Alectinib HCl
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MedKoo CAT#: 206629

CAS#: 1256589-74-8 (HCl)

Description: Alectinib, also known as AF802, or CH5424802 or RO5424802, is a potent, selective, and orally available ALK inhibitor with a unique chemical scaffold, showing preferential antitumor activity against cancers with gene alterations of ALK, such as nonsmall cell lung cancer (NSCLC) cells expressing EML4-ALK fusion and anaplastic large-cell lymphoma (ALCL) cells expressing NPM-ALK fusion in vitro and in vivo. Alectinib inhibited ALK L1196M, which corresponds to the gatekeeper mutation conferring common resistance to kinase inhibitors, and blocked EML4-ALK L1196M-driven cell growth. Alectinib (as HCl salt) was approved in Dec. 2015.


Price and Availability

Size
Price

25mg
USD 150
500mg
USD 950
10g
USD 5750
Size
Price

50mg
USD 250
1g
USD 1650
Size
Price

100mg
USD 450
5g
USD 3850

Alectinib HCl, purity > 98%, is in stock. The same day shipping out after order is received. Note: the estimated shipping out time for order > 200mg may be 2 weeks.


Chemical Structure

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Theoretical Analysis

MedKoo Cat#: 206629
Name: Alectinib HCl
CAS#: 1256589-74-8 (HCl)
Chemical Formula: C30H35ClN4O2
Exact Mass:
Molecular Weight: 519.086
Elemental Analysis: C, 69.42; H, 6.80; Cl, 6.83; N, 10.79; O, 6.16


Related CAS #: 1256580-46-7 (free base)   1256589-74-8 (HCl)    

Synonym: AF 802; AF-802; AF802; CH5424802; CH5424802; CH 5424802; RO5424802; RO 5424802; RO5424802, Alectinib; brand name: Alecensa

IUPAC/Chemical Name: 9-ethyl-6,6-dimethyl-8-(4-morpholinopiperidin-1-yl)-11-oxo-6,11-dihydro-5H-benzo[b]carbazole-3-carbonitrile hydrochloride

InChi Key: GYABBVHSRIHYJR-UHFFFAOYSA-N

InChi Code: InChI=1S/C30H34N4O2.ClH/c1-4-20-16-23-24(17-26(20)34-9-7-21(8-10-34)33-11-13-36-14-12-33)30(2,3)29-27(28(23)35)22-6-5-19(18-31)15-25(22)32-29;/h5-6,15-17,21,32H,4,7-14H2,1-3H3;1H

SMILES Code: N#CC1=CC2=C(C=C1)C3=C(C(C)(C)C4=CC(N5CCC(N6CCOCC6)CC5)=C(CC)C=C4C3=O)N2.[H]Cl


Technical Data

Appearance:
Solid powder

Purity:
>98% (or refer to the Certificate of Analysis)

Certificate of Analysis:

Safety Data Sheet (MSDS):

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).

Harmonized System Code:
293490


Additional Information

Related CAS#
CAS#1256580-46-7 (Alectinib free base)
CAS#1256589-74-8 (Alectinib HCl)


References

1: Ou SH, Weitz M, Jalas JR, Kelly DF, Wong V, Azada MC, Quines O, Klempner SJ. Alectinib induced CNS radiation necrosis in an ALK+NSCLC patient with a remote (7 years) history of brain radiation. Lung Cancer. 2016 Jun;96:15-8. doi: 10.1016/j.lungcan.2016.03.008. Epub 2016 Mar 26. PubMed PMID: 27133743.

2: Tchekmedyian N, Ali SM, Miller VA, Haura EB. Acquired ALK L1152R Mutation Confers Resistance to Ceritinib and Predicts Response to Alectinib. J Thorac Oncol. 2016 Apr 15. pii: S1556-0864(16)30081-8. doi: 10.1016/j.jtho.2016.03.018. [Epub ahead of print] PubMed PMID: 27091190.

3: Aikawa H, Hayashi M, Ryu S, Yamashita M, Ohtsuka N, Nishidate M, Fujiwara Y, Hamada A. Visualizing spatial distribution of alectinib in murine brain using quantitative mass spectrometry imaging. Sci Rep. 2016 Mar 30;6:23749. doi: 10.1038/srep23749. PubMed PMID: 27026287; PubMed Central PMCID: PMC4812395.

4: Dong X, Fernandez-Salas E, Li E, Wang S. Elucidation of Resistance Mechanisms to Second-Generation ALK Inhibitors Alectinib and Ceritinib in Non-Small Cell Lung Cancer Cells. Neoplasia. 2016 Mar;18(3):162-71. doi: 10.1016/j.neo.2016.02.001. PubMed PMID: 26992917; PubMed Central PMCID: PMC4796802.

5: Tanaka H, Taima K, Morimoto T, Nakamura K, Tanaka Y, Itoga M, Takanashi S, Okumura K. Dramatic response to alectinib in a patient of ALK-rearranged lung cancer with poor performance status. BMC Res Notes. 2016 Mar 17;9(1):173. doi: 10.1186/s13104-016-1983-9. PubMed PMID: 26987388; PubMed Central PMCID: PMC4794901.

6: Yoshida T, Hida T, Yatabe Y. Rapid and dramatic response to alectinib in an ALK rearranged non-small-cell lung cancer patient who are critically ill. Anticancer Drugs. 2016 Mar 2. [Epub ahead of print] PubMed PMID: 26938871.

7: Yoshimura Y, Kurasawa M, Yorozu K, Puig O, Bordogna W, Harada N. Antitumor activity of alectinib, a selective ALK inhibitor, in an ALK-positive NSCLC cell line harboring G1269A mutation : Efficacy of alectinib against ALK G1269A mutated cells. Cancer Chemother Pharmacol. 2016 Mar;77(3):623-8. doi: 10.1007/s00280-016-2977-y. Epub 2016 Feb 5. PubMed PMID: 26849637.

8: Gainor JF, Chi AS, Logan J, Hu R, Oh KS, Brastianos PK, Shih HA, Shaw AT. Alectinib Dose Escalation Reinduces Central Nervous System Responses in Patients with Anaplastic Lymphoma Kinase-Positive Non-Small Cell Lung Cancer Relapsing on Standard Dose Alectinib. J Thorac Oncol. 2016 Feb;11(2):256-60. doi: 10.1016/j.jtho.2015.10.010. Epub 2015 Dec 18. PubMed PMID: 26845119; PubMed Central PMCID: PMC4743545.

9: Takegawa N, Hayashi H, Iizuka N, Takahama T, Ueda H, Tanaka K, Takeda M, Nakagawa K. Transformation of ALK rearrangement-positive adenocarcinoma to small-cell lung cancer in association with acquired resistance to alectinib. Ann Oncol. 2016 May;27(5):953-5. doi: 10.1093/annonc/mdw032. Epub 2016 Jan 24. PubMed PMID: 26811347.

10: Pirker R, Filipits M. Alectinib in RET-rearranged non-small cell lung cancer-Another progress in precision medicine? Transl Lung Cancer Res. 2015 Dec;4(6):797-800. doi: 10.3978/j.issn.2218-6751.2015.03.08. PubMed PMID: 26798590; PubMed Central PMCID: PMC4700226.

11: Fujita S, Masago K, Katakami N, Yatabe Y. Transformation to SCLC after Treatment with the ALK Inhibitor Alectinib. J Thorac Oncol. 2016 Jan 2. pii: S1556-0864(15)00275-0. doi: 10.1016/j.jtho.2015.12.105. [Epub ahead of print] PubMed PMID: 26751586.

12: Alectinib Approved for ALK+ Lung Cancer. Cancer Discov. 2016 Feb;6(2):115. doi: 10.1158/2159-8290.CD-NB2016-001. Epub 2016 Jan 6. PubMed PMID: 26739884.

13: Isozaki H, Ichihara E, Takigawa N, Ohashi K, Ochi N, Yasugi M, Ninomiya T, Yamane H, Hotta K, Sakai K, Matsumoto K, Hosokawa S, Bessho A, Sendo T, Tanimoto M, Kiura K. Non-Small Cell Lung Cancer Cells Acquire Resistance to the ALK Inhibitor Alectinib by Activating Alternative Receptor Tyrosine Kinases. Cancer Res. 2016 Mar 15;76(6):1506-16. doi: 10.1158/0008-5472.CAN-15-1010. Epub 2015 Dec 30. PubMed PMID: 26719536.

14: Shaw AT, Gandhi L, Gadgeel S, Riely GJ, Cetnar J, West H, Camidge DR, Socinski MA, Chiappori A, Mekhail T, Chao BH, Borghaei H, Gold KA, Zeaiter A, Bordogna W, Balas B, Puig O, Henschel V, Ou SH; study investigators. Alectinib in ALK-positive, crizotinib-resistant, non-small-cell lung cancer: a single-group, multicentre, phase 2 trial. Lancet Oncol. 2016 Feb;17(2):234-42. doi: 10.1016/S1470-2045(15)00488-X. Epub 2015 Dec 19. PubMed PMID: 26708155; PubMed Central PMCID: PMC4752892.

15: Jassem J. Alectinib in crizotinib-resistant, ALK-positive NSCLC. Lancet Oncol. 2016 Feb;17(2):134-5. doi: 10.1016/S1470-2045(15)00555-0. Epub 2015 Dec 19. PubMed PMID: 26708154.

16: Tani T, Yasuda H, Hamamoto J, Kuroda A, Arai D, Ishioka K, Ohgino K, Miyawaki M, Kawada I, Naoki K, Hayashi Y, Betsuyaku T, Soejima K. Activation of EGFR Bypass Signaling by TGFα Overexpression Induces Acquired Resistance to Alectinib in ALK-Translocated Lung Cancer Cells. Mol Cancer Ther. 2016 Jan;15(1):162-71. doi: 10.1158/1535-7163.MCT-15-0084. Epub 2015 Dec 18. PubMed PMID: 26682573.

17: Miyamoto S, Ikushima S, Ono R, Awano N, Kondo K, Furuhata Y, Fukumoto K, Kumasaka T. Transformation to small-cell lung cancer as a mechanism of acquired resistance to crizotinib and alectinib. Jpn J Clin Oncol. 2016 Feb;46(2):170-3. doi: 10.1093/jjco/hyv173. Epub 2015 Nov 27. PubMed PMID: 26613679.

18: Ou SH, Ahn JS, De Petris L, Govindan R, Yang JC, Hughes B, Lena H, Moro-Sibilot D, Bearz A, Ramirez SV, Mekhail T, Spira A, Bordogna W, Balas B, Morcos PN, Monnet A, Zeaiter A, Kim DW. Alectinib in Crizotinib-Refractory ALK-Rearranged Non-Small-Cell Lung Cancer: A Phase II Global Study. J Clin Oncol. 2016 Mar 1;34(7):661-8. doi: 10.1200/JCO.2015.63.9443. Epub 2015 Nov 23. PubMed PMID: 26598747.

19: Song Z, Wang M, Zhang A. Alectinib: a novel second generation anaplastic lymphoma kinase (ALK) inhibitor for overcoming clinically-acquired resistance. Acta Pharm Sin B. 2015 Jan;5(1):34-7. doi: 10.1016/j.apsb.2014.12.007. Epub 2015 Jan 24. Review. PubMed PMID: 26579422; PubMed Central PMCID: PMC4629211.

20: Takeuchi K, Togashi Y, Kamihara Y, Fukuyama T, Yoshioka H, Inoue A, Katsuki H, Kiura K, Nakagawa K, Seto T, Maemondo M, Hida T, Harada M, Ohe Y, Nogami N, Yamamoto N, Nishio M, Tamura T. Prospective and clinical validation of ALK immunohistochemistry: results from the phase I/II study of alectinib for ALK-positive lung cancer (AF-001JP study). Ann Oncol. 2016 Jan;27(1):185-92. doi: 10.1093/annonc/mdv501. Epub 2015 Oct 20. PubMed PMID: 26487585; PubMed Central PMCID: PMC4684157.