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5-(4'-AMINO-1'-ETHYL-5',8'-DIFLUORO-1'H-SPIRO[PIPERIDINE-4,2'-QUINAZOLINE]-1-YLCARBONYL)PICOLINONITRILE

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Identification

Generic Name
5-(4'-AMINO-1'-ETHYL-5',8'-DIFLUORO-1'H-SPIRO[PIPERIDINE-4,2'-QUINAZOLINE]-1-YLCARBONYL)PICOLINONITRILE
DrugBank Accession Number
DB06879
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
3D
Similar Structures
Weight
Average: 412.4358
Monoisotopic: 412.182315766
Chemical Formula
C21H22F2N6O
Synonyms
Not Available
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Pharmacology

Indication

Not Available

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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
UNitric oxide synthase, inducibleNot 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 quinazolinamines. These are heterocyclic aromatic compounds containing a quianazoline moiety substituted by one or more amine groups.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Diazanaphthalenes
Sub Class
Benzodiazines
Direct Parent
Quinazolinamines
Alternative Parents
N-acylpiperidines / Dialkylarylamines / Dihydropyridines / Aryl fluorides / Benzenoids / Imidolactams / Tertiary carboxylic acid amides / Ketimines / Propargyl-type 1,3-dipolar organic compounds / Azacyclic compounds
show 8 more
Substituents
Amidine / Aromatic heteropolycyclic compound / Aryl fluoride / Aryl halide / Azacycle / Benzenoid / Carbonitrile / Carbonyl group / Carboxamide group / Carboximidamide
show 24 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
Not Available
Affected organisms
Not Available

Chemical Identifiers

UNII
Not Available
CAS number
Not Available
InChI Key
QCFIRACCCDFXIP-UHFFFAOYSA-N
InChI
InChI=1S/C21H22F2N6O/c1-2-29-18-16(23)6-5-15(22)17(18)19(25)27-21(29)7-9-28(10-8-21)20(30)13-3-4-14(11-24)26-12-13/h5-6,12H,2-4,7-10H2,1H3,(H2,25,27)
IUPAC Name
5-({4'-amino-1'-ethyl-5',8'-difluoro-1'H-spiro[piperidine-4,2'-quinazolin]-1-yl}carbonyl)-3,4-dihydropyridine-2-carbonitrile
SMILES
CCN1C2=C(F)C=CC(F)=C2C(N)=NC11CCN(CC1)C(=O)C1=CN=C(CC1)C#N

References

General References
Not Available
PubChem Compound
46937031
PubChem Substance
99443350
ChemSpider
25060849
ZINC
ZINC000039187980
PDBe Ligand
1A2
PDB Entries
3e6t

Clinical Trials

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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
PropertyValueSource
Water Solubility0.0733 mg/mLALOGPS
logP2.15ALOGPS
logP2.74Chemaxon
logS-3.8ALOGPS
pKa (Strongest Basic)5.63Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count6Chemaxon
Hydrogen Donor Count1Chemaxon
Polar Surface Area98.08 Å2Chemaxon
Rotatable Bond Count2Chemaxon
Refractivity108.79 m3·mol-1Chemaxon
Polarizability41.29 Å3Chemaxon
Number of Rings4Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.957
Blood Brain Barrier+0.9309
Caco-2 permeable-0.6125
P-glycoprotein substrateSubstrate0.8955
P-glycoprotein inhibitor IInhibitor0.903
P-glycoprotein inhibitor IIInhibitor0.7584
Renal organic cation transporterInhibitor0.6168
CYP450 2C9 substrateNon-substrate0.833
CYP450 2D6 substrateNon-substrate0.7164
CYP450 3A4 substrateSubstrate0.637
CYP450 1A2 substrateNon-inhibitor0.7429
CYP450 2C9 inhibitorNon-inhibitor0.6847
CYP450 2D6 inhibitorNon-inhibitor0.7286
CYP450 2C19 inhibitorNon-inhibitor0.5711
CYP450 3A4 inhibitorNon-inhibitor0.8309
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.58
Ames testNon AMES toxic0.5712
CarcinogenicityNon-carcinogens0.8636
BiodegradationNot ready biodegradable1.0
Rat acute toxicity2.7955 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.8824
hERG inhibition (predictor II)Inhibitor0.8277
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/MSsplash10-03di-0000900000-3c26a29152602dd8ff66
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-03di-0002900000-ffc01919dc884699ec25
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-03di-0000900000-d0cfab61d73cea84c47b
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-03di-0011900000-924286e49612d8a96851
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-029i-1269000000-78e4eba6a77e017a1771
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0f89-1139100000-49961d012dca10831018
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]-187.79488
predicted
DeepCCS 1.0 (2019)
[M+H]+190.15288
predicted
DeepCCS 1.0 (2019)
[M+Na]+197.06778
predicted
DeepCCS 1.0 (2019)

Targets

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Details1. Nitric oxide synthase, inducible
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Produces nitric oxide (NO) which is a messenger molecule with diverse functions throughout the body (PubMed:7504305, PubMed:7531687, PubMed:7544004, PubMed:7682706). In macrophages, NO mediates tumoricidal and bactericidal actions. Also has nitrosylase activity and mediates cysteine S-nitrosylation of cytoplasmic target proteins such PTGS2/COX2 (By similarity). As component of the iNOS-S100A8/9 transnitrosylase complex involved in the selective inflammatory stimulus-dependent S-nitrosylation of GAPDH on 'Cys-247' implicated in regulation of the GAIT complex activity and probably multiple targets including ANXA5, EZR, MSN and VIM (PubMed:25417112). Involved in inflammation, enhances the synthesis of pro-inflammatory mediators such as IL6 and IL8 (PubMed:19688109)
Specific Function
arginine binding
Gene Name
NOS2
Uniprot ID
P35228
Uniprot Name
Nitric oxide synthase, inducible
Molecular Weight
131116.3 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 21:17 / Updated at June 12, 2020 16:52