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Merck
CN

SML2869

Sigma-Aldrich

Ispinesib

≥98% (HPLC)

Synonym(s):

(R)-N-(3-Aminopropyl)-N-[1-(3-benzyl-7-chloro-4-oxo-3,4-dihydroquinazolin-2-yl)-2-methylpropyl]-4-methylbenzamide, CK0238273, N-(3-Aminopropyl)-N-[(1R)-1-[7-chloro-3,4-dihydro-4-oxo-3-(phenylmethyl)-2-quinazolinyl]-2-methylpropyl]-4-methylbenzamide, SB 715992, SB-715992, SB715992

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About This Item

Empirical Formula (Hill Notation):
C30H33ClN4O2
CAS Number:
336113-53-2
Molecular Weight:
517.06
MDL number:
MFCD22628831
UNSPSC Code:
12352200
NACRES:
NA.77

Key Documents

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Quality Level

100

Assay

≥98% (HPLC)

form

powder

optical activity

[α]/D +315 to +375°, c = 0.5 in chloroform-d

color

white to beige

solubility

DMSO: 2 mg/mL, clear

storage temp.

2-8°C

SMILES string

Clc1cc2nc([n]([c](c2cc1)=O)Cc4ccccc4)[C@H](N(CCCN)C(=O)c3ccc(cc3)C)C(C)C

InChI

1S/C30H33ClN4O2/c1-20(2)27(34(17-7-16-32)29(36)23-12-10-21(3)11-13-23)28-33-26-18-24(31)14-15-25(26)30(37)35(28)19-22-8-5-4-6-9-22/h4-6,8-15,18,20,27H,7,16-17,19,32H2,1-3H3/t27-/m1/s1

InChI key

QJZRFPJCWMNVAV-HHHXNRCGSA-N

Related Categories

Biochem/physiol Actions

Ispinesib (SB-715992) is a potent and highly selective kinesin spindle protein (KSP, KIF11, EG5) allosteric inhibtor that specifically inhibits microtubule (MT)-stimulated ATPase activity of KSP (Ki = 1.7 nM; 5 μM MT, 500 μM ATP, 0.75 nM human KSP), but not ubiquitous kinesin heavy chain KHC, neuronal kinesin KIF1A, or mitotic kinesins CENP-E, RabK6, MCAK, MKLP1. Ispinesib exhibits anti-cancer efficacy in cultures (GI50 = 45 nM/BT-474 & 19 nM/MDA-MB-468) and in cancer xenograft models in vivo (8 or 10 mg/kg q4d×3 ip. mice with MCF-7, HCC-1954, KPL4, BT-474 xenografts).
Potent and highly selective kinesin spindle protein (KSP, KIF11, EG5) allosteric inhibtor with in vitro and in vivo anti-cancer efficacy.

Pictograms

Skull and crossbonesHealth hazard
GHS06,GHS08

Signal Word

Danger

Hazard Statements

H300 + H330,H341

Hazard Classifications

Acute Tox. 2 Inhalation - Acute Tox. 2 Oral - Muta. 2

Storage Class Code

6.1A - Combustible acute toxic Cat. 1 and 2 / very toxic hazardous materials

WGK

WGK 3

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
0000471378
0000471378
0000174291
0000174291
0000105541

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Hung Yi Kristal Kaan et al.
The Journal of biological chemistry, 288(25), 18588-18598 (2013-05-10)
Kinesins comprise a superfamily of molecular motors that drive a wide variety of cellular physiologies, from cytoplasmic transport to formation of the bipolar spindle in mitosis. These differing roles are reflected in corresponding polymorphisms in key kinesin structural elements. One
Jasper Edgar Neggers et al.
Nature communications, 9(1), 502-502 (2018-02-07)
Unraveling the mechanism of action and molecular target of small molecules remains a major challenge in drug discovery. While many cancer drugs target genetic vulnerabilities, loss-of-function screens fail to identify essential genes in drug mechanism of action. Here, we report
Sandeep K Talapatra et al.
Journal of medicinal chemistry, 56(16), 6317-6329 (2013-07-24)
Development of drug resistance during cancer chemotherapy is one of the major causes of chemotherapeutic failure for the majority of clinical agents. The aim of this study was to investigate the underlying molecular mechanism of resistance developed by the mitotic
Geng-Yuan Chen et al.
ACS chemical biology, 12(4), 1038-1046 (2017-02-07)
To uncover their contrasting mechanisms, antimitotic drugs that inhibit Eg5 (kinesin-5) were analyzed in mixed-motor gliding assays of kinesin-1 and Eg5 motors in which Eg5 "braking" dominates motility. Loop-5 inhibitors (monastrol, STLC, ispinesib, and filanesib) increased gliding speeds, consistent with
David A Davis et al.
BMC cancer, 6, 22-22 (2006-01-26)
Kinesin spindle proteins (KSP) are motor proteins that play an essential role in mitotic spindle formation. HsEg5, a KSP, is responsible for the formation of the bipolar spindle, which is critical for proper cell division during mitosis. The function of
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