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Tigecycline information


Tigecycline
Clinical data
Pronunciation/ˌtɡəˈskln/
Trade namesTygacil
AHFS/Drugs.comMonograph
MedlinePlusa614002
License data
  • US DailyMed: Tigecycline
Pregnancy
category
  • AU: D[1]
Routes of
administration
Intravenous (IV)
ATC code
  • J01AA12 (WHO)
Legal status
Legal status
  • AU: S4 (Prescription only)[2]
  • US: ℞-only[3]
  • EU: Rx-only[4]
Pharmacokinetic data
Protein binding71–89%
MetabolismNot metabolized
Elimination half-life42.4 hours
Excretion59% Bile duct, 33% kidney
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[5]
CAS Number
  • 220620-09-7 checkY
PubChem CID
  • 5282044
DrugBank
  • DB00560 checkY
ChemSpider
  • 10482314 checkY
UNII
  • 70JE2N95KR
KEGG
  • D01079 checkY
ChEBI
  • CHEBI:149836 checkY
ChEMBL
  • ChEMBL376140 checkY
CompTox Dashboard (EPA)
  • DTXSID2048581 Edit this at Wikidata
ECHA InfoCard100.211.439 Edit this at Wikidata
Chemical and physical data
FormulaC29H39N5O8
Molar mass585.658 g·mol−1
3D model (JSmol)
  • 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 checkY
  • Key:FPZLLRFZJZRHSY-HJYUBDRYSA-N checkY
  (verify)

Tigecycline, sold under the brand name Tygacil, is a tetracycline antibiotic medication for a number of bacterial infections.[3][6][7] 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.[6] 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.[6][7] It was approved for medical use in the European Union in April 2006.[4]

It was removed from the World Health Organization's List of Essential Medicines in 2019.[8][9] The World Health Organization classifies tigecycline as critically important for human medicine.[10]

  1. ^ "Tigecycline (Tygacil) Use During Pregnancy". Drugs.com. 6 July 2020. Retrieved 26 September 2020.
  2. ^ "Prescription medicines: registration of new generic medicines and biosimilar medicines, 2017". Therapeutic Goods Administration (TGA). 21 June 2022. Retrieved 30 March 2024.
  3. ^ a b "Tygacil- tigecycline injection, powder, lyophilized, for solution". DailyMed. 20 July 2020. Retrieved 26 September 2020.
  4. ^ a b "Tygacil EPAR". European Medicines Agency (EMA) (in Aragonese). 17 September 2018. Retrieved 26 September 2020.
  5. ^ "EP2181330". European Patent Office. Retrieved 29 September 2017.
  6. ^ a b c Rose WE, Rybak MJ (August 2006). "Tigecycline: first of a new class of antimicrobial agents". Pharmacotherapy. 26 (8): 1099–1110. doi:10.1592/phco.26.8.1099. PMID 16863487. S2CID 29714610.
  7. ^ a b Kasbekar N (July 2006). "Tigecycline: a new glycylcycline antimicrobial agent". American Journal of Health-System Pharmacy. 63 (13): 1235–1243. doi:10.2146/ajhp050487. PMID 16790575.
  8. ^ World Health Organization (2019). Executive summary: the selection and use of essential medicines 2019: report of the 22nd WHO Expert Committee on the selection and use of essential medicines. Geneva: World Health Organization. hdl:10665/325773. WHO/MVP/EMP/IAU/2019.05. License: CC BY-NC-SA 3.0 IGO.
  9. ^ World Health Organization (2019). The selection and use of essential medicines: report of the WHO Expert Committee on Selection and Use of Essential Medicines, 2019 (including the 21st WHO Model List of Essential Medicines and the 7th WHO Model List of Essential Medicines for Children). Geneva: World Health Organization. hdl:10665/330668. ISBN 9789241210300. ISSN 0512-3054. WHO technical report series;1021.
  10. ^ World Health Organization (2019). Critically important antimicrobials for human medicine (6th revision ed.). Geneva: World Health Organization. hdl:10665/312266. ISBN 9789241515528.

and 26 Related for: Tigecycline information

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Tigecycline

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Tigecycline, sold under the brand name Tygacil, is a tetracycline antibiotic medication for a number of bacterial infections. It is a glycylcycline class...

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List of antibiotics

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acid Mupirocin (topical) Omadacycline Oritavancin Tedizolid Telavancin Tigecycline (also covers gram negatives) Antibiotics that cover Pseudomonas aeruginosa:...

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Tetracycline antibiotics

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mediated by acquired efflux pumps and/or ribosomal protection. In 2005, tigecycline, the first member of a new subgroup of tetracyclines named glycylcyclines...

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Bacteriostatic agent

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Nitrofurantoin Novobiocin Oxazolidinone Spectinomycin Sulfonamides Tetracyclines Tigecycline Trimethoprim List of antibiotics Oligodynamic effect Pankey GA, Sabath...

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Glycylcycline

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mediated by acquired efflux pumps and/or ribosomal protection. Presently, tigecycline is the only glycylcycline approved for antibiotic use. The development...

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Peritonitis

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moxifloxacin because this is the only fluoroquinolone that covers anaerobes. Tigecycline is a tetracycline that can be used due to its coverage of Gram-positives...

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Stenotrophomonas maltophilia

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increasing. It is usually susceptible to piperacillin and ceftazidime. Tigecycline is also an effective drug. Polymyxin B may be effective treatment, at...

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Tetracyclic

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various pharmaceutical uses, such as: tetracycline antibiotics Doxycycline Tigecycline Omadacycline Eravacycline tetracyclic antidepressants Benzoctamine Loxapine...

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Enterococcus faecium

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microbes to become entirely tolerant of alcohol. Linezolid, daptomycin, tigecycline and the streptogramins (e.g. quinupristin/dalfopristin) can have activity...

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Semisynthesis

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semisyntheses of the further novel antibiotics tetracycline, doxycycline, and tigecycline. Further examples of semisynthesis include the early commercial production...

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Wyeth

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for the treatment of Renal Cell Carcinoma (a type of cancer). Tygacil (tigecycline); an antibiotic developed for treatment of intra-abdominal and skin /...

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Protein synthesis inhibitor

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by binding to the bacterial 30S ribosomal subunit. Tetracyclines and Tigecycline (a glycylcycline related to tetracyclines) block the A site on the ribosome...

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Drug of last resort

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cost and risk of vision loss or myopathy (due to mitochondrial damage). Tigecycline — used to kill Acinetobacter and Legionella species; this drug is limited...

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Pseudomonas aeruginosa

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common first-line antibiotics, carbapenems, polymyxins, and more recently tigecycline were considered to be the drugs of choice; however, resistance to these...

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Zidovudine

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in combination with other active agents (e.g. fosfomycin, colistin, tigecycline). Most common side effects include nausea, vomiting, acid reflux (heartburn)...

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Enterococcus

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E. faecalis, which is implicated in the vast majority of VRE cases. Tigecycline has also been shown to have antienterococcal activity, as has rifampicin...

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Timeline of antibiotics

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oxazolidinone 2001 – telithromycin, the first ketolide 2003 – daptomycin 2005 – tigecycline, the first glycylcycline 2005 – doripenem 2009 – telavancin, the first...

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Ampicillin

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different mechanisms of action, like vancomycin, linezolid, daptomycin, and tigecycline. Ampicillin can be administered by mouth, an intramuscular injection...

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Nitrofurantoin

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of extended-spectrum beta-lactamases: fosfomycin, nitrofurantoin and tigecycline". Clinical Microbiology and Infection. 14 (Suppl 1): 198–202. doi:10...

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Diabetic foot

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suggested that ertapenem with or without vancomycin is more effective than tigecycline for resolving DFIs. It is also generally unclear whether different antibiotics...

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Antibiotic

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2010s: cyclic lipopeptides (such as daptomycin), glycylcyclines (such as tigecycline), oxazolidinones (such as linezolid), and lipiarmycins (such as fidaxomicin)...

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Ertapenem

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has been found to be more effective and have fewer side effects than tigecycline, but in severe cases it is less effective than piperacillin/tazobactam...

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ESKAPE

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development of novel and effective antibiotic treatments. Colistin and tigecycline are two of the only antibiotics currently used for treatment, and there...

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Enterococcus faecalis

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nitrofurantoin (in the case of uncomplicated UTIs), linezolid, quinupristin, tigecycline and daptomycin, although ampicillin is preferred if the bacteria are...

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Clostridioides difficile

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progressing to severe-complicated disease the addition of intravenous tigecycline merits considerations. Patients with high risk of relapse may also benefit...

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Eravacycline

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class antibiotic by Tetraphase Pharmaceuticals. It is closely related to tigecycline. It has a broad spectrum of activity including many multi-drug resistant...

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