Tigecycline

CAS 220620-09-7

About the API

Systematic name (4S,4aS,5aR,12aS)-9-[2-(tert-butylamino)acetamido]-4,7-bis(dimethylamino)-1,4,4a,5,5a,6,11,12a-octahydro-3,10,12,12a-tetrahydroxy-1,11-dioxo-2-naphthacenecarboxamide
Trade name(s) Tygacil
Technology Synthetic Organic Chemistry
Molecular Formula C29H39N5O8
Molecular Weight 585.65 g/mol
Physical properties Orange lyophilized powder or cake
Therapeutic category Infectious disease
Available formulations Injectables
Regulations Canada DMF Flag Canada DMF EU DMF Flag EU DMF Other Flag Other US DMF Flag US DMF

General Information

Tigecycline is an anti-bacterial agent for intravenous infusion. It is used to treat patients with complicated skin and skin structure infections, complicated intra-abdominal infections and community-acquired bacterial pneumonia.

Specifically, it is prescribed for adults (or adults and children older than eight years, according to country) with complicated skin and skin structure infections caused by susceptible isolates of Escherichia coli, Enterococcus faecalis (vancomycin-susceptible isolates), Staphylococcus aureus (methicillin-susceptible and -resistant isolates), Streptococcus agalactiae, Streptococcus anginosus grp. (includes S. anginosus, S. intermedius, and S. constellatus), Streptococcus pyogenes, Enterobacter cloacae, Klebsiella pneumoniae, and Bacteroides fragilis.

It is not intended for diabetic foot infections.

It is prescribed for adults with intra-abdominal infections caused by susceptible isolates of Citrobacter freundii, Enterobacter cloacae, Escherichia coli, Klebsiella oxytoca, Klebsiella pneumoniae, Enterococcus faecalis (vancomycin-susceptible isolates), Staphylococcus aureus (methicillin-susceptible and -resistant isolates), Streptococcus anginosus grp. (includes S. anginosus, S. intermedius, and S. constellatus), Bacteroides fragilis, Bacteroides thetaiotaomicron, Bacteroides uniformis, Bacteroides vulgatus, Clostridium perfringens, and Peptostreptococcus micros.

In addition, it is prescribed for the treatment of adults with community-acquired bacterial pneumonia caused by susceptible isolates of Streptococcus pneumonia (penicillin-susceptible isolates), including cases with concurrent bacteremia (the presence of bacteria in the blood), Haemophilus influenza and Legionella pneumophila.

In comparison with other anitbacterials, tigecycline has similar effectiveness. In studies of skin and skin structure infections, approximately 86% of the patients receiving tigecycline were cured, compared with approximately 89% of those receiving vancomycin and aztreonam. In studies of abdominal infection, approximately 86% of the patients receiving either Tygacil or imipenem/cilastatin were cured.

 

Tigecycline was approved by the FDA in 2005 after receiving fast-track approval. The following year it was approved by the EMA.

It is produced through a chemical process involving several steps.