Name: | tigecycline |
---|---|
PubChem Compound ID: | 5282044 |
Molecular formula: | C29H39N5O8 |
Molecular weight: | 585.649 g/mol |
Synonyms: |
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.
show more » |
Name: | tigecycline |
---|---|
Name (isomeric): | DB00560 |
Drug Type: | small molecule |
Synonyms: |
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>. |
---|---|
Pharmacology: |
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 ...
show more » |
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...
show more » |
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: |
|
---|