Paklitaksel

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Paklitaksel
Klinički podaci
Robne marke Abraxane, Epitaxol, Onxol, Paxceed
AHFS/Drugs.com Monografija
Identifikatori
CAS broj 33069-62-4
ATC kod L01CD01
PubChem[1][2] 36314
DrugBank DB01229
ChemSpider[3] 33395
KEGG[4] C07394 YesY
ChEBI CHEBI:7887 YesY
ChEMBL[5] CHEMBL48 YesY
Hemijski podaci
Formula C47H51NO14 
Mol. masa 853,906
SMILES eMolekuli & PubHem
Fizički podaci
Tačka topljenja 216-217 °C (-143 °F)
Farmakokinetički podaci
Poluvreme eliminacije 52,7 h
Izlučivanje Fekalno, renalno
Farmakoinformacioni podaci
Trudnoća  ?
Pravni status
Način primene Intravenozno

Paklitaksel je mitotički inhibitor koji se koristi u hemoterapiji kancera. Otkriven je u američkom programu Nacionalnog instituta za rak u Institutu istraživački trougao 1967. godine, kad je izolovan iz kore Taxus brevifolia drveta, i nazvan je taksol. Kasnije je otkriveno da endofitne gljive u kori sintetišu paklitaksel.[6][7][8][9][10][11][12][13]

Kad ga je kompanija Bristol-Myers Squibb (BMS) komercijalno razvila, njegovo generičko ime je promenjeno u paklitaksel i BMS jedinjenje je u prodaji pod imenom Taksol. U toj formulaciji, paklitaksel je rastvoren u Kolliphor EL i etanolu, kao agensima za isporuku. Novija formulacija, u kojoj je paklitaksel vazan za albumin, je u prodaji pod imenom Abraksan.

Paklitaksel je organsko jedinjenje, koje sadrži 47 atoma ugljenika i ima molekulsku masu od 853,906 Da.

Osobine[uredi - уреди | uredi izvor]

Osobina Vrednost
Broj akceptora vodonika 14
Broj donora vodonika 4
Broj rotacionih veza 14
Particioni koeficijent[14] (ALogP) 3,1
Rastvorljivost[15] (logS, log(mol/L)) -8,6
Polarna površina[16] (PSA, Å2) 221,3

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. Wall ME, Wani MC: Camptothecin and taxol: discovery to clinic--thirteenth Bruce F. Cain Memorial Award Lecture. Cancer Res. 1995 Feb 15;55(4):753-60. PMID 7850785
  7. Wani MC, Taylor HL, Wall ME, Coggon P, McPhail AT: Plant antitumor agents. VI. The isolation and structure of taxol, a novel antileukemic and antitumor agent from Taxus brevifolia. J Am Chem Soc. 1971 May 5;93(9):2325-7. PMID 5553076
  8. Fuchs DA, Johnson RK: Cytologic evidence that taxol, an antineoplastic agent from Taxus brevifolia, acts as a mitotic spindle poison. Cancer Treat Rep. 1978 Aug;62(8):1219-22. PMID 688258
  9. Saville MW, Lietzau J, Pluda JM, Feuerstein I, Odom J, Wilson WH, Humphrey RW, Feigal E, Steinberg SM, Broder S, et al.: Treatment of HIV-associated Kaposi's sarcoma with paclitaxel. Lancet. 1995 Jul 1;346(8966):26-8. PMID 7603142
  10. ABI 007. Drugs R D. 2004;5(3):155-9. PMID 15139776
  11. Gaitanis A, Staal S: Liposomal doxorubicin and nab-paclitaxel: nanoparticle cancer chemotherapy in current clinical use. Methods Mol Biol. 2010;624:385-92. PMID 20217610
  12. Knox C, Law V, Jewison T, Liu P, Ly S, Frolkis A, Pon A, Banco K, Mak C, Neveu V, Djoumbou Y, Eisner R, Guo AC, Wishart DS (2011). "DrugBank 3.0: a comprehensive resource for omics research on drugs". Nucleic Acids Res. 39 (Database issue): D1035–41. PMC 3013709. PMID 21059682. doi:10.1093/nar/gkq1126. 
  13. David S. Wishart, Craig Knox, An Chi Guo, Dean Cheng, Savita Shrivastava, Dan Tzur, Bijaya Gautam, and Murtaza Hassanali (2008). "DrugBank: a knowledgebase for drugs, drug actions and drug targets". Nucleic acids research 36 (Database issue): D901–6. PMC 2238889. PMID 18048412. doi:10.1093/nar/gkm958. 
  14. Ghose, A.K., Viswanadhan V.N., and Wendoloski, J.J. (1998). "Prediction of Hydrophobic (Lipophilic) Properties of Small Organic Molecules Using Fragment Methods: An Analysis of AlogP and CLogP Methods". J. Phys. Chem. A 102: 3762–3772. doi:10.1021/jp980230o. 
  15. Tetko IV, Tanchuk VY, Kasheva TN, Villa AE. (2001). "Estimation of Aqueous Solubility of Chemical Compounds Using E-State Indices". Chem Inf. Comput. Sci. 41: 1488–1493. PMID 11749573. doi:10.1021/ci000392t. 
  16. Ertl P., Rohde B., Selzer P. (2000). "Fast calculation of molecular polar surface area as a sum of fragment based contributions and its application to the prediction of drug transport properties". J. Med. Chem. 43: 3714–3717. PMID 11020286. doi:10.1021/jm000942e. 

Literatura[uredi - уреди | uredi izvor]

Spoljašnje veze[uredi - уреди | uredi izvor]

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