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Filanesib

Filanesib structure

CAS No:
885060-09-3
Formula:
C20H22F2N4O2S
Chemical Name:
Filanesib
Synonyms:
1,3,4-Thiadiazole-3(2H)-carboxamide,2-(3-aminopropyl)-5-(2,5-difluorophenyl)-N-methoxy-N-methyl-2-phenyl-,(2S)-;(2S)-2-(3-Aminopropyl)-5-(2,5-difluorophenyl)-N-methoxy-N-methyl-2-phenyl-1,3,4-thiadiazole-3(2H)-carboxamide;Filanesib;ARRY 520;(2S)-2-(3-Aminopropyl)-5-(2,5-difluorophenyl)-N-methoxy-N-methyl-2-phenyl-1,3,4-thiadiazole-3-carboxamide
Categories:
Pharmaceutical Intermediates > Bulk Drug Intermediates

Description

Filanesib (ARRY-520) is a synthetic kinesin spindle protein (KSP) inhibitor with IC50 of 6 nM.

Filanesib is a potent Kinesin Spindle Protein (KSP) inhibitor that caused marked tumor regression in preclinical models of human solid tumors and human leukemias, often leading to durable responses.|Filanesib is a synthetic, small molecule targeting the kinesin spindle protein (KSP) with potential antineoplastic activity. Filanesib specifically inhibits KSP (kinesin-5 or Eg5), resulting in activation of the spindle assembly checkpoint, induction of cell cycle arrest during the mitotic phase, and consequently cell death in tumor cells that are actively dividing. Because KSP is not involved in postmitotic processes, such as neuronal transport, this agent does not cause the peripheral neuropathy that is often associated with tubulin-targeting agents. KSP is an ATP-dependent microtubule motor protein that is essential for the formation of bipolar spindles and the proper segregation of sister chromatids during mitosis.

Filanesib Basic Attributes

Molecular Weight：

420.4760864

Exact Mass：

420.48

UNII：

8A49OSO368

DSSTox ID：

DTXSID50237086

NCI Thesaurus Code：

C68937

Characteristics

PSA：

96.5

XLogP3：

3.27

Density：

1.3±0.1 g/cm3

Boiling Point：

511.3±60.0 °C at 760 mmHg

Flash Point：

263.0±32.9 °C

Refractive Index：

1.604

Drug Information

Drug Indication：

Investigated for use/treatment in cancer/tumors (unspecified).

Pharmacology：

This compound is a highly potent KSP inhibitor that demonstrates subnanomolar potency in both enzymatic and cellular assays and causes mitotic arrest, leading to cell death or apoptosis of the immensely proliferating cancer cells.

MeSH：

Agents that arrest cells in MITOSIS, most notably TUBULIN MODULATORS. (See all compounds classified as Antimitotic Agents.)

Mechanism of Action：

KSP has been identified as an attractive drug target against cancer. Cancer results when normal cellular processes go awry and lead to a massive, uncontrolled cell division, proliferation, and growth. Inhibitors of KSP cause mitotic arrest by preventing the formation of bipolar spindle. The monopolar spindle thus prevents the separation of centrosomes, organizes the microtubules from a single locus in the cell, and aligns the chromosomes around this locus. This compound is a highly potent KSP inhibitor that demonstrates subnanomolar potency in both enzymatic and cellular assays and causes mitotic arrest, leading to cell death or apoptosis of the immensely proliferating cancer cells.

MeSH Entry Terms：

(2S)-2-(3-aminopropyl)-5-(2,5-difluorophenyl)-N-methoxy-N-methyl-2-phenyl-1,3,4-thiadiazole-3(2H)-carboxamide

Filanesib Use and Manufacturing

(2S)-2-(3-Aminopropyl)-5-(2,5-difluorophenyl)-N-methoxy-N-methyl-2-phenyl-1,3,4-thiadiazole-3(2H)-carboxamide is a known potent kinesin spindle protein inhibitor

Computed Properties

Molecular Weight:420.5
XLogP3:3.3
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:7
Rotatable Bond Count:6
Exact Mass:420.14315345
Monoisotopic Mass:420.14315345
Topological Polar Surface Area:96.5
Heavy Atom Count:29
Complexity:605
Defined Atom Stereocenter Count:1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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