Tigecycline

Tigecycline
Clinical data
Pronunciation	/ˌtaɪɡəˈsaɪkliːn/
Trade names	Tygacil
AHFS/Drugs.com	Monograph
MedlinePlus	a614002
License data	US DailyMed: Tigecycline;
Pregnancy; category	AU: D; ;
Routes of; administration	Intravenous (IV)
ATC code	J01AA12 (WHO) ;
Legal status
Legal status	AU: S4 (Prescription only); US: ℞-only; EU: Rx-only;
Pharmacokinetic data
Protein binding	71–89%
Metabolism	Not metabolized
Elimination half-life	42.4 hours
Excretion	59% 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;
CAS Number	220620-09-7 ;
PubChem CID	5282044;
DrugBank	DB00560 ;
ChemSpider	10482314 ;
UNII	70JE2N95KR;
KEGG	D01079 ;
ChEBI	CHEBI:149836 ;
ChEMBL	ChEMBL376140 ;
CompTox Dashboard (EPA)	DTXSID2048581 ;
ECHA InfoCard	100.211.439
Chemical and physical data
Formula	C29H39N5O8
Molar mass	585.658 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 ; Key:FPZLLRFZJZRHSY-HJYUBDRYSA-N ;
	(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]

^ "Tigecycline (Tygacil) Use During Pregnancy". Drugs.com. 6 July 2020. Retrieved 26 September 2020.
^ "Prescription medicines: registration of new generic medicines and biosimilar medicines, 2017". Therapeutic Goods Administration (TGA). 21 June 2022. Retrieved 30 March 2024.
^ ^a ^b "Tygacil- tigecycline injection, powder, lyophilized, for solution". DailyMed. 20 July 2020. Retrieved 26 September 2020.
^ ^a ^b "Tygacil EPAR". European Medicines Agency (EMA) (in Aragonese). 17 September 2018. Retrieved 26 September 2020.
^ "EP2181330". European Patent Office. Retrieved 29 September 2017.
^ ^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.
^ ^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.
^ 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.
^ 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.
^ World Health Organization (2019). Critically important antimicrobials for human medicine (6th revision ed.). Geneva: World Health Organization. hdl:10665/312266. ISBN 9789241515528.

[Drugs.com_pregnancy-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.

[Tygacil_FDA_label-3] "Tygacil- tigecycline injection, powder, lyophilized, for solution". DailyMed. 20 July 2020. Retrieved 26 September 2020.

[Tygacil_EPAR-4] "Tygacil EPAR". European Medicines Agency (EMA) (in Aragonese). 17 September 2018. Retrieved 26 September 2020.

[5] "EP2181330". European Patent Office. Retrieved 29 September 2017.

[Rose-Rybak-6] 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.

[Kasbekar-7] 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.

[WHO21st-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.

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