Tigeciklin

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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
Robne marke Tigacil
AHFS/Drugs.com Monografija
Identifikatori
CAS broj 220620-09-7
ATC kod J01AA12
PubChem[1][2] 5282044
DrugBank DB00560
ChemSpider[3] 10482314
UNII 70JE2N95KR YesY
KEGG[4] D01079 YesY
ChEBI CHEBI:149836 YesY
ChEMBL[5] CHEMBL376140 YesY
Hemijski podaci
Formula C29H39N5O8 
Mol. masa 585,65 g/mol
SMILES eMolekuli & PubHem
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
Farmakokinetički podaci
Bioraspoloživost NA
Vezivanje za proteine plazme 71-89%
Metabolizam ne metabolizuje se
Poluvreme eliminacije 42,4 sata
Izlučivanje 59% bilijarno, 33% renalno
Farmakoinformacioni podaci
Trudnoća D(AU) D(US)
Pravni status Samo na recept (S4) (AU) -only (SAD)
Način primene IV only

Tigeciklin je glicilciklinski antibiotik[6][7] koji je razvila kompanija Francis Tali[8] 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.[9]

Struktura[uredi - уреди | uredi izvor]

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[uredi - уреди | uredi izvor]

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.[10]

Sinonimi[uredi - уреди | uredi izvor]

Reference[uredi - уреди | uredi izvor]

  1. Li Q, Cheng T, Wang Y, Bryant SH (2010). "PubChem as a public resource for drug discovery.". Drug Discov Today 15 (23-24): 1052–7. PMID 20970519. doi:10.1016/j.drudis.2010.10.003.  edit
  2. Evan E. Bolton, Yanli Wang, Paul A. Thiessen, Stephen H. Bryant (2008). "Chapter 12 PubChem: Integrated Platform of Small Molecules and Biological Activities". Annual Reports in Computational Chemistry 4: 217–241. doi:10.1016/S1574-1400(08)00012-1. 
  3. Hettne KM, Williams AJ, van Mulligen EM, Kleinjans J, Tkachenko V, Kors JA. (2010). "Automatic vs. manual curation of a multi-source chemical dictionary: the impact on text mining". J Cheminform 2 (1): 3. PMID 20331846. doi:10.1186/1758-2946-2-3.  edit
  4. Joanne Wixon, Douglas Kell (2000). "Website Review: The Kyoto Encyclopedia of Genes and Genomes — KEGG". Yeast 17 (1): 48–55. doi:10.1002/(SICI)1097-0061(200004)17:1<48::AID-YEA2>3.0.CO;2-H. 
  5. Gaulton A, Bellis LJ, Bento AP, Chambers J, Davies M, Hersey A, Light Y, McGlinchey S, Michalovich D, Al-Lazikani B, Overington JP. (2012). "ChEMBL: a large-scale bioactivity database for drug discovery". Nucleic Acids Res 40 (Database issue): D1100–7. PMID 21948594. doi:10.1093/nar/gkr777.  edit
  6. 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. 
  7. Kasbekar N (2006). "Tigecycline: a new glycylcycline antimicrobial agent.". Am J Health Syst Pharm 63 (13): 1235–43. PMID 16790575. doi:10.2146/ajhp050487. 
  8. Projan, Steven J (January 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. 
  9. 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. 
  10. 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
  11. 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[uredi - уреди | uredi izvor]

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