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Imetelstat

Imetelstat

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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

Imetelstat

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 Formula	C₁₄₈H₂₁₁N₆₈O₅₃P₁₃S₁₃
Molecular Weight	4610 g/mol
XLogP3	-1.1
Hydrogen Bond Donor Count	45
Hydrogen Bond Acceptor Count	107
Rotatable Bond Count	95
Exact Mass	4607.8897749 g/mol
Monoisotopic Mass	4606.8864201 g/mol
Topological Polar Surface Area	2010 Å²
Heavy Atom Count	295
Formal Charge	0
Complexity	11900
Isotope Atom Count	0
Defined Atom Stereocenter Count	39
Undefined Atom Stereocenter Count	1
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

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.