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Merck
CN

SML2158

VX-680

≥98% (HPLC)

Synonym(s):

MK 0457, MK-0457, MK0457, N-[4-[[4-(4-Methyl-1-piperazinyl)-6-[(5-methyl-1H-pyrazol-3-yl)amino]-2-pyrimidinyl]thio]phenyl]cyclopropanecarboxamide, Tozasertib, VX 680, VX680

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About This Item

Empirical Formula (Hill Notation):
C23H28N8OS
CAS Number:
639089-54-6
Molecular Weight:
464.59
MDL number:
MFCD13185152
UNSPSC Code:
12352200
NACRES:
NA.77

Key Documents

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Assay

≥98% (HPLC)

form

powder

color

white to beige

solubility

DMSO: 2 mg/mL, clear

storage temp.

2-8°C

SMILES string

O=C(C1CC1)NC(C=C2)=CC=C2SC3=NC(N4CCN(C)CC4)=CC(NC5=NNC(C)=C5)=N3

InChI

1S/C23H28N8OS/c1-15-13-20(29-28-15)25-19-14-21(31-11-9-30(2)10-12-31)27-23(26-19)33-18-7-5-17(6-8-18)24-22(32)16-3-4-16/h5-8,13-14,16H,3-4,9-12H2,1-2H3,(H,24,32)(H2,25,26,27,28,29)

InChI key

GCIKSSRWRFVXBI-UHFFFAOYSA-N

Related Categories

Biochem/physiol Actions

ATP site-targeting potent aurora kinase and Abl inhibitor with in vitro and in vivo anticancer efficacy.
VX-680 is an ATP site-targeting potent aurora kinase inhibitor (Aurara A/B/C Ki(app) = 0.6/18/4.6 nM) that affects FLT3, BCR-Abl, BCR-Abl (T315I), Lck, ITK, Src, and Fyn only at higher concentrations (Ki(app) = 30, 30, 42, 80, 220, 350, 520 nM, respectively) and exhibits little inhibitory potency toward 52 other kinases (Ki(app) >1 μM). VX-680 exhibits potent antiproliferation activity in a wide variety of cancer cultures (IC50 from 15 to 113 nM) as a result of cell cycle arrest and apoptosis induction, as well as causes tumor retardation (by 98% on day 13; 75 mg/kg b.i.d i.p.; HL-60 in mice) and regression (2 mg/kg/h 3 d/wk i.v. infusion; HCT116 in rats) in vivo. Crystallography data reveal a tight association of VX-680 with a hydrophobic pocket present only in a closed, inactive kinase conformation, which forms the basis of its selectivity profile, including its activity toward wild-type and the Imatinib-resistant (T315I) Abl.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
0000225170
0000225170
0000281616
0000281616
0000159342

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Matthew A Young et al.
Cancer research, 66(2), 1007-1014 (2006-01-21)
We present a high-resolution (2.0 A) crystal structure of the catalytic domain of a mutant form of the Abl tyrosine kinase (H396P; Abl-1a numbering) that is resistant to the Abl inhibitor imatinib. The structure is determined in complex with the
Sukumar Sarkar et al.
Molecular cancer research : MCR, 15(8), 1063-1072 (2017-05-26)
Reducing the levels of the androgen receptor (AR) is one of the most viable approaches to combat castration-resistant prostate cancer. Previously, we observed that proteasomal-dependent degradation of AR in response to 2-methoxyestradiol (2-ME) depends primarily on the E3 ligase C-terminus
Derek Lessing et al.
Proceedings of the National Academy of Sciences of the United States of America, 113(50), 14366-14371 (2017-02-10)
X-chromosome inactivation is a mechanism of dosage compensation in which one of the two X chromosomes in female mammals is transcriptionally silenced. Once established, silencing of the inactive X (Xi) is robust and difficult to reverse pharmacologically. However, the Xi
Mindy I Davis et al.
Nature biotechnology, 29(11), 1046-1051 (2011-11-01)
We tested the interaction of 72 kinase inhibitors with 442 kinases covering >80% of the human catalytic protein kinome. Our data show that, as a class, type II inhibitors are more selective than type I inhibitors, but that there are
Farid Gizatullin et al.
Cancer research, 66(15), 7668-7677 (2006-08-04)
VX-680 is a potent inhibitor of Aurora kinases that induces the accumulation of cells with > or =4N DNA content, followed by cell death. Here, we define the role of p53 and p21(Waf1/Cip1) in cell cycle perturbations following exposure to
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