2-(4-ETHYLPIPERAZIN-1-YL)-4-(PHENYLAMINO)PYRAZOLO[1,5-A][1,3,5]TRIAZINE-8-CARBONITRILE

Identification

Generic Name
2-(4-ETHYLPIPERAZIN-1-YL)-4-(PHENYLAMINO)PYRAZOLO[1,5-A][1,3,5]TRIAZINE-8-CARBONITRILE
DrugBank Accession Number
DB08360
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
Weight
Average: 348.405
Monoisotopic: 348.18109268
Chemical Formula
C18H20N8
Synonyms
Not Available

Pharmacology

Indication

Not Available

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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
UCasein kinase II subunit alphaNot AvailableHumans
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
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 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
Pyrazolotriazines / Pyrazolo[1,5-a][1,3,5]triazines / Dialkylarylamines / Aniline and substituted anilines / 1,3,5-triazine-2,4-diamines / N-alkylpiperazines / 1,3,5-triazines / Pyrazoles / Heteroaromatic compounds / Trialkylamines
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Substituents
1,3,5-triazine / 2,4-diamine-s-triazine / Amine / Amino-1,3,5-triazine / Aminotriazine / Aniline or substituted anilines / Aromatic heteropolycyclic compound / Azacycle / Azole / Benzenoid
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Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
Not Available
Affected organisms
Not Available

Chemical Identifiers

UNII
Not Available
CAS number
Not Available
InChI Key
BIFHJPUTQBOBGJ-UHFFFAOYSA-N
InChI
InChI=1S/C18H20N8/c1-2-24-8-10-25(11-9-24)17-22-16-14(12-19)13-20-26(16)18(23-17)21-15-6-4-3-5-7-15/h3-7,13H,2,8-11H2,1H3,(H,21,22,23)
IUPAC Name
2-(4-ethylpiperazin-1-yl)-4-(phenylamino)pyrazolo[1,5-a][1,3,5]triazine-8-carbonitrile
SMILES
CCN1CCN(CC1)C1=NC2=C(C=NN2C(NC2=CC=CC=C2)=N1)C#N

References

General References
Not Available
PubChem Compound
24779677
PubChem Substance
99444831
ChemSpider
22377932
BindingDB
50214452
ChEMBL
CHEMBL230137
ZINC
ZINC000016052399
PDBe Ligand
P55
PDB Entries
2pvl

Clinical Trials

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PhaseStatusPurposeConditionsCountStart DateWhy Stopped100+ additional columns

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
PropertyValueSource
Water Solubility0.159 mg/mLALOGPS
logP1.81ALOGPS
logP2.94Chemaxon
logS-3.3ALOGPS
pKa (Strongest Acidic)14.88Chemaxon
pKa (Strongest Basic)7.59Chemaxon
Physiological Charge1Chemaxon
Hydrogen Acceptor Count7Chemaxon
Hydrogen Donor Count1Chemaxon
Polar Surface Area85.38 Å2Chemaxon
Rotatable Bond Count4Chemaxon
Refractivity111.8 m3·mol-1Chemaxon
Polarizability38.17 Å3Chemaxon
Number of Rings4Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+1.0
Blood Brain Barrier+0.9508
Caco-2 permeable+0.5086
P-glycoprotein substrateSubstrate0.7375
P-glycoprotein inhibitor IInhibitor0.5
P-glycoprotein inhibitor IIInhibitor0.7119
Renal organic cation transporterInhibitor0.6915
CYP450 2C9 substrateNon-substrate0.8839
CYP450 2D6 substrateNon-substrate0.742
CYP450 3A4 substrateNon-substrate0.5208
CYP450 1A2 substrateNon-inhibitor0.5766
CYP450 2C9 inhibitorNon-inhibitor0.7504
CYP450 2D6 inhibitorNon-inhibitor0.8394
CYP450 2C19 inhibitorNon-inhibitor0.5187
CYP450 3A4 inhibitorNon-inhibitor0.9474
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.6934
Ames testNon AMES toxic0.5242
CarcinogenicityNon-carcinogens0.8308
BiodegradationNot ready biodegradable1.0
Rat acute toxicity2.7927 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Strong inhibitor0.8324
hERG inhibition (predictor II)Inhibitor0.524
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-0002-0009000000-77a0ef385301fdefcaba
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0002-0009000000-0193c76331fd42401205
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0002-0009000000-7745e4d02428de26d1d5
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0002-0029000000-03d8b81f4bb96fb9ad20
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-00fs-0197000000-45227ec7448eeaaeb847
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0kbf-1592000000-87eef2009eac57a39c4f
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]-175.57924
predicted
DeepCCS 1.0 (2019)
[M+H]+177.93724
predicted
DeepCCS 1.0 (2019)
[M+Na]+185.26341
predicted
DeepCCS 1.0 (2019)

Targets

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Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Catalytic subunit of a constitutively active serine/threonine-protein kinase complex that phosphorylates a large number of substrates containing acidic residues C-terminal to the phosphorylated serine or threonine (PubMed:11239457, PubMed:11704824, PubMed:16193064, PubMed:18411307, PubMed:18583988, PubMed:18678890, PubMed:19188443, PubMed:20545769, PubMed:20625391, PubMed:22017874, PubMed:22406621, PubMed:24962073, PubMed:30898438, PubMed:31439799). Regulates numerous cellular processes, such as cell cycle progression, apoptosis and transcription, as well as viral infection (PubMed:12631575, PubMed:19387551, PubMed:19387552). May act as a regulatory node which integrates and coordinates numerous signals leading to an appropriate cellular response (PubMed:12631575, PubMed:19387551, PubMed:19387552). During mitosis, functions as a component of the p53/TP53-dependent spindle assembly checkpoint (SAC) that maintains cyclin-B-CDK1 activity and G2 arrest in response to spindle damage (PubMed:11704824, PubMed:19188443). Also required for p53/TP53-mediated apoptosis, phosphorylating 'Ser-392' of p53/TP53 following UV irradiation (PubMed:11239457). Phosphorylates a number of DNA repair proteins in response to DNA damage, such as MDC1, MRE11, RAD9A, RAD51 and HTATSF1, promoting their recruitment to DNA damage sites (PubMed:18411307, PubMed:18583988, PubMed:18678890, PubMed:20545769, PubMed:21482717, PubMed:22325354, PubMed:26811421, PubMed:28512243, PubMed:30898438, PubMed:35597237). Can also negatively regulate apoptosis (PubMed:16193064, PubMed:22184066). Phosphorylates the caspases CASP9 and CASP2 and the apoptotic regulator NOL3 (PubMed:16193064). Phosphorylation protects CASP9 from cleavage and activation by CASP8, and inhibits the dimerization of CASP2 and activation of CASP8 (PubMed:16193064). Phosphorylates YY1, protecting YY1 from cleavage by CASP7 during apoptosis (PubMed:22184066). Regulates transcription by direct phosphorylation of RNA polymerases I, II, III and IV (PubMed:12631575, PubMed:19387550, PubMed:19387551, PubMed:19387552, PubMed:23123191). Also phosphorylates and regulates numerous transcription factors including NF-kappa-B, STAT1, CREB1, IRF1, IRF2, ATF1, ATF4, SRF, MAX, JUN, FOS, MYC and MYB (PubMed:12631575, PubMed:19387550, PubMed:19387551, PubMed:19387552, PubMed:23123191). Phosphorylates Hsp90 and its co-chaperones FKBP4 and CDC37, which is essential for chaperone function (PubMed:19387550). Mediates sequential phosphorylation of FNIP1, promoting its gradual interaction with Hsp90, leading to activate both kinase and non-kinase client proteins of Hsp90 (PubMed:30699359). Regulates Wnt signaling by phosphorylating CTNNB1 and the transcription factor LEF1 (PubMed:19387549). Acts as an ectokinase that phosphorylates several extracellular proteins (PubMed:12631575, PubMed:19387550, PubMed:19387551, PubMed:19387552). During viral infection, phosphorylates various proteins involved in the viral life cycles of EBV, HSV, HBV, HCV, HIV, CMV and HPV (PubMed:12631575, PubMed:19387550, PubMed:19387551, PubMed:19387552). Phosphorylates PML at 'Ser-565' and primes it for ubiquitin-mediated degradation (PubMed:20625391, PubMed:22406621). Plays an important role in the circadian clock function by phosphorylating BMAL1 at 'Ser-90' which is pivotal for its interaction with CLOCK and which controls CLOCK nuclear entry (By similarity). Phosphorylates CCAR2 at 'Thr-454' in gastric carcinoma tissue (PubMed:24962073). Phosphorylates FMR1, promoting FMR1-dependent formation of a membraneless compartment (PubMed:30765518, PubMed:31439799). May phosphorylate histone H2A on 'Ser-1' (PubMed:38334665)
Specific Function
ATP binding
Gene Name
CSNK2A1
Uniprot ID
P68400
Uniprot Name
Casein kinase II subunit alpha
Molecular Weight
45143.25 Da
References
  1. 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]

Drug created at September 15, 2010 21:31 / Updated at June 12, 2020 16:52