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    Silatecan

    ACTIVE PHARMA INGREDIENTS

    DEVELOPMENTS

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    2D Structure
    Also known as: Ar-67, 220913-32-6, Db-67, Ar67, Db 67; silatecan, Db 67
    Molecular Formula
    C26H30N2O5Si
    Molecular Weight
    478.6  g/mol
    InChI Key
    XUSKJHCMMWAAHV-SANMLTNESA-N
    FDA UNII
    3YEA04NV6H
    Silatecan AR-67 is a synthetic, highly lipophilic derivative of camptothecin, with potential antineoplastic and radiosensitizing activities. 7-tert-butyldimethylsilyl-10-hydroxycamptothecin binds to and stabilizes the topoisomerase I-DNA covalent complex. This inhibits the religation of topoisomerase I-mediated single-stranded DNA breaks and produces lethal double-stranded DNA breaks when encountered by the DNA replication machinery, thereby inhibiting DNA replication and inducing apoptosis. Camptothecin readily undergoes hydrolysis at physiological pH, changing its conformation from the active lactone structure to an inactive carboxylate form. Modifications on the E ring of camptothecin prevent binding of human serum albumin, which prefers the inactive carboxylate form, thereby enhancing the stability of the active lactone structure and resulting in prolonged agent activity. In addition, this agent sensitizes tumor cells toward radiation treatment.
    1 2D Structure

    2D Structure

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    (19S)-10-[tert-butyl(dimethyl)silyl]-19-ethyl-7,19-dihydroxy-17-oxa-3,13-diazapentacyclo[11.8.0.02,11.04,9.015,20]henicosa-1(21),2,4(9),5,7,10,15(20)-heptaene-14,18-dione
    2.1.2 InChI
    InChI=1S/C26H30N2O5Si/c1-7-26(32)18-11-20-21-16(12-28(20)23(30)17(18)13-33-24(26)31)22(34(5,6)25(2,3)4)15-10-14(29)8-9-19(15)27-21/h8-11,29,32H,7,12-13H2,1-6H3/t26-/m0/s1
    2.1.3 InChI Key
    XUSKJHCMMWAAHV-SANMLTNESA-N
    2.1.4 Canonical SMILES
    CCC1(C2=C(COC1=O)C(=O)N3CC4=C(C5=C(C=CC(=C5)O)N=C4C3=C2)[Si](C)(C)C(C)(C)C)O
    2.1.5 Isomeric SMILES
    CC[C@@]1(C2=C(COC1=O)C(=O)N3CC4=C(C5=C(C=CC(=C5)O)N=C4C3=C2)[Si](C)(C)C(C)(C)C)O
    2.2 Other Identifiers
    2.2.1 UNII
    3YEA04NV6H
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. 1h-pyrano(3',4':6,7)indolizino(1,2-b)quinoline-3,14(4h,12h)- Dione, 11-((1,1-dimethylethyl)dimethylsilyl)-4-ethyl-4,9- Dihydroxy-, (4s)-

    2. 7-t-butyldimethylsilyl-10-hydroxycamptothecin

    3. 7-tert-butyldimethylsilyl-10-hydroxycamptothecin

    4. Ar 67 Cpd

    5. Ar-67 Cpd

    6. Db 67

    7. Db-67

    2.3.2 Depositor-Supplied Synonyms

    1. Ar-67

    2. 220913-32-6

    3. Db-67

    4. Ar67

    5. Db 67; Silatecan

    6. Db 67

    7. Nsc-708298

    8. 3yea04nv6h

    9. Db67

    10. (s)-11-(tert-butyldimethylsilyl)-4-ethyl-4,9-dihydroxy-1h-pyrano[3',4':6,7]indolizino[1,2-b]quinoline-3,14(4h,12h)-dione

    11. (20s)-7-t-butyldimethylsilyl-10-hydroxycamptothecin

    12. 1h-pyrano(3',4':6,7)indolizino(1,2-b)quinoline-3,14(4h,12h)-dione, 11-((1,1-dimethylethyl)dimethylsilyl)-4-ethyl-4,9-dihydroxy-, (4s)-

    13. Nci60_038363

    14. Ar 67 Cpd

    15. Ar-67 Cpd

    16. Unii-3yea04nv6h

    17. Chembl412309

    18. Gtpl8919

    19. Schembl1266162

    20. Dtxsid00176592

    21. Ar 67

    22. Nsc708298

    23. Zinc170020689

    24. Compound 14 [pmid:11052802]

    25. Db12384

    26. Nsc 708298

    27. Q27074492

    28. (20s)-7-tert-butyldimethysilyl-10-hydroxycamptothecin

    29. (19s)-10-[tert-butyl(dimethyl)silyl]-19-ethyl-7,19-dihydroxy-17-oxa-3,13-diazapentacyclo[11.8.0.02,11.04,9.015,20]henicosa-1(21),2,4(9),5,7,10,15(20)-heptaene-14,18-dione

    30. 1h-pyrano[3',7]indolizino[1,2-b]quinoline-3,14(4h,12h)dione, 11-[(1,1-dimethylethyl)dimethylsilyl]-4-ethyl-4,9-dihydroxy-, (4s)-

    2.4 Create Date
    2006-06-05
    3 Chemical and Physical Properties
    Molecular Weight 478.6 g/mol
    Molecular Formula C26H30N2O5Si
    Hydrogen Bond Donor Count2
    Hydrogen Bond Acceptor Count6
    Rotatable Bond Count3
    Exact Mass478.19239860 g/mol
    Monoisotopic Mass478.19239860 g/mol
    Topological Polar Surface Area100 Ų
    Heavy Atom Count34
    Formal Charge0
    Complexity982
    Isotope Atom Count0
    Defined Atom Stereocenter Count1
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count0
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count1