Auranofin

Auranofin
Klinički podaci
Drugs.comMonografija
Način primeneOralno
Farmakokinetički podaci
IzlučivanjeRenalno
Identifikatori
CAS broj34031-32-8 ДаY
ATC kodM01CB03 (WHO)
PubChemCID 6333901
DrugBankDB00995 ДаY
ChemSpider21229878 ДаY
ChEBICHEBI:2922 ДаY
ChEMBLCHEMBL1366 ДаY
Hemijski podaci
FormulaC20H34AuO9PS
Molarna masa678,484
SMILES
  • CCP(CC)(CC)=[Au]S[C@@H]1O[C@H](COC(C)=O)[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@H]1OC(C)=O
InChI
  • InChI=1S/C14H20O9S.C6H15P.Au/c1-6(15)19-5-10-11(20-7(2)16)12(21-8(3)17)13(14(24)23-10)22-9(4)18;1-4-7(5-2)6-3;/h10-14,24H,5H2,1-4H3;4-6H2,1-3H3;/q;;+1/p-1/t10-,11-,12+,13-,14+;;/m1../s1 ДаY
  • Key:AUJRCFUBUPVWSZ-XTZHGVARSA-M ДаY

Auranofin je organsko jedinjenje, koje sadrži 20 atoma ugljenika i ima molekulsku masu od 678,484 Da.[1][2][3][4][5][6][7]

Osobine

Osobina Vrednost
Broj akceptora vodonika 10
Broj donora vodonika 0
Broj rotacionih veza 14
Particioni koeficijent[8] (ALogP) 1,4
Rastvorljivost[9] (logS, log(mol/L)) -3,3
Polarna površina[10] (PSA, Å2) 149,5

Reference

  1. ^ Jeon KI, Byun MS, Jue DM: Gold compound auranofin inhibits IkappaB kinase (IKK) by modifying Cys-179 of IKKbeta subunit. Exp Mol Med. 2003 Apr 30;35(2):61-6. PMID 12754408
  2. ^ Kim IS, Jin JY, Lee IH, Park SJ: Auranofin induces apoptosis and when combined with retinoic acid enhances differentiation of acute promyelocytic leukaemia cells in vitro. Br J Pharmacol. 2004 Jun;142(4):749-55. Epub 2004 May 24. PMID 15159275
  3. ^ Venardos K, Harrison G, Headrick J, Perkins A: Auranofin increases apoptosis and ischaemia-reperfusion injury in the rat isolated heart. Clin Exp Pharmacol Physiol. 2004 May-Jun;31(5-6):289-94. PMID 15191400
  4. ^ Hafejee A, Winhoven S, Coulson IH: Jessner's lymphocytic infiltrate responding to oral auranofin. J Dermatolog Treat. 2004 Sep;15(5):331-2. PMID 15370403
  5. ^ Rigobello MP, Folda A, Baldoin MC, Scutari G, Bindoli A: Effect of auranofin on the mitochondrial generation of hydrogen peroxide. Role of thioredoxin reductase. Free Radic Res. 2005 Jul;39(7):687-95. PMID 16036347
  6. ^ 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 Слободан приступ. PMID 21059682. doi:10.1093/nar/gkq1126. 
  7. ^ David S. Wishart; Craig Knox; An Chi Guo; Dean Cheng; Savita Shrivastava; Dan Tzur; Bijaya Gautam; Murtaza Hassanali (2008). „DrugBank: a knowledgebase for drugs, drug actions and drug targets”. Nucleic acids research. 36 (Database issue): D901—6. PMC 2238889 Слободан приступ. PMID 18048412. doi:10.1093/nar/gkm958. 
  8. ^ Ghose, A.K.; Viswanadhan V.N. & 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. 
  9. ^ 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. 
  10. ^ 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

  • Hardman JG, Limbird LE, Gilman AG (2001). Goodman & Gilman's The Pharmacological Basis of Therapeutics (10. изд.). New York: McGraw-Hill. ISBN 0071354697. doi:10.1036/0071422803. 
  • Thomas L. Lemke; David A. Williams, ур. (2007). Foye's Principles of Medicinal Chemistry (6. изд.). Baltimore: Lippincott Willams & Wilkins. ISBN 0781768799. 

Spoljašnje veze

  • Auranofin
  • п
  • р
  • у
Jedinjenja zlata
Zlato(-I)
Zlato(I)
  • AuBr
  • AuCl
  • AuI
  • AuOH
  • Au2S
  • (C2H5)3PAuSC5H5O(CO2CH3)3CH2OCOCH3
  • AuSC5H5O(OH)3CH2OH
  • NaAuSCH2CHOHCH2SO3
  • BrAuSC4H8
  • ClAuSC4H8
  • ClAuS(CH3)2
  • ClAuP(C6H5)3
  • Na2AuSCHCO2CH2CO2
  • NaAuSCHCO2CH2CO2H
  • Na3Au(S2O3)2
Organozlato(I) jedinjenja
  • (AuC6H2(CH3)3)5
    • Zlato(II)
    • AuXe4(Sb2F11)2
    Zlato(I,III)
    • Au4Cl8
    Zlato(III)
    • HAuCl4
    • HAuBr4
    • AuBr3
    • AuCl3
    • AuF3
    • Au2O3
    • Au(OH)3
    • Au2S3
    Zlato(V)
    • AuF5
    • AuF5·F2
    • Au2(C2O4)5


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