Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C30H33ClN4O2.CH4O3S |
| Molecular Weight | 613.167 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 1 / 1 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
CS(O)(=O)=O.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=MRKSDPIHUJSKRA-HZPIKELBSA-N
InChI=1S/C30H33ClN4O2.CH4O3S/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;1-5(2,3)4/h4-6,8-15,18,20,27H,7,16-17,19,32H2,1-3H3;1H3,(H,2,3,4)/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 |
| Molecular Formula | CH4O3S |
| Molecular Weight | 96.106 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
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 |
|---|---|---|
| American Chemical Society--233rd National Meeting. Kinesin spindle protein inhibitors. 25-29 March 2007, Chicago, IL, USA. | 2007 May |
|
| ATP-competitive inhibitors of the mitotic kinesin KSP that function via an allosteric mechanism. | 2007 Nov |
|
| 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 |
|
| Initial testing (stage 1) of the kinesin spindle protein inhibitor ispinesib by the pediatric preclinical testing program. | 2009 Dec 15 |
|
| Functional characterisation and drug target validation of a mitotic kinesin-13 in Trypanosoma brucei. | 2010 Aug 19 |
|
| Activity of the kinesin spindle protein inhibitor ispinesib (SB-715992) in models of breast cancer. | 2010 Jan 15 |
|
| Novel benzimidazole inhibitors bind to a unique site in the kinesin spindle protein motor domain. | 2010 Sep 28 |
|
| 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 15:52:35 UTC 2023
by
admin
on
Fri Dec 15 15:52:35 UTC 2023
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| Record UNII |
R6ZMD4UH3D
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| Record Status |
Validated (UNII)
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C67440
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