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Merck
CN

SML2672

Tandutinib hydrochloride

≥98% (HPLC)

Synonym(s):

4-[6-Methoxy-7-[3-(1-piperidinyl)propoxy]-4-quinazolinyl]-N-[4-(1-methylethoxy)phenyl]-1-piperazinecarboxamide hydrochloride, CT 53518 hydrochloride, CT-53518 hydrochloride, CT53518 hydrochloride, MLN 518 hydrochloride, MLN-518 hydrochloride, MLN518 hydrochloride, N-(4-Isopropoxyphenyl)-4-(6-methoxy-7-(3-(piperidin-1-yl)propoxy)quinazolin-4-yl)piperazine-1-carboxamide hydrochloride

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About This Item

Empirical Formula (Hill Notation):
C31H42N6O4 · xHCl
CAS Number:
387867-13-2
Molecular Weight:
562.70 (free base basis)
UNSPSC Code:
12352200
NACRES:
NA.77

Key Documents

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Assay

≥98% (HPLC)

form

powder

storage condition

desiccated

color

white to beige

solubility

H2O: 2 mg/mL, clear

storage temp.

2-8°C

SMILES string

N5(CCCCC5)CCCOc1cc2ncnc(c2cc1OC)N3CCN(CC3)C(=O)Nc4ccc(cc4)OC(C)C

InChI

1S/C31H42N6O4/c1-23(2)41-25-10-8-24(9-11-25)34-31(38)37-17-15-36(16-18-37)30-26-20-28(39-3)29(21-27(26)32-22-33-30)40-19-7-14-35-12-5-4-6-13-35/h8-11,20-23H,4-7,12-19H2,1-3H3,(H,34,38)

InChI key

UXXQOJXBIDBUAC-UHFFFAOYSA-N

Related Categories

Biochem/physiol Actions

Orally active, potent βPDGFR, c-Kit, Flt3 (Flk2, Stk1) receptor tyrosine kinase inhibitor with anti-leukemia efficacy in vitro and in vivo.
Tandutinib (CT53518, MLN518) is a potent receptor tyrosine kinase inhibitor against PDGFRβ, c-Kit, Flt3 (IC50 = 0.20, 0.17, 0.22, 3.43 μM, respectively, against 8 nM PDGF-BB induced autophosphorylation of βPDGFR, βPDGFR/c-Kit, βPDGFR/Flt3, βPDGFR/CSF-1R chimera expressed in CHO cells; IC50 =30 μM against KDR, EFGR, FGFR, InsR, Abl, Src, PKA, PKC, ERK2, MEK1, MKK4/6, p38). Tandutinib prolongs the survival in murine CMML (Baf3 with Tel/βPDGFR chimera) and Flt-3/ITD AML leukemia models (60 mg/kg bid p.o.) with good oral bioavailability.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
0000076353
0000076354
0000072557

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Nimitha R Mathew et al.
Nature medicine, 24(3), 282-291 (2018-02-13)
Individuals with acute myeloid leukemia (AML) harboring an internal tandem duplication (ITD) in the gene encoding Fms-related tyrosine kinase 3 (FLT3) who relapse after allogeneic hematopoietic cell transplantation (allo-HCT) have a 1-year survival rate below 20%. We observed that sorafenib
Sivapriya Ponnurangam et al.
Molecular cancer therapeutics, 12(5), 598-609 (2013-02-22)
The c-Kit receptor can activate distinct signaling pathways including phosphoinositide 3-kinase (PI3K)/Akt and mTOR. Aberrant c-Kit activation protects cells from apoptosis and enhances invasion of colon carcinoma cells. Tandutinib is a novel quinazoline-based inhibitor of the type III receptor tyrosine
Yousef Salama et al.
Biochemical and biophysical research communications, 490(2), 209-216 (2017-06-12)
Thymic regeneration is a crucial function that allows for the generation of mature T cells after myelosuppression like irradiation. However molecular drivers involved in this process remain undefined. Here, we report that the angiogenic factor, epidermal growth factor-like domain 7
Louise M Kelly et al.
Cancer cell, 1(5), 421-432 (2002-07-19)
Up to 30% of acute myelogenous leukemia (AML) patients harbor an activating internal tandem duplication (ITD) within the juxtamembrane domain of the FLT3 receptor, suggesting that it may be a target for kinase inhibitor therapy. For this purpose we have
Anjali Pandey et al.
Journal of medicinal chemistry, 45(17), 3772-3793 (2002-08-09)
We have previously found that the 4-[4-(N-substituted carbamoyl)-1-piperazinyl]-6,7-dimethoxyquinazolines can function as potent and selective inhibitors of platelet-derived growth factor receptor (PDGFR) phosphorylation. A series of highly potent, specific, orally active, small molecule kinase inhibitors directed against members of PDGFR receptor
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