Filanesib

This drug entry is a stub and has not been fully annotated. It is scheduled to be annotated soon.

Identification

Generic Name
Filanesib
DrugBank Accession Number
DB06040
Background

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.

Type
Small Molecule
Groups
Investigational
Structure
Thumb
Weight
Average: 420.48
Monoisotopic: 420.143153464
Chemical Formula
C20H22F2N4O2S
Synonyms
  • Filanesib
External IDs
  • ARRY-520

Pharmacology

Indication

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

Pharmacology
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Contraindications & Blackbox Warnings
Contraindications
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Pharmacodynamics

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.

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.

TargetActionsOrganism
UKinesin-like protein KIF11Not AvailableHumans
Absorption

Not Available

Volume of distribution

Not Available

Protein binding

Not Available

Metabolism
Not Available
Route of elimination

Not Available

Half-life

Not Available

Clearance

Not Available

Adverse Effects
Adverseeffects
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Toxicity

Not Available

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
Darbepoetin alfaThe risk or severity of Thrombosis can be increased when Darbepoetin alfa is combined with Filanesib.
ErythropoietinThe risk or severity of Thrombosis can be increased when Erythropoietin is combined with Filanesib.
Methoxy polyethylene glycol-epoetin betaThe risk or severity of Thrombosis can be increased when Methoxy polyethylene glycol-epoetin beta is combined with Filanesib.
PeginesatideThe risk or severity of Thrombosis can be increased when Peginesatide is combined with Filanesib.
Interactions
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Food Interactions
Not Available

Products

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Product Ingredients
IngredientUNIICASInChI Key
Filanesib HydrochlorideN98S79PF2I1385020-40-5CTAIFVHCDONNPS-BDQAORGHSA-N

Categories

Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as phenylbutylamines. These are compounds containing a phenylbutylamine moiety, which consists of a phenyl group substituted at the fourth carbon by an butan-1-amine.
Kingdom
Organic compounds
Super Class
Benzenoids
Class
Benzene and substituted derivatives
Sub Class
Phenylbutylamines
Direct Parent
Phenylbutylamines
Alternative Parents
Fluorobenzenes / Aralkylamines / Aryl fluorides / Thiadiazolines / Semicarbazides / Azacyclic compounds / Organofluorides / Organic oxides / Monoalkylamines / Hydrocarbon derivatives
show 1 more
Substituents
Amine / Aralkylamine / Aromatic heteromonocyclic compound / Aryl fluoride / Aryl halide / Azacycle / Carbonyl group / Fluorobenzene / Halobenzene / Hydrocarbon derivative
show 13 more
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
Not Available
Affected organisms
Not Available

Chemical Identifiers

UNII
8A49OSO368
CAS number
885060-09-3
InChI Key
LLXISKGBWFTGEI-FQEVSTJZSA-N
InChI
InChI=1S/C20H22F2N4O2S/c1-25(28-2)19(27)26-20(11-6-12-23,14-7-4-3-5-8-14)29-18(24-26)16-13-15(21)9-10-17(16)22/h3-5,7-10,13H,6,11-12,23H2,1-2H3/t20-/m0/s1
IUPAC Name
(2S)-2-(3-aminopropyl)-5-(2,5-difluorophenyl)-N-methoxy-N-methyl-2-phenyl-2,3-dihydro-1,3,4-thiadiazole-3-carboxamide
SMILES
CON(C)C(=O)N1N=C(S[C@@]1(CCCN)C1=CC=CC=C1)C1=CC(F)=CC=C1F

References

General References
  1. Bayes M, Rabasseda X, Prous JR: Gateways to clinical trials. Methods Find Exp Clin Pharmacol. 2007 Nov;29(9):625-55. [Article]
ChemSpider
25069697
BindingDB
50431893
ChEMBL
CHEMBL2347655
ZINC
ZINC000043204022
PDBe Ligand
GCE
Wikipedia
Filanesib
PDB Entries
6hkx / 6hky

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
2CompletedTreatmentAdvanced Multiple Myeloma2
1CompletedTreatmentLeukemia, Plasma Cell / Recurrent Plasma Cell Myeloma / Refractory Plasma Cell Myeloma1
1CompletedTreatmentMultiple Myeloma, Plasma Cell Leukemia1
1CompletedTreatmentSolid Tumors, Advanced Solid Tumors1
1, 2CompletedTreatmentAcute Myeloid Leukemia (AML) / Advanced MDS1
1, 2CompletedTreatmentLeukemia, Plasma Cell / Multiple Myeloma (MM)1
1, 2CompletedTreatmentMultiple Myeloma (MM)1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.0045 mg/mLALOGPS
logP3.31ALOGPS
logP4.08ChemAxon
logS-5ALOGPS
pKa (Strongest Basic)9.9ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area71.16 Å2ChemAxon
Rotatable Bond Count6ChemAxon
Refractivity109.66 m3·mol-1ChemAxon
Polarizability42.09 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted ADMET Features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Targets

Drugtargets2
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Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Protein kinase binding
Specific Function
Motor protein required for establishing a bipolar spindle. Blocking of KIF11 prevents centrosome migration and arrest cells in mitosis with monoastral microtubule arrays.
Gene Name
KIF11
Uniprot ID
P52732
Uniprot Name
Kinesin-like protein KIF11
Molecular Weight
119158.025 Da
References
  1. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [Article]

Drug created on November 18, 2007 18:29 / Updated on February 21, 2021 18:51