Thenalidine

Identification

Generic Name

Thenalidine

DrugBank Accession Number

DB04826

Background

Withdrawn from the Canadian, US, and UK markets in 1963 due to concerns involving neutropenia.

Type

Small Molecule

Groups

Approved, Withdrawn

Structure

3D

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MOLSDF3D-SDFPDBSMILESInChI

Similar Structures

Structure for Thenalidine (DB04826)

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Weight

Average: 286.435
Monoisotopic: 286.150369404

Chemical Formula

C₁₇H₂₂N₂S

Synonyms

• 1-Methyl-4-amino-N-phenyl-N-(2-thenyl)piperidine
• 1-Methyl-4-N-2-thenylanilinopiperidine
• Tenalidina
• Thenalidine
• Thenalidinum
• Thenophenopiperidine

External IDs

• AS 716

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Pharmacology

Indication

Not Available

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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

Adverse Effects

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Toxicity

Not Available

Pathways

Pathway	Category
Thenalidine H1-Antihistamine Action	Drug action

Pharmacogenomic Effects/ADRs

Not Available

Interactions

Drug Interactions

This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.

• Approved
• Vet approved
• Nutraceutical
• Illicit
• Withdrawn
• Investigational
• Experimental
• All Drugs

Drug	Interaction
Integrate drug-drug interactions in your software
Droxidopa	The therapeutic efficacy of Droxidopa can be increased when used in combination with Thenalidine.
Ephedrine	The therapeutic efficacy of Ephedrine can be increased when used in combination with Thenalidine.
Epinephrine	The therapeutic efficacy of Epinephrine can be increased when used in combination with Thenalidine.
Levonordefrin	The therapeutic efficacy of Levonordefrin can be increased when used in combination with Thenalidine.
Norepinephrine	The therapeutic efficacy of Norepinephrine can be increased when used in combination with Thenalidine.

Food Interactions

Not Available

Products

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International/Other Brands

Sanbosten / Sandostene

Categories

ATC Codes

R06AX03 — Thenalidine

• R06AX — Other antihistamines for systemic use
• R06A — ANTIHISTAMINES FOR SYSTEMIC USE
• R06 — ANTIHISTAMINES FOR SYSTEMIC USE
• R — RESPIRATORY SYSTEM

R06AX53 — Thenalidine, combinations

• R06AX — Other antihistamines for systemic use
• R06A — ANTIHISTAMINES FOR SYSTEMIC USE
• R06 — ANTIHISTAMINES FOR SYSTEMIC USE
• R — RESPIRATORY SYSTEM

D04AA03 — Thenalidine

• D04AA — Antihistamines for topical use
• D04A — ANTIPRURITICS, INCL. ANTIHISTAMINES, ANESTHETICS, ETC.
• D04 — ANTIPRURITICS, INCL. ANTIHISTAMINES, ANESTHETICS, ETC.
• D — DERMATOLOGICALS

Drug Categories

• Antihistamines for Systemic Use
• Antihistamines for Topical Use
• Antipruritics, Incl. Antihistamines, Anesthetics, Etc.
• Dermatologicals

Chemical TaxonomyProvided by Classyfire

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

4-aminopiperidine / Aniline or substituted anilines / Aralkylamine / Aromatic heteromonocyclic compound / Azacycle / Benzenoid / Dialkylarylamine / Heteroaromatic compound / Hydrocarbon derivative / Monocyclic benzene moiety

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

Not Available

Affected organisms

Not Available

Chemical Identifiers

UNII

6U94N2D00F

CAS number

86-12-4

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

References

General References

Not Available

External Links

PubChem Compound

27901

PubChem Substance

46504731

ChemSpider

25957

ChEBI

135187

ChEMBL

CHEMBL2105458

ZINC

ZINC000000002146

Wikipedia

Thenalidine

Clinical Trials

Clinical Trials

Phase	Status	Purpose	Conditions	Count

Pharmacoeconomics

Manufacturers

Not Available

Packagers

Not Available

Dosage Forms

Not Available

Prices

Not Available

Patents

Not Available

Properties

State

Solid

Experimental Properties

Property	Value	Source
melting point (°C)	96 °C	PhysProp
boiling point (°C)	159 °C at 2.00E-02 mm Hg	PhysProp

Predicted Properties

Property	Value	Source
Water Solubility	0.0883 mg/mL	ALOGPS
logP	4.47	ALOGPS
logP	3.75	Chemaxon
logS	-3.5	ALOGPS
pKa (Strongest Basic)	8.69	Chemaxon
Physiological Charge	1	Chemaxon
Hydrogen Acceptor Count	2	Chemaxon
Hydrogen Donor Count	0	Chemaxon
Polar Surface Area	6.48 Å2	Chemaxon
Rotatable Bond Count	4	Chemaxon
Refractivity	87.44 m3·mol-1	Chemaxon
Polarizability	32.89 Å3	Chemaxon
Number of Rings	3	Chemaxon
Bioavailability	1	Chemaxon
Rule of Five	Yes	Chemaxon
Ghose Filter	Yes	Chemaxon
Veber's Rule	Yes	Chemaxon
MDDR-like Rule	No	Chemaxon

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 inhibitor	Non-inhibitor	0.8589
CYP450 2D6 inhibitor	Inhibitor	0.8765
CYP450 2C19 inhibitor	Non-inhibitor	0.7584
CYP450 3A4 inhibitor	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

ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)

Not Available

Spectra

Spectrum	Spectrum Type	Splash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)	Predicted LC-MS/MS	splash10-000i-0090000000-a79ba6bf2f3a2f82fbfa
Predicted MS/MS Spectrum - 10V, Negative (Annotated)	Predicted LC-MS/MS	splash10-000i-0090000000-102a409e3e0c058e6189
Predicted MS/MS Spectrum - 20V, Negative (Annotated)	Predicted LC-MS/MS	splash10-000i-3890000000-7adc1d7fb7f9eec4851d
Predicted MS/MS Spectrum - 20V, Positive (Annotated)	Predicted LC-MS/MS	splash10-000i-0090000000-0ce14139273174530e90
Predicted MS/MS Spectrum - 40V, Positive (Annotated)	Predicted LC-MS/MS	splash10-0a4i-9510000000-fb5e46014e2d06a8f1de
Predicted MS/MS Spectrum - 40V, Negative (Annotated)	Predicted LC-MS/MS	splash10-0wa0-2930000000-896cdcb951efb7085ddc
Predicted 1H NMR Spectrum	1D NMR	Not Applicable
Predicted 13C NMR Spectrum	1D NMR	Not Applicable

Chromatographic Properties

Collision Cross Sections (CCS)

Adduct	CCS Value (Å2)	Source type	Source
[M-H]-	171.9160397	predicted	DarkChem Lite v0.1.0
[M-H]-	164.13934	predicted	DeepCCS 1.0 (2019)
[M+H]+	172.2117397	predicted	DarkChem Lite v0.1.0
[M+H]+	166.49734	predicted	DeepCCS 1.0 (2019)
[M+Na]+	172.1862397	predicted	DarkChem Lite v0.1.0
[M+Na]+	172.5905	predicted	DeepCCS 1.0 (2019)

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Drug created at September 11, 2007 20:30 / Updated at February 21, 2021 18:51