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Entrectinib

CAT: 0013-GTR19163650-03Size: 1 gDry Ice: NoHazardous: No
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Description
Entrectinib (NMS-E628, RXDX-101, NMS-01191372) is a potent, ATP-competitive, orally available pan-TRK, ROS1 and ALK inhibitor with IC50 of 1/3/5/12/7 nM for TRKA/TRKB/TRKC/ALK/ROS1, respectively; exhibits high antiproliferative activity against colorectal carcinoma cell line KM12 with IC50 of 17 nM, abolishes autophosphorylation of TPM3-TRKA, concomitant with complete inhibition of the phosphorylation of PLCγ1, AKT, and MAPK; induces regression in relevant human xenograft tumors, including the TRKA-dependent colorectal carcinoma KM12, ROS1-driven tumors, and several ALK-dependent models.Lung Cancer Phase 2 Clinical (In Vitro) :Entrectinib (NMS-E628) is found to be exquisitely active in inhibiting the proliferation of a limited number of cell lines: the TRKA-driven colorectal carcinoma cell line KM12 (IC50 of 17 nM), the ALK-dependent ALCL cell lines SU-DHL-1, Karpas-299, SUP-M2 and SR-786 (IC50 of 20, 31, 41, and 81 nM, respectively), the ALK-dependent NSCLC cell line NCI-H2228 (IC50 of 68 nM) and the FLT3-dependent AML cell line MV-4-11 (IC50 of 81 nM) . Entrectinib potently blocks proliferation of Ba/F3-TEL-TRKB (IC50 of 2.9 nM), Ba/F3-TEL-TRKC (IC50 of 3.3 nM), and Ba/F3-TEL-ROS1 (IC50 of 5.3 nM) cells, with a high degree of selectivity versus parental Ba/F3 cells or those transformed by nontargeted kinases such as ABL and RET, which are inhibited with IC50s in the range of 2 to 3 μM. Entrectinib significantly inhibits the growth of TrkB-expressing NB cells in vitro, and it significantly enhances the growth inhibition of Irino-TMZ when used in combination. (In Vivo) :Oral administration of entrectinib to tumor-bearing mice induces regression in relevant human xenograft tumors, including the TRKA-dependent colorectal carcinoma KM12, ROS1-driven tumors, and several ALK-dependent models of different tissue origins, including a model of brain-localized lung cancer metastasis. Single agent therapy results in significant tumor growth inhibition in animals treated with entrectinib compared to control animals.
CAS Number
1108743-60-7
Product Name Alternative
NMS-E628 | RXDX-101 | NMS-01191372
Field of Research
Pharmacology & Drug Discovery
Purity
>98% (HPLC)
Solubility
DMSO: ≥ 31 mg/mL
Smiles
O=C (NC1=NNC2=C1C=C (CC3=CC (F) =CC (F) =C3) C=C2) C4=CC=C (N5CCN (C) CC5) C=C4NC6CCOCC6
Molecular Formula
C31H34F2N6O2
Molecular Weight
560.6375
Storage Conditions
Storage temperature: -20°C. Stability: ≥ 2 years
Notes
For research use only.
Other Product Names
Benzamide, N-[5-[ (3,5-difluorophenyl) methyl]-1H-indazol-3-yl]-4- (4-methyl-1-piperazinyl) -2-[ (tetrahydro-2H-pyran-4-yl) amino]-

Chemical Information

Entrectinib

Entrectinib is a member of the class of indazoles that is 1H-indazole substituted by [4-(4-methylpiperazin-1-yl)-2-(tetrahydro-2H-pyran-4-ylamino)benzoyl]amino and 3,5-difluorobenzyl groups at positions 3 and 5, respectively. It is a potent inhibitor of TRKA, TRKB, TRKC, ROS1, and ALK (IC50 values of 0.1 to 1.7 nM), and used for the treatment of NTRK, ROS1 and ALK gene fusion-positive solid tumours. It has a role as an antibacterial agent, an antineoplastic agent, an EC 2.7.10.1 (receptor protein-tyrosine kinase) inhibitor and an apoptosis inducer. It is a secondary carboxamide, a member of benzamides, a difluorobenzene, a member of indazoles, a N-methylpiperazine, a member of oxanes and a secondary amino compound.

CAS Number1108743-60-7
PubChem CID25141092
IUPAC NameN-[5-[(3,5-difluorophenyl)methyl]-1H-indazol-3-yl]-4-(4-methylpiperazin-1-yl)-2-(oxan-4-ylamino)benzamide
Molecular FormulaC31H34F2N6O2
Molecular Weight560.6
XLogP5.7
Topological Polar Surface Area85.5
Hydrogen Bond Donor Count3
Hydrogen Bond Acceptor Count8
Rotatable Bond Count7
Heavy Atom Count41
Formal Charge0
Complexity846
SMILES
CN1CCN(CC1)C2=CC(=C(C=C2)C(=O)NC3=NNC4=C3C=C(C=C4)CC5=CC(=CC(=C5)F)F)NC6CCOCC6
InChI
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)
InChIKey
HAYYBYPASCDWEQ-UHFFFAOYSA-N
Chemical Structure
2D Structure
2D structure of Entrectinib
CAS: 1108743-60-7
CID: 25141092
Formula: C31H34F2N6O2
MW: 560.6
Interactive 3D Structure
Loading 3D structure...
View on PubChemRaw 3D data
Computed Properties
PropertyValue
Molecular Weight560.6
XLogP35.7
Hydrogen Bond Donor Count3
Hydrogen Bond Acceptor Count8
Rotatable Bond Count7
Exact Mass560.27113067
Monoisotopic Mass560.27113067
Topological Polar Surface Area85.5 Ų
Heavy Atom Count41
Formal Charge0
Complexity846
Isotope Atom Count0
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently-Bonded Unit Count1
Compound Is CanonicalizedYes

Alternative Products

CatalogName
S7998-5mgEntrectinib

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