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Details

Stereochemistry ACHIRAL
Molecular Formula C19H21N5O2
Molecular Weight 351.4023
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of PIRENZEPINE

SMILES

CN1CCN(CC(=O)N2C3=CC=CC=C3C(=O)NC4=C2N=CC=C4)CC1

InChI

InChIKey=RMHMFHUVIITRHF-UHFFFAOYSA-N
InChI=1S/C19H21N5O2/c1-22-9-11-23(12-10-22)13-17(25)24-16-7-3-2-5-14(16)19(26)21-15-6-4-8-20-18(15)24/h2-8H,9-13H2,1H3,(H,21,26)

HIDE SMILES / InChI

Molecular Formula C19H21N5O2
Molecular Weight 351.4023
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Pirenzepine is a M1 muscarinic receptor antagonist, which is prescribed for the treatment of gastric and duodenal ulcer in Europe. The drug preferentially acts on the gastric mucosa to inhibit secretion of both gastric acid and pepsin. Experiment with healthy volunteers demonstrated that pirenzepine passes the blood-brain barrier, but only to a small extent.

CNS Activity

Curator's Comment: Pirenzepine passes the blood-brain barrier, but only to a small extent.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Target ID: P11229
Gene ID: 1128.0
Gene Symbol: CHRM1
Target Organism: Homo sapiens (Human)
192.0 nM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
GASTROZEPIN

Approved Use

GASTROZEPIN is used for a duodenal ulcer and a benign stomach ulcer.
Primary
GASTROZEPIN

Approved Use

GASTROZEPIN is used for a duodenal ulcer and a benign stomach ulcer.
PubMed

PubMed

TitleDatePubMed
First experiences in combination therapy using olanzapine with SSRIs (citalopram, paroxetine) in delusional depression.
2001
Superior efficacy of olanzapine over haloperidol: analysis of patients with schizophrenia from a multicenter international trial.
2001
Rapid tranquilization with olanzapine in acute psychosis: a case series.
2001
Effect of amantadine on weight gain during olanzapine treatment.
2001 Apr
Regulation of phospholipase Cbeta activity by muscarinic acetylcholine and 5-HT(2) receptors in crude and synaptosomal membranes from human cerebral cortex.
2001 Apr
Comment: olanzapine-induced acute pancreatitis.
2001 Apr
Ondansetron for tardive dyskinesia.
2001 Apr
Neuroleptic malignant syndrome after addition of haloperidol to atypical antipsychotic.
2001 Apr
Acetylcholine increases the free intracellular calcium concentration in podocytes in intact rat glomeruli via muscarinic M(5) receptors.
2001 Apr
Reply to comments on "Olanzapine treatment of children, adolescents, and adults with pervasive developmental disorders: an open-label pilot study".
2001 Apr
Olanzapine and Huntington's disease.
2001 Apr
Functional characterization of rat submaxillary gland muscarinic receptors using microphysiometry.
2001 Apr
Ca(2+) signaling in porcine duodenal glands by muscarinic receptor activation.
2001 Apr
Acetylcholine increases intracellular Ca2+ in the rat pituitary folliculostellate cells in primary culture.
2001 Apr
Effects of brucine, a plant alkaloid, on M(1) muscarinic receptors and alpha(1)-adrenoceptors in the rabbit vas deferens preparation.
2001 Apr
Treatment of psychogenic polydipsia: comparison of risperidone and olanzapine, and the effects of an adjunctive angiotensin-II receptor blocking drug (irbesartan).
2001 Feb
[Anti-ulcer drug pirenzepin: new use as an aid for prevention of myopia?].
2001 Feb
Long-term olanzapine treatment: weight change and weight-related health factors in schizophrenia.
2001 Feb
Olanzapine and hypertriglyceridemia.
2001 Feb
Olanzapine plasma concentrations and clinical response: acute phase results of the North American Olanzapine Trial.
2001 Feb
Traditional and new antipsychotic drugs differentially alter neurotransmission markers in basal ganglia-thalamocortical neural pathways.
2001 Feb
Characterisation of the prejunctional inhibitory muscarinic receptor on cholinergic nerves in the rat urinary bladder.
2001 Feb 16
Short-term effects of olanzapine in Huntington disease.
2001 Jan
Misdiagnosis of schizophrenia for a patient with epilepsy.
2001 Jan
A novel augmentation strategy for treating resistant major depression.
2001 Jan
Allelic variation in the 5-HT2C receptor (HT2RC) and the increase in slow wave sleep produced by olanzapine.
2001 Jan 1
Consistency of atypical antipsychotic superiority to placebo in recent clinical trials.
2001 Jan 1
Double-blind comparison of olanzapine versus clozapine in schizophrenic patients clinically eligible for treatment with clozapine.
2001 Jan 1
[Olanzapine and pregnancy].
2001 Jan 21
[Subjective and objective evaluation of treating schizophrenia with classic or atypical drugs].
2001 Jan-Feb
[Obsessive-compulsive disorders in adolescents with diagnosed schizophrenia].
2001 Jan-Feb
[Viewpoint of schizophrenic patients: a European survey].
2001 Jan-Feb
Analysis of the QTc interval during olanzapine treatment of patients with schizophrenia and related psychosis.
2001 Mar
Dementia with Lewy bodies in Down's syndrome.
2001 Mar
Serine/threonine protein phosphatases and synaptic inhibition regulate the expression of cholinergic-dependent plateau potentials.
2001 Mar
Atypical antipsychotics and hyperglycaemia.
2001 Mar
The allosteric interaction of otenzepad (AF-DX 116) at muscarinic M2 receptors in guinea pig atria.
2001 Mar 30
Quantitative determination of olanzapine in rat brain tissue by high-performance liquid chromatography with electrochemical detection.
2001 Mar 5
Haloperidol-stomach lesions attenuation by pentadecapeptide BPC 157, omeprazole, bromocriptine, but not atropine, lansoprazole, pantoprazole, ranitidine, cimetidine and misoprostol in mice.
2001 Mar 9
The antinociceptive and sedative effects of carbachol and oxycodone administered into brainstem pontine reticular formation and spinal subarachnoid space in rats.
2001 May
Nitric oxide modulates cardiac performance in the heart of Anguilla anguilla.
2001 May
Expression of multiple subtypes of muscarinic receptors and cellular distribution in the human heart.
2001 May
Pharmacological properties of (2R)-N-[1-(6-aminopyridin-2-ylmethyl)piperidin-4-yl]-2-[(1R)-3,3-difluorocyclopentyl]-2-hydroxy-2-phenylacetamide: a novel mucarinic antagonist with M(2)-sparing antagonistic activity.
2001 May
Molecular and pharmacological characterization of muscarinic receptor subtypes in a rat parotid gland cell line: comparison with native parotid gland.
2001 May
Long-term effects of olanzapine, risperidone, and quetiapine on dopamine receptor types in regions of rat brain: implications for antipsychotic drug treatment.
2001 May
Agonist activation of cytosolic Ca2+ in subfornical organ cells projecting to the supraoptic nucleus.
2001 May
Patents

Patents

Sample Use Guides

Gastric and duodenal ulcers: 1 tablet (GASTROZEPIN 50 mg) 2 times daily (morning and evening). Severe and complicated gastric and duodenal ulcers: 1 tablet (GASTROZEPINE 50 mg) 3 times daily.
Route of Administration: Oral
In Vitro Use Guide
Muscle strips from the canine gall-bladder were treated with pirenzepine (10(-9)-10(-5) M). Pirenzepine antagonized muscle contractions in response to acetylcholine (10(-9)-10(-2) M) and CCK-8 (10(-11)-10(-6) M) in a significant manner.
Substance Class Chemical
Created
by admin
on Sat Dec 16 17:10:31 GMT 2023
Edited
by admin
on Sat Dec 16 17:10:31 GMT 2023
Record UNII
3G0285N20N
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
PIRENZEPINE
INN   MI   VANDF   WHO-DD  
INN  
Official Name English
PIRENZEPINE [MI]
Common Name English
pirenzepine [INN]
Common Name English
6H-PYRIDO(2,3-B)(1,4)BENZODIAZEPIN-6-ONE, 5,11-DIHYDRO-11-((4-METHYL-1-PIPERAZINYL)ACETYL)-
Systematic Name English
ACI-91
Code English
PIRENZEPINE [VANDF]
Common Name English
11-((4-METHYL-1-PIPERAZINYL)ACETYL)-5,11-DIHYDRO-6H-PYRIDO(2,3-B)(1,4)BENZODIAZEPIN-6-ONE
Systematic Name English
Pirenzepine [WHO-DD]
Common Name English
5,11-DIHYDRO-11-((4-METHYL-1-PIPERAZINYL)ACETYL)-6H-PYRIDO(2,3-B)(1,4)BENZODIAZEPIN-6-ONE
Systematic Name English
WST-057
Code English
Classification Tree Code System Code
WHO-ATC A02BX03
Created by admin on Sat Dec 16 17:10:32 GMT 2023 , Edited by admin on Sat Dec 16 17:10:32 GMT 2023
NCI_THESAURUS C29704
Created by admin on Sat Dec 16 17:10:33 GMT 2023 , Edited by admin on Sat Dec 16 17:10:33 GMT 2023
WHO-VATC QA02BX03
Created by admin on Sat Dec 16 17:10:33 GMT 2023 , Edited by admin on Sat Dec 16 17:10:33 GMT 2023
Code System Code Type Description
MESH
D010890
Created by admin on Sat Dec 16 17:10:33 GMT 2023 , Edited by admin on Sat Dec 16 17:10:33 GMT 2023
PRIMARY
CAS
28797-61-7
Created by admin on Sat Dec 16 17:10:32 GMT 2023 , Edited by admin on Sat Dec 16 17:10:32 GMT 2023
PRIMARY
SMS_ID
100000081663
Created by admin on Sat Dec 16 17:10:33 GMT 2023 , Edited by admin on Sat Dec 16 17:10:33 GMT 2023
PRIMARY
DRUG CENTRAL
2200
Created by admin on Sat Dec 16 17:10:33 GMT 2023 , Edited by admin on Sat Dec 16 17:10:33 GMT 2023
PRIMARY
DRUG BANK
DB00670
Created by admin on Sat Dec 16 17:10:32 GMT 2023 , Edited by admin on Sat Dec 16 17:10:32 GMT 2023
PRIMARY
PUBCHEM
4848
Created by admin on Sat Dec 16 17:10:33 GMT 2023 , Edited by admin on Sat Dec 16 17:10:33 GMT 2023
PRIMARY
MERCK INDEX
m8874
Created by admin on Sat Dec 16 17:10:33 GMT 2023 , Edited by admin on Sat Dec 16 17:10:33 GMT 2023
PRIMARY Merck Index
WIKIPEDIA
PIRENZEPINE
Created by admin on Sat Dec 16 17:10:33 GMT 2023 , Edited by admin on Sat Dec 16 17:10:33 GMT 2023
PRIMARY
EPA CompTox
DTXSID7023487
Created by admin on Sat Dec 16 17:10:33 GMT 2023 , Edited by admin on Sat Dec 16 17:10:33 GMT 2023
PRIMARY
IUPHAR
328
Created by admin on Sat Dec 16 17:10:33 GMT 2023 , Edited by admin on Sat Dec 16 17:10:33 GMT 2023
PRIMARY
FDA UNII
3G0285N20N
Created by admin on Sat Dec 16 17:10:33 GMT 2023 , Edited by admin on Sat Dec 16 17:10:33 GMT 2023
PRIMARY
ChEMBL
CHEMBL9967
Created by admin on Sat Dec 16 17:10:32 GMT 2023 , Edited by admin on Sat Dec 16 17:10:32 GMT 2023
PRIMARY
NCI_THESAURUS
C76002
Created by admin on Sat Dec 16 17:10:33 GMT 2023 , Edited by admin on Sat Dec 16 17:10:33 GMT 2023
PRIMARY
RXCUI
8352
Created by admin on Sat Dec 16 17:10:33 GMT 2023 , Edited by admin on Sat Dec 16 17:10:33 GMT 2023
PRIMARY RxNorm
CHEBI
8247
Created by admin on Sat Dec 16 17:10:32 GMT 2023 , Edited by admin on Sat Dec 16 17:10:32 GMT 2023
PRIMARY
INN
3476
Created by admin on Sat Dec 16 17:10:33 GMT 2023 , Edited by admin on Sat Dec 16 17:10:33 GMT 2023
PRIMARY
EVMPD
SUB09904MIG
Created by admin on Sat Dec 16 17:10:32 GMT 2023 , Edited by admin on Sat Dec 16 17:10:32 GMT 2023
PRIMARY
ECHA (EC/EINECS)
249-228-4
Created by admin on Sat Dec 16 17:10:33 GMT 2023 , Edited by admin on Sat Dec 16 17:10:33 GMT 2023
PRIMARY
Related Record Type Details
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
LABELED -> NON-LABELED
TARGET -> INHIBITOR
BINDING
IC50
BINDER->LIGAND
BINDING
TARGET -> INHIBITOR
Pirenzepine is a selective muscarinic M1 receptor antagonist
SOLVATE->ANHYDROUS
OFF-TARGET->INHIBITOR
IC50
Related Record Type Details
ACTIVE MOIETY