Entrectinib
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MedKoo CAT#: 206181

CAS#: 1108743-60-7

Description: Entrectinib, also known as RXDX-101 and NMS-E628, is an oral small molecule inhibitor of TrkA, TrkB and TrkC, as well as ROS1 and ALK, with high potency and selectivity. RXDX-101 has demonstrated potent pharmacological activity in preclinical studies and has the potential to be first-in-class against the Trk family of kinases. PXDX-101 has been well tolerated in patients with advanced solid tumors. PXDX-101 is currently in clinical trials, and is being developed by Ignyta.


Price and Availability

Size Price Shipping out time Quantity
50mg USD 150 Same day
100mg USD 250 Same day
200mg USD 450 Same day
500mg USD 950 Same day
1g USD 1750 Same day
2g USD 3250 Same day
5g USD 5250 Same day
10g USD 8950 2 weeks
Inquire bulk and customized quantity

Pricing updated 2020-06-02. Prices are subject to change without notice.

Entrectinib, purity > 98%, is in stock. The same day shipping out after order is received.


Chemical Structure

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Theoretical Analysis

MedKoo Cat#: 206181
Name: Entrectinib
CAS#: 1108743-60-7
Chemical Formula: C31H34F2N6O2
Exact Mass: 560.27113
Molecular Weight: 560.64
Elemental Analysis: C, 66.41; H, 6.11; F, 6.78; N, 14.99; O, 5.71


Synonym: RXDX101; RXDX 101; RXDX-101; NMS E628; NMSE628; NMS-E628; Entrectinib

IUPAC/Chemical Name: N-(5-(3,5-difluorobenzyl)-1H-indazol-3-yl)-4-(4-methylpiperazin-1-yl)-2-((tetrahydro-2H-pyran-4-yl)amino)benzamide

InChi Key: HAYYBYPASCDWEQ-UHFFFAOYSA-N

InChi Code: InChI=1S/C31H34F2N6O2/c1-38-8-10-39(11-9-38)25-3-4-26(29(19-25)34-24-6-12-41-13-7-24)31(40)35-30-27-17-20(2-5-28(27)36-37-30)14-21-15-22(32)18-23(33)16-21/h2-5,15-19,24,34H,6-14H2,1H3,(H2,35,36,37,40)

SMILES Code: O=C(NC1=NNC2=C1C=C(CC3=CC(F)=CC(F)=C3)C=C2)C4=CC=C(N5CCN(C)CC5)C=C4NC6CCOCC6


Technical Data

Appearance:
Solid powder

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

Certificate of Analysis:

Safety Data Sheet (SDS):

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


Additional Information

  
 
 
 


References

  1: Facchinetti F, Friboulet L. Profile of entrectinib and its potential in the treatment of ROS1-positive NSCLC: evidence to date. Lung Cancer (Auckl). 2019 Sep 9;10:87-94. doi: 10.2147/LCTT.S190786. eCollection 2019. PubMed PMID: 31572036; PubMed Central PMCID: PMC6747675.

2: Entrectinib OK'd for Cancers with NTRK Fusions, NSCLC. Cancer Discov. 2019 Oct;9(10):OF2. doi: 10.1158/2159-8290.CD-NB2019-101. Epub 2019 Aug 30. PubMed PMID: 31471291.

3: Menichincheri M, Ardini E, Magnaghi P, Avanzi N, Banfi P, Bossi R, Buffa L, Canevari G, Ceriani L, Colombo M, Corti L, Donati D, Fasolini M, Felder E, Fiorelli C, Fiorentini F, Galvani A, Isacchi A, Borgia AL, Marchionni C, Nesi M, Orrenius C, Panzeri A, Pesenti E, Rusconi L, Saccardo MB, Vanotti E, Perrone E, Orsini P. Correction to Discovery of Entrectinib: A New 3-Aminoindazole as a Potent Anaplastic Lymphoma Kinase (ALK), c-ros Oncogene 1 Kinase (ROS1), and Pan-Tropomyosin Receptor Kinases (Pan-TRKs) inhibitor. J Med Chem. 2019 Sep 12;62(17):8364. doi: 10.1021/acs.jmedchem.9b01259. Epub 2019 Aug 19. PubMed PMID: 31424209.

4: Al-Salama ZT, Keam SJ. Entrectinib: First Global Approval. Drugs. 2019 Sep;79(13):1477-1483. doi: 10.1007/s40265-019-01177-y. Review. PubMed PMID: 31372957.

5: Ku BM, Bae YH, Lee KY, Sun JM, Lee SH, Ahn JS, Park K, Ahn MJ. Entrectinib resistance mechanisms in ROS1-rearranged non-small cell lung cancer. Invest New Drugs. 2019 May 24. doi: 10.1007/s10637-019-00795-3. [Epub ahead of print] PubMed PMID: 31124056.

6: Entrectinib Shows Pediatric Potential. Cancer Discov. 2019 Jul;9(7):OF4. doi: 10.1158/2159-8290.CD-NB2019-060. Epub 2019 May 21. PubMed PMID: 31113803.

7: Wang Q, Fang P, Zheng L, Ye L. Quantification and pharmacokinetic study of entrectinib in rat plasma using ultra-performance liquid chromatography tandem mass spectrometry. Biomed Chromatogr. 2019 Apr;33(4):e4467. doi: 10.1002/bmc.4467. Epub 2019 Jan 7. PubMed PMID: 30549079.

8: Entrectinib Effective across NTRK Fusion-Positive Cancers. Cancer Discov. 2019 Jan;9(1):OF4. doi: 10.1158/2159-8290.CD-NB2018-156. Epub 2018 Nov 27. PubMed PMID: 30482804.

9: Pacenta HL, Macy ME. Entrectinib and other ALK/TRK inhibitors for the treatment of neuroblastoma. Drug Des Devel Ther. 2018 Oct 23;12:3549-3561. doi: 10.2147/DDDT.S147384. eCollection 2018. Review. PubMed PMID: 30425456; PubMed Central PMCID: PMC6204873.

10: Attwa MW, Kadi AA, Alrabiah H, Darwish HW. LC-MS/MS reveals the formation of iminium and quinone methide reactive intermediates in entrectinib metabolism: In vivo and in vitro metabolic investigation. J Pharm Biomed Anal. 2018 Oct 25;160:19-30. doi: 10.1016/j.jpba.2018.07.032. Epub 2018 Jul 22. PubMed PMID: 30055343.

11: Liu D, Offin M, Harnicar S, Li BT, Drilon A. Entrectinib: an orally available, selective tyrosine kinase inhibitor for the treatment of NTRK, ROS1, and ALK fusion-positive solid tumors. Ther Clin Risk Manag. 2018 Jul 20;14:1247-1252. doi: 10.2147/TCRM.S147381. eCollection 2018. Review. PubMed PMID: 30050303; PubMed Central PMCID: PMC6055893.

12: Attwa MW, Darwish HW, Alhazmi HA, Kadi AA. Investigation of metabolic degradation of new ALK inhibitor: Entrectinib by LC-MS/MS. Clin Chim Acta. 2018 Oct;485:298-304. doi: 10.1016/j.cca.2018.07.009. Epub 2018 Jul 10. PubMed PMID: 30006284.

13: Nishiyama A, Yamada T, Kita K, Wang R, Arai S, Fukuda K, Tanimoto A, Takeuchi S, Tange S, Tajima A, Furuya N, Kinoshita T, Yano S. Foretinib Overcomes Entrectinib Resistance Associated with the NTRK1 G667C Mutation in NTRK1 Fusion-Positive Tumor Cells in a Brain Metastasis Model. Clin Cancer Res. 2018 May 15;24(10):2357-2369. doi: 10.1158/1078-0432.CCR-17-1623. Epub 2018 Feb 20. PubMed PMID: 29463555.

14: Ambati SR, Slotkin EK, Chow-Maneval E, Basu EM. Entrectinib in Two Pediatric Patients With Inflammatory Myofibroblastic Tumors Harboring ROS1 or ALK Gene Fusions. JCO Precis Oncol. 2018;2018. pii: https://ascopubs.org/doi/10.1200/PO.18.00095. Epub 2018 Sep 13. PubMed PMID: 31763577.

15: Smith KM, Fagan PC, Pomari E, Germano G, Frasson C, Walsh C, Silverman I, Bonvini P, Li G. Antitumor Activity of Entrectinib, a Pan-TRK, ROS1, and ALK Inhibitor, in ETV6-NTRK3-Positive Acute Myeloid Leukemia. Mol Cancer Ther. 2018 Feb;17(2):455-463. doi: 10.1158/1535-7163.MCT-17-0419. Epub 2017 Dec 13. PubMed PMID: 29237803.

16: Sigal D, Tartar M, Xavier M, Bao F, Foley P, Luo D, Christiansen J, Hornby Z, Maneval EC, Multani P. Activity of Entrectinib in a Patient With the First Reported NTRK Fusion in Neuroendocrine Cancer. J Natl Compr Canc Netw. 2017 Nov;15(11):1317-1322. doi: 10.6004/jnccn.2017.7029. PubMed PMID: 29118225.

17: Drilon A, Siena S, Ou SI, Patel M, Ahn MJ, Lee J, Bauer TM, Farago AF, Wheler JJ, Liu SV, Doebele R, Giannetta L, Cerea G, Marrapese G, Schirru M, Amatu A, Bencardino K, Palmeri L, Sartore-Bianchi A, Vanzulli A, Cresta S, Damian S, Duca M, Ardini E, Li G, Christiansen J, Kowalski K, Johnson AD, Patel R, Luo D, Chow-Maneval E, Hornby Z, Multani PS, Shaw AT, De Braud FG. Safety and Antitumor Activity of the Multitargeted Pan-TRK, ROS1, and ALK Inhibitor Entrectinib: Combined Results from Two Phase I Trials (ALKA-372-001 and STARTRK-1). Cancer Discov. 2017 Apr;7(4):400-409. doi: 10.1158/2159-8290.CD-16-1237. Epub 2017 Feb 9. PubMed PMID: 28183697; PubMed Central PMCID: PMC5380583.

18: Menichincheri M, Ardini E, Magnaghi P, Avanzi N, Banfi P, Bossi R, Buffa L, Canevari G, Ceriani L, Colombo M, Corti L, Donati D, Fasolini M, Felder E, Fiorelli C, Fiorentini F, Galvani A, Isacchi A, Borgia AL, Marchionni C, Nesi M, Orrenius C, Panzeri A, Pesenti E, Rusconi L, Saccardo MB, Vanotti E, Perrone E, Orsini P. Discovery of Entrectinib: A New 3-Aminoindazole As a Potent Anaplastic Lymphoma Kinase (ALK), c-ros Oncogene 1 Kinase (ROS1), and Pan-Tropomyosin Receptor Kinases (Pan-TRKs) inhibitor. J Med Chem. 2016 Apr 14;59(7):3392-408. doi: 10.1021/acs.jmedchem.6b00064. Epub 2016 Mar 30. Erratum in: J Med Chem. 2019 Sep 12;62(17):8364. PubMed PMID: 27003761.

19: Ardini E, Menichincheri M, Banfi P, Bosotti R, De Ponti C, Pulci R, Ballinari D, Ciomei M, Texido G, Degrassi A, Avanzi N, Amboldi N, Saccardo MB, Casero D, Orsini P, Bandiera T, Mologni L, Anderson D, Wei G, Harris J, Vernier JM, Li G, Felder E, Donati D, Isacchi A, Pesenti E, Magnaghi P, Galvani A. Entrectinib, a Pan-TRK, ROS1, and ALK Inhibitor with Activity in Multiple Molecularly Defined Cancer Indications. Mol Cancer Ther. 2016 Apr;15(4):628-39. doi: 10.1158/1535-7163.MCT-15-0758. Epub 2016 Mar 3. PubMed PMID: 26939704.

20: Drilon A, Li G, Dogan S, Gounder M, Shen R, Arcila M, Wang L, Hyman DM, Hechtman J, Wei G, Cam NR, Christiansen J, Luo D, Maneval EC, Bauer T, Patel M, Liu SV, Ou SH, Farago A, Shaw A, Shoemaker RF, Lim J, Hornby Z, Multani P, Ladanyi M, Berger M, Katabi N, Ghossein R, Ho AL. What hides behind the MASC: clinical response and acquired resistance to entrectinib after ETV6-NTRK3 identification in a mammary analogue secretory carcinoma (MASC). Ann Oncol. 2016 May;27(5):920-6. doi: 10.1093/annonc/mdw042. Epub 2016 Feb 15. PubMed PMID: 26884591; PubMed Central PMCID: PMC4843186.