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
• 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

Properties

• Quality Segment: 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

Description

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 (K_i = 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.

Safety Information

• pictograms: GHS06,GHS08
• signalword: Danger
• hcodes: H300 + H330,H341
• pcodes: P202 - P260 - P264 - P271 - P280 - P304 + P340 + P310
• 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