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MedKoo Cat#: 206868 | Name: Pimitespib
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Description:

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

TAS-​116, also known as Pimitespib, is a potent and selective inhibitor of heat shock protein 90 (Hsp90) subtypes alpha and beta, with potential antineoplastic and chemo/radiosensitizing activities. TAS-116 specifically binds to and inhibits the activity of Hsp90 alpha and beta; this results in the proteasomal degradation of oncogenic client proteins, which inhibits client protein dependent-signaling, induces apoptosis, and inhibits the proliferation of cells overexpressing HSP90alpha/beta.

Chemical Structure

Pimitespib
Pimitespib
CAS#1260533-36-5

Theoretical Analysis

MedKoo Cat#: 206868

Name: Pimitespib

CAS#: 1260533-36-5

Chemical Formula: C25H26N8O

Exact Mass: 454.2230

Molecular Weight: 454.54

Elemental Analysis: C, 66.06; H, 5.77; N, 24.65; O, 3.52

Price and Availability

Size Price Availability Quantity
25mg USD 450.00 2 Weeks
50mg USD 750.00 2 Weeks
100mg USD 1,650.00 2 Weeks
200mg USD 2,950.00 2 Weeks
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Synonym
TAS-​116; TAS ​116; TAS116; Pimitespib
IUPAC/Chemical Name
3-Ethyl-4-[4-[4-(1-methylpyrazol-4-yl)imidazol-1-yl]-3-propan-2-ylpyrazolo[3,4-b]pyridin-1-yl]benzamide
InChi Key
NVVPMZUGELHVMH-UHFFFAOYSA-N
InChi Code
InChI=1S/C25H26N8O/c1-5-16-10-17(24(26)34)6-7-20(16)33-25-22(23(30-33)15(2)3)21(8-9-27-25)32-13-19(28-14-32)18-11-29-31(4)12-18/h6-15H,5H2,1-4H3,(H2,26,34)
SMILES Code
O=C(N)C1=CC=C(N2N=C(C(C)C)C3=C(N4C=C(C5=CN(C)N=C5)N=C4)C=CN=C32)C(CC)=C1
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
Soluble in DMSO
Shelf Life
>3 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
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
Product Data
Product Data
Instruction
View handling instruction
Biological target:
TAS-116, also known as Pimitespib, is a potent and selective inhibitor of heat shock protein 90 (Hsp90) subtypes alpha and beta.
In vitro activity:
TAS-116 achieved IC50 values of less than 0.5 μmol/L in 10 ATL-related cell lines and less than 1 μmol/L in primary peripheral blood cells of nine ATL patients; no toxicity was observed toward CD4+ lymphocytes from healthy donors, indicating the safety of this agent. Furthermore, gene expression profiling of TAS-116-treated Tax-positive or -negative cell lines and primary ATL cells using DNA microarray and multiple pathway analysis revealed the significant downregulation of the NF-κB pathway in Tax-positive cells and cell-cycle arrest in Tax-negative cells and primary ATL cells. TAS-116 suppressed the activator protein-1 and tumor necrosis factor pathways in all examined cells. Reference: Cancer Sci. 2022 Feb;113(2):684-696. https://pubmed.ncbi.nlm.nih.gov/34794206/
In vivo activity:
Oral administration of TAS-116 led to tumor shrinkage in human tumor xenograft mouse models accompanied by depletion of multiple HSP90 clients, demonstrating that the inhibition of HSP90α and β alone was sufficient to exert antitumor activity in certain tumor models. Importantly, in a rat model, the antitumor activity of TAS-116 was accompanied by a higher distribution of the compound in subcutaneously xenografted NCI-H1975 non-small cell lung carcinoma tumors than in retina. Moreover, TAS-116 showed activity against orthotopically transplanted NCI-H1975 lung tumors. Reference: Mol Cancer Ther. 2015 Jan;14(1):14-22. https://pubmed.ncbi.nlm.nih.gov/25416789/
Solvent mg/mL mM comments
Solubility
DMSO 125.0 275.00
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 454.54 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.

Recalculate based on batch purity %
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
Formulation protocol:
1. Ikebe E, Shimosaki S, Hasegawa H, Iha H, Tsukamoto Y, Wang Y, Sasaki D, Imaizumi Y, Miyazaki Y, Yanagihara K, Hamaguchi I, Morishita K. TAS-116 (pimitespib), a heat shock protein 90 inhibitor, shows efficacy in preclinical models of adult T-cell leukemia. Cancer Sci. 2022 Feb;113(2):684-696. doi: 10.1111/cas.15204. Epub 2021 Nov 27. PMID: 34794206; PMCID: PMC8819293. 2. Ranta-Aho S, Piippo N, Korhonen E, Kaarniranta K, Hytti M, Kauppinen A. TAS-116, a Well-Tolerated Hsp90 Inhibitor, Prevents the Activation of the NLRP3 Inflammasome in Human Retinal Pigment Epithelial Cells. Int J Mol Sci. 2021 May 5;22(9):4875. doi: 10.3390/ijms22094875. PMID: 34062977; PMCID: PMC8125426. 3. Solopov PA, Colunga Biancatelli RML, Dimitropolou C, Day T, Catravas JD. Optimizing antidotal treatment with the oral HSP90 inhibitor TAS-116 against hydrochloric acid-induced pulmonary fibrosis in mice. Front Pharmacol. 2022 Nov 7;13:1034464. doi: 10.3389/fphar.2022.1034464. PMID: 36419627; PMCID: PMC9676235. 4. Ohkubo S, Kodama Y, Muraoka H, Hitotsumachi H, Yoshimura C, Kitade M, Hashimoto A, Ito K, Gomori A, Takahashi K, Shibata Y, Kanoh A, Yonekura K. TAS-116, a highly selective inhibitor of heat shock protein 90α and β, demonstrates potent antitumor activity and minimal ocular toxicity in preclinical models. Mol Cancer Ther. 2015 Jan;14(1):14-22. doi: 10.1158/1535-7163.MCT-14-0219. Epub 2014 Nov 21. PMID: 25416789.
In vitro protocol:
1. Ikebe E, Shimosaki S, Hasegawa H, Iha H, Tsukamoto Y, Wang Y, Sasaki D, Imaizumi Y, Miyazaki Y, Yanagihara K, Hamaguchi I, Morishita K. TAS-116 (pimitespib), a heat shock protein 90 inhibitor, shows efficacy in preclinical models of adult T-cell leukemia. Cancer Sci. 2022 Feb;113(2):684-696. doi: 10.1111/cas.15204. Epub 2021 Nov 27. PMID: 34794206; PMCID: PMC8819293. 2. Ranta-Aho S, Piippo N, Korhonen E, Kaarniranta K, Hytti M, Kauppinen A. TAS-116, a Well-Tolerated Hsp90 Inhibitor, Prevents the Activation of the NLRP3 Inflammasome in Human Retinal Pigment Epithelial Cells. Int J Mol Sci. 2021 May 5;22(9):4875. doi: 10.3390/ijms22094875. PMID: 34062977; PMCID: PMC8125426.
In vivo protocol:
1. Solopov PA, Colunga Biancatelli RML, Dimitropolou C, Day T, Catravas JD. Optimizing antidotal treatment with the oral HSP90 inhibitor TAS-116 against hydrochloric acid-induced pulmonary fibrosis in mice. Front Pharmacol. 2022 Nov 7;13:1034464. doi: 10.3389/fphar.2022.1034464. PMID: 36419627; PMCID: PMC9676235. 2. Ohkubo S, Kodama Y, Muraoka H, Hitotsumachi H, Yoshimura C, Kitade M, Hashimoto A, Ito K, Gomori A, Takahashi K, Shibata Y, Kanoh A, Yonekura K. TAS-116, a highly selective inhibitor of heat shock protein 90α and β, demonstrates potent antitumor activity and minimal ocular toxicity in preclinical models. Mol Cancer Ther. 2015 Jan;14(1):14-22. doi: 10.1158/1535-7163.MCT-14-0219. Epub 2014 Nov 21. PMID: 25416789.
1: Teranishi R, Takahashi T, Kurokawa Y, Saito T, Yamamoto K, Momose K, Yamashita K, Tanaka K, Makino T, Nakajima K, Eguchi H, Doki Y. Pimitespib, a Novel Heat Shock Protein 90 Inhibitor, Is Effective in Treating Renal Cell Carcinoma by Anti-angiogenetic Signaling. Anticancer Res. 2024 Aug;44(8):3343-3348. doi: 10.21873/anticanres.17154. PMID: 39060043. 2: Naoki K, Igawa S, Uojima H, Tsumura H, Sengoku N, Karayama M, Shimomura A, Ohtake T, Shio Y, Hosokawa A, Komatsu Y, Kumagai Y. Cardiovascular safety of pimitespib in patients with advanced solid tumors: An open-label, nonrandomized, phase 1 study. Cancer. 2024 Jul 10. doi: 10.1002/cncr.35447. Epub ahead of print. PMID: 38985885. 3: Rastogi S, Joshi A, Sato N, Lee S, Lee MJ, Trepel JB, Neckers L. An update on the status of HSP90 inhibitors in cancer clinical trials. Cell Stress Chaperones. 2024 Jun 13;29(4):519-539. doi: 10.1016/j.cstres.2024.05.005. Epub ahead of print. PMID: 38878853; PMCID: PMC11260857. 4: Liu J, Shu H, Xia Q, You Q, Wang L. Recent developments of HSP90 inhibitors: an updated patent review (2020-present). Expert Opin Ther Pat. 2024 Jan- Feb;34(1-2):1-15. doi: 10.1080/13543776.2024.2327295. Epub 2024 Mar 8. PMID: 38441084. 5: Doi T, Yamamoto N, Ohkubo S. Pimitespib for the treatment of advanced gastrointestinal stromal tumors and other tumors. Future Oncol. 2024 Mar;20(9):507-519. doi: 10.2217/fon-2022-1172. Epub 2023 Dec 5. PMID: 38050698. 6: Ohnuma T, Mijiddorj MT, Kajihara I, Sawamura S, Sakamoto R, Maeda-Otsuka S, Yamada-Kanazawa S, Makino K, Aoi J, Masuguchi S, Fukushima S. Overexpression of heat shock protein 90 through the downregulation of miR-9-5p in extramammary Paget's disease. J Dermatol. 2023 Sep;50(9):1216-1221. doi: 10.1111/1346-8138.16825. Epub 2023 May 19. PMID: 37208828. 7: Hu K, Zhang H, Shu M, Wang X. Efficacy of post-first-line agents for advanced gastrointestinal stromal tumors following imatinib failure: A network meta- analysis. Cancer Med. 2023 Jun;12(11):12187-12197. doi: 10.1002/cam4.5912. Epub 2023 Apr 21. PMID: 37084005; PMCID: PMC10278495. 8: Teranishi R, Takahashi T, Kurokawa Y, Saito T, Yamamoto K, Yamashita K, Tanaka K, Makino T, Nakajima K, Eguchi H, Doki Y. Long-term response to pimitespib in postoperative recurrent gastrointestinal stromal tumors with PDGFRA D842V mutation: a case report. Surg Case Rep. 2023 Apr 7;9(1):54. doi: 10.1186/s40792-023-01637-4. PMID: 37027098; PMCID: PMC10082137. 9: Wang J, Zou J, Zhao C, Yu H, Teng J, Dong L. Syringaresinol inhibits cardiorenal fibrosis through HSP90 in a cardiorenal syndrome type 2. Hum Exp Toxicol. 2023 Jan-Dec;42:9603271231165678. doi: 10.1177/09603271231165678. PMID: 36960691. 10: Kagawa Y, Hayashida T, Liu J, Mori S, Izumi H, Kumagai S, Udagawa H, Hattori N, Goto K, Kobayashi SS. The EGFR C797S Mutation Confers Resistance to a Novel EGFR Inhibitor CLN-081 to EGFR Exon 20 Insertion Mutations. JTO Clin Res Rep. 2023 Jan 24;4(3):100462. doi: 10.1016/j.jtocrr.2023.100462. PMID: 36915628; PMCID: PMC10006853. 11: Naito Y, Nishida T, Doi T. Current status of and future prospects for the treatment of unresectable or metastatic gastrointestinal stromal tumours. Gastric Cancer. 2023 May;26(3):339-351. doi: 10.1007/s10120-023-01381-6. Epub 2023 Mar 13. PMID: 36913072; PMCID: PMC10115693. 12: Sano D, Kihara T, Yuan J, Kimura N, Ohkouchi M, Hashikura Y, Ohkubo S, Hirota S. Characterization of cell line with dedifferentiated GIST-like features established from cecal GIST of familial GIST model mice. Pathol Int. 2023 May;73(5):181-187. doi: 10.1111/pin.13315. Epub 2023 Feb 24. PMID: 36825754. 13: Teranishi R, Takahashi T, Obata Y, Nishida T, Ohkubo S, Kazuno H, Saito Y, Serada S, Fujimoto M, Kurokawa Y, Saito T, Yamamoto K, Yamashita K, Tanaka K, Makino T, Nakajima K, Hirota S, Naka T, Eguchi H, Doki Y. Combination of pimitespib (TAS-116) with sunitinib is an effective therapy for imatinib- resistant gastrointestinal stromal tumors. Int J Cancer. 2023 Jun 15;152(12):2580-2593. doi: 10.1002/ijc.34461. Epub 2023 Feb 21. PMID: 36752576. 14: Xiao X, Yuan W, Wang C, Song H. A systematic review and network meta- analysis of the efficacy and safety of third-line and over third-line therapy after imatinib and TKI resistance in advanced gastrointestinal stromal tumor. Front Pharmacol. 2022 Nov 21;13:978885. doi: 10.3389/fphar.2022.978885. PMID: 36479203; PMCID: PMC9720279. 15: El-Kashef DH, Youssef ME, Nasr M, Alrouji M, Alhajlah S, AlOmeir O, El Adle Khalaf N, Ghaffar DMA, Jamil L, Abdel-Nasser ZM, Ibrahim S, Abdeldaiem MSI, Donia SS, Mohammed OA, Morsy NE, Shata A, Saber S. Pimitespib, an HSP90 inhibitor, augments nifuroxazide-induced disruption in the IL-6/STAT3/HIF-1α autocrine loop in rats with bleomycin-challenged lungs: Evolutionary perspective in managing pulmonary fibrosis. Biomed Pharmacother. 2022 Sep;153:113487. doi: 10.1016/j.biopha.2022.113487. Epub 2022 Jul 31. PMID: 36076505. 16: Hoy SM. Pimitespib: First Approval. Drugs. 2022 Sep;82(13):1413-1418. doi: 10.1007/s40265-022-01764-6. PMID: 35986838. 17: Komatsu Y, Shimokawa T, Akiyoshi K, Karayama M, Shimomura A, Kawamoto Y, Yuki S, Tambo Y, Kasahara K. An open-label, crossover study to compare different formulations and evaluate effect of food on pharmacokinetics of pimitespib in patients with advanced solid tumors. Invest New Drugs. 2022 Oct;40(5):1011-1020. doi: 10.1007/s10637-022-01285-9. Epub 2022 Aug 6. PMID: 35932386; PMCID: PMC9395490. 18: Kurokawa Y, Honma Y, Sawaki A, Naito Y, Iwagami S, Komatsu Y, Takahashi T, Nishida T, Doi T. Pimitespib in patients with advanced gastrointestinal stromal tumor (CHAPTER-GIST-301): a randomized, double-blind, placebo-controlled phase III trial. Ann Oncol. 2022 Sep;33(9):959-967. doi: 10.1016/j.annonc.2022.05.518. Epub 2022 Jun 8. PMID: 35688358. 19: Ikebe E, Shimosaki S, Hasegawa H, Iha H, Tsukamoto Y, Wang Y, Sasaki D, Imaizumi Y, Miyazaki Y, Yanagihara K, Hamaguchi I, Morishita K. TAS-116 (pimitespib), a heat shock protein 90 inhibitor, shows efficacy in preclinical models of adult T-cell leukemia. Cancer Sci. 2022 Feb;113(2):684-696. doi: 10.1111/cas.15204. Epub 2021 Nov 27. PMID: 34794206; PMCID: PMC8819293. 20: Kihara T, Yuan J, Watabe T, Kitajima K, Kimura N, Ohkouchi M, Hashikura Y, Ohkubo S, Takahashi T, Hirota S. Pimitespib is effective on cecal GIST in a mouse model of familial GISTs with KIT-Asp820Tyr mutation through KIT signaling inhibition. Exp Mol Pathol. 2021 Dec;123:104692. doi: 10.1016/j.yexmp.2021.104692. Epub 2021 Oct 1. PMID: 34606780.

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