Ispinesib
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MedKoo CAT#: 201600

CAS#: 336113-53-2 (free base)

Description: Ispinesib is a synthetic small molecule, derived from quinazolinone, with antineoplastic properties. Ispinesib selectively inhibits the mitotic motor protein, kinesin spindle protein (KSP), resulting in inhibition of mitotic spindle assembly, induction of cell cycle arrest during the mitotic phase, and cell death in tumor cells that are actively dividing. Because KSP is not involved in nonmitotic processes, such as neuronal transport, ispinesib may be less likely to cause the peripheral neuropathy often associated with the tubulin-targeting agents. Check for active clinical trials or closed clinical trials using this agent. (NCI Thesaurus).

Chemical Structure

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Ispinesib
CAS# 336113-53-2 (free base)
Product data Instruction

Theoretical Analysis

MedKoo Cat#: 201600
Name: Ispinesib
CAS#: 336113-53-2 (free base)
Chemical Formula: C30H33ClN4O2
Exact Mass: 516.23
Molecular Weight: 517.070
Elemental Analysis: C, 69.69; H, 6.43; Cl, 6.86; N, 10.84; O, 6.19

Price and Availability

Size Price Availability Quantity
10mg USD 500 2 Weeks
5mg USD 290
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Related CAS #: 336113-53-2 (free base), 514820-03-2 (mesylate),

Synonym: SB715992; SB-715992; SB 715992; CK 0238273; CK-0238273; CK0238273.

IUPAC/Chemical Name: (R)-N-(3-aminopropyl)-N-(1-(3-benzyl-7-chloro-4-oxo-3,4-dihydroquinazolin-2-yl)-2-methylpropyl)-4-methylbenzamide

InChi Key: QJZRFPJCWMNVAV-HHHXNRCGSA-N

InChi Code: 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

SMILES Code: O=C(N(CCCN)[C@@H](C(N1CC2=CC=CC=C2)=NC3=C(C=CC(Cl)=C3)C1=O)C(C)C)C4=CC=C(C)C=C4

Appearance: Solid powder

Purity: >98%

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO, not in water

Shelf Life: >5 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

Product Data:
Product Data
Instruction:
View handling instruction
Biological target: Ispinesib is a specific inhibitor of kinesin spindle protein (KSP), with a Ki app of 1.7 nM.
In vitro activity: Ispinesib was effective against tumor cells in the different growth conditions. This may additionally indicate the efficacy of ispinesib against cancer stem cell population of ATRT cells growing as neurospheres in-vitro in growth factors-enriched cancer stem cell media (Figs. 4e, S7C). Tumor cell proliferation was effectively inhibited between IC50 range of 4.5 nM–527 nM on Day 7 for all 7 cell lines (Fig. S7C). Ispinesib concentration of 5 nM–1.25 µM demonstrated sustained time-dependent killing-effect on all 7 cell lines over 13 days (Fig. S7C). Reference: Sci Rep. 2021 Jun 2;11(1):11580. https://pubmed.ncbi.nlm.nih.gov/34079014/
In vivo activity: Tumor growth was significantly inhibited by 3 mg/kg of ispinesib. Furthermore, 10 mg/kg dose treatment inhibited tumor growth more markedly, demonstrating a dose‐dependent inhibitory effect of ispinesib treatment (tumor volume and tumor weight, P < .01, by Kruskal‐Wallis test). Representative images of the tumors performed in these mouse xenograft experiments are shown in Figure S3A,B. Reference: Cancer Sci. 2021 Nov;112(11):4641-4654. https://pubmed.ncbi.nlm.nih.gov/34510663/

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMF 30.0 58.02
DMSO 77.4 149.74
Ethanol 61.6 119.07
Ethanol:PBS (pH 7.2) (1:1) 0.5 0.97

Preparing Stock Solutions

The following data is based on the product molecular weight 517.070000000000000000000000000000 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol: 1. Elghetany MT, Ho JM, Shi-Qi LH, Karthik S, Su JMF, Lin Q, Du Y, Shen J, Chow WY, Lau CC, Adesina A, Major A, Erdreich-Epstein A, Hui KM, Li XN, Teo WY. Maximizing the potential of aggressive mouse tumor models in preclinical drug testing. Sci Rep. 2021 Jun 2;11(1):11580. doi: 10.1038/s41598-021-91167-6. PMID: 34079014; PMCID: PMC8172610. 2. Murase Y, Ono H, Ogawa K, Yoshioka R, Ishikawa Y, Ueda H, Akahoshi K, Ban D, Kudo A, Tanaka S, Tanabe M. Inhibitor library screening identifies ispinesib as a new potential chemotherapeutic agent for pancreatic cancers. Cancer Sci. 2021 Nov;112(11):4641-4654. doi: 10.1111/cas.15134. Epub 2021 Oct 2. PMID: 34510663; PMCID: PMC8586681. 3. Purcell JW, Davis J, Reddy M, Martin S, Samayoa K, Vo H, Thomsen K, Bean P, Kuo WL, Ziyad S, Billig J, Feiler HS, Gray JW, Wood KW, Cases S. Activity of the kinesin spindle protein inhibitor ispinesib (SB-715992) in models of breast cancer. Clin Cancer Res. 2010 Jan 15;16(2):566-76. doi: 10.1158/1078-0432.CCR-09-1498. Epub 2010 Jan 12. PMID: 20068098; PMCID: PMC2844774.
In vitro protocol: 1. Elghetany MT, Ho JM, Shi-Qi LH, Karthik S, Su JMF, Lin Q, Du Y, Shen J, Chow WY, Lau CC, Adesina A, Major A, Erdreich-Epstein A, Hui KM, Li XN, Teo WY. Maximizing the potential of aggressive mouse tumor models in preclinical drug testing. Sci Rep. 2021 Jun 2;11(1):11580. doi: 10.1038/s41598-021-91167-6. PMID: 34079014; PMCID: PMC8172610.
In vivo protocol: 1. Murase Y, Ono H, Ogawa K, Yoshioka R, Ishikawa Y, Ueda H, Akahoshi K, Ban D, Kudo A, Tanaka S, Tanabe M. Inhibitor library screening identifies ispinesib as a new potential chemotherapeutic agent for pancreatic cancers. Cancer Sci. 2021 Nov;112(11):4641-4654. doi: 10.1111/cas.15134. Epub 2021 Oct 2. PMID: 34510663; PMCID: PMC8586681. 2. Purcell JW, Davis J, Reddy M, Martin S, Samayoa K, Vo H, Thomsen K, Bean P, Kuo WL, Ziyad S, Billig J, Feiler HS, Gray JW, Wood KW, Cases S. Activity of the kinesin spindle protein inhibitor ispinesib (SB-715992) in models of breast cancer. Clin Cancer Res. 2010 Jan 15;16(2):566-76. doi: 10.1158/1078-0432.CCR-09-1498. Epub 2010 Jan 12. PMID: 20068098; PMCID: PMC2844774.

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