Tigecycline

Tigecycline

Clinical data
Pronunciation	/ˌtaɪɡəˈsaɪkliːn/
Trade names	Tygacil
AHFS/Drugs.com	Monograph
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
Protein binding	71–89%
Metabolism	Not metabolized
Biological 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-5,5a,6,6a,7,8,9,10,10a,11-decahydrotetracen-2-yl]-2-(tert-butylamino)acetamide
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
CAS Number	220620-09-7 Y
PubChem CID	5282044
DrugBank	DB00560 Y
ChemSpider	10482314 Y
UNII	70JE2N95KR
KEGG	D01079 Y
ChEBI	CHEBI:149836 Y
ChEMBL	CHEMBL376140 Y
ECHA InfoCard	100.211.439
Chemical and physical data
Formula	C29H39N5O8
Molar mass	585.65 g/mol
3D model (Jmol)	Interactive image
SMILES CC(C)(C)NCC(=O)Nc1cc(c2C[C@H]3C[C@H]4[C@H](N(C)C)C(\O)=C(\C(N)=O)C(=O)[C@@]4(O)C(/O)=C3/C(=O)c2c1O)N(C)C
InChI InChI=1S/C29H39N5O8/c1-28(2,3)31-11-17(35)32-15-10-16(33(4)5)13-8-12-9-14-21(34(6)7)24(38)20(27(30)41)26(40)29(14,42)25(39)18(12)23(37)19(13)22(15)36/h10,12,14,21,31,36,38-39,42H,8-9,11H2,1-7H3,(H2,30,41)(H,32,35)/t12-,14-,21-,29-/m0/s1 Y Key:FPZLLRFZJZRHSY-HJYUBDRYSA-N Y

Tigecycline is an antibiotic used to treat a number of bacterial infections. It is a glycylcycline that is administered intravenously. It was developed in response to the growing rate of antibiotic resistance in bacteria such as Staphylococcus aureus, Acinetobacter baumannii, and E. coli. As a tetracycline derivative antibiotic, its structural modifications has expanded its therapeutic activity to include Gram-positive and Gram-negative organisms, including those of multi-drug resistance.

Tigecycline is marketed by Pfizer 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.

Tigecycline is used to treat different kinds of bacterial infections, including complicated skin and structure infections, complicated intra-abdominal infections and community-acquired bacterial pneumonia. The spectrum of activity of tigecycline is discussed below.

Tigecycline is given intravenously and has activity against a variety of Gram-positive and Gram-negative bacterial pathogens, many of which are resistant to existing antibiotics. Tigecycline successfully completed phase III trials in which it was at least equal to intravenous vancomycin and aztreonam to treat complicated skin and skin structure infections, and to intravenous imipenem and cilastatian to treat complicated intra-abdominal infections. Tigecycline is active against many Gram-positive bacteria, Gram-negative bacteria and anaerobes – including activity against methicillin-resistant Staphylococcus aureus (MRSA), Stenotrophomonas maltophilia, Haemophilus influenzae, and Neisseria gonorrhoeae (with MIC values reported at 2 µg/mL) and multi-drug resistant strains of Acinetobacter baumannii. It has no activity against Pseudomonas spp. or Proteus spp. The drug is licensed for the treatment of skin and soft tissue infections as well as intra-abdominal infections.