THENALIDINE

US Previously Marketed

First approved in 1956

Details

Stereochemistry	ACHIRAL
Molecular Formula	C17H22N2S
Molecular Weight	286.435
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CN1CCC(CC1)N(CC2=CC=CS2)C3=CC=CC=C3

InChI

InChIKey=KLOHYVOVXOUKQI-UHFFFAOYSA-N

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

HIDE SMILES / InChI

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/6266359
Curator's Comment: Description was created based on several sources, including http://www.drugbank.ca/drugs/DB04826 http://www.un.org/esa/coordination/CL12.pdf

Thenalidine is an antihistamine with anticholinergic properties used as an antipruritic drug. It was withdrawn from the US, Canadian, and UK markets due to a risk of neutropenia. Thenalidine is an antagonist of the H1-receptor.

CNS Activity

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Histamine H1 receptor 315 Target ID: CHEMBL231 Sources: https://www.ncbi.nlm.nih.gov/pubmed/6266359 \| http://www.genome.jp/dbget-bin/www_bget?drug+D07194	Antagonist 2778

Conditions

Condition	Modality	Targets	Highest Phase	Product
Atopic dermatitis 43 Sources: https://www.ncbi.nlm.nih.gov/pubmed/13573282	Primary		Approved 8429	Sandostene Approved Use for the management of dermatologic and allergic conditions Launch Date 1952

Doses

Dose	Population	Adverse events
25 mg 3 times / day multiple, oral (starting) Dose: 25 mg, 3 times / day Route: oral Route: multiple Dose: 25 mg, 3 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/13762246 https://pubmed.ncbi.nlm.nih.gov/13917095	unhealthy, 41 years n = 1 Health Status: unhealthy Age Group: 41 years Sex: M Population Size: 1 Sources: https://pubmed.ncbi.nlm.nih.gov/13762246 https://pubmed.ncbi.nlm.nih.gov/13917095	Disc. AE: Agranulocytosis... AEs leading to discontinuation/dose reduction: Agranulocytosis (grade 5) Sources: https://pubmed.ncbi.nlm.nih.gov/13762246 https://pubmed.ncbi.nlm.nih.gov/13917095

AEs

AE	Significance	Dose	Population
Agranulocytosis	grade 5 Disc. AE	25 mg 3 times / day multiple, oral (starting) Dose: 25 mg, 3 times / day Route: oral Route: multiple Dose: 25 mg, 3 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/13762246 https://pubmed.ncbi.nlm.nih.gov/13917095	unhealthy, 41 years n = 1 Health Status: unhealthy Age Group: 41 years Sex: M Population Size: 1 Sources: https://pubmed.ncbi.nlm.nih.gov/13762246 https://pubmed.ncbi.nlm.nih.gov/13917095

Sourcing

Vendor/Aggregator	ID	URL
001 Chemical	DY575262	https://www.001chemical.com/chem/86-12-4
ABI Chem	AC1L1E77
Alfa Chemistry	86-12-4	https://www.alfa-chemistry.com/cas_86-12-4.htm
ChemMol	99169221	http://www.chemmol.com/chemmol/99169221.html
Chemieliva Pharmaceutical Co., Ltd	PBCM0000229
Clearsynth	CS-T-86728	https://www.clearsynth.com/en/CST86728.html
Compound Cloud	27901
Molcore	MC575262	https://www.molcore.com/product/86-12-4
MuseChem	R027335
Norris Pharm	NSZB-A064135
NovoSeek	27901
Smolecule	S545158	http://www.smolecule.com/products/s545158
THE BioTek	bt-284248	https://www.thebiotek.com/product/inhibitors/bt-284248
Toronto Research Chemicals	T343000
ZINC	ZINC000000002146	http://zinc15.docking.org/substances/ZINC000000002146

PubMed

Title	Date	PubMed

Patents

Sample Use Guides

In Vivo Use Guide

Thenalidine was given in coated tablets, each containing 25 mg. of the active ingredient. The initial dosage was 2 tablets 4 times a day until the patient improved, or for at least one week. The maintenance dose varied between 3 and 6 tablets daily, 4 tablets daily being the average. Intravenous injection of 10 ml. of thenalidine tartrate plus calcium (50 mg. of Sandostene and 1.375 g. of calcium gluconogalactogluconate) was given in a few severe and acute cases only.

Route of Administration: Other

In Vitro Use Guide

Unknown

Name

Type

Language

THENALIDINE

Official Name

English

1-METHYL-4-N-2-THENYLANILINOPIPERIDINE

Common Name

English

4-PIPERIDINAMINE, 1-METHYL-N-PHENYL-N-(2-THIENYLMETHYL)-

Systematic Name

English

Thenalidine [WHO-DD]

Common Name

English

THENOPHENOPIPERIDINE

Common Name

English

thenalidine [INN]

Common Name

English

THENALDINE [MI]

Common Name

English

Classification Tree Code System Code

WHO-VATC

QD04AA03