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Identification
NameThenalidine
Accession NumberDB04826
TypeSmall Molecule
GroupsWithdrawn
Description

Withdrawn from the Canadian, US, and UK markets in 1963 due to concerns involving neutropenia.

Structure
Thumb
Synonyms
SynonymLanguageCode
1-Methyl-4-amino-N-phenyl-N-(2-thenyl)piperidineNot AvailableNot Available
1-Methyl-4-N-2-thenylanilinopiperidineNot AvailableNot Available
TenalidinaSpanishINN
ThenaldineNot AvailableNot Available
ThenalidinumLatinINN
ThenophenopiperidineNot AvailableNot Available
Prescription ProductsNot Available
Generic Prescription ProductsNot Available
Over the Counter ProductsNot Available
International Brands
NameCompany
SanbostenNot Available
SandosteneNot Available
Brand mixturesNot Available
SaltsNot Available
CategoriesNot Available
CAS number86-12-4
WeightAverage: 286.435
Monoisotopic: 286.150369404
Chemical FormulaC17H22N2S
InChI KeyKLOHYVOVXOUKQI-UHFFFAOYSA-N
InChI
InChI=1S/C17H22N2S/c1-18-11-9-16(10-12-18)19(14-17-8-5-13-20-17)15-6-3-2-4-7-15/h2-8,13,16H,9-12,14H2,1H3
IUPAC Name
1-methyl-N-phenyl-N-(thiophen-2-ylmethyl)piperidin-4-amine
SMILES
CN1CCC(CC1)N(CC1=CC=CS1)C1=CC=CC=C1
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
  • Aralkylamine
  • Aniline
  • 4-aminopiperidine
  • Benzenoid
  • Piperidine
  • Monocyclic benzene moiety
  • Heteroaromatic compound
  • Thiophene
  • Tertiary aliphatic amine
  • Azacycle
  • Organoheterocyclic compound
  • Hydrocarbon derivative
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic 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+0.9679
Blood Brain Barrier+0.9862
Caco-2 permeable+0.6921
P-glycoprotein substrateSubstrate0.6784
P-glycoprotein inhibitor INon-inhibitor0.7908
P-glycoprotein inhibitor IINon-inhibitor0.542
Renal organic cation transporterInhibitor0.7914
CYP450 2C9 substrateNon-substrate0.7078
CYP450 2D6 substrateSubstrate0.5511
CYP450 3A4 substrateNon-substrate0.5881
CYP450 1A2 substrateInhibitor0.6618
CYP450 2C9 substrateNon-inhibitor0.8589
CYP450 2D6 substrateInhibitor0.8765
CYP450 2C19 substrateNon-inhibitor0.7584
CYP450 3A4 substrateNon-inhibitor0.9589
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.5834
Ames testNon AMES toxic0.8307
CarcinogenicityNon-carcinogens0.9578
BiodegradationNot ready biodegradable0.9913
Rat acute toxicity2.4636 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.771
hERG inhibition (predictor II)Inhibitor0.6166
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point96 °CPhysProp
boiling point159 °C at 2.00E-02 mm HgPhysProp
Predicted Properties
PropertyValueSource
Water Solubility0.0883 mg/mLALOGPS
logP4.47ALOGPS
logP3.75ChemAxon
logS-3.5ALOGPS
pKa (Strongest Basic)8.69ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area6.48 Å2ChemAxon
Rotatable Bond Count4ChemAxon
Refractivity87.44 m3·mol-1ChemAxon
Polarizability32.89 Å3ChemAxon
Number of Rings3ChemAxon
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 14:30 / Updated on September 16, 2013 17:25