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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Withdrawn from the Canadian, US, and UK markets in 1963 due to concerns involving neutropenia.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
SaltsNot Available
Brand names
NameCompany
SanbostenNot Available
SandosteneNot Available
Brand mixturesNot 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
Mass SpecNot Available
Taxonomy
KingdomOrganic Compounds
SuperclassHeterocyclic Compounds
ClassPiperidines
SubclassAminopiperidines
Direct parentAminopiperidines
Alternative parentsBenzene and Substituted Derivatives; Thiophenes; Tertiary Amines; Polyamines
Substituentsbenzene; thiophene; tertiary amine; polyamine; amine; organonitrogen compound
Classification descriptionThis compound belongs to the aminopiperidines.
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 organismsNot Available
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
Property Value Probability
Human Intestinal Absorption + 0.9679
Blood Brain Barrier + 0.9862
Caco-2 permeable + 0.6921
P-glycoprotein substrate Substrate 0.6784
P-glycoprotein inhibitor I Non-inhibitor 0.7908
P-glycoprotein inhibitor II Non-inhibitor 0.542
Renal organic cation transporter Inhibitor 0.7914
CYP450 2C9 substrate Non-substrate 0.7078
CYP450 2D6 substrate Substrate 0.5511
CYP450 3A4 substrate Non-substrate 0.5881
CYP450 1A2 substrate Inhibitor 0.6618
CYP450 2C9 substrate Non-inhibitor 0.8589
CYP450 2D6 substrate Inhibitor 0.8765
CYP450 2C19 substrate Non-inhibitor 0.7584
CYP450 3A4 substrate Non-inhibitor 0.9589
CYP450 inhibitory promiscuity High CYP Inhibitory Promiscuity 0.5834
Ames test Non AMES toxic 0.8307
Carcinogenicity Non-carcinogens 0.9578
Biodegradation Not ready biodegradable 0.9913
Rat acute toxicity 2.4636 LD50, mol/kg Not applicable
hERG inhibition (predictor I) Weak inhibitor 0.771
hERG inhibition (predictor II) Inhibitor 0.6166
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 Solubility0.0883ALOGPS
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 RuleNoChemAxon
Spectra
SpectraNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
External Links
ResourceLink
PubChem Compound27901
PubChem Substance46504731
ChemSpider25957
WikipediaThenalidine
ATC CodesD04AA03R06AX03
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