Structure via PubChem · Public domain (PubChem)
tigecycline
Sign in to saveAlso 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- Tigecycline antibacterial activity, clinical effectiveness, and mechanisms and epidemiology of resistance: narrative review.European journal of clinical microbiology & infectious diseases : official publication of the European Society of Clinical Microbiology · 2022
- Tigecycline.Drugs · 2005
- Tigecycline-induced coagulopathy: a literature review.International journal of clinical pharmacy · 2019
- Effectiveness and Safety of High Dose Tigecycline for the Treatment of Severe Infections: A Systematic Review and Meta-Analysis.Advances in therapy · 2020
- The tigecycline resistance mechanisms in Gram-negative bacilli.Frontiers in cellular and infection microbiology · 2024
via PubMed
~6 min read
Encyclopedic overview
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.
Excerpted from Wikipedia’s “tigecycline” article, available under the CC BY-SA 4.0 licence.