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Details

Stereochemistry ACHIRAL
Molecular Formula C28H30N6OS
Molecular Weight 498.642
Optical Activity UNSPECIFIED
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of MASITINIB

SMILES

CN1CCN(CC2=CC=C(C=C2)C(=O)NC3=CC(NC4=NC(=CS4)C5=CN=CC=C5)=C(C)C=C3)CC1

InChI

InChIKey=WJEOLQLKVOPQFV-UHFFFAOYSA-N
InChI=1S/C28H30N6OS/c1-20-5-10-24(16-25(20)31-28-32-26(19-36-28)23-4-3-11-29-17-23)30-27(35)22-8-6-21(7-9-22)18-34-14-12-33(2)13-15-34/h3-11,16-17,19H,12-15,18H2,1-2H3,(H,30,35)(H,31,32)

HIDE SMILES / InChI

Molecular Formula C28H30N6OS
Molecular Weight 498.642
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description

Masitinib is a new orally administered tyrosine kinase inhibitor that targets mast cells and macrophages, important cells for immunity, through inhibiting a limited number of kinases. Based on its unique mechanism of action, masitinib can be developed in a large number of conditions in oncology, in inflammatory diseases, and in certain diseases of the central nervous system. In oncology due to its immunotherapy effect, masitinib can have an effect on survival, alone or in combination with chemotherapy. Through its activity on mast cells and consequently the inhibition of the activation of the inflammatory process, masitinib can have an effect on the symptoms associated with some inflammatory and central nervous system diseases and the degeneration of these diseases. AB Science is developing masitinib in multiple sclerosis and alzheimer's disease. Masitinib targets kinases, including c-Kit, PDGFR, and Lyn. It is used in the treatment of mast cell tumors in animals, specifically dogs. Since its introduction in November 2008 it has been distributed under the commercial name Masivet. It has been available in Europe since the second part of 2009. In the USA it is distributed under the name Kinavet.

CNS Activity

Originator

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Primary
Primary
Primary
Primary
Masivet
Primary
Primary
Primary
Primary
Primary
Primary
Primary
PubMed

PubMed

TitleDatePubMed
[Gastrointestinal stromal tumors: molecular aspects and therapeutic implications].
2008 Jan
Masitinib is safe and effective for the treatment of canine mast cell tumors.
2008 Nov-Dec
More about masitinib.
2009
Masitinib in the treatment of active rheumatoid arthritis: results of a multicentre, open-label, dose-ranging, phase 2a study.
2009
Masitinib, a c-kit/PDGF receptor tyrosine kinase inhibitor, improves disease control in severe corticosteroid-dependent asthmatics.
2009 Aug
Pharmacokinetics of masitinib in cats.
2009 Dec
Phase 1 dose-escalation study of oral tyrosine kinase inhibitor masitinib in advanced and/or metastatic solid cancers.
2009 Sep
Clinically relevant advances in rheumatoid arthritis therapy.
2009 Sep 14
Masitinib (AB1010), a potent and selective tyrosine kinase inhibitor targeting KIT.
2009 Sep 30
[New drugs for small animals in 2009].
2010
c-Fms-mediated differentiation and priming of monocyte lineage cells play a central role in autoimmune arthritis.
2010
Churg and Strauss vasculitis in the course of masitinib treatment: a first report.
2010 Aug
Masitinib for the treatment of systemic and cutaneous mastocytosis with handicap: a phase 2a study.
2010 Dec
Update on the treatment of gastrointestinal stromal tumors (GISTs): role of imatinib.
2010 Feb 4
Masitinib for the treatment of canine atopic dermatitis: a pilot study.
2010 Jan
"Masitinib" is safe and effective for the treatment of canine mast cell tumors.
2010 Jan-Feb
Safety and activity of masitinib in combination with gemcitabine in patients with advanced pancreatic cancer.
2010 Jul
[Focus on GIST management].
2010 Jun
Masitinib combined with standard gemcitabine chemotherapy: in vitro and in vivo studies in human pancreatic tumour cell lines and ectopic mouse model.
2010 Mar 4
Drug-induced minimal change nephropathy in a dog.
2010 Mar-Apr
Phase II study of oral masitinib mesilate in imatinib-naïve patients with locally advanced or metastatic gastro-intestinal stromal tumour (GIST).
2010 May
The complexity of the complicity of mast cells in cancer.
2010 May
Evaluation of 12- and 24-month survival rates after treatment with masitinib in dogs with nonresectable mast cell tumors.
2010 Nov
Activation state-dependent binding of small molecule kinase inhibitors: structural insights from biochemistry.
2010 Nov 24
Clinical trial on the efficacy of masitinib in canine IBD.
2010 Nov 6
Canine and human gastrointestinal stromal tumors display similar mutations in c-KIT exon 11.
2010 Oct 15
Comprehensive analysis of kinase inhibitor selectivity.
2011 Oct 30
Comprehensive assay of kinase catalytic activity reveals features of kinase inhibitor selectivity.
2011 Oct 30
A broad activity screen in support of a chemogenomic map for kinase signalling research and drug discovery.
2013 Apr 15
Patents

Sample Use Guides

In Vivo Use Guide
6 mg/kg/day
Route of Administration: Oral
In Vitro Use Guide
In Ba/F3 cells expressing human wild-type Kit, Masitinib inhibits SCF (stem cell factor)-induced cell proliferation with an IC50 of 150 nM, while the IC50 for inhibition of IL-3-stimulated proliferation is at approximately >10 µM. In Ba/F3 cells expressing PDGFRα, Masitinib inhibits PDGF-BB-stimulated proliferation and PDGFRα tyrosine phosphorylation with IC50 of 300 nM.
Substance Class Chemical
Created
by admin
on Mon Oct 21 20:18:27 UTC 2019
Edited
by admin
on Mon Oct 21 20:18:27 UTC 2019
Record UNII
M59NC4E26P
Record Status Validated (UNII)
Record Version
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Name Type Language
MASITINIB
DASH   INN   MART.   MI   WHO-DD  
INN  
Official Name English
MASITINIB [WHO-DD]
Common Name English
4-((4-METHYLPIPERAZIN-1-YL)METHYL)-N-(4-METHYL-3-((4-PYRIDIN-3-YL-1,3-THIAZOL-2-YL)AMINO)PHENYL)BENZAMIDE
Systematic Name English
MASITINIB [MI]
Common Name English
MASITINIB [INN]
Common Name English
MASITINIB [MART.]
Common Name English
KINAVET
Brand Name English
Classification Tree Code System Code
NCI_THESAURUS C1967
Created by admin on Mon Oct 21 20:18:27 UTC 2019 , Edited by admin on Mon Oct 21 20:18:27 UTC 2019
EU-Orphan Drug EU/3/04/251
Created by admin on Mon Oct 21 20:18:27 UTC 2019 , Edited by admin on Mon Oct 21 20:18:27 UTC 2019
WHO-VATC QL01XE22
Created by admin on Mon Oct 21 20:18:27 UTC 2019 , Edited by admin on Mon Oct 21 20:18:27 UTC 2019
FDA ORPHAN DRUG 210505
Created by admin on Mon Oct 21 20:18:27 UTC 2019 , Edited by admin on Mon Oct 21 20:18:27 UTC 2019
EMA ASSESSMENT REPORTS MASIVIERA (REFUSED: PANCREATIC NEOPLASMS)
Created by admin on Mon Oct 21 20:18:27 UTC 2019 , Edited by admin on Mon Oct 21 20:18:27 UTC 2019
EU-Orphan Drug EU/3/05/286
Created by admin on Mon Oct 21 20:18:27 UTC 2019 , Edited by admin on Mon Oct 21 20:18:27 UTC 2019
FDA ORPHAN DRUG 201005
Created by admin on Mon Oct 21 20:18:27 UTC 2019 , Edited by admin on Mon Oct 21 20:18:27 UTC 2019
EMA ASSESSMENT REPORTS MASICAN (REFUSED: GASTROINTESTINAL STROMAL TUMORS)
Created by admin on Mon Oct 21 20:18:27 UTC 2019 , Edited by admin on Mon Oct 21 20:18:27 UTC 2019
EU-Orphan Drug EU/3/04/251
Created by admin on Mon Oct 21 20:18:27 UTC 2019 , Edited by admin on Mon Oct 21 20:18:27 UTC 2019
EU-Orphan Drug EU/3/04/242
Created by admin on Mon Oct 21 20:18:27 UTC 2019 , Edited by admin on Mon Oct 21 20:18:27 UTC 2019
Code System Code Type Description
EU-Orphan Drug
EU/3/04/251(POSITIVE)
Created by admin on Mon Oct 21 20:18:27 UTC 2019 , Edited by admin on Mon Oct 21 20:18:27 UTC 2019
PRIMARY TREATMENT OF MALIGNANT GASTROINTESTINAL STROMAL TUMOURS 20/12/2004 POSITIVE
CAS
790299-79-5
Created by admin on Mon Oct 21 20:18:27 UTC 2019 , Edited by admin on Mon Oct 21 20:18:27 UTC 2019
PRIMARY
NCI_THESAURUS
C79910
Created by admin on Mon Oct 21 20:18:27 UTC 2019 , Edited by admin on Mon Oct 21 20:18:27 UTC 2019
PRIMARY
ChEMBL
CHEMBL1908391
Created by admin on Mon Oct 21 20:18:27 UTC 2019 , Edited by admin on Mon Oct 21 20:18:27 UTC 2019
PRIMARY
MESH
C526575
Created by admin on Mon Oct 21 20:18:27 UTC 2019 , Edited by admin on Mon Oct 21 20:18:27 UTC 2019
PRIMARY
MERCK INDEX
M7092
Created by admin on Mon Oct 21 20:18:27 UTC 2019 , Edited by admin on Mon Oct 21 20:18:27 UTC 2019
PRIMARY Merck Index
EVMPD
SUB32266
Created by admin on Mon Oct 21 20:18:27 UTC 2019 , Edited by admin on Mon Oct 21 20:18:27 UTC 2019
PRIMARY
Related Record Type Details
TARGET -> INHIBITOR
TARGET -> INHIBITOR
TARGET -> INHIBITOR
TARGET -> INHIBITOR
TRANSPORTER -> INHIBITOR
TARGET -> INHIBITOR
Kd
BINDING
TARGET -> INHIBITOR
SALT/SOLVATE -> PARENT
Related Record Type Details
ACTIVE MOIETY