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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
Salts
Name/CAS Structure Properties
Methapyrilene Hydrochloride
135-23-9
Thumb
  • InChI Key: BONORRGKLJBGRV-UHFFFAOYSA-N
  • Monoisotopic Mass: 297.106646052
  • Average Mass: 297.847
DBSALT000334
Brand names
NameCompany
Co-PyronilNot Available
HistadylNot Available
LullaminNot Available
Brand mixturesNot Available
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
Mass SpecNot Available
Taxonomy
KingdomOrganic Compounds
SuperclassHeterocyclic Compounds
ClassPyridines and Derivatives
SubclassAminopyridines and Derivatives
Direct parentAminopyridines and Derivatives
Alternative parentsThiophenes; Tertiary Amines; Polyamines
Substituentsthiophene; tertiary amine; polyamine; amine; organonitrogen compound
Classification descriptionThis compound belongs to the aminopyridines and derivatives. These are organic heterocyclic compounds containing an amino group attached to a pyridine ring.
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
Property Value Probability
Human Intestinal Absorption + 0.9873
Blood Brain Barrier + 0.9492
Caco-2 permeable + 0.6224
P-glycoprotein substrate Substrate 0.6832
P-glycoprotein inhibitor I Non-inhibitor 0.9755
P-glycoprotein inhibitor II Non-inhibitor 0.9142
Renal organic cation transporter Inhibitor 0.5832
CYP450 2C9 substrate Non-substrate 0.7548
CYP450 2D6 substrate Non-substrate 0.7717
CYP450 3A4 substrate Non-substrate 0.5307
CYP450 1A2 substrate Inhibitor 0.831
CYP450 2C9 substrate Non-inhibitor 0.8932
CYP450 2D6 substrate Inhibitor 0.8168
CYP450 2C19 substrate Non-inhibitor 0.7581
CYP450 3A4 substrate Non-inhibitor 0.9942
CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.7722
Ames test Non AMES toxic 0.888
Carcinogenicity Non-carcinogens 0.9043
Biodegradation Not ready biodegradable 1.0
Rat acute toxicity 2.5098 LD50, mol/kg Not applicable
hERG inhibition (predictor I) Weak inhibitor 0.847
hERG inhibition (predictor II) Non-inhibitor 0.6318
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 RuleNoChemAxon
Spectra
SpectraNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
External Links
ResourceLink
KEGG CompoundC11114
PubChem Compound8667
PubChem Substance46505007
ChemSpider8345
ChEBI6820
ChEMBL
WikipediaMethapyrilene
ATC CodesR06AC05
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