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SML2869

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
UNSPSC Code:
12352200
NACRES:
NA.77
MDL number:
MFCD22628831
Assay:
≥98% (HPLC)
Form:
powder
Quality level:
100
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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

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

signalword

Danger

Hazard Classifications

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

Storage Class

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
0000534534
0000534534
0000471378
0000471378
0000174291

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James W Purcell et al.
Clinical cancer research : an official journal of the American Association for Cancer Research, 16(2), 566-576 (2010-01-14)
Ispinesib (SB-715992) is a potent inhibitor of kinesin spindle protein, a kinesin motor protein essential for the formation of a bipolar mitotic spindle and cell cycle progression through mitosis. Clinical studies of ispinesib have shown a 9% response rate in
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
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Global Trade Item Number

SKUGTIN
SML2869-25MG04061842495030
SML2869-5MG04061842495047