N-[4-Methyl-3-[[4-(3-Pyridinyl)-2-Pyrimidinyl]Amino]Phenyl]-3-Pyridinecarboxamide
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Identification
- Generic Name
- N-[4-Methyl-3-[[4-(3-Pyridinyl)-2-Pyrimidinyl]Amino]Phenyl]-3-Pyridinecarboxamide
- DrugBank Accession Number
- DB03878
- Background
Not Available
- Type
- Small Molecule
- Groups
- Experimental
- Structure
- Weight
- Average: 382.4179
Monoisotopic: 382.154209228 - Chemical Formula
- C22H18N6O
- Synonyms
- Not Available
Pharmacology
- Indication
Not Available
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- Pharmacodynamics
Not Available
- Mechanism of action
Target Actions Organism UTyrosine-protein kinase ABL1 Not Available Humans UTyrosine-protein kinase transforming protein Abl Not Available Abelson murine leukemia virus - 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
- 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
Categories
- Drug Categories
- Not Available
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as aromatic anilides. These are aromatic compounds containing an anilide group in which the carboxamide group is substituted with an aromatic group. They have the general structure RNC(=O)R', where R= benzene, and R = aryl group.
- Kingdom
- Organic compounds
- Super Class
- Benzenoids
- Class
- Benzene and substituted derivatives
- Sub Class
- Anilides
- Direct Parent
- Aromatic anilides
- Alternative Parents
- Pyridinylpyrimidines / Nicotinamides / Diaminotoluenes / Aniline and substituted anilines / Aminopyrimidines and derivatives / Heteroaromatic compounds / Secondary carboxylic acid amides / Amino acids and derivatives / Secondary amines / Azacyclic compounds show 4 more
- Substituents
- Amine / Amino acid or derivatives / Aminopyrimidine / Aniline or substituted anilines / Aromatic anilide / Aromatic heteromonocyclic compound / Azacycle / Carboxamide group / Carboxylic acid derivative / Diaminotoluene show 18 more
- Molecular Framework
- Aromatic heteromonocyclic compounds
- External Descriptors
- pyrimidylpyridine, pyridinecarboxamide (CHEBI:45090)
- Affected organisms
- Not Available
Chemical Identifiers
- UNII
- Q8SP783P3P
- CAS number
- Not Available
- InChI Key
- YWQVBESSYLICRX-UHFFFAOYSA-N
- InChI
- InChI=1S/C22H18N6O/c1-15-6-7-18(26-21(29)17-5-3-10-24-14-17)12-20(15)28-22-25-11-8-19(27-22)16-4-2-9-23-13-16/h2-14H,1H3,(H,26,29)(H,25,27,28)
- IUPAC Name
- N-(4-methyl-3-{[4-(pyridin-3-yl)pyrimidin-2-yl]amino}phenyl)pyridine-3-carboxamide
- SMILES
- CC1=CC=C(NC(=O)C2=CC=CN=C2)C=C1NC1=NC=CC(=N1)C1=CC=CN=C1
References
- General References
- Not Available
- External Links
- PubChem Compound
- 4327
- PubChem Substance
- 46505112
- ChemSpider
- 4174
- ZINC
- ZINC000008656718
- PDBe Ligand
- PRC
- PDB Entries
- 1fpu
Clinical Trials
- Clinical Trials
Clinical Trial & Rare Diseases Add-on Data Package
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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
Property Value Source Water Solubility 0.00873 mg/mL ALOGPS logP 2.81 ALOGPS logP 3.37 Chemaxon logS -4.6 ALOGPS pKa (Strongest Acidic) 12.69 Chemaxon pKa (Strongest Basic) 4.33 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 6 Chemaxon Hydrogen Donor Count 2 Chemaxon Polar Surface Area 92.69 Å2 Chemaxon Rotatable Bond Count 5 Chemaxon Refractivity 112.18 m3·mol-1 Chemaxon Polarizability 40.66 Å3 Chemaxon Number of Rings 4 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
Property Value Probability Human Intestinal Absorption + 0.9929 Blood Brain Barrier + 0.926 Caco-2 permeable + 0.5355 P-glycoprotein substrate Non-substrate 0.7543 P-glycoprotein inhibitor I Non-inhibitor 0.5204 P-glycoprotein inhibitor II Non-inhibitor 0.8511 Renal organic cation transporter Non-inhibitor 0.8769 CYP450 2C9 substrate Non-substrate 0.7356 CYP450 2D6 substrate Non-substrate 0.9005 CYP450 3A4 substrate Non-substrate 0.6436 CYP450 1A2 substrate Inhibitor 0.922 CYP450 2C9 inhibitor Non-inhibitor 0.7281 CYP450 2D6 inhibitor Non-inhibitor 0.9765 CYP450 2C19 inhibitor Non-inhibitor 0.5459 CYP450 3A4 inhibitor Non-inhibitor 0.8529 CYP450 inhibitory promiscuity High CYP Inhibitory Promiscuity 0.5284 Ames test Non AMES toxic 0.6244 Carcinogenicity Non-carcinogens 0.8933 Biodegradation Not ready biodegradable 0.965 Rat acute toxicity 2.3615 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9784 hERG inhibition (predictor II) Non-inhibitor 0.6749
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS splash10-001i-0209000000-6eb509d2b67273663f6c Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS splash10-001i-0019000000-73111d2374351aace2ca Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS splash10-001i-0119000000-7b5a5f0771b868a145e3 Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS splash10-00ai-2139000000-3467fee392a8077b33a5 Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS splash10-0a7i-9513000000-401bca0957e62463f7be Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS splash10-056u-3629000000-2bc020eee6721636f2ab 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]- 186.91751 predictedDeepCCS 1.0 (2019) [M+H]+ 189.27553 predictedDeepCCS 1.0 (2019) [M+Na]+ 196.18286 predictedDeepCCS 1.0 (2019)
Targets
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1. DetailsTyrosine-protein kinase ABL1
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Non-receptor tyrosine-protein kinase that plays a role in many key processes linked to cell growth and survival such as cytoskeleton remodeling in response to extracellular stimuli, cell motility and adhesion, receptor endocytosis, autophagy, DNA damage response and apoptosis. Coordinates actin remodeling through tyrosine phosphorylation of proteins controlling cytoskeleton dynamics like WASF3 (involved in branch formation); ANXA1 (involved in membrane anchoring); DBN1, DBNL, CTTN, RAPH1 and ENAH (involved in signaling); or MAPT and PXN (microtubule-binding proteins). Phosphorylation of WASF3 is critical for the stimulation of lamellipodia formation and cell migration. Involved in the regulation of cell adhesion and motility through phosphorylation of key regulators of these processes such as BCAR1, CRK, CRKL, DOK1, EFS or NEDD9 (PubMed:22810897). Phosphorylates multiple receptor tyrosine kinases and more particularly promotes endocytosis of EGFR, facilitates the formation of neuromuscular synapses through MUSK, inhibits PDGFRB-mediated chemotaxis and modulates the endocytosis of activated B-cell receptor complexes. Other substrates which are involved in endocytosis regulation are the caveolin (CAV1) and RIN1. Moreover, ABL1 regulates the CBL family of ubiquitin ligases that drive receptor down-regulation and actin remodeling. Phosphorylation of CBL leads to increased EGFR stability. Involved in late-stage autophagy by regulating positively the trafficking and function of lysosomal components. ABL1 targets to mitochondria in response to oxidative stress and thereby mediates mitochondrial dysfunction and cell death. In response to oxidative stress, phosphorylates serine/threonine kinase PRKD2 at 'Tyr-717' (PubMed:28428613). ABL1 is also translocated in the nucleus where it has DNA-binding activity and is involved in DNA-damage response and apoptosis. Many substrates are known mediators of DNA repair: DDB1, DDB2, ERCC3, ERCC6, RAD9A, RAD51, RAD52 or WRN. Activates the proapoptotic pathway when the DNA damage is too severe to be repaired. Phosphorylates TP73, a primary regulator for this type of damage-induced apoptosis. Phosphorylates the caspase CASP9 on 'Tyr-153' and regulates its processing in the apoptotic response to DNA damage. Phosphorylates PSMA7 that leads to an inhibition of proteasomal activity and cell cycle transition blocks. ABL1 acts also as a regulator of multiple pathological signaling cascades during infection. Several known tyrosine-phosphorylated microbial proteins have been identified as ABL1 substrates. This is the case of A36R of Vaccinia virus, Tir (translocated intimin receptor) of pathogenic E.coli and possibly Citrobacter, CagA (cytotoxin-associated gene A) of H.pylori, or AnkA (ankyrin repeat-containing protein A) of A.phagocytophilum. Pathogens can highjack ABL1 kinase signaling to reorganize the host actin cytoskeleton for multiple purposes, like facilitating intracellular movement and host cell exit. Finally, functions as its own regulator through autocatalytic activity as well as through phosphorylation of its inhibitor, ABI1. Regulates T-cell differentiation in a TBX21-dependent manner (By similarity). Positively regulates chemokine-mediated T-cell migration, polarization, and homing to lymph nodes and immune-challenged tissues, potentially via activation of NEDD9/HEF1 and RAP1 (By similarity). Phosphorylates TBX21 on tyrosine residues leading to an enhancement of its transcriptional activator activity (By similarity)
- Specific Function
- actin filament binding
- Gene Name
- ABL1
- Uniprot ID
- P00519
- Uniprot Name
- Tyrosine-protein kinase ABL1
- Molecular Weight
- 122871.435 Da
References
- 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]
- Kind
- Protein
- Organism
- Abelson murine leukemia virus
- Pharmacological action
- Unknown
- General Function
- Not Available
- Specific Function
- ATP binding
- Gene Name
- ABL
- Uniprot ID
- P00521
- Uniprot Name
- Tyrosine-protein kinase transforming protein Abl
- Molecular Weight
- 81871.395 Da
References
Drug created at June 13, 2005 13:24 / Updated at June 12, 2020 16:52