NAV

Masitinib

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

Identification

Generic Name
Masitinib
DrugBank Accession Number
DB11526
Background

Masitinib is a tyrosine-kinase inhibitor used in the treatment of mast cell tumors in dogs. It has been available in Europe since 2009, under the brand name Masivet. In the USA it is distributed under the name Kinavet and has been available for veterinaries since 2011.

Type
Small Molecule
Groups
Investigational, Vet approved
Structure
3D
Similar Structures
Weight
Average: 498.65
Monoisotopic: 498.220180784
Chemical Formula
C28H30N6OS
Synonyms
  • 4-((4-METHYLPIPERAZIN-1-YL)METHYL)-N-(4-METHYL-3-((4-PYRIDIN-3-YL-1,3-THIAZOL-2-YL)AMINO)PHENYL)BENZAMIDE
  • Masitinib
External IDs
  • AB 1010
  • AB-1010
  • AB1010
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Pharmacology

Indication

Not Available

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Contraindications & Blackbox Warnings
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Pharmacodynamics

Not Available

Mechanism of action
Not Available
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
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Toxicity

Not Available

Pathways
Not Available
Pharmacogenomic Effects/ADRs Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">
Not Available

Interactions

Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">
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.
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AmbroxolThe risk or severity of methemoglobinemia can be increased when Masitinib is combined with Ambroxol.
ArticaineThe risk or severity of methemoglobinemia can be increased when Masitinib is combined with Articaine.
BenzocaineThe risk or severity of methemoglobinemia can be increased when Masitinib is combined with Benzocaine.
Benzyl alcoholThe risk or severity of methemoglobinemia can be increased when Masitinib is combined with Benzyl alcohol.
BupivacaineThe risk or severity of methemoglobinemia can be increased when Masitinib is combined with Bupivacaine.
Food Interactions
Not Available

Products

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Product Ingredients
IngredientUNIICASInChI Key
Masitinib mesylateZK89EG3A181048007-93-7TXCWBWKVIZGWEQ-UHFFFAOYSA-N
International/Other Brands
Kinavet / Masivet

Categories

ATC Codes
L01EX06 — Masitinib
Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as benzanilides. These are aromatic compounds containing an anilide group in which the carboxamide group is substituted with a benzene ring. They have the general structure RNC(=O)R', where R,R'= benzene.
Kingdom
Organic compounds
Super Class
Benzenoids
Class
Benzene and substituted derivatives
Sub Class
Anilides
Direct Parent
Benzanilides
Alternative Parents
Diaminotoluenes / Benzamides / Phenylmethylamines / Aniline and substituted anilines / Benzylamines / Benzoyl derivatives / 2,4-disubstituted thiazoles / N-methylpiperazines / Aralkylamines / Pyridines and derivatives
show 11 more
Substituents
1,3-thiazol-2-amine / 1,4-diazinane / 2,4-disubstituted 1,3-thiazole / Amine / Amino acid or derivatives / Aniline or substituted anilines / Aralkylamine / Aromatic heteromonocyclic compound / Azacycle / Azole
show 28 more
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
1,3-thiazole, benzamides, pyridines, N-alkylpiperazine (CHEBI:63450)
Affected organisms
Not Available

Chemical Identifiers

UNII
M59NC4E26P
CAS number
790299-79-5
InChI Key
WJEOLQLKVOPQFV-UHFFFAOYSA-N
InChI
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)
IUPAC Name
N-(4-methyl-3-{[4-(pyridin-3-yl)-1,3-thiazol-2-yl]amino}phenyl)-4-[(4-methylpiperazin-1-yl)methyl]benzamide
SMILES
CN1CCN(CC2=CC=C(C=C2)C(=O)NC2=CC=C(C)C(NC3=NC(=CS3)C3=CN=CC=C3)=C2)CC1

References

General References
  1. Walker UA: More about masitinib. Arthritis Res Ther. 2009;11(4):120. doi: 10.1186/ar2734. Epub 2009 Jul 13. [Article]
  2. Bellamy F, Bader T, Moussy A, Hermine O: Pharmacokinetics of masitinib in cats. Vet Res Commun. 2009 Dec;33(8):831-7. doi: 10.1007/s11259-009-9231-6. [Article]
  3. Chaigne B, Lagier L, Aubourg A, de Muret A, Jonville-Bera AP, Machet L, Samimi M: Stevens-Johnson Syndrome induced by masitinib. Acta Derm Venereol. 2012 Mar;92(2):210-2. doi: 10.2340/00015555-1196. [Article]
  4. Daly M, Sheppard S, Cohen N, Nabity M, Moussy A, Hermine O, Wilson H: Safety of masitinib mesylate in healthy cats. J Vet Intern Med. 2011 Mar-Apr;25(2):297-302. doi: 10.1111/j.1939-1676.2011.0687.x. Epub 2011 Feb 11. [Article]
  5. Procoli F: Clinical trial on the efficacy of masitinib in canine IBD. Vet Rec. 2010 Nov 6;167(19):760. doi: 10.1136/vr.c6030. [Article]
  6. Hahn KA, Ogilvie G, Rusk T, Devauchelle P, Leblanc A, Legendre A, Powers B, Leventhal PS, Kinet JP, Palmerini F, Dubreuil P, Moussy A, Hermine O: Masitinib is safe and effective for the treatment of canine mast cell tumors. J Vet Intern Med. 2008 Nov-Dec;22(6):1301-9. doi: 10.1111/j.1939-1676.2008.0190.x. Epub 2008 Sep 24. [Article]
  7. Gentilini F: "Masitinib" is safe and effective for the treatment of canine mast cell tumors. J Vet Intern Med. 2010 Jan-Feb;24(1):6; author reply 7. [Article]
  8. Thamm DH, Rose B, Kow K, Humbert M, Mansfield CD, Moussy A, Hermine O, Dubreuil P: Masitinib as a chemosensitizer of canine tumor cell lines: a proof of concept study. Vet J. 2012 Jan;191(1):131-4. doi: 10.1016/j.tvjl.2011.01.001. Epub 2011 Feb 17. [Article]
  9. Tebib J, Mariette X, Bourgeois P, Flipo RM, Gaudin P, Le Loet X, Gineste P, Guy L, Mansfield CD, Moussy A, Dubreuil P, Hermine O, Sibilia J: Masitinib in the treatment of active rheumatoid arthritis: results of a multicentre, open-label, dose-ranging, phase 2a study. Arthritis Res Ther. 2009;11(3):R95. doi: 10.1186/ar2740. Epub 2009 Jun 23. [Article]
  10. Dubreuil P, Letard S, Ciufolini M, Gros L, Humbert M, Casteran N, Borge L, Hajem B, Lermet A, Sippl W, Voisset E, Arock M, Auclair C, Leventhal PS, Mansfield CD, Moussy A, Hermine O: Masitinib (AB1010), a potent and selective tyrosine kinase inhibitor targeting KIT. PLoS One. 2009 Sep 30;4(9):e7258. doi: 10.1371/journal.pone.0007258. [Article]
  11. Daigle J, Moussy A, Mansfield CD, Hermine O: Masitinib for the treatment of canine atopic dermatitis: a pilot study. Vet Res Commun. 2010 Jan;34(1):51-63. doi: 10.1007/s11259-009-9332-2. Epub 2009 Dec 23. [Article]
  12. Le Cesne A, Blay JY, Bui BN, Bouche O, Adenis A, Domont J, Cioffi A, Ray-Coquard I, Lassau N, Bonvalot S, Moussy A, Kinet JP, Hermine O: Phase II study of oral masitinib mesilate in imatinib-naive patients with locally advanced or metastatic gastro-intestinal stromal tumour (GIST). Eur J Cancer. 2010 May;46(8):1344-51. doi: 10.1016/j.ejca.2010.02.014. Epub 2010 Mar 6. [Article]
  13. Hahn KA, Legendre AM, Shaw NG, Phillips B, Ogilvie GK, Prescott DM, Atwater SW, Carreras JK, Lana SE, Ladue T, Rusk A, Kinet JP, Dubreuil P, Moussy A, Hermine O: Evaluation of 12- and 24-month survival rates after treatment with masitinib in dogs with nonresectable mast cell tumors. Am J Vet Res. 2010 Nov;71(11):1354-61. doi: 10.2460/ajvr.71.11.1354. [Article]
  14. Piette F, Belmin J, Vincent H, Schmidt N, Pariel S, Verny M, Marquis C, Mely J, Hugonot-Diener L, Kinet JP, Dubreuil P, Moussy A, Hermine O: Masitinib as an adjunct therapy for mild-to-moderate Alzheimer's disease: a randomised, placebo-controlled phase 2 trial. Alzheimers Res Ther. 2011 Apr 19;3(2):16. doi: 10.1186/alzrt75. [Article]
  15. Cadot P, Hensel P, Bensignor E, Hadjaje C, Marignac G, Beco L, Fontaine J, Jamet JF, Georgescu G, Campbell K, Cannon A, Osborn SC, Messinger L, Gogny-Goubert M, Dubreuil P, Moussy A, Hermine O: Masitinib decreases signs of canine atopic dermatitis: a multicentre, randomized, double-blind, placebo-controlled phase 3 trial. Vet Dermatol. 2011 Dec;22(6):554-64. doi: 10.1111/j.1365-3164.2011.00990.x. Epub 2011 Jun 13. [Article]
  16. Holtermann N, Kiupel M, Kessler M, Teske E, Betz D, Hirschberger J: Masitinib monotherapy in canine epitheliotropic lymphoma. Vet Comp Oncol. 2015 Sep 14. doi: 10.1111/vco.12157. [Article]
Human Metabolome Database
HMDB0254344
KEGG Drug
D10229
ChemSpider
8250179
BindingDB
50355495
ChEBI
63450
ChEMBL
CHEMBL1908391
ZINC
ZINC000034177219
PDBe Ligand
G65
Wikipedia
Masitinib
PDB Entries
5mql / 7ju7 / 7tvx

Clinical Trials

Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
PhaseStatusPurposeConditionsCount
3CompletedTreatmentAlzheimer's Disease (AD)1
3CompletedTreatmentAsthma2
3CompletedTreatmentGastrointestinal Stromal Tumor (GIST)1
3CompletedTreatmentIndolent Systemic Mastocytosis1
3CompletedTreatmentLocally Advanced or Metastatic Pancreatic Cancer1

Pharmacoeconomics

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

Properties

State
Not Available
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.00289 mg/mLALOGPS
logP4.18ALOGPS
logP4.97Chemaxon
logS-5.2ALOGPS
pKa (Strongest Acidic)15.12Chemaxon
pKa (Strongest Basic)7.84Chemaxon
Physiological Charge1Chemaxon
Hydrogen Acceptor Count6Chemaxon
Hydrogen Donor Count2Chemaxon
Polar Surface Area73.39 Å2Chemaxon
Rotatable Bond Count7Chemaxon
Refractivity147 m3·mol-1Chemaxon
Polarizability55.33 Å3Chemaxon
Number of Rings5Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleYesChemaxon
Predicted ADMET Features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
LC-MS/MS Spectrum - LC-ESI-qTof , PositiveLC-MS/MSsplash10-0002-0236920000-165320b13f69ca2a3a29
MS/MS Spectrum - , positiveLC-MS/MSsplash10-0udi-1291000000-f2e2f823b1870c00bb6d
MS/MS Spectrum - , positiveLC-MS/MSsplash10-0002-0236920000-165320b13f69ca2a3a29
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-0002-0010900000-cb5d88cf514415cfa83d
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-000i-0009100000-c8124b66a7caf632e108
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0002-0002900000-219c068231ee93cbf7df
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-00kb-0203900000-d8a63cb18b35754129cf
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-00kk-0715900000-2b5a79ceeacf9298c3d7
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-000e-3719600000-7740019128ee89751e1b
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-208.7431
predicted
DeepCCS 1.0 (2019)
[M+H]+211.13866
predicted
DeepCCS 1.0 (2019)
[M+Na]+217.05118
predicted
DeepCCS 1.0 (2019)

Drug created at February 26, 2016 17:35 / Updated at July 18, 2023 22:56