WARNING: This product is for research use only, not for human or veterinary use.
MedKoo CAT#: 414533
CAS#: 190977-41-4
Description: Oblimersen Na targets the Bcl-2 oncogene good efficacy with low toxicity tumour regressions
MedKoo Cat#: 414533
Name: Oblimersen Na
CAS#: 190977-41-4
Chemical Formula: C172H204N62Na17O91P17S17
Exact Mass: 6054.2294
Molecular Weight: 6058.27
Elemental Analysis: C, 34.10; H, 3.39; N, 14.33; Na, 6.45; O, 24.03; P, 8.69; S, 9.00
This product is not in stock, which may be available by custom synthesis.
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Synonym: Oblimersen sodium; Oblimersen Na; G3139; G-3139; G 3139
IUPAC/Chemical Name: P-Thiothymidylyl-(3'to 5')-2'-deoxy-P-thiocytidylyl-(3'to 5')-P-thiothymidylyl-(3'to 5')-2'-deoxy-P-thiocytidylyl-(3'to 5')-2'-deoxy-P-thiocytidylyl-(3'to 5')-2'-deoxy-P-thiocytidylyl-(3'to 5')-2'-deoxy-P-thioadenylyl-(3'to 5')-2'-deoxy-P-thioguanylyl-(3'to 5')-2'-deoxy-P-thiocytidylyl-(3'to 5')-2'-deoxy-P-thioguanylyl-(3'to 5')-P-thiothymidylyl-(3'to 5')-2'-deoxy-P-thioguanylyl-(3'to 5')-2'-deoxy-P-thiocytidylyl-(3'to 5')-2'-deoxy-P-thioguanylyl-(3'to 5')-2'-deoxy-P-thiocytidylyl-(3'to 5')-2'-deoxy-P-thiocytidylyl-(3'to 5')-2'-deoxy-P-thioadenylyl-(3'to 5')-thymidine heptadecasodium salt
InChi Key: IBXPAFBDJCXCDW-MHFPCNPESA-A
InChi Code: InChI=1S/C172H221N62O91P17S17.17Na/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);;;;;;;;;;;;;;;;;/q;17*+1/p-17/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
SMILES Code: CC1=CN(C(NC1=O)=O)[C@H]2C[C@@H]([C@H](O2)COP([S-])(O[C@H]3C[C@H](n(cn4)c5c4c(N)ncn5)O[C@@H]3COP([S-])(O[C@H]6C[C@H](N7C=CC(N)=NC7=O)O[C@@H]6COP([S-])(O[C@H]8C[C@H](N9C=CC(N)=NC9=O)O[C@@H]8COP([S-])(O[C@H]%10C[C@H](n%11c%12c(C(NC(N)=N%12)=O)nc%11)O[C@@H]%10COP([S-])(O[C@H]%13C[C@H](N%14C=CC(N)=NC%14=O)O[C@@H]%13COP([S-])(O[C@H]%15C[C@H](n%16c%17c(C(NC(N)=N%17)=O)nc%16)O[C@@H]%15COP([S-])(O[C@H]%18C[C@H](N%19C=C(C(NC%19=O)=O)C)O[C@@H]%18COP([S-])(O[C@H]%20C[C@H](n%21c%22c(C(NC(N)=N%22)=O)nc%21)O[C@@H]%20COP([S-])(O[C@H]%23C[C@H](N%24C=CC(N)=NC%24=O)O[C@@H]%23COP([S-])(O[C@H]%25C[C@H](n%26c%27c(C(NC(N)=N%27)=O)nc%26)O[C@@H]%25COP([S-])(O[C@H]%28C[C@H](n(cn%29)c%30c%29c(N)ncn%30)O[C@@H]%28COP([S-])(O[C@H]%31C[C@H](N%32C=CC(N)=NC%32=O)O[C@@H]%31COP([S-])(O[C@H]%33C[C@H](N%34C=CC(N)=NC%34=O)O[C@@H]%33COP([S-])(O[C@H]%35C[C@H](N%36C=CC(N)=NC%36=O)O[C@@H]%35COP([S-])(O[C@H]%37C[C@H](N%38C=C(C(NC%38=O)=O)C)O[C@@H]%37COP([S-])(O[C@H]%39C[C@H](N%40C=CC(N)=NC%40=O)O[C@@H]%39COP([S-])(O[C@H]%41C[C@H](N%42C=C(C(NC%42=O)=O)C)O[C@@H]%41CO)=O)=O)=O)=O)=O)=O)=O)=O)=O)=O)=O)=O)=O)=O)=O)=O)=O)O.[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+]
Appearance: Solid powder
Purity: >98% (or refer to the Certificate of Analysis)
Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility: To be determined
Shelf Life: >2 years if stored properly
Drug Formulation: To be determined
Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code: 2934.99.9001
The following data is based on the product molecular weight 6058.27 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.
| Concentration / Solvent Volume / Mass | 1 mg | 5 mg | 10 mg |
|---|---|---|---|
| 1 mM | 1.15 mL | 5.76 mL | 11.51 mL |
| 5 mM | 0.23 mL | 1.15 mL | 2.3 mL |
| 10 mM | 0.12 mL | 0.58 mL | 1.15 mL |
| 50 mM | 0.02 mL | 0.12 mL | 0.23 mL |
1: Herbst RS, Frankel SR. Oblimersen sodium (Genasense bcl-2 antisense oligonucleotide): a rational therapeutic to enhance apoptosis in therapy of lung cancer. Clin Cancer Res. 2004 Jun 15;10(12 Pt 2):4245s-4248s. doi: 10.1158/1078-0432.CCR-040018. PMID: 15217967.
2: Frankel SR. Oblimersen sodium (G3139 Bcl-2 antisense oligonucleotide) therapy in Waldenstrom's macroglobulinemia: a targeted approach to enhance apoptosis. Semin Oncol. 2003 Apr;30(2):300-4. doi: 10.1053/sonc.2003.50041. PMID: 12720157.
3: Advani PP, Paulus A, Masood A, Sher T, Chanan-Khan A. Pharmacokinetic evaluation of oblimersen sodium for the treatment of chronic lymphocytic leukemia. Expert Opin Drug Metab Toxicol. 2011 Jun;7(6):765-74. doi: 10.1517/17425255.2011.579105. Epub 2011 Apr 27. PMID: 21521129.
4: Moreira JN, Santos A, Simões S. Bcl-2-targeted antisense therapy (Oblimersen sodium): towards clinical reality. Rev Recent Clin Trials. 2006 Sep;1(3):217-35. doi: 10.2174/157488706778250050. PMID: 18473975.
5: Oblimersen: Augmerosen, BCL-2 antisense oligonucleotide - Genta, G 3139, GC 3139, oblimersen sodium. Drugs R D. 2007;8(5):321-34. doi: 10.2165/00126839-200708050-00006. PMID: 17767397.
6: Klasa RJ, Gillum AM, Klem RE, Frankel SR. Oblimersen Bcl-2 antisense: facilitating apoptosis in anticancer treatment. Antisense Nucleic Acid Drug Dev. 2002 Jun;12(3):193-213. doi: 10.1089/108729002760220798. PMID: 12162702.
7: Bedikian AY, Millward M, Pehamberger H, Conry R, Gore M, Trefzer U, Pavlick AC, DeConti R, Hersh EM, Hersey P, Kirkwood JM, Haluska FG; Oblimersen Melanoma Study Group. Bcl-2 antisense (oblimersen sodium) plus dacarbazine in patients with advanced melanoma: the Oblimersen Melanoma Study Group. J Clin Oncol. 2006 Oct 10;24(29):4738-45. doi: 10.1200/JCO.2006.06.0483. Epub 2006 Sep 11. PMID: 16966688.
8: Tarhini AA, Kirkwood JM. Oblimersen in the treatment of metastatic melanoma. Future Oncol. 2007 Jun;3(3):263-71. doi: 10.2217/14796694.3.3.263. PMID: 17547520.
9: Koziner B. Potential therapeutic applications of oblimersen in CLL. Oncology (Williston Park). 2004 Nov;18(13 Suppl 10):32-8. PMID: 15651175.
10: Sternberg CN, Dumez H, Van Poppel H, Skoneczna I, Sella A, Daugaard G, Gil T, Graham J, Carpentier P, Calabro F, Collette L, Lacombe D; EORTC Genitourinary Tract Cancer Group. Docetaxel plus oblimersen sodium (Bcl-2 antisense oligonucleotide): an EORTC multicenter, randomized phase II study in patients with castration-resistant prostate cancer. Ann Oncol. 2009 Jul;20(7):1264-9. doi: 10.1093/annonc/mdn784. Epub 2009 Mar 17. PMID: 19297314.
