteneTigecycline may enhance the adverse/toxic effect of Retinoic Acid Derivatives. The development of pseudotumor cerebri (intracranial hypertension) is of particular concern. Avoid this combination.
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