tigecycline
Also known as (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
Tigecycline, sold under the brand name Tygacil, is a tetracycline antibiotic medication for a number of bacterial infections. It is a glycylcycline class drug that is administered intravenously. It was developed in response to the growing rate of antibiotic resistant 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.
Chemical data
- Formula
- C29H39N5O8
- Molecular weight
- 585.6 g/mol
- 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
- SMILES
- CC(C)(C)NCC(=O)NC1=CC(=C2C[C@H]3C[C@H]4[C@@H](C(=O)/C(=C(\N)/O)/C(=O)[C@]4(C(=O)C3=C(C2=C1O)O)O)N(C)C)N(C)C
- InChIKey
- ZXGBRIBPJBHLMO-SBMFAFPZSA-N
- XLogP
- -0.2
- Polar surface area
- 206 Ų
- H-bond donors
- 7
- H-bond acceptors
- 12
- Formal charge
- 0
via PubChem
Research
6,072 papers~6 min read
Article
17 sectionsContents
- Medical uses
- Antibacterial use
- Non-antibacterial use
- Susceptibility data
- Liver or kidney problems
- Resistance mechanisms
- Side effects
- Precautions
- Black box warning
- Drug interactions
- History
- Mechanism of action
- Pharmacokinetics
- Society and culture
- Approval
- Other names
- References
Tigecycline, sold under the brand name Tygacil, is a tetracycline antibiotic medication for a number of bacterial infections. It is a glycylcycline class drug that is administered intravenously. It was developed in response to the growing rate of antibiotic resistant 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.
It was given a U.S. Food and Drug Administration (FDA) fast-track approval and was approved on 17 June 2005. It was approved for medical use in the European Union in April 2006.