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=C(NC(=O)C4=C2N=CC=C4)C=CC=C3

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
Quinolizidinyl derivatives of 5,11-dihydro-6H-pyrido[2,3-b][1,4]benzodiazepin-6-one as ligands for muscarinic receptors.	1999-10-18	10571170
Muscarinic M1 and M3 receptor antagonist effects of a new pirenzepine analogue in isolated guinea-pig ileal longitudinal muscle-myenteric plexus.	1994-03-11	7515819
Affinity profiles of pizotifen, ketotifen and other tricyclic antimuscarinics at muscarinic receptor subtypes M1, M2 and M3.	1992-02-18	1377628

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 `Mon Mar 31 18:31:09 GMT 2025` Edited by `admin` on `Mon Mar 31 18:31:09 GMT 2025`
Record UNII	8OMO7K4W74
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

NUVENZEPINE

Official Name

English

nuvenzepine [INN]

Preferred Name

English

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

Systematic Name

English

Classification Tree Code System Code

NCI_THESAURUS

C29704