Apatorsen Free Base | CAS# 1002331-21-6 (free base) | Antineoplastic

MedKoo Cat#: 414557 | Name: Apatorsen Free Base

Description:

WARNING: This product is for research use only, not for human or veterinary use.

Apatorsen Free Base is an antisense oligonucleotide that targets Hsp27 for support of cancer therapy.

Chemical Structure

Apatorsen Free Base

CAS#1002331-21-6 (free base)

Theoretical Analysis

MedKoo Cat#: 414557

Name: Apatorsen Free Base

CAS#: 1002331-21-6 (free base)

Chemical Formula: C224H304N79O116P19S19

Exact Mass: 7152.0026

Molecular Weight: 7156.97

Elemental Analysis: C, 37.59; H, 4.28; N, 15.46; O, 25.93; P, 8.22; S, 8.51

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.

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Related CAS #

1002331-21-6 (free base); 915443-09-3 (Na)

Synonym

Apatorsen Free Base; OGX427; OGX-427; OGX 427

IUPAC/Chemical Name

DNA, d(P-thio)((2'-O-(2-methoxyethyl))rG-(2'-O-(2-methoxyethyl))rG-(2'-O-(2-methoxyethyl))rG-(2'-O-(2-methoxyethyl))rA-m5C-G-m5C-G-G-m5C-G-m5C-T-m5C-G-G-(2'-O-(2-methoxyethyl))m5rU-(2'-O-(2-methoxyethyl))m5rC-(2'-O-(2-methoxyethyl))rA-(2'-O-(2-methoxyethyl))m5rU)

InChi Key

RMTMMKNSPRRFHW-SVAVBUBPSA-N

InChi Code

InChI=1S/C224H304N79O116P19S19/c1-88-46-284(216(318)257-168(88)225)129-34-97(401-420(327,439)363-60-114-102(39-134(386-114)289-52-94(7)187(306)281-222(289)324)406-421(328,440)362-56-110-98(35-130(381-110)285-47-89(2)169(226)258-217(285)319)402-422(329,441)368-63-119-107(44-139(390-119)297-81-252-147-182(297)267-211(237)276-194(147)313)411-430(337,449)372-66-121-108(45-140(392-121)298-82-253-148-183(298)268-212(238)277-195(148)314)412-431(338,450)375-69-123-154(163(357-29-21-349-13)201(396-123)292-54-96(9)189(308)283-224(292)326)414-435(342,454)377-70-124-155(162(356-28-20-348-12)200(395-124)290-51-93(6)173(230)262-221(290)323)415-436(343,455)378-72-126-157(165(359-31-23-351-15)203(398-126)300-84-247-142-175(232)243-76-245-177(142)300)417-433(340,452)374-68-122-152(305)160(354-26-18-346-10)199(394-122)291-53-95(8)188(307)282-223(291)325)111(382-129)57-364-426(333,445)407-103-40-135(293-77-248-143-178(293)263-207(233)272-190(143)309)387-116(103)61-367-423(330,442)403-99-36-131(286-48-90(3)170(227)259-218(286)320)384-113(99)59-366-428(335,447)409-105-42-137(295-79-250-145-180(295)265-209(235)274-192(145)311)391-120(105)65-371-429(336,448)410-106-43-138(296-80-251-146-181(296)266-210(236)275-193(146)312)389-118(106)62-369-424(331,443)404-100-37-132(287-49-91(4)171(228)260-219(287)321)383-112(100)58-365-427(334,446)408-104-41-136(294-78-249-144-179(294)264-208(234)273-191(144)310)388-117(104)64-370-425(332,444)405-101-38-133(288-50-92(5)172(229)261-220(288)322)385-115(101)67-373-432(339,451)416-156-125(397-202(164(156)358-30-22-350-14)299-83-246-141-174(231)242-75-244-176(141)299)71-379-437(344,456)419-159-128(400-206(167(159)361-33-25-353-17)303-87-256-151-186(303)271-215(241)280-198(151)317)74-380-438(345,457)418-158-127(399-205(166(158)360-32-24-352-16)302-86-255-150-185(302)270-214(240)279-197(150)316)73-376-434(341,453)413-153-109(55-304)393-204(161(153)355-27-19-347-11)301-85-254-149-184(301)269-213(239)278-196(149)315/h46-54,75-87,97-140,152-167,199-206,304-305H,18-45,55-74H2,1-17H3,(H,327,439)(H,328,440)(H,329,441)(H,330,442)(H,331,443)(H,332,444)(H,333,445)(H,334,446)(H,335,447)(H,336,448)(H,337,449)(H,338,450)(H,339,451)(H,340,452)(H,341,453)(H,342,454)(H,343,455)(H,344,456)(H,345,457)(H2,225,257,318)(H2,226,258,319)(H2,227,259,320)(H2,228,260,321)(H2,229,261,322)(H2,230,262,323)(H2,231,242,244)(H2,232,243,245)(H,281,306,324)(H,282,307,325)(H,283,308,326)(H3,233,263,272,309)(H3,234,264,273,310)(H3,235,265,274,311)(H3,236,266,275,312)(H3,237,267,276,313)(H3,238,268,277,314)(H3,239,269,278,315)(H3,240,270,279,316)(H3,241,271,280,317)/t97?,98?,99?,100?,101?,102?,103?,104?,105?,106?,107?,108?,109-,110-,111-,112-,113-,114-,115-,116-,117-,118-,119-,120-,121-,122-,123-,124-,125-,126-,127-,128-,129-,130-,131-,132-,133-,134-,135-,136-,137-,138-,139-,140-,152?,153?,154?,155?,156?,157?,158?,159?,160?,161?,162?,163?,164?,165?,166?,167?,199-,200-,201-,202-,203-,204-,205-,206-,420?,421?,422?,423?,424?,425?,426?,427?,428?,429?,430?,431?,432?,433?,434?,435?,436?,437?,438?/m1/s1

SMILES Code

COCCOC1C([C@H](O[C@H]1N2C=C(C(NC2=O)=O)C)COP(S)(OC3[C@H](O[C@@H](n4c5c(C(NC=N5)=N)nc4)C3OCCOC)COP(S)(OC6[C@H](O[C@@H](N7C=C(C(N)=NC7=O)C)C6OCCOC)COP(S)(OC8[C@H](O[C@@H](N9C=C(C(NC9=O)=O)C)C8OCCOC)COP(S)(OC%10C[C@H](n%11c%12c(C(NC(N)=N%12)=O)nc%11)O[C@@H]%10COP(S)(OC%13C[C@H](n%14c%15c(C(NC(N)=N%15)=O)nc%14)O[C@@H]%13COP(S)(OC%16C[C@H](N%17C=C(C(N)=NC%17=O)C)O[C@@H]%16COP(S)(OC%18C[C@H](N%19C=C(C(NC%19=O)=O)C)O[C@@H]%18COP(S)(OC%20C[C@H](N%21C=C(C(N)=NC%21=O)C)O[C@@H]%20COP(S)(OC%22C[C@H](n%23c%24c(C(NC(N)=N%24)=O)nc%23)O[C@@H]%22COP(S)(OC%25C[C@H](N%26C=C(C(N)=NC%26=O)C)O[C@@H]%25COP(S)(OC%27C[C@H](n%28c%29c(C(NC(N)=N%29)=O)nc%28)O[C@@H]%27COP(S)(OC%30C[C@H](n%31c%32c(C(NC(N)=N%32)=O)nc%31)O[C@@H]%30COP(S)(OC%33C[C@H](N%34C=C(C(N)=NC%34=O)C)O[C@@H]%33COP(S)(OC%35C[C@H](n%36c%37c(C(NC(N)=N%37)=O)nc%36)O[C@@H]%35COP(S)(OC%38C[C@H](N%39C=C(C(N)=NC%39=O)C)O[C@@H]%38COP(S)(OC%40[C@H](O[C@@H](n(cn%41)c%42c%41c(N)ncn%42)C%40OCCOC)COP(S)(OC%43[C@H](O[C@@H](n%44c%45c(C(NC(N)=N%45)=O)nc%44)C%43OCCOC)COP(S)(OC%46[C@H](O[C@@H](n%47c%48c(C(NC(N)=N%48)=O)nc%47)C%46OCCOC)COP(S)(OC%49[C@H](O[C@@H](n%50c%51c(C(NC(N)=N%51)=O)nc%50)C%49OCCOC)CO)=O)=O)=O)=O)=O)=O)=O)=O)=O)=O)=O)=O)=O)=O)=O)=O)=O)=O)=O)O

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

More Info

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 7,156.97 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: Rosenberg JE, Hahn NM, Regan MM, Werner L, Alva A, George S, Picus J, Alter R, Balar A, Hoffman-Censits J, Grivas P, Lauer R, Guancial EA, Hoimes C, Sonpavde G, Albany C, Stein MN, Breen T, Jacobs C, Anderson K, Bellmunt J, Lalani AA, Pal S, Choueiri TK. Apatorsen plus docetaxel versus docetaxel alone in platinum-resistant metastatic urothelial carcinoma (Borealis-2). Br J Cancer. 2018 May;118(11):1434-1441. doi: 10.1038/s41416-018-0087-9. Epub 2018 May 16. PMID: 29765151; PMCID: PMC5988804. 2: Spigel DR, Shipley DL, Waterhouse DM, Jones SF, Ward PJ, Shih KC, Hemphill B, McCleod M, Whorf RC, Page RD, Stilwill J, Mekhail T, Jacobs C, Burris HA 3rd, Hainsworth JD. A Randomized, Double-Blinded, Phase II Trial of Carboplatin and Pemetrexed with or without Apatorsen (OGX-427) in Patients with Previously Untreated Stage IV Non-Squamous-Non-Small-Cell Lung Cancer: The SPRUCE Trial. Oncologist. 2019 Dec;24(12):e1409-e1416. doi: 10.1634/theoncologist.2018-0518. Epub 2019 Aug 16. PMID: 31420467; PMCID: PMC6975937. 3: Bellmunt J, Eigl BJ, Senkus E, Loriot Y, Twardowski P, Castellano D, Blais N, Sridhar SS, Sternberg CN, Retz M, Pal S, Blumenstein B, Jacobs C, Stewart PS, Petrylak DP. Borealis-1: a randomized, first-line, placebo-controlled, phase II study evaluating apatorsen and chemotherapy for patients with advanced urothelial cancer. Ann Oncol. 2017 Oct 1;28(10):2481-2488. doi: 10.1093/annonc/mdx400. PMID: 28961845. 4: Yu EY, Ellard SL, Hotte SJ, Gingerich JR, Joshua AM, Gleave ME, Chi KN. A randomized phase 2 study of a HSP27 targeting antisense, apatorsen with prednisone versus prednisone alone, in patients with metastatic castration resistant prostate cancer. Invest New Drugs. 2018 Apr;36(2):278-287. doi: 10.1007/s10637-017-0553-x. Epub 2017 Dec 18. PMID: 29250742. 5: Chi KN, Yu EY, Jacobs C, Bazov J, Kollmannsberger C, Higano CS, Mukherjee SD, Gleave ME, Stewart PS, Hotte SJ. A phase I dose-escalation study of apatorsen (OGX-427), an antisense inhibitor targeting heat shock protein 27 (Hsp27), in patients with castration-resistant prostate cancer and other advanced cancers. Ann Oncol. 2016 Jun;27(6):1116-1122. doi: 10.1093/annonc/mdw068. Epub 2016 Feb 18. PMID: 27022067. 6: Ko AH, Murphy PB, Peyton JD, Shipley DL, Al-Hazzouri A, Rodriguez FA, Womack MS 4th, Xiong HQ, Waterhouse DM, Tempero MA, Guo S, Lane CM, Earwood C, DeBusk LM, Bendell JC. A Randomized, Double-Blinded, Phase II Trial of Gemcitabine and Nab-Paclitaxel Plus Apatorsen or Placebo in Patients with Metastatic Pancreatic Cancer: The RAINIER Trial. Oncologist. 2017 Dec;22(12):1427-e129. doi: 10.1634/theoncologist.2017-0066. Epub 2017 Sep 21. PMID: 28935773; PMCID: PMC5728028. 7: Shimada T, Tsuruta M, Hasegawa H, Okabayashi K, Shigeta K, Ishida T, Asada Y, Suzumura H, Koishikawa K, Akimoto S, Kitagawa Y. Heat shock protein 27 knockdown using nucleotide‑based therapies enhances sensitivity to 5-FU chemotherapy in SW480 human colon cancer cells. Oncol Rep. 2018 Mar;39(3):1119-1124. doi: 10.3892/or.2018.6180. Epub 2018 Jan 3. PMID: 29328475. 8: Dellis AE, Papatsoris AG. Perspectives on the current and emerging chemical androgen receptor antagonists for the treatment of prostate cancer. Expert Opin Pharmacother. 2019 Feb;20(2):163-172. doi: 10.1080/14656566.2018.1548611. Epub 2018 Nov 21. PMID: 30462924. 9: Shevtsov M, Multhoff G, Mikhaylova E, Shibata A, Guzhova I, Margulis B. Combination of Anti-Cancer Drugs with Molecular Chaperone Inhibitors. Int J Mol Sci. 2019 Oct 24;20(21):5284. doi: 10.3390/ijms20215284. PMID: 31652993; PMCID: PMC6862641. 10: Chan L, Yokota T. Development and Clinical Applications of Antisense Oligonucleotide Gapmers. Methods Mol Biol. 2020;2176:21-47. doi: 10.1007/978-1-0716-0771-8_2. PMID: 32865780.