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Identification
Name6-CHLORO-1-(2-{[(5-CHLORO-1-BENZOTHIEN-3-YL)METHYL]AMINO}ETHYL)-3-[(2-PYRIDIN-2-YLETHYL)AMINO]-1,4-DIHYDROPYRAZIN-2-OL
Accession NumberDB07521
TypeSmall Molecule
GroupsExperimental
DescriptionNot Available
Structure
Thumb
SynonymsNot Available
Prescription ProductsNot Available
Generic Prescription ProductsNot Available
Over the Counter ProductsNot Available
International BrandsNot Available
Brand mixturesNot Available
SaltsNot Available
CategoriesNot Available
CAS numberNot Available
WeightAverage: 484.485
Monoisotopic: 483.162636743
Chemical FormulaC22H31Cl2N5OS
InChI KeyYHTGPUXGIBWHPN-WEYGHZABSA-N
InChI
InChI=1S/C22H31Cl2N5OS/c23-16-4-5-19-18(11-16)15(14-31-19)12-25-9-10-29-20(24)13-28-21(22(29)30)27-8-6-17-3-1-2-7-26-17/h4-5,11,14,17,20,22,25-26,30H,1-3,6-10,12-13H2,(H,27,28)/t17-,20+,22-/m0/s1
IUPAC Name
(2S,6S)-6-chloro-1-(2-{[(5-chloro-1-benzothiophen-3-yl)methyl]amino}ethyl)-3-({2-[(2S)-piperidin-2-yl]ethyl}amino)-1,2,5,6-tetrahydropyrazin-2-ol
SMILES
[H][C@@]1(CCNC2=NC[C@]([H])(Cl)N(CCNCC3=CSC4=CC=C(Cl)C=C34)[C@@]2([H])O)CCCCN1
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as benzothiophenes. These are organic compounds containing a benzene fused to a thiepine ring (a five-membered ring with six carbon atoms and one sulfur atom).
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassBenzothiophenes
Sub ClassNot Available
Direct ParentBenzothiophenes
Alternative Parents
Substituents
  • Benzothiophene
  • Aralkylamine
  • Chlorobenzene
  • Aminopyrazine
  • Imidolactam
  • Benzenoid
  • Piperidine
  • Aryl halide
  • Aryl chloride
  • Heteroaromatic compound
  • Thiophene
  • Tertiary aliphatic amine
  • Tertiary amine
  • Azacycle
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Carboximidamide
  • Secondary amine
  • Secondary aliphatic amine
  • Carboxylic acid amidine
  • Amidine
  • Alkanolamine
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Organochloride
  • Organohalogen compound
  • Amine
  • Alkyl halide
  • Alkyl chloride
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Pharmacology
IndicationNot Available
PharmacodynamicsNot Available
Mechanism of actionNot Available
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
MetabolismNot Available
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityNot Available
Affected organismsNot Available
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.891
Blood Brain Barrier-0.5596
Caco-2 permeable-0.647
P-glycoprotein substrateSubstrate0.847
P-glycoprotein inhibitor INon-inhibitor0.5327
P-glycoprotein inhibitor IIInhibitor0.8471
Renal organic cation transporterInhibitor0.5157
CYP450 2C9 substrateNon-substrate0.6413
CYP450 2D6 substrateNon-substrate0.7325
CYP450 3A4 substrateSubstrate0.5644
CYP450 1A2 substrateInhibitor0.6045
CYP450 2C9 substrateNon-inhibitor0.5912
CYP450 2D6 substrateNon-inhibitor0.527
CYP450 2C19 substrateInhibitor0.5376
CYP450 3A4 substrateNon-inhibitor0.7988
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.5778
Ames testNon AMES toxic0.6147
CarcinogenicityNon-carcinogens0.9024
BiodegradationNot ready biodegradable1.0
Rat acute toxicity2.5621 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.8216
hERG inhibition (predictor II)Inhibitor0.856
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
StateSolid
Experimental PropertiesNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.00388 mg/mLALOGPS
logP2.76ALOGPS
logP3.1ChemAxon
logS-5.1ALOGPS
pKa (Strongest Acidic)12.21ChemAxon
pKa (Strongest Basic)10.51ChemAxon
Physiological Charge2ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area71.92 Å2ChemAxon
Rotatable Bond Count8ChemAxon
Refractivity128.43 m3·mol-1ChemAxon
Polarizability52.39 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
SpectraNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
External Links
ATC CodesNot Available
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSNot Available
Interactions
Drug InteractionsNot Available
Food InteractionsNot Available

Targets

1. Prothrombin

Kind: protein

Organism: Human

Pharmacological action: unknown

Components

Name UniProt ID Details
Prothrombin P00734 Details

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. Pubmed

Comments
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Drug created on September 15, 2010 15:23 / Updated on September 16, 2013 18:06