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Wikipedia - Tigecycline

Tigecycline
Systematic (IUPAC) name
N-[(5aR,6aS,7S,9Z,10aS)-9-[amino(hydroxy)methylidene]-4,7-bis(dimethylamino)-1,10a,12-trihydroxy-8,10,11-trioxo-5,5a,6,6a,7,8,9,10,10a,11-decahydrotetracen-2-yl]-2-(tert-butylamino)acetamide
Identifiers
CAS number 220620-09-7
ATC code J01AA12
PubChem CID 5282044
DrugBank APRD01307
Chemical data
Formula C29H39N5O8 
Mol. mass 585.65 g/mol
Synonyms N-[(5aR,6aS,7S,9Z,10aS)-9-(amino-hydroxy-methylidene)-4,7-bis(dimethylamino)-1,10a,12-trihydroxy-8,10,11-trioxo-5a,6,6a,7-tetrahydro-5H-tetracen-2-yl]-2-(tert-butylamino)acetamide
Pharmacokinetic data
Bioavailability NA
Protein binding 71-89%
Metabolism not metabolised
Half-life 42.4 hours
Excretion 59% biliary, 33% renal
Therapeutic considerations
Pregnancy cat. D(AU) D(US)
Legal status Prescription Only (S4) (AU) ?-only (US)
Routes IV only
 YesY(what is this?)  (verify)

Tigecycline (INN) (pronounced /?ta?g?'sa?kli?n/) is a glycylcycline antibiotic[1][2] developed by Francis Tally[3] and marketed by Wyeth under the brand name Tygacil. It was given a U.S. Food and Drug Administration (FDA) fast-track approval and was approved on June 17, 2005. It was developed in response to the growing prevalence of antibiotic resistance in bacteria such as Staphylococcus aureus and acinetobacter baumanii.

Contents

[edit] Structure

This antibiotic is the first clinically-available drug in a new class of antibiotics called the glycylcyclines. It is structurally similar to the tetracyclines in that it contains a central four-ring carbocyclic skeleton and is actually a derivative of minocycline. Tigecycline has a substitution at the D-9 position which is believed to confer broad spectrum activity.

[edit] Mechanism of action

Tigecycline is bacteriostatic and is a protein synthesis inhibitor by binding to the 30S ribosomal subunit of bacteria and thereby blocking entry of Aminoacyl-tRNA into the A site of the ribosome during prokaryotic translation.[4]

[edit] Indications

Tigecycline is active against many Gram-positive bacteria, Gram-negative bacteria and anaerobes – including activity against methicillin-resistant Staphylococcus aureus (MRSA) and multi-drug resistant strains of Acinetobacter baumannii. It has no activity against Pseudomonas spp. or Proteus spp. The drug is licenced for the treatment of skin and soft tissue infections as well as intra-abdominal infections.

[edit] Dosing

Tigecycline is given by slow intravenous infusion (30 to 60 minutes). A single dose of 100 mg is given first, followed by 50 mg every twelve hours after that. Patients with impaired liver function need to be given a lower dose. No adjustment is needed for patients with impaired kidney function. It is not licensed for use in children. There is no oral form available.

[edit] Side effects

Tigecycline has similar side effects to the tetracyclines. The most common side effects of tigecycline are diarrhea, nausea and vomiting. Nausea and vomiting is mild or moderate and usually occurs during the first two days of therapy. Other side effects include pain at the injection site, swelling and irritation; increased or decreased heart rate and infections. Also avoid use in children and pregnancy, due to its affects on teeth and bone. As with other antibiotics, overgrowth of organisms that are not susceptible to tigecycline can occur.

[edit] Synonyms

  • GAR-936[5]
  • Tygacil

[edit] References

  1. ^ Rose W, Rybak M (2006). "Tigecycline: first of a new class of antimicrobial agents.". Pharmacotherapy 26 (8): 1099–110. doi:10.1592/phco.26.8.1099. PMID 16863487. 
  2. ^ Kasbekar N (2006). "Tigecycline: a new glycylcycline antimicrobial agent.". Am J Health Syst Pharm 63 (13): 1235–43. doi:10.2146/ajhp050487. PMID 16790575. 
  3. ^ Projan, Steven J (Jan. 2010). "Francis Tally and the discovery and development of tigecycline: a personal reminiscence". Clin. Infect. Dis. (United States) 50 Suppl 1: S24–5. doi:10.1086/647941. PMID 20067389. 
  4. ^ Tigecycline: A Novel Broad-Spectrum Antimicrobial: Pharmacology and Mechanism of Action Christine M. Slover, PharmD, Infectious Diseases Fellow, Keith A. Rodvold, PharmD and Larry H. Danziger, PharmD, Professor, Department of Pharmacy Practice, University of Illinois at Chicago, Chicago, IL
  5. ^ Betriu C, Rodríguez-Avial I, Sánchez BA, Gómez M, Picazo JJ (2002). "Comparative in vitro activities of tigecycline (GAR-936) and other antimicrobial agents against Stenotrophomonas maltophilia". J Antimicrob Chemother 50 (5): 758–59. doi:10.1093/jac/dkf196. PMID 12407139. 

[edit] External links

v • d • e
Antibacterials: protein synthesis inhibitors (J01A, J01B, J01F, J01G, QJ01XQ)
30S
-mycin (Streptomyces)
Tetracyclines
Tigecycline
50S
EF-G
Steroid antibacterials
#WHO-EM. ‡Withdrawn from market. CLINICAL TRIALS: †Phase III. §Never to phase III

M: BAC

drug(J1p, w, n, m, vacc)
Retrieved from "http://en.wikipedia.org/wiki/Tigecycline"

This article is licensed under the GNU Free Documentation License. It uses material from the Wikipedia article "Tigecycline".

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