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Substance Name: Imetelstat sodium [USAN:INN]
RN: 1007380-31-5
UNII: 2AW48LAZ4I
InChIKey: IEVORMRANFJJFR-NMZIRJKDSA-A

Note

  • A lipid derivative of GRN163 that inhibits telomerase.

    NCI: /Imetelstat sodium/ The sodium salt of imetelstat, a synthetic lipid-conjugated, 13-mer oligonucleotide N3' P5'-thio-phosphoramidate with potential antineoplastic activity. Complementary to the template region of telomerase RNA (hTR), imetelstat acts as a competitive enzyme inhibitor that binds and blocks the active site of the enzyme (a "telomerase template antagonist"), a mechanism of action which differs from that for the antisense oligonucleotide-mediated inhibition of telomerase activity through telomerase mRNA binding. Inhibition of telomerase activity in tumor cells by imetelstat results in telomere shortening, which leads to cell cycle arrest or apoptosis. Check for active clinical trials or closed clinical trials using this agent. (NCI Thesaurus)

Molecular Formula

  • C148-H198-N68-Na13-O53-P13-S13

Molecular Weight

  • 4896.0052
 

Classification Code

  • Antineoplastic
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Names and Synonyms

Name of Substance

  • Imetelstat sodium [USAN:INN]

Synonyms

  • 5'-(O-(2-hydroxy-3-((1-oxohexadecyl)amino)propyl)phosphorothioate)-d(3'-amino-3'-deoxy-p-thio)(t-a-g-g-g-t-t-a-g-a-c-a-a), sodium salt (13)
  • DNA, d(3'-amino-3'-deoxy-p-thio)(T-A-G-G-G-T-T-A-G-A-C-A-A), 5'-(o-(2-hydroxy-3-((1-oxohexadecyl)amino)propyl) hydrogen phosphorothioate), sodium salt (1:13)
  • GRN 163L sodium salt
  • GRN-163L tridecasodium salt
  • GRN163L
  • GRN163L tridecasodium salt
  • Imetelstat sodium
  • UNII-2AW48LAZ4I

Registry Numbers

CAS Registry Number

  • 1007380-31-5

FDA UNII

  • 2AW48LAZ4I

System Generated Number

  • 1007380315

Structure Descriptors

InChI

1S/C148H211N68O53P13S13.13Na/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);;;;;;;;;;;;;/q;13*+1/p-13/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

InChIKey

IEVORMRANFJJFR-NMZIRJKDSA-A

Smiles

CCCCCCCCCCCCCCCC(=O)NCC(COP(=O)(OC[C@@H]1[C@H](C[C@@H](O1)n2cc(c(=O)[nH]c2=O)C)NP(=O)(OC[C@@H]3[C@H](C[C@@H](O3)n4cnc5c4ncnc5N)NP(=O)(OC[C@@H]6[C@H](C[C@@H](O6)n7cnc8c7nc([nH]c8=O)N)NP(=O)(OC[C@@H]9[C@H](C[C@@H](O9)n1cnc2c1nc([nH]c2=O)N)NP(=O)(OC[C@@H]1[C@H](C[C@@H](O1)n1cnc2c1nc([nH]c2=O)N)NP(=O)(OC[C@@H]1[C@H](C[C@@H](O1)n1cc(c(=O)[nH]c1=O)C)NP(=O)(OC[C@@H]1[C@H](C[C@@H](O1)n1cc(c(=O)[nH]c1=O)C)NP(=O)(OC[C@@H]1[C@H](C[C@@H](O1)n1cnc2c1ncnc2N)NP(=O)(OC[C@@H]1[C@H](C[C@@H](O1)n1cnc2c1nc([nH]c2=O)N)NP(=O)(OC[C@@H]1[C@H](C[C@@H](O1)n1cnc2c1ncnc2N)NP(=O)(OC[C@@H]1[C@H](C[C@@H](O1)n1ccc(nc1=O)N)NP(=O)(OC[C@@H]1[C@H](C[C@@H](O1)n1cnc2c1ncnc2N)NP(=O)(OC[C@@H]1[C@H](C[C@@H](O1)n1cnc2c1ncnc2N)N)[S-])[S-])[S-])[S-])[S-])[S-])[S-])[S-])[S-])[S-])[S-])[S-])[S-])O.[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+]