Details
Stereochemistry | ACHIRAL |
Molecular Formula | C28H30N6OS |
Molecular Weight | 498.642 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
CN1CCN(CC2=CC=C(C=C2)C(=O)NC3=CC=C(C)C(NC4=NC(=CS4)C5=CN=CC=C5)=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)
Molecular Formula | C28H30N6OS |
Molecular Weight | 498.642 |
Charge | 0 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
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.
Originator
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
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Target ID: CHEMBL1936 Sources: https://www.ncbi.nlm.nih.gov/pubmed/19789626 |
200.0 nM [IC50] | ||
Target ID: CHEMBL2007 Sources: https://www.ncbi.nlm.nih.gov/pubmed/19789626 |
540.0 nM [IC50] | ||
Target ID: CHEMBL1913 Sources: https://www.ncbi.nlm.nih.gov/pubmed/19789626 |
800.0 nM [IC50] | ||
Target ID: CHEMBL3905 Sources: https://www.ncbi.nlm.nih.gov/pubmed/19789626 |
510.0 nM [IC50] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Primary | Unknown Approved UseUnknown |
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Primary | Unknown Approved UseUnknown |
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Primary | Unknown Approved UseUnknown |
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Primary | Unknown Approved UseUnknown |
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Primary | Unknown Approved UseUnknown |
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Primary | Unknown Approved UseUnknown |
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Primary | Unknown Approved UseUnknown |
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Primary | Unknown Approved UseUnknown |
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Primary | Unknown Approved UseUnknown |
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Primary | Unknown Approved UseUnknown |
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Primary | Unknown Approved UseUnknown |
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Primary | Masivet Approved UseTreatment of non-resectable dog mast cell tumours (Grade 2 or 3) with confirmed mutated c-kit
tyrosine kinase receptor. Launch Date2008 |
PubMed
Title | Date | PubMed |
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[Gastrointestinal stromal tumors: molecular aspects and therapeutic implications]. | 2008 Jan |
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Masitinib is safe and effective for the treatment of canine mast cell tumors. | 2008 Nov-Dec |
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More about masitinib. | 2009 |
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Masitinib in the treatment of active rheumatoid arthritis: results of a multicentre, open-label, dose-ranging, phase 2a study. | 2009 |
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Masitinib, a c-kit/PDGF receptor tyrosine kinase inhibitor, improves disease control in severe corticosteroid-dependent asthmatics. | 2009 Aug |
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Pharmacokinetics of masitinib in cats. | 2009 Dec |
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Phase 1 dose-escalation study of oral tyrosine kinase inhibitor masitinib in advanced and/or metastatic solid cancers. | 2009 Sep |
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Clinically relevant advances in rheumatoid arthritis therapy. | 2009 Sep 14 |
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Masitinib (AB1010), a potent and selective tyrosine kinase inhibitor targeting KIT. | 2009 Sep 30 |
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[New drugs for small animals in 2009]. | 2010 |
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c-Fms-mediated differentiation and priming of monocyte lineage cells play a central role in autoimmune arthritis. | 2010 |
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Churg and Strauss vasculitis in the course of masitinib treatment: a first report. | 2010 Aug |
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Masitinib for the treatment of systemic and cutaneous mastocytosis with handicap: a phase 2a study. | 2010 Dec |
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Update on the treatment of gastrointestinal stromal tumors (GISTs): role of imatinib. | 2010 Feb 4 |
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Masitinib for the treatment of canine atopic dermatitis: a pilot study. | 2010 Jan |
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Safety and activity of masitinib in combination with gemcitabine in patients with advanced pancreatic cancer. | 2010 Jul |
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[Focus on GIST management]. | 2010 Jun |
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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 |
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Drug-induced minimal change nephropathy in a dog. | 2010 Mar-Apr |
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Phase II study of oral masitinib mesilate in imatinib-naïve patients with locally advanced or metastatic gastro-intestinal stromal tumour (GIST). | 2010 May |
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The complexity of the complicity of mast cells in cancer. | 2010 May |
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Evaluation of 12- and 24-month survival rates after treatment with masitinib in dogs with nonresectable mast cell tumors. | 2010 Nov |
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Activation state-dependent binding of small molecule kinase inhibitors: structural insights from biochemistry. | 2010 Nov 24 |
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Clinical trial on the efficacy of masitinib in canine IBD. | 2010 Nov 6 |
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Canine and human gastrointestinal stromal tumors display similar mutations in c-KIT exon 11. | 2010 Oct 15 |
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Comprehensive analysis of kinase inhibitor selectivity. | 2011 Oct 30 |
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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
Sources: https://clinicaltrials.gov/ct2/show/NCT01470131
6 mg/kg/day
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/19789626
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
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Record UNII |
M59NC4E26P
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Record Status |
Validated (UNII)
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Record Version |
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Official Name | English | ||
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Systematic Name | English | ||
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NCI_THESAURUS |
C1967
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EU-Orphan Drug |
EU/3/04/251
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WHO-VATC |
QL01XE22
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FDA ORPHAN DRUG |
285309
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FDA ORPHAN DRUG |
210505
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EMA ASSESSMENT REPORTS |
MASIVIERA (REFUSED: PANCREATIC NEOPLASMS)
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EU-Orphan Drug |
EU/3/05/286
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FDA ORPHAN DRUG |
201005
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EMA ASSESSMENT REPORTS |
MASICAN (REFUSED: GASTROINTESTINAL STROMAL TUMORS)
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FDA ORPHAN DRUG |
201505
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EU-Orphan Drug |
EU/3/04/251
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EU-Orphan Drug |
EU/3/04/242
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EU/3/04/251(POSITIVE)
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PRIMARY | TREATMENT OF MALIGNANT GASTROINTESTINAL STROMAL TUMOURS 20/12/2004 POSITIVE | ||
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63450
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DTXSID001000207
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100000124415
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790299-79-5
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C79910
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Masitinib
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CHEMBL1908391
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10074640
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DB11526
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C526575
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M59NC4E26P
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8779
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m7092
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PRIMARY | Merck Index | ||
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SUB32266
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Related Record | Type | Details | ||
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TARGET -> INHIBITOR | |||
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TARGET -> INHIBITOR |
INHIBITOR
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TARGET -> INHIBITOR | |||
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TARGET -> INHIBITOR | |||
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TARGET -> INHIBITOR | |||
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TRANSPORTER -> INHIBITOR |
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TARGET -> INHIBITOR | |||
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SALT/SOLVATE -> PARENT |
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ACTIVE MOIETY |