Tigecycline

Tigecycline

File:Tigecycline structure.svg
Clinical data
Pregnancy category	AU: D US: D (Evidence of risk)
Routes of administration	IV only
ATC code	J01AA12 (WHO)
Legal status
Legal status	AU: S4 (Prescription only) US: ℞-only
Pharmacokinetic data
Bioavailability	NA
Protein binding	71-89%
Metabolism	not metabolised
Elimination half-life	42.4 hours
Excretion	59% biliary, 33% renal
Identifiers
IUPAC name 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
CAS Number	220620-09-7
PubChem CID	5282044
DrugBank	APRD01307
E number	{{#property:P628}}
ECHA InfoCard	{{#property:P2566}}
Chemical and physical data
Formula	C19H39N5O8
Molar mass	585.65 g/mol

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Tigecycline (INN) (IPA: Template:IPA) is an glycylcycline antibiotic developed 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.

Pharmacology

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. The drug inhibits the bacterial 30S ribosome and is bacteriostatic.

Indications

Tigecycline is active against many Gram-positive bacteria, Gram-negative bacteria and anaerobes – including activity against methicillin-resistant Staphylococcus aureus (MRSA). 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.

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.

Side Effects

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. As tigecycline is similar to the tetracycline antibiotics,they have similar side effects such as increased sensitivity to sunlight. 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.

References

• Rose W, Rybak M (2006). "Tigecycline: first of a new class of antimicrobial agents". Pharmacotherapy. 26 (8): 1099–110. PMID 16863487.
• Kasbekar N (2006). "Tigecycline: a new glycylcycline antimicrobial agent". Am J Health Syst Pharm. 63 (13): 1235–43. PMID 16790575.

External links

• Tygacil ® ( tigecycline iv ): Antibiotic for Skin Infections