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    Imetelstat

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    2D Structure
    Also known as: Grn163l, F60ne4xb53, 5'-(o-(2-hydroxy-3-((1-oxohexadecyl)amino)propyl) hydrogen phosphorothioate)-d(3'-amino-3'-deoxy-p-thio)(t-a-g-g-g-t-t-a-g-a-c-a-a), Grn163l peptide, Imetelstat [inn], Imetelstat [usan]
    Molecular Formula
    C148H211N68O53P13S13
    Molecular Weight
    4610  g/mol
    InChI Key
    LVZYXEALRXBLJZ-ISQYCPACSA-N
    FDA UNII
    F60NE4XB53
    GRN163L is a novel anti-cancer drug. It has been characterized preclinically and shown to inhibit telomerase in human tumor cells of many cancer types (including lung, breast, prostate, liver, and early stage of human breast cancer), in both cell culture systems and animal models. Study of this drug shows the its potential utility in the treatment of patients with hematologic and solid tumor malignancies.
    1 2D Structure

    2D Structure

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    N-[3-[[(2S,3S,5R)-3-[[[(2S,3S,5R)-3-[[[(2S,3S,5R)-3-[[[(2S,3S,5R)-3-[[[(2S,3S,5R)-3-[[[(2S,3S,5R)-3-[[[(2S,3S,5R)-3-[[[(2S,3S,5R)-3-[[[(2S,3S,5R)-3-[[[(2S,3S,5R)-3-[[[(2S,3S,5R)-3-[[[(2S,3S,5R)-3-[[[(2S,3S,5R)-3-amino-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-sulfanylphosphoryl]amino]-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphinothioyl]amino]-5-(4-amino-2-oxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphinothioyl]amino]-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphinothioyl]amino]-5-(2-amino-6-oxo-1H-purin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphinothioyl]amino]-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphinothioyl]amino]-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphinothioyl]amino]-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphinothioyl]amino]-5-(2-amino-6-oxo-1H-purin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphinothioyl]amino]-5-(2-amino-6-oxo-1H-purin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphinothioyl]amino]-5-(2-amino-6-oxo-1H-purin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphinothioyl]amino]-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphinothioyl]amino]-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphinothioyl]oxy-2-hydroxypropyl]hexadecanamide
    2.1.2 InChI
    InChI=1S/C148H211N68O53P13S13/c1-5-6-7-8-9-10-11-12-13-14-15-16-17-18-97(218)160-34-69(217)38-255-282(242,295)256-51-95-74(25-102(261-95)207-37-68(4)136(221)191-148(207)229)195-274(234,287)249-45-89-78(29-106(264-89)212-61-175-115-124(155)165-56-170-129(115)212)199-277(237,290)252-48-92-81(32-109(267-92)215-64-178-118-132(215)183-143(158)187-139(118)224)202-280(240,293)254-50-94-82(33-110(269-94)216-65-179-119-133(216)184-144(159)188-140(119)225)203-281(241,294)253-49-93-79(30-107(268-93)213-62-176-116-130(213)181-141(156)185-137(116)222)200-278(238,291)246-42-86-72(23-100(260-86)205-35-66(2)134(219)189-146(205)227)193-272(232,285)245-41-85-73(24-101(259-85)206-36-67(3)135(220)190-147(206)228)194-273(233,286)248-44-88-77(28-105(263-88)211-60-174-114-123(154)164-55-169-128(114)211)198-276(236,289)251-47-91-80(31-108(266-91)214-63-177-117-131(214)182-142(157)186-138(117)223)201-279(239,292)250-46-90-76(27-104(265-90)210-59-173-113-122(153)163-54-168-127(113)210)197-275(235,288)244-40-84-71(22-99(258-84)204-20-19-96(150)180-145(204)226)192-271(231,284)247-43-87-75(26-103(262-87)209-58-172-112-121(152)162-53-167-126(112)209)196-270(230,283)243-39-83-70(149)21-98(257-83)208-57-171-111-120(151)161-52-166-125(111)208/h19-20,35-37,52-65,69-95,98-110,217H,5-18,21-34,38-51,149H2,1-4H3,(H,160,218)(H,242,295)(H2,150,180,226)(H2,151,161,166)(H2,152,162,167)(H2,153,163,168)(H2,154,164,169)(H2,155,165,170)(H,189,219,227)(H,190,220,228)(H,191,221,229)(H2,192,231,284)(H2,193,232,285)(H2,194,233,286)(H2,195,234,287)(H2,196,230,283)(H2,197,235,288)(H2,198,236,289)(H2,199,237,290)(H2,200,238,291)(H2,201,239,292)(H2,202,240,293)(H2,203,241,294)(H3,156,181,185,222)(H3,157,182,186,223)(H3,158,183,187,224)(H3,159,184,188,225)/t69?,70-,71-,72-,73-,74-,75-,76-,77-,78-,79-,80-,81-,82-,83+,84+,85+,86+,87+,88+,89+,90+,91+,92+,93+,94+,95+,98+,99+,100+,101+,102+,103+,104+,105+,106+,107+,108+,109+,110+,270?,271?,272?,273?,274?,275?,276?,277?,278?,279?,280?,281?,282?/m0/s1
    2.1.3 InChI Key
    LVZYXEALRXBLJZ-ISQYCPACSA-N
    2.1.4 Canonical SMILES
    CCCCCCCCCCCCCCCC(=O)NCC(COP(=S)(O)OCC1C(CC(O1)N2C=C(C(=O)NC2=O)C)NP(=S)(O)OCC3C(CC(O3)N4C=NC5=C(N=CN=C54)N)NP(=S)(O)OCC6C(CC(O6)N7C=NC8=C7N=C(NC8=O)N)NP(=S)(O)OCC9C(CC(O9)N1C=NC2=C1N=C(NC2=O)N)NP(=S)(O)OCC1C(CC(O1)N1C=NC2=C1N=C(NC2=O)N)NP(=S)(O)OCC1C(CC(O1)N1C=C(C(=O)NC1=O)C)NP(=S)(O)OCC1C(CC(O1)N1C=C(C(=O)NC1=O)C)NP(=S)(O)OCC1C(CC(O1)N1C=NC2=C(N=CN=C21)N)NP(=S)(O)OCC1C(CC(O1)N1C=NC2=C1N=C(NC2=O)N)NP(=S)(O)OCC1C(CC(O1)N1C=NC2=C(N=CN=C21)N)NP(=S)(O)OCC1C(CC(O1)N1C=CC(=NC1=O)N)NP(=S)(O)OCC1C(CC(O1)N1C=NC2=C(N=CN=C21)N)NP(=O)(OCC1C(CC(O1)N1C=NC2=C(N=CN=C21)N)N)S)O
    2.1.5 Isomeric SMILES
    CCCCCCCCCCCCCCCC(=O)NCC(COP(=S)(O)OC[C@@H]1[C@H](C[C@@H](O1)N2C=C(C(=O)NC2=O)C)NP(=S)(O)OC[C@@H]3[C@H](C[C@@H](O3)N4C=NC5=C(N=CN=C54)N)NP(=S)(O)OC[C@@H]6[C@H](C[C@@H](O6)N7C=NC8=C7N=C(NC8=O)N)NP(=S)(O)OC[C@@H]9[C@H](C[C@@H](O9)N1C=NC2=C1N=C(NC2=O)N)NP(=S)(O)OC[C@@H]1[C@H](C[C@@H](O1)N1C=NC2=C1N=C(NC2=O)N)NP(=S)(O)OC[C@@H]1[C@H](C[C@@H](O1)N1C=C(C(=O)NC1=O)C)NP(=S)(O)OC[C@@H]1[C@H](C[C@@H](O1)N1C=C(C(=O)NC1=O)C)NP(=S)(O)OC[C@@H]1[C@H](C[C@@H](O1)N1C=NC2=C(N=CN=C21)N)NP(=S)(O)OC[C@@H]1[C@H](C[C@@H](O1)N1C=NC2=C1N=C(NC2=O)N)NP(=S)(O)OC[C@@H]1[C@H](C[C@@H](O1)N1C=NC2=C(N=CN=C21)N)NP(=S)(O)OC[C@@H]1[C@H](C[C@@H](O1)N1C=CC(=NC1=O)N)NP(=S)(O)OC[C@@H]1[C@H](C[C@@H](O1)N1C=NC2=C(N=CN=C21)N)NP(=O)(OC[C@@H]1[C@H](C[C@@H](O1)N1C=NC2=C(N=CN=C21)N)N)S)O
    2.2 Other Identifiers
    2.2.1 UNII
    F60NE4XB53
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. Imetelstat

    2.3.2 Depositor-Supplied Synonyms

    1. Grn163l

    2. F60ne4xb53

    3. 5'-(o-(2-hydroxy-3-((1-oxohexadecyl)amino)propyl) Hydrogen Phosphorothioate)-d(3'-amino-3'-deoxy-p-thio)(t-a-g-g-g-t-t-a-g-a-c-a-a)

    4. Grn163l Peptide

    5. Imetelstat [inn]

    6. Imetelstat [usan]

    7. Imetelstat [who-dd]

    8. Unii-f60ne4xb53

    9. Grn 163l

    10. Grn-163l

    2.4 Create Date
    2013-07-08
    3 Chemical and Physical Properties
    Molecular Weight 4610 g/mol
    Molecular Formula C148H211N68O53P13S13
    XLogP3-1.1
    Hydrogen Bond Donor Count45
    Hydrogen Bond Acceptor Count107
    Rotatable Bond Count95
    Exact Mass4607.8897749 g/mol
    Monoisotopic Mass4606.8864201 g/mol
    Topological Polar Surface Area2010 Ų
    Heavy Atom Count295
    Formal Charge0
    Complexity11900
    Isotope Atom Count0
    Defined Atom Stereocenter Count39
    Undefined Atom Stereocenter Count1
    Defined Bond Stereocenter Count0
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count1
    4 Drug and Medication Information
    4.1 Drug Indication

    Investigated for use/treatment in leukemia (lymphoid) and solid tumors.

    5 Pharmacology and Biochemistry
    5.1 MeSH Pharmacological Classification

    Enzyme Inhibitors

    Compounds or agents that combine with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction. (See all compounds classified as Enzyme Inhibitors.)

    5.2 Mechanism of Action

    GRN163L has been characterized preclinically and shown to inhibit telomerase in human tumor cells of many cancer types. It targets the template region, or active site, of telomerase. GRN163L does not exhibit antisense activity (binding to messenger RNA), but rather directly bind to the RNA component of telomerase at the active site of the enzyme, thereby acting like a conventional pharmaceutical drug. Inhibiting telomerase activity should result in telomere shortening and therefore cause aging and death of cancer cells.