Thenalidine

Identification

Name
Thenalidine
Accession Number
DB04826
Type
Small Molecule
Groups
Withdrawn
Description

Withdrawn from the Canadian, US, and UK markets in 1963 due to concerns involving neutropenia.

Structure
Thumb
Synonyms
  • 1-Methyl-4-amino-N-phenyl-N-(2-thenyl)piperidine
  • 1-Methyl-4-N-2-thenylanilinopiperidine
  • Tenalidina
  • Thenaldine
  • Thenalidinum
  • Thenophenopiperidine
International/Other Brands
Sanbosten / Sandostene
Categories
UNII
6U94N2D00F
CAS number
86-12-4
Weight
Average: 286.435
Monoisotopic: 286.150369404
Chemical Formula
C17H22N2S
InChI Key
KLOHYVOVXOUKQI-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-yl)methyl]piperidin-4-amine
SMILES
CN1CCC(CC1)N(CC1=CC=CS1)C1=CC=CC=C1

Pharmacology

Indication
Not Available
Pharmacodynamics
Not Available
Mechanism of action
Not Available
Absorption
Not Available
Volume of distribution
Not Available
Protein binding
Not Available
Metabolism
Not Available
Route of elimination
Not Available
Half life
Not Available
Clearance
Not Available
Toxicity
Not Available
Affected organisms
Not Available
Pathways
PathwayCategory
Thenalidine H1-Antihistamine ActionDrug action
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
Not Available
Food Interactions
Not Available

References

General References
Not Available
External Links
PubChem Compound
27901
PubChem Substance
46504731
ChemSpider
25957
ChEBI
135187
ChEMBL
CHEMBL2105458
Wikipedia
Thenalidine
ATC Codes
R06AX03 — ThenalidineD04AA03 — ThenalidineR06AX53 — Thenalidine, combinations

Clinical Trials

Clinical Trials
Not Available

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)96 °CPhysProp
boiling point (°C)159 °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 RuleNoChemAxon
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 inhibitorNon-inhibitor0.8589
CYP450 2D6 inhibitorInhibitor0.8765
CYP450 2C19 inhibitorNon-inhibitor0.7584
CYP450 3A4 inhibitorNon-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
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Taxonomy

Description
This 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.
Kingdom
Organic compounds
Super Class
Organic nitrogen compounds
Class
Organonitrogen compounds
Sub Class
Amines
Direct Parent
Dialkylarylamines
Alternative Parents
Aniline and substituted anilines / Aralkylamines / Aminopiperidines / Thiophenes / Heteroaromatic compounds / Trialkylamines / Azacyclic compounds / Organopnictogen compounds / Hydrocarbon derivatives
Substituents
Aniline or substituted anilines / Dialkylarylamine / Aralkylamine / 4-aminopiperidine / Benzenoid / Piperidine / Monocyclic benzene moiety / Heteroaromatic compound / Thiophene / Tertiary aliphatic amine
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
Not Available

Drug created on September 11, 2007 14:30 / Updated on June 02, 2018 07:35