Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C30H33ClN4O2 |
Molecular Weight | 517.062 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 1 / 1 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
CC(C)[C@@H](N(CCCN)C(=O)C1=CC=C(C)C=C1)C2=NC3=CC(Cl)=CC=C3C(=O)N2CC4=CC=CC=C4
InChI
InChIKey=QJZRFPJCWMNVAV-HHHXNRCGSA-N
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
DescriptionSources: https://www.ncbi.nlm.nih.gov/pubmed/18290633
Sources: https://www.ncbi.nlm.nih.gov/pubmed/18290633
Ispinesib (SB-715992) is a potent, specific and reversible inhibitor of kinesin spindle protein (KSP). KSP, also known as HsEg5, is a kinesin that plays an essential role in the formation of a bipolar mitotic spindle and is required for cell cycle progression through mitosis. Ispinesib is the highly specific small-molecule inhibitor of KSP tested for the treatment of human disease. It causes mitotic arrest and growth inhibition in several human tumor cell lines and is currently being tested in multiple phase II clinical trials for treatment of the breast cancer and renal cell cancer.
Originator
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
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Target ID: CHEMBL4581 Sources: https://www.ncbi.nlm.nih.gov/pubmed/18290633 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Primary | Unknown Approved UseUnknown |
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Primary | Unknown Approved UseUnknown |
PubMed
Title | Date | PubMed |
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American Chemical Society--233rd National Meeting. Kinesin spindle protein inhibitors. 25-29 March 2007, Chicago, IL, USA. | 2007 May |
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A phase II and pharmacokinetic study of SB-715992, in patients with metastatic hepatocellular carcinoma: a study of the National Cancer Institute of Canada Clinical Trials Group (NCIC CTG IND.168). | 2008 Jun |
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Conformation-dependent ligand regulation of ATP hydrolysis by human KSP: activation of basal hydrolysis and inhibition of microtubule-stimulated hydrolysis by a single, small molecule modulator. | 2008 Jun 18 |
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A Bayesian population PK-PD model for ispinesib/docetaxel combination-induced myelosuppression. | 2009 Feb |
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KIF11 inhibition for glioblastoma treatment: reason to hope or a struggle with the brain? | 2009 Jun 22 |
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Thermodynamics of nucleotide and inhibitor binding to wild-type and ispinesib-resistant forms of human kinesin spindle protein. | 2009 Nov 24 |
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Activity of the kinesin spindle protein inhibitor ispinesib (SB-715992) in models of breast cancer. | 2010 Jan 15 |
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Discovery of (+)-N-(3-aminopropyl)-N-[1-(5-benzyl-3-methyl-4-oxo-[1,2]thiazolo[5,4-d]pyrimidin-6-yl)-2-methylpropyl]-4-methylbenzamide (AZD4877), a kinesin spindle protein inhibitor and potential anticancer agent. | 2011 Oct 13 |
Patents
Sample Use Guides
Patients receive ispinesib (SB-715992) IV over 1 hour on days 1, 8, and 15. Courses repeat every 28 days in the absence of disease progression or unacceptable toxicity.
Route of Administration:
Intravenous
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/20068098
In vitro, ispinesib at concentrations of 3.3 × 10−5 to 8.5 × 10−11 mol/L inhibited proliferation of all 53 breast cell lines tested. GI50 values spanned a 100-fold range and fall between 10 and 100 nmol/L for most cell lines. (The GI50 value is the drug concentration that results in 50% growth inhibition after 72 h of drug exposure relative to control). Ispinesib exhibited no apparent specificity for histopathologic subtype (luminal A, luminal B, basal) or receptor status (HER2, ER/PR).
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C67440
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ACTIVE MOIETY
SALT/SOLVATE (PARENT)