Amuvatinib
Identification
- Generic Name
- Amuvatinib
- DrugBank Accession Number
- DB12742
- Background
Amuvatinib has been used in trials studying the treatment of Solid Tumors and Small Cell Lung Carcinoma. Amuvatinib is an oral, selective multi-targeted tyrosine kinase inhibitor that suppresses c-MET, c-RET and the mutant forms of c-KIT, PDGFR and FLT3. Amuvatinib also suppresses Rad51 protein, a critical component of double-stranded DNA repair in cancer cells.
- Type
- Small Molecule
- Groups
- Investigational
- Structure
- Weight
- Average: 447.51
Monoisotopic: 447.13651073 - Chemical Formula
- C23H21N5O3S
- Synonyms
- 1-Piperazinecarbothioamide, N-(1,3-benzodioxol-5-ylmethyl)-4-benzofuro(3,2-d)pyrimidin-4-yl-
- 4-[1]Benzofuro[3,2-D]Pyrimidin-4-Yl-N-(1,3-Benzodioxol-5-Ylmethyl)Piperazine-1-Carbothioamide
- Amuvatinib
- N-(1,3-Benzodioxol-5-ylmethyl)-4-(benzofuro(3,2-d)pyrimidin-4-yl)piperazine-1- carbothioamide
- External IDs
- HPK 56
- HPK-56
- HPK56
- MP 470
- MP-470
- MP470
Pharmacology
- Indication
Amuvatinib is a selective multi-targeted tyrosine kinase inhibitor that suppresses c-MET, c-RET and the mutant forms of c-KIT, PDGFR and FLT3. Amuvatinib also suppresses Rad51 protein, a critical component of double-stranded DNA repair in cancer cells.
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- Pharmacodynamics
Not Available
- Mechanism of action
Target Actions Organism UMast/stem cell growth factor receptor Kit Not Available Humans UHepatocyte growth factor receptor Not Available Humans UProto-oncogene tyrosine-protein kinase receptor Ret Not Available Humans UPlatelet-derived growth factor receptor alpha Not Available Humans UReceptor-type tyrosine-protein kinase FLT3 Not Available Humans UDNA repair protein RAD51 homolog 1 Not Available Humans - Absorption
Orally 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
- Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.
- 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.Not Available
- Food Interactions
- Not Available
Products
- Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.
- Product Ingredients
Ingredient UNII CAS InChI Key Amuvatinib hydrochloride 14L8O2K12B 1055986-67-8 IKQFRXPMBGQJGE-UHFFFAOYSA-N
Categories
- Drug Categories
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as n-arylpiperazines. These are organic compounds containing a piperazine ring where the nitrogen ring atom carries an aryl group.
- Kingdom
- Organic compounds
- Super Class
- Organoheterocyclic compounds
- Class
- Diazinanes
- Sub Class
- Piperazines
- Direct Parent
- N-arylpiperazines
- Alternative Parents
- Benzofurans / Benzodioxoles / Dialkylarylamines / Aminopyrimidines and derivatives / Imidolactams / Benzenoids / Heteroaromatic compounds / Furans / Thioureas / Oxacyclic compounds show 4 more
- Substituents
- Acetal / Aminopyrimidine / Aromatic heteropolycyclic compound / Azacycle / Benzenoid / Benzodioxole / Benzofuran / Dialkylarylamine / Furan / Heteroaromatic compound show 12 more
- Molecular Framework
- Aromatic heteropolycyclic compounds
- External Descriptors
- Not Available
- Affected organisms
- Not Available
Chemical Identifiers
- UNII
- SO9S6QZB4R
- CAS number
- 850879-09-3
- InChI Key
- FOFDIMHVKGYHRU-UHFFFAOYSA-N
- InChI
- InChI=1S/C23H21N5O3S/c32-23(24-12-15-5-6-18-19(11-15)30-14-29-18)28-9-7-27(8-10-28)22-21-20(25-13-26-22)16-3-1-2-4-17(16)31-21/h1-6,11,13H,7-10,12,14H2,(H,24,32)
- IUPAC Name
- N-[(2H-1,3-benzodioxol-5-yl)methyl]-4-{8-oxa-3,5-diazatricyclo[7.4.0.0^{2,7}]trideca-1(9),2(7),3,5,10,12-hexaen-6-yl}piperazine-1-carbothioamide
- SMILES
- S=C(NCC1=CC=C2OCOC2=C1)N1CCN(CC1)C1=NC=NC2=C1OC1=C2C=CC=C1
References
- General References
- Mahadevan D, Cooke L, Riley C, Swart R, Simons B, Della Croce K, Wisner L, Iorio M, Shakalya K, Garewal H, Nagle R, Bearss D: A novel tyrosine kinase switch is a mechanism of imatinib resistance in gastrointestinal stromal tumors. Oncogene. 2007 Jun 7;26(27):3909-19. Epub 2007 Feb 26. [Article]
- Product Announcement [Link]
- External Links
- Human Metabolome Database
- HMDB0248369
- PubChem Compound
- 11282283
- PubChem Substance
- 347828932
- ChemSpider
- 9457280
- BindingDB
- 50172081
- ChEBI
- 91389
- ChEMBL
- CHEMBL2103851
- ZINC
- ZINC000034951302
Clinical Trials
- Clinical Trials
Phase Status Purpose Conditions Count 2 Completed Treatment Small Cell Lung Cancer (SCLC) 1 1 Completed Treatment Malignant Diseases 1 1 Completed Treatment Solid Tumors 1 Not Available Terminated Treatment Lymphoma / Unspecified Adult Solid Tumor, Protocol Specific 1
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
Property Value Source Water Solubility 0.0741 mg/mL ALOGPS logP 2.79 ALOGPS logP 3.52 Chemaxon logS -3.8 ALOGPS pKa (Strongest Acidic) 14.11 Chemaxon pKa (Strongest Basic) 1.37 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 5 Chemaxon Hydrogen Donor Count 1 Chemaxon Polar Surface Area 75.89 Å2 Chemaxon Rotatable Bond Count 3 Chemaxon Refractivity 124.53 m3·mol-1 Chemaxon Polarizability 47.82 Å3 Chemaxon Number of Rings 6 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
- Not Available
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS splash10-0002-0000900000-bd47e1ff7b3fa90fa215 Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS splash10-03dj-0000900000-ac798471f13b65ed487e Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS splash10-0002-0000900000-5a5c89e2ce002105d6f7 Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS splash10-06rb-0190300000-110d01ac795cbf7154d2 Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS splash10-0002-1010900000-06e7d1578e033e7e7b52 Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS splash10-0hha-1491600000-97558b648cd8a272d72e Predicted 1H NMR Spectrum 1D NMR Not Applicable Predicted 13C NMR Spectrum 1D NMR Not Applicable - Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 222.4357574 predictedDarkChem Lite v0.1.0 [M-H]- 194.4301 predictedDeepCCS 1.0 (2019) [M+H]+ 223.2029574 predictedDarkChem Lite v0.1.0 [M+H]+ 196.78812 predictedDeepCCS 1.0 (2019) [M+Na]+ 223.1092574 predictedDarkChem Lite v0.1.0 [M+Na]+ 203.40129 predictedDeepCCS 1.0 (2019)
Targets
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Transmembrane receptor protein tyrosine kinase activity
- Specific Function
- Tyrosine-protein kinase that acts as cell-surface receptor for the cytokine KITLG/SCF and plays an essential role in the regulation of cell survival and proliferation, hematopoiesis, stem cell main...
- Gene Name
- KIT
- Uniprot ID
- P10721
- Uniprot Name
- Mast/stem cell growth factor receptor Kit
- Molecular Weight
- 109863.655 Da
References
- Mahadevan D, Cooke L, Riley C, Swart R, Simons B, Della Croce K, Wisner L, Iorio M, Shakalya K, Garewal H, Nagle R, Bearss D: A novel tyrosine kinase switch is a mechanism of imatinib resistance in gastrointestinal stromal tumors. Oncogene. 2007 Jun 7;26(27):3909-19. Epub 2007 Feb 26. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Protein tyrosine kinase activity
- Specific Function
- Receptor tyrosine kinase that transduces signals from the extracellular matrix into the cytoplasm by binding to hepatocyte growth factor/HGF ligand. Regulates many physiological processes including...
- Gene Name
- MET
- Uniprot ID
- P08581
- Uniprot Name
- Hepatocyte growth factor receptor
- Molecular Weight
- 155540.035 Da
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Transmembrane receptor protein tyrosine kinase activity
- Specific Function
- Receptor tyrosine-protein kinase involved in numerous cellular mechanisms including cell proliferation, neuronal navigation, cell migration, and cell differentiation upon binding with glial cell de...
- Gene Name
- RET
- Uniprot ID
- P07949
- Uniprot Name
- Proto-oncogene tyrosine-protein kinase receptor Ret
- Molecular Weight
- 124317.465 Da
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Vascular endothelial growth factor-activated receptor activity
- Specific Function
- Tyrosine-protein kinase that acts as a cell-surface receptor for PDGFA, PDGFB and PDGFC and plays an essential role in the regulation of embryonic development, cell proliferation, survival and chem...
- Gene Name
- PDGFRA
- Uniprot ID
- P16234
- Uniprot Name
- Platelet-derived growth factor receptor alpha
- Molecular Weight
- 122668.46 Da
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Vascular endothelial growth factor-activated receptor activity
- Specific Function
- Tyrosine-protein kinase that acts as cell-surface receptor for the cytokine FLT3LG and regulates differentiation, proliferation and survival of hematopoietic progenitor cells and of dendritic cells...
- Gene Name
- FLT3
- Uniprot ID
- P36888
- Uniprot Name
- Receptor-type tyrosine-protein kinase FLT3
- Molecular Weight
- 112902.51 Da
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Single-stranded dna-dependent atpase activity
- Specific Function
- Participates in a common DNA damage response pathway associated with the activation of homologous recombination and double-strand break repair. Binds to single and double-stranded DNA and exhibits ...
- Gene Name
- RAD51
- Uniprot ID
- Q06609
- Uniprot Name
- DNA repair protein RAD51 homolog 1
- Molecular Weight
- 36965.82 Da
Drug created at October 20, 2016 23:58 / Updated at December 01, 2022 11:27