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MedKoo Cat#: 565088 | Name: Amuvatinib Hydrochloride

Description:

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

Amuvatinib Hydrochloride is a multitargeted receptor tyrosine kinase inhibitor which binds to and inhibits mutant forms of the stem cell factor receptor (c-Kit; SCFR). Amuvatinib Hydrochloride also inhibits c-Met, Ret oncoprotein, and mutant forms of Flt3 and PDGFR alpha, thereby suppressing the induction of DNA repair protein Rad51.

Chemical Structure

Amuvatinib Hydrochloride
Amuvatinib Hydrochloride
CAS#1055986-67-8 (HCl)

Theoretical Analysis

MedKoo Cat#: 565088

Name: Amuvatinib Hydrochloride

CAS#: 1055986-67-8 (HCl)

Chemical Formula: C23H22ClN5O3S

Exact Mass: 0.0000

Molecular Weight: 483.97

Elemental Analysis: C, 57.08; H, 4.58; Cl, 7.32; N, 14.47; O, 9.92; S, 6.62

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Related CAS #
850879-09-3 (free) 1055986-67-8 (HCl)
Synonym
MP470 Hydrochloride; MP-470 Hydrochloride; MP 470 Hydrochloride; MP470 HCl; MP-470 HCl; MP 470 HCl; Amuvatinib HCl; Amuvatinib Hydrochloride
IUPAC/Chemical Name
N-(1,3-Benzodioxol-5-ylmethyl)-4-([1]benzofuro[3,2-d]pyrimidin-4-yl)piperazine-1-carbothioamide hydrochloride
InChi Key
IKQFRXPMBGQJGE-UHFFFAOYSA-N
InChi Code
InChI=1S/C23H21N5O3S.ClH/c32-23(24-12-15-5-6-18-19(11-15)30-14-29-18)28-9-7-27(8-10-28)22-21-20(25-13-26-22)16-3-1-2-4-17(16)31-21;/h1-6,11,13H,7-10,12,14H2,(H,24,32);1H
SMILES Code
S=C(N1CCN(C2=C(OC3=C4C=CC=C3)C4=NC=N2)CC1)NCC5=CC=C(OCO6)C6=C5.[H]Cl
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

Preparing Stock Solutions

The following data is based on the product molecular weight 483.97 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.

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
1: Marciano R, David HB, Akabayov B, Rotblat B. The Amuvatinib Derivative, N-(2H -1,3-Benzodioxol-5-yl)-4-{thieno[3,2-d]pyrimidin-4-yl}piperazine-1-carboxamide, Inhibits Mitochondria and Kills Tumor Cells under Glucose Starvation. Int J Mol Sci. 2020 Feb 4;21(3):1041. doi: 10.3390/ijms21031041. PMID: 32033217; PMCID: PMC7036964. 2: Huynh TTX, Pham TX, Lee GH, Lee JB, Lee SG, Tark D, Lim YS, Hwang SB. Amuvatinib Blocks SARS-CoV-2 Infection at the Entry Step of the Viral Life Cycle. Microbiol Spectr. 2023 Mar 30:e0510522. doi: 10.1128/spectrum.05105-22. Epub ahead of print. PMID: 36995225. 3: Fedorenko IV, Fang B, Koomen JM, Gibney GT, Smalley KS. Amuvatinib has cytotoxic effects against NRAS-mutant melanoma but not BRAF-mutant melanoma. Melanoma Res. 2014 Oct;24(5):448-53. doi: 10.1097/CMR.0000000000000103. PMID: 24950457; PMCID: PMC4384823. 4: Chang JY, Verma V, Welsh JW, Formenti SC. Radiotherapy plus immune checkpoint blockade in PD(L)-1-resistant metastatic NSCLC. Lancet Oncol. 2022 Apr;23(4):e156. doi: 10.1016/S1470-2045(22)00134-6. PMID: 35358456. 5: Choy G, Joshi-Hangal R, Oganesian A, Fine G, Rasmussen S, Collier J, Kissling J, Sahai A, Azab M, Redkar S. Safety, tolerability, and pharmacokinetics of amuvatinib from three phase 1 clinical studies in healthy volunteers. Cancer Chemother Pharmacol. 2012 Jul;70(1):183-90. doi: 10.1007/s00280-012-1821-2. Epub 2012 Feb 15. PMID: 22349808. 6: Chen D, Barsoumian HB, Yang L, Younes AI, Verma V, Hu Y, Menon H, Wasley M, Masropour F, Mosaffa S, Ozgen T, Klein K, Cortez MA, Welsh JW. SHP-2 and PD-L1 Inhibition Combined with Radiotherapy Enhances Systemic Antitumor Effects in an Anti-PD-1-Resistant Model of Non-Small Cell Lung Cancer. Cancer Immunol Res. 2020 Jul;8(7):883-894. doi: 10.1158/2326-6066.CIR-19-0744. Epub 2020 Apr 16. PMID: 32299915; PMCID: PMC10173258. 7: Chen D, Barsoumian HB, Fischer G, Yang L, Verma V, Younes AI, Hu Y, Masropour F, Klein K, Vellano C, Marszalek J, Davies M, Cortez MA, Welsh J. Combination treatment with radiotherapy and a novel oxidative phosphorylation inhibitor overcomes PD-1 resistance and enhances antitumor immunity. J Immunother Cancer. 2020 Jun;8(1):e000289. doi: 10.1136/jitc-2019-000289. PMID: 32581056; PMCID: PMC7319777. 8: Mita M, Gordon M, Rosen L, Kapoor N, Choy G, Redkar S, Taverna P, Oganesian A, Sahai A, Azab M, Bristow R, Tolcher AW. Phase 1B study of amuvatinib in combination with five standard cancer therapies in adults with advanced solid tumors. Cancer Chemother Pharmacol. 2014 Jul;74(1):195-204. doi: 10.1007/s00280-014-2481-1. Epub 2014 May 22. PMID: 24849582. 9: Zhao H, Luoto KR, Meng AX, Bristow RG. The receptor tyrosine kinase inhibitor amuvatinib (MP470) sensitizes tumor cells to radio- and chemo-therapies in part by inhibiting homologous recombination. Radiother Oncol. 2011 Oct;101(1):59-65. doi: 10.1016/j.radonc.2011.08.013. Epub 2011 Sep 6. PMID: 21903282. 10: Byers LA, Horn L, Ghandi J, Kloecker G, Owonikoko T, Waqar SN, Krzakowski M, Cardnell RJ, Fujimoto J, Taverna P, Azab M, Camidge DR. A phase 2, open-label, multi-center study of amuvatinib in combination with platinum etoposide chemotherapy in platinum-refractory small cell lung cancer patients. Oncotarget. 2017 Aug 3;8(46):81441-81454. doi: 10.18632/oncotarget.19888. PMID: 29113403; PMCID: PMC5655298. 11: Tibes R, Fine G, Choy G, Redkar S, Taverna P, Oganesian A, Sahai A, Azab M, Tolcher AW. A phase I, first-in-human dose-escalation study of amuvatinib, a multi-targeted tyrosine kinase inhibitor, in patients with advanced solid tumors. Cancer Chemother Pharmacol. 2013 Feb;71(2):463-71. doi: 10.1007/s00280-012-2019-3. Epub 2012 Nov 23. PMID: 23178951. 12: Phillip CJ, Zaman S, Shentu S, Balakrishnan K, Zhang J, Baladandayuthapani V, Taverna P, Redkar S, Wang M, Stellrecht CM, Gandhi V. Targeting MET kinase with the small-molecule inhibitor amuvatinib induces cytotoxicity in primary myeloma cells and cell lines. J Hematol Oncol. 2013 Dec 10;6:92. doi: 10.1186/1756-8722-6-92. Erratum in: J Hematol Oncol. 2016 Oct 13;9(1):110. PMID: 24326130; PMCID: PMC3878866. 13: Brayford S, Duly A, Teo WS, Dwarte T, Gonzales-Aloy E, Ma Z, McVeigh L, Failes TW, Arndt GM, McCarroll JA, Kavallaris M. βIII-tubulin suppression enhances the activity of Amuvatinib to inhibit cell proliferation in c-Met positive non-small cell lung cancer cells. Cancer Med. 2023 Feb;12(4):4455-4471. doi: 10.1002/cam4.5128. Epub 2022 Aug 10. PMID: 35946957; PMCID: PMC9972117. 14: Phillip CJ, Zaman S, Shentu S, Balakrishnan K, Zhang J, Baladandayuthapani V, Taverna P, Redkar S, Wang M, Stellrecht CM, Gandhi V. Erratum to: Targeting MET kinase with the small-molecule inhibitor amuvatinib induces cytotoxicity in primary myeloma cells and cell lines. J Hematol Oncol. 2016 Oct 13;9(1):110. doi: 10.1186/s13045-016-0335-5. Erratum for: J Hematol Oncol. 2013 Dec 10;6:92. PMID: 27737688; PMCID: PMC5064904. 15: Padda S, Neal JW, Wakelee HA. MET inhibitors in combination with other therapies in non-small cell lung cancer. Transl Lung Cancer Res. 2012 Dec;1(4):238-53. doi: 10.3978/j.issn.2218-6751.2012.10.08. PMID: 25806189; PMCID: PMC4367550. 16: Son J, Hsieh RC, Lin HY, Krause KJ, Yuan Y, Biter AB, Welsh J, Curran MA, Hong DS. Inhibition of the CD47-SIRPα axis for cancer therapy: A systematic review and meta-analysis of emerging clinical data. Front Immunol. 2022 Nov 11;13:1027235. doi: 10.3389/fimmu.2022.1027235. PMID: 36439116; PMCID: PMC9691650. 17: Salem MSH, Abdel Aziz YM, Elgawish MS, Said MM, Abouzid KAM. Design, synthesis, biological evaluation and molecular modeling study of new thieno[2,3-d]pyrimidines with anti-proliferative activity on pancreatic cancer cell lines. Bioorg Chem. 2020 Jan;94:103472. doi: 10.1016/j.bioorg.2019.103472. Epub 2019 Nov 30. PMID: 31813475. 18: Cortez MA, Masrorpour F, Ivan C, Zhang J, Younes AI, Lu Y, Estecio MR, Barsoumian HB, Menon H, Caetano MDS, Ramapriyan R, Schoenhals JE, Wang X, Skoulidis F, Wasley MD, Calin G, Hwu P, Welsh JW. Bone morphogenetic protein 7 promotes resistance to immunotherapy. Nat Commun. 2020 Sep 24;11(1):4840. doi: 10.1038/s41467-020-18617-z. Erratum in: Nat Commun. 2020 Oct 8;11(1):5144. PMID: 32973129; PMCID: PMC7519103. 19: Sezen D, Barsoumian HB, He K, Hu Y, Wang Q, Abana CO, Puebla-Osorio N, Hsu EY, Wasley M, Masrorpour F, Wang J, Cortez MA, Welsh JW. Pulsed radiotherapy to mitigate high tumor burden and generate immune memory. Front Immunol. 2022 Oct 6;13:984318. doi: 10.3389/fimmu.2022.984318. PMID: 36275767; PMCID: PMC9582356. 20: Nazha B, Owonikoko TK. The clinical conundrum of managing relapsed small cell lung cancer. Cancer. 2019 Apr 1;125(7):1022-1026. doi: 10.1002/cncr.31849. Epub 2018 Dec 18. PMID: 30561759.