Tigeciklin

Tigeciklin
IUPAC ime
	N-[(5aR,6aS,7S,9Z,10aS)-9-[amino(hidroksi)metiliden]-4,7-bis(dimetilamino)-1,10a,12-trihidroksi-8,10,11-triokso-5,5a,6,6a,7,8,9,10,10a,11-dekahidrotetracen-2-il]-2-(tert-butilamino)acetamid
Klinički podaci
Prodajno ime	Tigacil
Drugs.com	Monografija
Kategorija trudnoće	AU: D ; US: D (Evidencija rizika) ; ;
Način primene	IV only;
Pravni status
Pravni status	AU: S4 (Prescription only) ; US: ℞-only ;
Farmakokinetički podaci
Bioraspoloživost	NA
Vezivanje proteina	71-89%
Metabolizam	ne metabolizuje se
Poluvreme eliminacije	42,4 sata
Izlučivanje	59% bilijarno, 33% renalno;
Identifikatori
CAS broj	220620-09-7
ATC kod	J01AA12 (WHO)
PubChem	CID 5282044
DrugBank	DB00560
ChemSpider	10482314
UNII	70JE2N95KR
KEGG	D01079
ChEBI	CHEBI:149836
ChEMBL	; CHEMBL376140;
Sinonimi	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
Hemijski podaci
Formula	C29H39N5O8
Molarna masa	585,65 g/mol
	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 ;

Tigeciklin je glicilciklinski antibiotik^[1]^[2] koji je razvila kompanija Francis Tali^[3] i koji proizvodi i prodaje Wyeth pod iemnom Tigacil. Ovaj lek je FDA odobrila 2005. On je razvijen u responsu na rastuću prevalenciju otpornosti na antibiotike kod bakterija poput Staphylococcus aureus i Acinetobacter baumannii. Enterobacteriaceae otporne na višestruke lekove usled dejstva enzima Nju Delhi metalo-beta-laktamaza su isto tako podložen tigeciklinu.^[4]

Struktura

Ovaj antibiotik je prvi klinički dostupan lek u novoj klasi antibiotika zavanih glicilciklini. On je strukturno sličan sa tetraciklinima po tome što sadrži centralni skeleton sa četiri prstena. On je derivat minociklina. Tigeciklin je supstitutuisan na D-9 poziciji za šta se smatra da uzrokuje širok spektar aktivnosti.

Mehanizam dejstva

Tigeciklin je bakteriostatik i inhibitor proteinske sinteze putem vezivanja za 30S ribozomalnu podjedinicu bakterija čime blokira pristup Aminoacil-tRNK u A mesto ribozoma tokom prokariotske translacije.^[5]

Sinonimi

GAR-936^[6]
Tigacil

Reference

^ Rose W, Rybak M (2006). „Tigecycline: first of a new class of antimicrobial agents.”. Pharmacotherapy. 26 (8): 1099—110. PMID 16863487. doi:10.1592/phco.26.8.1099.
^ N, Kasbekar (2006). „Tigecycline: a new glycylcycline antimicrobial agent.”. Am J Health Syst Pharm. 63 (13): 1235—43. PMID 16790575. doi:10.2146/ajhp050487.
^ Projan, Steven J (2010). „Francis Tally and the discovery and development of tigecycline: a personal reminiscence”. Clin. Infect. Dis. United States. 50 Suppl 1: S24—5. PMID 20067389. doi:10.1086/647941.
^ Kumarasamy et. al.; Toleman, Mark A; Walsh, Timothy R; Bagaria, Jay; Butt, Fafhana; Balakrishnan, Ravikumar; Chaudhary, Uma; Doumith, Michel; Giske, Christian G (2010). „Emergence of a new antibiotic resistance mechanism in India, Pakistan, and the UK: a molecular, biological, and epidemiological study”. The Lancet Infectious Diseases. 10 (9): 597—602. PMC 2933358 . PMID 20705517. doi:10.1016/S1473-3099(10)70143-2.
^ Tigecycline: A Novel Broad-Spectrum Antimicrobial: Pharmacology and Mechanism of Action Christine M. Slover, PharmD, Infectious Diseases Fellow, Keith A. Rodvold, PharmD and Larry H. Danziger, PharmD, Professor, Department of Pharmacy Practice, University of Illinois at Chicago, Chicago, IL
^ Betriu C, Rodríguez-Avial I, Sánchez BA, Gómez M, Picazo JJ (2002). „Comparative in vitro activities of tigecycline (GAR-936) and other antimicrobial agents against Stenotrophomonas maltophilia”. J Antimicrob Chemother. 50 (5): 758–59. PMID 12407139. doi:10.1093/jac/dkf196.

Spoljašnje veze

Tygacil ( tigecycline iv ): Antibiotic for Skin Infections Архивирано на сајту Wayback Machine (6. јул 2008)

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[1] Rose W, Rybak M (2006). „Tigecycline: first of a new class of antimicrobial agents.”. Pharmacotherapy. 26 (8): 1099—110. PMID 16863487. doi:10.1592/phco.26.8.1099.

[2] N, Kasbekar (2006). „Tigecycline: a new glycylcycline antimicrobial agent.”. Am J Health Syst Pharm. 63 (13): 1235—43. PMID 16790575. doi:10.2146/ajhp050487.

[3] Projan, Steven J (2010). „Francis Tally and the discovery and development of tigecycline: a personal reminiscence”. Clin. Infect. Dis. United States. 50 Suppl 1: S24—5. PMID 20067389. doi:10.1086/647941.

[Kumarasamy-4] Kumarasamy et. al.; Toleman, Mark A; Walsh, Timothy R; Bagaria, Jay; Butt, Fafhana; Balakrishnan, Ravikumar; Chaudhary, Uma; Doumith, Michel; Giske, Christian G (2010). „Emergence of a new antibiotic resistance mechanism in India, Pakistan, and the UK: a molecular, biological, and epidemiological study”. The Lancet Infectious Diseases. 10 (9): 597—602. PMC 2933358 . PMID 20705517. doi:10.1016/S1473-3099(10)70143-2.

[5] Tigecycline: A Novel Broad-Spectrum Antimicrobial: Pharmacology and Mechanism of Action Christine M. Slover, PharmD, Infectious Diseases Fellow, Keith A. Rodvold, PharmD and Larry H. Danziger, PharmD, Professor, Department of Pharmacy Practice, University of Illinois at Chicago, Chicago, IL

[6] Betriu C, Rodríguez-Avial I, Sánchez BA, Gómez M, Picazo JJ (2002). „Comparative in vitro activities of tigecycline (GAR-936) and other antimicrobial agents against Stenotrophomonas maltophilia”. J Antimicrob Chemother. 50 (5): 758–59. PMID 12407139. doi:10.1093/jac/dkf196.

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