NUVENZEPINE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C19H20N4O2
Molecular Weight	336.3877
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CN1CCC(CC1)C(=O)N2C3=NC=CC=C3C(=O)NC4=C2C=CC=C4

InChI

InChIKey=HPKYRXAEGNUARA-UHFFFAOYSA-N

InChI=1S/C19H20N4O2/c1-22-11-8-13(9-12-22)19(25)23-16-7-3-2-6-15(16)21-18(24)14-5-4-10-20-17(14)23/h2-7,10,13H,8-9,11-12H2,1H3,(H,21,24)

HIDE SMILES / InChI

Molecular Formula	C19H20N4O2
Molecular Weight	336.3877
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/1377628 | https://www.ncbi.nlm.nih.gov/pubmed/7816744 | https://www.ncbi.nlm.nih.gov/pubmed/2095154

Nuvenzepine is an mAChR antagonist previously in phase I clinical trials for the treatment of gastrospasm. Nuvenzepine substantially shares the antimuscarinic properties of pirenzepine but it is also endowed with a (weak) H1-blocking action. Nuvenzepine is selective for M1 receptors (pA2 = 6.63-7.74). Nuvenzepine, administered intraduodenally, displayed a long-lasting and dose-dependent inhibition of neostigmine-induced intestinal motility in anaesthetized cats. On ileal motor activity, the compound showed a potency 10 times greater than that of pirenzepine, and, although to a lesser extent, it was also active, unlike pirenzepine, on colonic stimulated motility. In conscious cats, nuvenzepine inhibited pentagastrin-stimulated gastric acid secretion resulting 25-30 times more potent than pirenzepine.

Approval Year

PubMed

Title	Date	PubMed
Affinity profiles of pizotifen, ketotifen and other tricyclic antimuscarinics at muscarinic receptor subtypes M1, M2 and M3.	1992 Feb 18	1377628
Muscarinic M1 and M3 receptor antagonist effects of a new pirenzepine analogue in isolated guinea-pig ileal longitudinal muscle-myenteric plexus.	1994 Mar 11	7515819
Quinolizidinyl derivatives of 5,11-dihydro-6H-pyrido[2,3-b][1,4]benzodiazepin-6-one as ligands for muscarinic receptors.	1999 Oct 18	10571170

Sample Use Guides

In Vivo Use Guide

Healthy volunteers treated PO with 15 or 25 mg of nuvenzepine.

Route of Administration: Oral

In Vitro Use Guide

Nuvenzepine showed a four-fold higher affinity than pirenzepine in competitively antagonizing acetylcholine-induced contractions on isolated ileal musculature (pA2 = 7.08 +/- 0.15) and on longitudinal ileum dispersed cells (pA2 = 7.11 +/- 0.19). Nuvenzepine inhibited histamine-induced ileal motor activity in a dualistic manner, behaving as an irreversible competitive H1 antagonist (pA2 = 5.02 +/- 0.11). Nuvenzepine was almost equipotent to pirenzepine in competitively preventing bethanechol-induced gall-bladder contractions (pA2 = 7.23 +/- 0.16) and it displayed a four-fold higher potency than pirenzepine in blocking vagal-stimulated tracheal constrictions (pIC50 = 6.77 +/- 0.06).

Substance Class	Chemical Created by `admin` on `Fri Dec 15 16:33:09 GMT 2023` Edited by `admin` on `Fri Dec 15 16:33:09 GMT 2023`
Record UNII	8OMO7K4W74
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

NUVENZEPINE

Official Name

English

6,11-DIHYDRO-11-(1-METHYLISONIPECOTOYL)-5H-PYRIDO(2,3-B)(1,5)BENZODIAZEPIN-5-ONE

Systematic Name

English

nuvenzepine [INN]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C29704