oblimersen   Click here for help

GtoPdb Ligand ID: 8269

Synonyms: DNA, D(P-thio)(T-C-T-C-C-C-A-G-C-G-T-G-C-G-C-C-A-T) | G3139 | Genasense®
Compound class: Nucleic acid
Comment: Oblimersen (G3139) is an 18mer phosphorothioate DNA antisense oligonucleotide (ASO) complementary to the first six codons of the open reading frame of Bcl-2 messenger RNA [1].
2D Structure
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2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

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SMILES / InChI / InChIKey
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SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)

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Canonical SMILES CC1=CN([C@H]2C[C@@H]([C@@H](COP(=S)(O)O[C@H]3C[C@H](N4C=NC5=C4N=CN=C5N)O[C@@H]3COP(=S)(O)O[C@H]6C[C@H](N7C=CC(=NC7=O)N)O[C@@H]6COP(=S)(O)O[C@H]8C[C@H](N9C=CC(=NC9=O)N)O[C@@H]8COP(=S)(O)O[C@H]%10C[C@H](N%11C=NC%12=C%11N=C(N)NC%12=O)O[C@@H]%10COP(=S)(O)O[C@H]%13C[C@H](N%14C=CC(=NC%14=O)N)O[C@@H]%13COP(=S)(O)O[C@H]%15C[C@H](N%16C=NC%17=C%16N=C(N)NC%17=O)O[C@@H]%15COP(=S)(O)O[C@H]%18C[C@H](N%19C=C(C)C(=O)NC%19=O)O[C@@H]%18COP(=S)(O)O[C@H]%20C[C@H](N%21C=NC%22=C%21N=C(N)NC%22=O)O[C@@H]%20COP(=S)(O)O[C@H]%23C[C@H](N%24C=CC(=NC%24=O)N)O[C@@H]%23COP(=S)(O)O[C@H]%25C[C@H](N%26C=NC%27=C%26N=C(N)NC%27=O)O[C@@H]%25COP(=S)(O)O[C@H]%28C[C@H](N%29C=NC%30=C%29N=CN=C%30N)O[C@@H]%28COP(=S)(O)O[C@H]%31C[C@H](N%32C=CC(=NC%32=O)N)O[C@@H]%31COP(=S)(O)O[C@H]%33C[C@H](N%34C=CC(=NC%34=O)N)O[C@@H]%33COP(=S)(O)O[C@H]%35C[C@H](N%36C=CC(=NC%36=O)N)O[C@@H]%35COP(=S)(O)O[C@H]%37C[C@H](N%38C=C(C)C(=O)NC%38=O)O[C@@H]%37COP(=S)(O)O[C@H]%39C[C@H](N%40C=CC(=NC%40=O)N)O[C@@H]%39COP(=S)(O)O[C@H]%41C[C@H](N%42C=C(C)C(=O)NC%42=O)O[C@@H]%41CO)O2)O)C(=O)NC1=O
Isomeric SMILES CC1=CN(C(=O)NC1=O)[C@H]2C[C@@H]([C@H](O2)COP(=S)(O)O[C@H]3C[C@@H](O[C@@H]3COP(=S)(O)O[C@H]4C[C@@H](O[C@@H]4COP(=S)(O)O[C@H]5C[C@@H](O[C@@H]5COP(=S)(O)O[C@H]6C[C@@H](O[C@@H]6COP(=S)(O)O[C@H]7C[C@@H](O[C@@H]7COP(=S)(O)O[C@H]8C[C@@H](O[C@@H]8COP(=S)(O)O[C@H]9C[C@@H](O[C@@H]9COP(=S)(O)O[C@H]%10C[C@@H](O[C@@H]%10COP(=S)(O)O[C@H]%11C[C@@H](O[C@@H]%11COP(=S)(O)O[C@H]%12C[C@@H](O[C@@H]%12COP(=S)(O)O[C@H]%13C[C@@H](O[C@@H]%13COP(=S)(O)O[C@H]%14C[C@@H](O[C@@H]%14COP(=S)(O)O[C@H]%15C[C@@H](O[C@@H]%15COP(=S)(O)O[C@H]%16C[C@@H](O[C@@H]%16COP(=S)(O)O[C@H]%17C[C@@H](O[C@@H]%17COP(=S)(O)O[C@H]%18C[C@@H](O[C@@H]%18COP(=S)(O)O[C@H]%19C[C@@H](O[C@@H]%19CO)N%20C=C(C(=O)NC%20=O)C)N%21C=CC(=NC%21=O)N)N%22C=C(C(=O)NC%22=O)C)N%23C=CC(=NC%23=O)N)N%24C=CC(=NC%24=O)N)N%25C=CC(=NC%25=O)N)N%26C=NC%27=C(N=CN=C%27%26)N)N%28C=NC%29=C%28N=C(NC%29=O)N)N%30C=CC(=NC%30=O)N)N%31C=NC%32=C%31N=C(NC%32=O)N)N%33C=C(C(=O)NC%33=O)C)N%34C=NC%35=C%34N=C(NC%35=O)N)N%36C=CC(=NC%36=O)N)N%37C=NC%38=C%37N=C(NC%38=O)N)N%39C=CC(=NC%39=O)N)N%40C=CC(=NC%40=O)N)N%41C=NC%42=C(N=CN=C%42%41)N)O
InChI InChI=1S/C172H221N62O91P17S17/c1-69-39-225(169(253)213-149(69)237)117-21-73(236)92(292-117)44-274-326(257,343)320-85-33-129(229-63-191-135-141(181)187-61-189-143(135)229)303-103(85)55-285-332(263,349)314-79-27-122(221-17-9-113(177)201-165(221)249)295-95(79)47-278-330(261,347)312-78-26-121(220-16-8-112(176)200-164(220)248)298-98(78)50-280-338(269,355)322-87-35-131(231-65-193-137-145(231)205-157(183)209-153(137)241)305-105(87)57-287-334(265,351)316-81-29-124(223-19-11-115(179)203-167(223)251)299-99(81)51-281-339(270,356)323-88-36-132(232-66-194-138-146(232)206-158(184)210-154(138)242)307-107(88)59-289-337(268,354)319-84-32-128(228-42-72(4)152(240)216-172(228)256)302-102(84)54-284-341(272,358)325-90-38-134(234-68-196-140-148(234)208-160(186)212-156(140)244)306-106(90)58-288-335(266,352)317-82-30-125(224-20-12-116(180)204-168(224)252)300-100(82)52-282-340(271,357)324-89-37-133(233-67-195-139-147(233)207-159(185)211-155(139)243)308-108(89)60-290-342(273,359)321-86-34-130(230-64-192-136-142(182)188-62-190-144(136)230)304-104(86)56-286-333(264,350)315-80-28-123(222-18-10-114(178)202-166(222)250)296-96(80)48-277-328(259,345)310-76-24-119(218-14-6-110(174)198-162(218)246)294-94(76)46-276-329(260,346)311-77-25-120(219-15-7-111(175)199-163(219)247)297-97(77)49-279-336(267,353)318-83-31-127(227-41-71(3)151(239)215-171(227)255)301-101(83)53-283-331(262,348)313-75-23-118(217-13-5-109(173)197-161(217)245)293-93(75)45-275-327(258,344)309-74-22-126(291-91(74)43-235)226-40-70(2)150(238)214-170(226)254/h5-20,39-42,61-68,73-108,117-134,235-236H,21-38,43-60H2,1-4H3,(H,257,343)(H,258,344)(H,259,345)(H,260,346)(H,261,347)(H,262,348)(H,263,349)(H,264,350)(H,265,351)(H,266,352)(H,267,353)(H,268,354)(H,269,355)(H,270,356)(H,271,357)(H,272,358)(H,273,359)(H2,173,197,245)(H2,174,198,246)(H2,175,199,247)(H2,176,200,248)(H2,177,201,249)(H2,178,202,250)(H2,179,203,251)(H2,180,204,252)(H2,181,187,189)(H2,182,188,190)(H,213,237,253)(H,214,238,254)(H,215,239,255)(H,216,240,256)(H3,183,205,209,241)(H3,184,206,210,242)(H3,185,207,211,243)(H3,186,208,212,244)/t73-,74-,75-,76-,77-,78-,79-,80-,81-,82-,83-,84-,85-,86-,87-,88-,89-,90-,91+,92+,93+,94+,95+,96+,97+,98+,99+,100+,101+,102+,103+,104+,105+,106+,107+,108+,117+,118+,119+,120+,121+,122+,123+,124+,125+,126+,127+,128+,129+,130+,131+,132+,133+,134+,326?,327?,328?,329?,330?,331?,332?,333?,334?,335?,336?,337?,338?,339?,340?,341?,342?/m0/s1
InChI Key MIMNFCVQODTQDP-NDLVEFNKSA-N

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
No information available.
Summary of Clinical Use Click here for help
The FDA granted oblimersen orphan drug designation for the treatment of multiple myeloma (MM), acute myelocytic leukemia (AML), chronic lymphocytic leukemia (CLL) and advanced malignant melanoma. The efficacy of oblimersen has been assessed in many Phase 3 clinical trials, for several types of solid malignancies and lymphomas. It should be noted that several of these studies were terminated early. Click here to link to ClinicalTrials.gov's list of Phase 3 oblimersen trials. A review of oblimersen clinical trials was published in 2023 [2].
Mechanism Of Action and Pharmacodynamic Effects Click here for help
Bcl-2 is an important apoptosis-regulating protein associated with chemoresistance and inhibition of apoptisis in malignant cells. Using an antisense technique to block the translation of Bcl-2 mRNA in to protein has an antitumour effect [1].