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Identification
NameMethapyrilene
Accession NumberDB04819
TypeSmall Molecule
GroupsWithdrawn
Description

Methapyrilene, formerly marketed in many drug products, was shown to be
a potent carcinogen. Manufacturers voluntarily withdrew methapyriline
drug products from the market in May and June 1979.

Structure
Thumb
Synonyms
SynonymLanguageCode
2-[[2-(Dimethylamino)ethyl]-2-thenylamino]pyridineNot AvailableNot Available
MethypyrileneNot AvailableNot Available
N,N-Dimethyl-N'-pyrid-2-yl-N'-2-thenylethylenediamineNot AvailableNot Available
ThenylpyramineNot AvailableNot Available
Prescription ProductsNot Available
Generic Prescription ProductsNot Available
Over the Counter ProductsNot Available
International Brands
NameCompany
Co-PyronilNot Available
HistadylNot Available
LullaminNot Available
Brand mixturesNot Available
Salts
Name/CASStructureProperties
Methapyrilene Hydrochloride
135-23-9
Thumb
  • InChI Key: BONORRGKLJBGRV-UHFFFAOYSA-N
  • Monoisotopic Mass: 297.106646052
  • Average Mass: 297.847
DBSALT000334
Categories
CAS number91-80-5
WeightAverage: 297.847
Monoisotopic: 297.106646052
Chemical FormulaC14H20ClN3S
InChI KeyBONORRGKLJBGRV-UHFFFAOYSA-N
InChI
InChI=1S/C14H19N3S.ClH/c1-16(2)9-10-17(12-13-6-5-11-18-13)14-7-3-4-8-15-14;/h3-8,11H,9-10,12H2,1-2H3;1H
IUPAC Name
N-[2-(dimethylamino)ethyl]-N-(thiophen-2-ylmethyl)pyridin-2-amine hydrochloride
SMILES
Cl.CN(C)CCN(CC1=CC=CS1)C1=CC=CC=N1
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as dialkylarylamines. These are aliphatic aromatic amines in which the amino group is linked to two aliphatic chains and one aromatic group.
KingdomOrganic compounds
Super ClassOrganonitrogen compounds
ClassAmines
Sub ClassTertiary amines
Direct ParentDialkylarylamines
Alternative Parents
Substituents
  • Dialkylarylamine
  • Aminopyridine
  • Imidolactam
  • Pyridine
  • Heteroaromatic compound
  • Thiophene
  • Tertiary aliphatic amine
  • Azacycle
  • Organoheterocyclic compound
  • Hydrocarbon derivative
  • Hydrochloride
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Pharmacology
IndicationNot Available
PharmacodynamicsNot Available
Mechanism of actionNot Available
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
Metabolism
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityNot Available
Affected organisms
  • Humans and other mammals
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9873
Blood Brain Barrier+0.9492
Caco-2 permeable+0.6224
P-glycoprotein substrateSubstrate0.6832
P-glycoprotein inhibitor INon-inhibitor0.9755
P-glycoprotein inhibitor IINon-inhibitor0.9142
Renal organic cation transporterInhibitor0.5832
CYP450 2C9 substrateNon-substrate0.7548
CYP450 2D6 substrateNon-substrate0.7717
CYP450 3A4 substrateNon-substrate0.5307
CYP450 1A2 substrateInhibitor0.831
CYP450 2C9 substrateNon-inhibitor0.8932
CYP450 2D6 substrateInhibitor0.8168
CYP450 2C19 substrateNon-inhibitor0.7581
CYP450 3A4 substrateNon-inhibitor0.9942
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.7722
Ames testNon AMES toxic0.888
CarcinogenicityNon-carcinogens0.9043
BiodegradationNot ready biodegradable1.0
Rat acute toxicity2.5098 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.847
hERG inhibition (predictor II)Non-inhibitor0.6318
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
StateSolid
Experimental Properties
PropertyValueSource
boiling point173-175 °C at 3.00E+00 mm HgNot Available
water solubility601 mg/L (at 30 °C)YALKOWSKY,SH & DANNENFELSER,RM (1992)
logP2.87SANGSTER (1994)
logS-2.64ADME Research, USCD
pKa8.85 (at 20 °C)PERRIN,DD (1965)
Predicted Properties
PropertyValueSource
logP3.11ChemAxon
pKa (Strongest Basic)8.76ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area19.37 Å2ChemAxon
Rotatable Bond Count6ChemAxon
Refractivity78.16 m3·mol-1ChemAxon
Polarizability29.5 Å3ChemAxon
Number of Rings2ChemAxon
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
Comments
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Drug created on September 11, 2007 14:19 / Updated on September 16, 2013 17:25