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ChemicalBook--->CAS DataBase List--->1802220-02-5

1802220-02-5

1802220-02-5 Structure

1802220-02-5 Structure
IdentificationBack Directory
[Name]

TPX-0005
[CAS]

1802220-02-5
[Synonyms]

CS-2479
TPX-005
TPX-0005
Repotrectinib
Ropotrectinib
Repotrectinib(TPX-005)
Repotrectinib,TPX-0005
TPX0005(Ropotrectinib)
Ropotrectinib(TPX0005)
TPX-0005,Repotrectinib
TPX-0005;TPX 0005;TPX0005
1,15-Etheno-1H-pyrazolo[4,3-f][1,4,8,10]benzoxatriazacyclotridecin-4(5H)-one,11-fluoro-6,7,13,14-tetrahydro-7,13-dimethyl-, (7S,13R)-
[EINECS(EC#)]

125-417-3
[Molecular Formula]

C18H18FN5O2
[MDL Number]

MFCD31544350
[MOL File]

1802220-02-5.mol
[Molecular Weight]

355.37
Chemical PropertiesBack Directory
[density ]

1.46±0.1 g/cm3(Predicted)
[storage temp. ]

Store at -20°C
[solubility ]

DMSO:35.0(Max Conc. mg/mL);98.5(Max Conc. mM)
Ethanol:10.0(Max Conc. mg/mL);28.1(Max Conc. mM)
[form ]

A crystalline solid
[pka]

10.79±0.60(Predicted)
[color ]

White to off-white
[InChI]

InChI=1S/C18H18FN5O2/c1-10-8-20-18(25)14-9-21-24-6-5-16(23-17(14)24)22-11(2)13-7-12(19)3-4-15(13)26-10/h3-7,9-11H,8H2,1-2H3,(H,20,25)(H,22,23)/t10-,11+/m0/s1
[InChIKey]

FIKPXCOQUIZNHB-WDEREUQCSA-N
[SMILES]

O1C2=CC=C(F)C=C2[C@@H](C)NC2C=CN3C(N=2)=C(C=N3)C(=O)NC[C@@H]1C
Safety DataBack Directory
[Symbol(GHS) ]


GHS07
[Signal word ]

Warning
[Hazard statements ]

H302-H315-H319-H335
[Precautionary statements ]

P261-P305+P351+P338
Hazard InformationBack Directory
[Description]

Ropotrectinib (TPX-0005; TP Therapeutics, San Diego, CA, USA) is a nextgeneration ROS1 inhibitor, a novel three-dimensional macrocyle with a much smaller size (MW <370) than current ROS1 inhibitors. It was specifically designed to overcome resistance mutations. Preclinical studies have shown activity against gatekeeper and solvent mutations, including G2032R, D2033N, L2026M, S1986F/Y, L1951R, and kinases involved in bypass signaling such as focal adhesion kinase, SRC proto-oncogene, and non-receptor tyrosine kinase [102, 103].
[General Description]

Class: receptor tyrosine kinase; Treatment: NSCLC; Other name: TPX-0005
[Biological Activity]

Repotrectinib is a potent inhibitor targeting solvent-front mutations (SFMs) of ROS1, pan-TRK, and ALK. It effectively inhibits the kinase activity of wild-type ROS1, TRKA-C, and ALK, along with their SFMs, with IC50 values ranging from 0.071 to 4.46 nM. The compound shows high potency against ROS1 and TRKA-C, with approximately 15-fold selectivity over ALK.
[Clinical Use]

Repotrectinib has advantage with central nervous system (CNS) penetration, aimed to target both wide-type (WT) and solvent-front mutations (SFM) kinases and other resistance mutations including ROS1-G2032R and ROS1-D2033N, TRKA-G595R, TRKB-G639R, TRKC-G623R, and ALK-G1202R.
[target]

Primary targets: NTRK, ROS, ALT
Questions And AnswerBack Directory
[Binding Mode]

The cocrystal structures of repotrectinib with TRK proteins are yet to be reported. However, a docking model with TRKA suggests that the pyrazole nitrogen forms hydrogen bonds with Met592 in the hinge area. The fluorophenyl group, positioned in a hydrophobic pocket, aligns perpendicularly to the macrocycle, and the lactam oxygen atom engages in a water-mediated hydrogen bond with Met592 in the hinge region (Figs. 1,2).
Figure 1. Docking of repotrectinib with TRKA.Figure 2. Putative interactions of repotrectinib–TRKA.
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