Abivertinib maleate

MedKoo Cat#: 207122 | Name: Abivertinib HCl

Description:

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

Abivertinib, also known as AC0010 and Avitinib, is a third-generation EGFR tyrosine kinase inhibitor and BTK Inhibitor that demonstrated clinical efficacy and manageable adverse events (AEs). Abivertinib inhibits cell proliferation, reduces colony-forming capacity, and induces apoptosis and cell cycle arrest in AML cells, especially those harboring FLT3-ITD mutations. Abivertinib was also found to be more sensitive than ibrutinib in treating AML. Abivertinib may be a promising novel agent for AML, with potential for combination treatment with HHT.

Chemical Structure

Abivertinib HCl

CAS#1557268-90-2 (2HCl)

Theoretical Analysis

MedKoo Cat#: 207122

Name: Abivertinib HCl

CAS#: 1557268-90-2 (2HCl)

Chemical Formula: C26H28Cl2FN7O2

Exact Mass:

Molecular Weight: 560.46

Elemental Analysis: C, 55.72; H, 5.04; Cl, 12.65; F, 3.39; N, 17.49; O, 5.71

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 #

1557267-42-1 (free base) 1557268-88-8 (maleate) 1822357-78-7 (maleate hydrate) 1557268-90-2 (2HCl) 1801879-16-2 (HCl)

Synonym

Abivertinib maleate, Abivertinib; AC0010; AC-0010; AC 0010; Avitinib;

IUPAC/Chemical Name

N-(3-((2-((3-fluoro-4-(4-methylpiperazin-1-yl)phenyl)amino)-7H-pyrrolo[2,3-d]pyrimidin-4-yl)oxy)phenyl)acrylamide dihydrochloride

InChi Key

NFPCFFZEIWPSBM-UHFFFAOYSA-N

InChi Code

InChI=1S/C26H26FN7O2.2ClH/c1-3-23(35)29-17-5-4-6-19(15-17)36-25-20-9-10-28-24(20)31-26(32-25)30-18-7-8-22(21(27)16-18)34-13-11-33(2)12-14-34;;/h3-10,15-16H,1,11-14H2,2H3,(H,29,35)(H2,28,30,31,32);2*1H

SMILES Code

C=CC(NC1=CC=CC(OC2=C3C(NC=C3)=NC(NC4=CC=C(N5CCN(C)CC5)C(F)=C4)=N2)=C1)=O.[H]Cl.[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

Resistance to third-generation epidermal growth factor receptor (EGFR) tyrosine kinase inhibitors (TKIs) presents a major clinical challenge in advanced non-small cell lung cancer (NSCLC).

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 560.46 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

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J Thorac Oncol. 2021 May;16(5):740-763. doi: 10.1016/j.jtho.2020.11.028. Epub 2020 Dec 15. PMID: 33338652. 5: Huang S, Li C, Zhang X, Pan J, Li F, Lv Y, Huang J, Ling Q, Ye W, Mao S, Huang X, Jin J. Abivertinib synergistically strengthens the anti-leukemia activity of venetoclax in acute myeloid leukemia in a BTK-dependent manner. Mol Oncol. 2020 Oct;14(10):2560-2573. doi: 10.1002/1878-0261.12742. Epub 2020 Jul 3. PMID: 32519423; PMCID: PMC7530784. 6: Tang Q, Chen H, Mai Z, Sun H, Xu L, Wu G, Tu Z, Cheng X, Wang X, Chen T. Bim- and Bax-mediated mitochondrial pathway dominates abivertinib-induced apoptosis and ferroptosis. Free Radic Biol Med. 2022 Feb 20;180:198-209. doi: 10.1016/j.freeradbiomed.2022.01.013. Epub 2022 Jan 19. PMID: 35063650. 7: Huang S, Pan J, Jin J, Li C, Li X, Huang J, Huang X, Yan X, Li F, Yu M, Hu C, Jin J, Xu Y, Ling Q, Ye W, Wang Y, Jin J. Abivertinib, a novel BTK inhibitor: Anti-Leukemia effects and synergistic efficacy with homoharringtonine in acute myeloid leukemia. Cancer Lett. 2019 Oct 1;461:132-143. doi: 10.1016/j.canlet.2019.07.008. Epub 2019 Jul 13. PMID: 31310800. 8: Wang L, Guo L, Wang Y, Guo R, Xu Z, Gao Z, Xie L, Chen J, Chen Y, Liu Y, Zhang H, Bao L, Xu W, Zhu M, Shao F, Shu Y. Metabolic disposition of [14 C]-abivertinib, an epidermal growth factor receptor tyrosine kinase inhibitor: Role of glutathione conjugation. Br J Clin Pharmacol. 2021 Mar;87(3):1475-1485. doi: 10.1111/bcp.14555. Epub 2020 Nov 5. PMID: 32959915. 9: Zhou Q, Wu L, Hu P, An T, Zhou J, Zhang L, Liu XQ, Luo F, Zheng X, Cheng Y, Yang N, Li J, Feng J, Han B, Song Y, Wang K, Zhang L, Fang J, Zhao H, Shu Y, Lin XY, Chen Z, Gan B, Xu WH, Tang W, Zhang X, Yang JJ, Xu X, Wu YL. A Novel Third- generation EGFR Tyrosine Kinase Inhibitor Abivertinib for EGFR T790M-mutant Non- Small Cell Lung Cancer: a Multicenter Phase I/II Study. Clin Cancer Res. 2022 Mar 15;28(6):1127-1135. doi: 10.1158/1078-0432.CCR-21-2595. PMID: 34740925; PMCID: PMC9365372. 10: Huang S, Yu M, Shi N, Zhou Y, Li F, Li X, Huang X, Jin J. Apigenin and Abivertinib, a novel BTK inhibitor synergize to inhibit diffuse large B-cell lymphoma in vivo and vitro. J Cancer. 2020 Feb 3;11(8):2123-2132. doi: 10.7150/jca.34981. PMID: 32127939; PMCID: PMC7052937. 11: Zhang YC, Chen ZH, Zhang XC, Xu CR, Yan HH, Xie Z, Chuai SK, Ye JY, Han- Zhang H, Zhang Z, Bai XY, Su J, Gan B, Yang JJ, Li WF, Tang W, Luo FR, Xu X, Wu YL, Zhou Q. Analysis of resistance mechanisms to abivertinib, a third-generation EGFR tyrosine kinase inhibitor, in patients with EGFR T790M-positive non-small cell lung cancer from a phase I trial. EBioMedicine. 2019 May;43:180-187. doi: 10.1016/j.ebiom.2019.04.030. Epub 2019 Apr 23. PMID: 31027916; PMCID: PMC6558024. 12: Zheng X, Wang W, Zhang Y, Ma Y, Zhao H, Gao H, Hu P, Jiang J. Development of an LC-MS/MS method for quantifying two main metabolites of abivertinib in human plasma. Biomed Chromatogr. 2020 Feb;34(2):e4704. doi: 10.1002/bmc.4704. Epub 2019 Dec 23. PMID: 31629371. 13: Tan S, Lu R, Yao D, Wang J, Gao P, Xie G, Liu H, Yao X. Identification of LRRK2 Inhibitors through Computational Drug Repurposing. ACS Chem Neurosci. 2023 Feb 1;14(3):481-493. doi: 10.1021/acschemneuro.2c00672. Epub 2023 Jan 17. PMID: 36649061. 14: Schein CH. Repurposing approved drugs for cancer therapy. Br Med Bull. 2021 Mar 25;137(1):13-27. doi: 10.1093/bmb/ldaa045. PMID: 33517358; PMCID: PMC7929227. 15: Alizadehmohajer N, Behmardi A, Najafgholian S, Moradi S, Mohammadi F, Nedaeinia R, Haghjooy Javanmard S, Sohrabi E, Salehi R, Ferns GA, Emami Nejad A, Manian M. Screening of potential inhibitors of COVID-19 with repurposing approach via molecular docking. Netw Model Anal Health Inform Bioinform. 2022;11(1):11. doi: 10.1007/s13721-021-00341-3. Epub 2022 Feb 4. PMID: 35136710; PMCID: PMC8814570. 16: Jade D, Ayyamperumal S, Tallapaneni V, Joghee Nanjan CM, Barge S, Mohan S, Nanjan MJ. Virtual high throughput screening: Potential inhibitors for SARS- CoV-2 PLPRO and 3CLPRO proteases. Eur J Pharmacol. 2021 Jun 15;901:174082. doi: 10.1016/j.ejphar.2021.174082. Epub 2021 Apr 3. PMID: 33823185; PMCID: PMC8018918. 17: Miao Y, Wang Y, Bi Z, Huang K, Gao J, Li X, Li S, Wei L, Zhou H, Yang C. Antifibrotic mechanism of avitinib in bleomycin-induced pulmonary fibrosis in mice. BMC Pulm Med. 2023 Mar 22;23(1):94. doi: 10.1186/s12890-023-02385-9. PMID: 36949426; PMCID: PMC10031887. 18: Wu Q, Jiang H, Wang S, Dai D, Chen F, Meng D, Geng P, Tong H, Zhou Y, Pan D, Zhou Q, Wang C. Effects of avitinib on the pharmacokinetics of osimertinib in vitro and in vivo in rats. Thorac Cancer. 2020 Oct;11(10):2775-2781. doi: 10.1111/1759-7714.13587. Epub 2020 Aug 19. PMID: 32812378; PMCID: PMC7529555. 19: Shi Y, Meng D, Wang S, Geng P, Xu T, Zhou Q, Zhou Y, Li W, Chen X. Effects of Avitinib on CYP450 Enzyme Activity in vitro and in vivo in Rats. Drug Des Devel Ther. 2021 Aug 21;15:3661-3673. doi: 10.2147/DDDT.S323186. PMID: 34456561; PMCID: PMC8387736. 20: Attwa MW, Kadi AA, Abdelhameed AS. Reactive intermediates and bioactivation pathways characterization of avitinib by LC-MS/MS: In vitro metabolic investigation. J Pharm Biomed Anal. 2019 Feb 5;164:659-667. doi: 10.1016/j.jpba.2018.11.033. Epub 2018 Nov 17. PMID: 30472584.

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