TELENZEPINE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C19H22N4O2S
Molecular Weight	370.469
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CN1CCN(CC(=O)N2C3=C(C)SC=C3C(=O)NC4=CC=CC=C24)CC1

InChI

InChIKey=VSWPGAIWKHPTKX-UHFFFAOYSA-N

InChI=1S/C19H22N4O2S/c1-13-18-14(12-26-13)19(25)20-15-5-3-4-6-16(15)23(18)17(24)11-22-9-7-21(2)8-10-22/h3-6,12H,7-11H2,1-2H3,(H,20,25)

HIDE SMILES / InChI

Molecular Formula	C19H22N4O2S
Molecular Weight	370.469
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/2695806 | https://www.ncbi.nlm.nih.gov/pubmed/8081076 | https://adisinsight.springer.com/drugs/800000603

Telenzepine is a selective muscarinic M1 receptor antagonist that was studied for selective inhibition of gastric acid secretion. Telenzepine was used in clinical trials in patients with acute duodenal ulcer, where was found that once daily administration of 3 mg in the evening must be regarded as the optimal dosage regimen of telenzepine. However, the preregistration for peptic ulcer in Germany was discontinued. In addition, the drug was studied in patients with nocturnal asthma. It was shown that telenzepine via the oral route at a dose of up to 5 mg was not effective in preventing nocturnal asthma.

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Muscarinic acetylcholine receptor M1 169 Target ID: CHEMBL276 Sources: https://www.ncbi.nlm.nih.gov/pubmed/2066986 \| https://www.ncbi.nlm.nih.gov/pubmed/2695806	Antagonist 2778		0.0018 µM [Ki]

PubMed

Title	Date	PubMed
The existence of stable enantiomers of telenzepine and their stereoselective interaction with muscarinic receptor subtypes.	1989 Apr	2704371
Correlation of brain levels of 9-amino-1,2,3,4-tetrahydroacridine (THA) with neurochemical and behavioral changes.	1989 Nov 28	2606156
Assessment of the muscarinic receptor subtypes involved in pilocarpine-induced seizures in mice.	1994 Feb 28	8028781
Characterization of the muscarinic receptor subtype mediating pilocarpine-induced tremulous jaw movements in rats.	1999 Jan 1	9920179
Distinct muscarinic receptors enhance spontaneous GABA release and inhibit electrically evoked GABAergic synaptic transmission in the chick lateral spiriform nucleus.	2001	11457590
Cholinergic modulation of basal and amphetamine-induced dopamine release in rat medial prefrontal cortex and nucleus accumbens.	2002 Dec 20	12468043
Miniaturization of fluorescence polarization receptor-binding assays using CyDye-labeled ligands.	2003 Aug	14567793
PMA decreases the proliferation of retinal cells in vitro: the involvement of acetylcholine and BDNF.	2003 Jan	12441170
Cholinergic modulation of memory in the basolateral amygdala involves activation of both m1 and m2 receptors.	2003 May	12799522
Muscarinic acetylcholine receptors potentiate the GABAergic transmission in the developing rat inferior colliculus.	2003 Sep	12907311
Acetylcholine mediates the release of IL-8 in human bronchial epithelial cells by a NFkB/ERK-dependent mechanism.	2008 Mar 17	18242599

Sample Use Guides

In Vivo Use Guide

120 patients with endoscopically proven, florid duodenal ulcer were treated with either 1.5 mg, 3 mg or 5 mg telenzepine once daily at bedtime (40 patients per dose group).

Route of Administration: Oral

Substance Class	Chemical Created by `admin` on `Fri Dec 15 16:32:36 GMT 2023` Edited by `admin` on `Fri Dec 15 16:32:36 GMT 2023`
Record UNII	0990EG3K10
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

TELENZEPINE

Official Name

English

NSC-758679

Code

English

10H-THIENO(3,4-B)(1,5)BENZODIAZEPIN-10-ONE, 4,9-DIHYDRO-3-METHYL-4-(2-(4-METHYL-1-PIPERAZINYL)ACETYL)-

Common Name

English

TELENZEPINE [MART.]

Common Name

English

telenzepine [INN]

Common Name

English

TELENZEPINE [MI]

Common Name

English

4,9-DIHYDRO-3-METHYL-4-(2-(4-METHYL-1-PIPERAZINYL)ACETYL)-10H-THIENO(3,4-B)(1,5)BENZODIAZEPIN-10-ONE

Systematic Name

English

Telenzepine [WHO-DD]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C29704