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
| Molecular Formula | C30H33ClN4O2 |
| Molecular Weight | 517.062 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ABSOLUTE |
| Additional Stereochemistry | No |
| Defined Stereocenters | 1 / 1 |
| E/Z Centers | 0 |
| Optical Activity | UNSPECIFIED |
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
PubMed
| Title | Date | PubMed |
|---|---|---|
| Promising novel cytotoxic agents and combinations in metastatic prostate cancer. | 2008 Jan-Feb |
|
| 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 |
|
| Phase II study of ispinesib in recurrent or metastatic squamous cell carcinoma of the head and neck. | 2008 Jun |
|
| A University of Chicago consortium phase II trial of SB-715992 in advanced renal cell cancer. | 2008 Mar |
|
| Mechanism of inhibition of human KSP by ispinesib. | 2008 Mar 18 |
|
| Thermodynamics of nucleotide and inhibitor binding to wild-type and ispinesib-resistant forms of human kinesin spindle protein. | 2009 Nov 24 |
|
| Activity of the kinesin spindle protein inhibitor ispinesib (SB-715992) in models of breast cancer. | 2010 Jan 15 |
|
| 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, 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).
| Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Dec 15 16:29:05 UTC 2023
by
admin
on
Fri Dec 15 16:29:05 UTC 2023
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| Record UNII |
BKT5F9C2NI
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| Record Status |
Validated (UNII)
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| Record Version |
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NCI_THESAURUS |
C67440
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C508757
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6851740
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C38131
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SUB33489
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336113-53-2
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BKT5F9C2NI
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100000127443
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| Related Record | Type | Details | ||
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SALT/SOLVATE -> PARENT | |||
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TARGET -> INHIBITOR |
IC50
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ACTIVE MOIETY |
