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MedKoo Cat#: 206083 | Name: Olmutinib free base
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Description:

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

Olmutinib, also known as HM61713 and BI-1482694, is a potent small molecule inhibitor of Bruton's tyrosine kinase (BTK). BTK is a member of the Tec family of non-receptor protein tyrosine kinases. BTK is mostly expressed in hematopoietic cells such as B cells, mast cells and macrophages. BTK plays key roles in multiple cell signaling pathways including B-Cell Receptor (BCR) and Fc receptor (FcR) signaling cascades and is an essential mediator not only in B-cell dependent but also in myeloid cell dependent inflammatory arthritis. HM71224 has been selected as a novel therapeutic agent for the treatment of autoimmune diseases such as RA.

Chemical Structure

Olmutinib free base
Olmutinib free base
CAS#1353550-13-6 (free base)

Theoretical Analysis

MedKoo Cat#: 206083

Name: Olmutinib free base

CAS#: 1353550-13-6 (free base)

Chemical Formula: C26H26N6O2S

Exact Mass: 486.1838

Molecular Weight: 486.59

Elemental Analysis: C, 64.18; H, 5.39; N, 17.27; O, 6.58; S, 6.59

Price and Availability

Size Price Availability Quantity
100mg USD 150.00 Ready to ship
200mg USD 250.00 Ready to ship
500mg USD 450.00 Ready to ship
1g USD 750.00 Ready to ship
2g USD 1,350.00 Ready to ship
5g USD 2,950.00 Ready to ship
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Related CAS #
1842366-97-5 (2HCl) 2102670-48-2 (HCl) 1353550-13-6 (free base) 2102714-68-9 (HCl hydrate)
Synonym
HM61713; HM 61713; HM-61713; BI 1482694; BI-1482694; BI1482694; Olmutinib.
IUPAC/Chemical Name
N-(3-((2-((4-(4-methylpiperazin-1-yl)phenyl)amino)thieno[3,2-d]pyrimidin-4-yl)oxy)phenyl)acrylamide
InChi Key
FDMQDKQUTRLUBU-UHFFFAOYSA-N
InChi Code
InChI=1S/C26H26N6O2S/c1-3-23(33)27-19-5-4-6-21(17-19)34-25-24-22(11-16-35-24)29-26(30-25)28-18-7-9-20(10-8-18)32-14-12-31(2)13-15-32/h3-11,16-17H,1,12-15H2,2H3,(H,27,33)(H,28,29,30)
SMILES Code
C=CC(NC1=CC=CC(OC2=C3C(C=CS3)=NC(NC4=CC=C(N5CCN(C)CC5)C=C4)=N2)=C1)=O
Appearance
Light yellow 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, not in water
Shelf Life
>2 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
Related CAS# 1353550-13-6 (free base); 1842366-97-5 (HCl). 1802181-20-9 (deleted CAS#) Note: Olmutinib was previously mistakely cited as "HM71224". As of 9/12/2016, there are many vendor still cit      
Biological target:
Olmutinib (HM61713; BI-1482694) is an irreversible third EGFR tyrosine kinase inhibitor that binds to a cysteine residue near the kinase domain.
In vitro activity:
As compared with the NCI-H460 and HEK293/pcDNA3.1 cell lines, olmutinib significantly decreased the IC50 values of MX and SN-38 in the NCI-H460/MX20 and HEK293/ABCG2 cell lines, but it did not affect the values of paclitaxel and vincristine in the KB-C2 and HEK293/ABCB1 cell lines, compared to parental KB-3-1 and HEK293/pcDNA3.1 cell lines. It also did not affect the IC50 values of vinblastine and vincristine in KB-CV60 and HEK293/MRP1 cell lines, compared to parental KB-3-1 and HEK293/pcDNA3.1 cell lines. Cisplatin is not a substrate for ABCB1 and ABCG2. It has no reversal effect on ABCB1-mediated and ABCG2-mediated MDR. So there was no significant change in the IC50 values of cisplatin in the human cancer cell lines (KB-C2, NCI-H460/MX20, and KB-CV60) or transfected cell lines (HEK293/ABCB1, HEK293/G2, and HEK293/MRP1) compared with the corresponding parental cells (Tables Tables11–33). These results indicate that olmutinib could selectively reverse MDR mediated by ABCG2-overexpression but could not reverse ABCB1- and ABCC1-overexpressing mediated MDR. Reference: Front Pharmacol. 2018; 9: 1097. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6189370/
In vivo activity:
An ETS1-overexpressing K562/ADR cell xenograft model was established in athymic nude mice to estimate whether olmutinib could reverse the resistance of leukemia to Dox in vivo. As shown in Figure 5, there was an obvious inhibition of tumor growth in animals under the olmutinib and Dox synergistic treatment group, compared with that in the other monotherapy groups. The mean tumor weights were 2.43±0.09 g, 2.38±0.16 g, 2.38±0.22 g, and 1.82±0.98 g in the saline, olmutinib, Dox, and olmutinib plus Dox groups, respectively. Moreover, there was no palpable weight loss or mortality in the combination treatment group (Figure 5F), suggesting that olmutinib effectively reversed ETS1-mediated Dox resistance in vivo without causing additional toxicity. Reference: Med Sci Monit. 2020; 26: e924922-1–e924922-9. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7466836/
Solvent mg/mL mM
Solubility
DMSO 40.0 82.20
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 486.59 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. Zhang W, Fan YF, Cai CY, Wang JQ, Teng QX, Lei ZN, Zeng L, Gupta P, Chen ZS. Olmutinib (BI1482694/HM61713), a Novel Epidermal Growth Factor Receptor Tyrosine Kinase Inhibitor, Reverses ABCG2-Mediated Multidrug Resistance in Cancer Cells. Front Pharmacol. 2018 Oct 9;9:1097. doi: 10.3389/fphar.2018.01097. PMID: 30356705; PMCID: PMC6189370. 2. Zhang Z, Guo X, To KKW, Chen Z, Fang X, Luo M, Ma C, Xu J, Yan S, Fu L. Olmutinib (HM61713) reversed multidrug resistance by inhibiting the activity of ATP-binding cassette subfamily G member 2 in vitro and in vivo. Acta Pharm Sin B. 2018 Jul;8(4):563-574. doi: 10.1016/j.apsb.2018.06.002. Epub 2018 Jun 15. PMID: 30109181; PMCID: PMC6089862. 3. Zhong J, Zhang J, Yu X, Zhang X, Dian L. Olmutinib Reverses Doxorubicin Resistance in ETS1-Overexpressing Leukemia Cells. Med Sci Monit. 2020 Aug 24;26:e924922. doi: 10.12659/MSM.924922. PMID: 32830792; PMCID: PMC7466836. 4. Zhang Z, Guo X, To KKW, Chen Z, Fang X, Luo M, Ma C, Xu J, Yan S, Fu L. Olmutinib (HM61713) reversed multidrug resistance by inhibiting the activity of ATP-binding cassette subfamily G member 2 in vitro and in vivo. Acta Pharm Sin B. 2018 Jul;8(4):563-574. doi: 10.1016/j.apsb.2018.06.002. Epub 2018 Jun 15. PMID: 30109181; PMCID: PMC6089862.
In vitro protocol:
1. Zhang W, Fan YF, Cai CY, Wang JQ, Teng QX, Lei ZN, Zeng L, Gupta P, Chen ZS. Olmutinib (BI1482694/HM61713), a Novel Epidermal Growth Factor Receptor Tyrosine Kinase Inhibitor, Reverses ABCG2-Mediated Multidrug Resistance in Cancer Cells. Front Pharmacol. 2018 Oct 9;9:1097. doi: 10.3389/fphar.2018.01097. PMID: 30356705; PMCID: PMC6189370. 2. Zhang Z, Guo X, To KKW, Chen Z, Fang X, Luo M, Ma C, Xu J, Yan S, Fu L. Olmutinib (HM61713) reversed multidrug resistance by inhibiting the activity of ATP-binding cassette subfamily G member 2 in vitro and in vivo. Acta Pharm Sin B. 2018 Jul;8(4):563-574. doi: 10.1016/j.apsb.2018.06.002. Epub 2018 Jun 15. PMID: 30109181; PMCID: PMC6089862.
In vivo protocol:
1. Zhong J, Zhang J, Yu X, Zhang X, Dian L. Olmutinib Reverses Doxorubicin Resistance in ETS1-Overexpressing Leukemia Cells. Med Sci Monit. 2020 Aug 24;26:e924922. doi: 10.12659/MSM.924922. PMID: 32830792; PMCID: PMC7466836. 2. Zhang Z, Guo X, To KKW, Chen Z, Fang X, Luo M, Ma C, Xu J, Yan S, Fu L. Olmutinib (HM61713) reversed multidrug resistance by inhibiting the activity of ATP-binding cassette subfamily G member 2 in vitro and in vivo. Acta Pharm Sin B. 2018 Jul;8(4):563-574. doi: 10.1016/j.apsb.2018.06.002. Epub 2018 Jun 15. PMID: 30109181; PMCID: PMC6089862.
1: Park K, Han JY, Kim DW, Bazhenova LA, Ou SH, Pang YK, Hin HS, Juan O, Son J, Jänne P. 190TiP: ELUXA 1: Phase II study of BI 1482694 (HM61713) in patients (pts) with T790M-positive non-small cell lung cancer (NSCLC) after treatment with an epidermal growth factor receptor tyrosine kinase inhibitor (EGFR TKI). J Thorac Oncol. 2016 Apr;11(4 Suppl):S139. doi: 10.1016/S1556-0864(16)30299-4. Epub 2016 Apr 15. PubMed PMID: 27198328. 2: Park K, Lee JS, Han JY, Lee KH, Kim JH, Cho EK, Cho JY, Min YJ, Kim JS, Kim DW. 1300: Efficacy and safety of BI 1482694 (HM61713), an EGFR mutant-specific inhibitor, in T790M-positive NSCLC at the recommended phase II dose. J Thorac Oncol. 2016 Apr;11(4 Suppl):S113. doi: 10.1016/S1556-0864(16)30243-X. Epub 2016 Apr 15. PubMed PMID: 27198272. 3: Wang S, Cang S, Liu D. Third-generation inhibitors targeting EGFR T790M mutation in advanced non-small cell lung cancer. J Hematol Oncol. 2016 Apr 12;9:34. doi: 10.1186/s13045-016-0268-z. Review. PubMed PMID: 27071706; PubMed Central PMCID: PMC4830020. 4: Tan CS, Cho BC, Soo RA. Next-generation epidermal growth factor receptor tyrosine kinase inhibitors in epidermal growth factor receptor -mutant non-small cell lung cancer. Lung Cancer. 2016 Mar;93:59-68. doi: 10.1016/j.lungcan.2016.01.003. Epub 2016 Jan 8. Review. PubMed PMID: 26898616. 5: Song HN, Jung KS, Yoo KH, Cho J, Lee JY, Lim SH, Kim HS, Sun JM, Lee SH, Ahn JS, Park K, Choi YL, Park W, Ahn MJ. Acquired C797S Mutation upon Treatment with a T790M-Specific Third-Generation EGFR Inhibitor (HM61713) in Non-Small Cell Lung Cancer. J Thorac Oncol. 2016 Apr;11(4):e45-7. doi: 10.1016/j.jtho.2015.12.093. Epub 2015 Dec 31. PubMed PMID: 26749488. 6: Pirker R. Third-generation epidermal growth factor receptor tyrosine kinase inhibitors in advanced nonsmall cell lung cancer. Curr Opin Oncol. 2016 Mar;28(2):115-21. doi: 10.1097/CCO.0000000000000260. PubMed PMID: 26720671. 7: Ou SH, Soo RA. Dacomitinib in lung cancer: a "lost generation" EGFR tyrosine-kinase inhibitor from a bygone era? Drug Des Devel Ther. 2015 Oct 15;9:5641-53. doi: 10.2147/DDDT.S52787. eCollection 2015. Review. PubMed PMID: 26508839; PubMed Central PMCID: PMC4610796. 8: Tartarone A, Lerose R. Clinical approaches to treat patients with non-small cell lung cancer and epidermal growth factor receptor tyrosine kinase inhibitor acquired resistance. Ther Adv Respir Dis. 2015 Oct;9(5):242-50. doi: 10.1177/1753465815587820. Epub 2015 May 27. Review. PubMed PMID: 26016841. 9: Wang H, Guo R, Zhang L. [TKI Resistance for T790M Mutation]. Zhongguo Fei Ai Za Zhi. 2015 Apr;18(4):245-50. doi: 10.3779/j.issn.1009-3419.2015.04.10. Review. Chinese. PubMed PMID: 25936890. 10: Liao BC, Lin CC, Yang JC. Second and third-generation epidermal growth factor receptor tyrosine kinase inhibitors in advanced nonsmall cell lung cancer. Curr Opin Oncol. 2015 Mar;27(2):94-101. doi: 10.1097/CCO.0000000000000164. Review. PubMed PMID: 25611025. 11: Stinchcombe TE. Recent advances in the treatment of non-small cell and small cell lung cancer. F1000Prime Rep. 2014 Dec 1;6:117. doi: 10.12703/P6-117. eCollection 2014. Review. PubMed PMID: 25580271; PubMed Central PMCID: PMC4251418. 12: Steuer CE, Khuri FR, Ramalingam SS. The next generation of epidermal growth factor receptor tyrosine kinase inhibitors in the treatment of lung cancer. Cancer. 2015 Apr 15;121(8):E1-6. doi: 10.1002/cncr.29139. Epub 2014 Dec 17. Review. PubMed PMID: 25521095. 13: Peters S, Zimmermann S, Adjei AA. Oral epidermal growth factor receptor tyrosine kinase inhibitors for the treatment of non-small cell lung cancer: comparative pharmacokinetics and drug-drug interactions. Cancer Treat Rev. 2014 Sep;40(8):917-26. doi: 10.1016/j.ctrv.2014.06.010. Epub 2014 Jul 1. PubMed PMID: 25027951.