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Details

Stereochemistry ACHIRAL
Molecular Formula C19H21N5O2
Molecular Weight 351.4031
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of PIRENZEPINE

SMILES

CN1CCN(CC1)CC(=O)N2c3ccccc3C(=Nc4cccnc42)O

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 351.4031
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
M3 muscarinic receptor activation of a delayed rectifier potassium current in canine atrial myocytes.
1999
A double-blind placebo-controlled case study of the use of donepezil to improve cognition in a schizoaffective disorder patient: functional MRI correlates.
2001
Pharmacology, distribution and development of muscarinic acetylcholine receptor subtypes in the optic tectum of Rana pipiens.
2001
First experiences in combination therapy using olanzapine with SSRIs (citalopram, paroxetine) in delusional depression.
2001
Weight change and atypical antipsychotic treatment in patients with schizophrenia.
2001
Cardiac safety parameters of olanzapine: comparison with other atypical and typical antipsychotics.
2001
Evidence for the effectiveness of olanzapine among patients nonresponsive and/or intolerant to risperidone.
2001
An efficacy analysis of olanzapine treatment data in schizophrenia patients with catatonic signs and symptoms.
2001
Rapid tranquilization with olanzapine in acute psychosis: a case series.
2001
Atypical antipsychotics: new directions and new challenges in the treatment of schizophrenia.
2001
Manic symptoms induced by olanzapine.
2001 Apr
Comment: olanzapine-induced acute pancreatitis.
2001 Apr
Olanzapine overdose.
2001 Apr
Olanzapine-associated priapism.
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
Long-term olanzapine treatment: weight change and weight-related health factors in schizophrenia.
2001 Feb
Effects of newer atypical antipsychotics on autonomic neurocardiac function: a comparison between amisulpride, olanzapine, sertindole, and clozapine.
2001 Feb
Olanzapine plasma concentrations and clinical response: acute phase results of the North American Olanzapine Trial.
2001 Feb
The economic consequences of a drug-drug interaction.
2001 Feb
Repeated episodes of hypothermia in a subject treated with haloperidol, levomepromazine, olanzapine, and thioridazine.
2001 Feb
Atypical antipsychotics and cardiovascular risk in schizophrenic patients.
2001 Feb
Pharmacological characterization of muscarinic receptors in dog isolated ciliary and urinary bladder smooth muscle.
2001 Feb
Traditional and new antipsychotic drugs differentially alter neurotransmission markers in basal ganglia-thalamocortical neural pathways.
2001 Feb
Modulation by muscarinic antagonists of the response to carbon dioxide challenge in panic disorder.
2001 Feb
Rehospitalization rates of chronically ill schizophrenic patients discharged on a regimen of risperidone, olanzapine, or conventional antipsychotics.
2001 Feb
Muscarinic receptor subtypes and calcium signaling in Fischer rat thyroid cells.
2001 Feb 1
Characterisation of the prejunctional inhibitory muscarinic receptor on cholinergic nerves in the rat urinary bladder.
2001 Feb 16
A novel augmentation strategy for treating resistant major depression.
2001 Jan
Lowered seizure threshold on olanzapine.
2001 Jan
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
Dopamine transporter density in young patients with schizophrenia assessed with [123]FP-CIT SPECT.
2001 Jan 15
[Olanzapine and pregnancy].
2001 Jan 21
Interleukin-2 and interleukin-4 increase the survival of retinal ganglion cells in culture.
2001 Jan 22
[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
Dementia with Lewy bodies in Down's syndrome.
2001 Mar
Effects of antimanic mood-stabilizing drugs on fetuses, neonates, and nursing infants.
2001 Mar
Olanzapine-lnduced hyperglycemic nonketonic coma.
2001 Mar
Autoantibodies against neonatal heart M1 muscarinic acetylcholine receptor in children with congenital heart block.
2001 Mar
5-HT(2A) and D(2) receptor blockade increases cortical DA release via 5-HT(1A) receptor activation: a possible mechanism of atypical antipsychotic-induced cortical dopamine release.
2001 Mar
Low blood glucose and olanzapine.
2001 Mar
Insulin and leptin levels in patients with schizophrenia or related psychoses--a comparison between different antipsychotic agents.
2001 Mar 1
Quantitative determination of olanzapine in rat brain tissue by high-performance liquid chromatography with electrochemical detection.
2001 Mar 5
Separation of olanzapine, carbamazepine and their main metabolites by capillary electrophoresis with pseudo-stationary phases.
2001 Mar 5
The antinociceptive and sedative effects of carbachol and oxycodone administered into brainstem pontine reticular formation and spinal subarachnoid space in rats.
2001 May
Expression of multiple subtypes of muscarinic receptors and cellular distribution in the human heart.
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
Antibodies against human putamen in adolescents with anorexia nervosa.
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 Jun 26 04:03:26 UTC 2021
Edited
by admin
on Sat Jun 26 04:03:26 UTC 2021
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
PIRENZEPINE [WHO-DD]
Common 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
5,11-DIHYDRO-11-((4-METHYL-1-PIPERAZINYL)ACETYL)-6H-PYRIDO(2,3-B)(1,4)BENZODIAZEPIN-6-ONE
Systematic Name English
Classification Tree Code System Code
WHO-ATC A02BX03
Created by admin on Sat Jun 26 04:03:26 UTC 2021 , Edited by admin on Sat Jun 26 04:03:26 UTC 2021
NCI_THESAURUS C29704
Created by admin on Sat Jun 26 04:03:26 UTC 2021 , Edited by admin on Sat Jun 26 04:03:26 UTC 2021
WHO-VATC QA02BX03
Created by admin on Sat Jun 26 04:03:26 UTC 2021 , Edited by admin on Sat Jun 26 04:03:26 UTC 2021
Code System Code Type Description
MESH
D010890
Created by admin on Sat Jun 26 04:03:26 UTC 2021 , Edited by admin on Sat Jun 26 04:03:26 UTC 2021
PRIMARY
CAS
28797-61-7
Created by admin on Sat Jun 26 04:03:26 UTC 2021 , Edited by admin on Sat Jun 26 04:03:26 UTC 2021
PRIMARY
DRUG CENTRAL
2200
Created by admin on Sat Jun 26 04:03:26 UTC 2021 , Edited by admin on Sat Jun 26 04:03:26 UTC 2021
PRIMARY
DRUG BANK
DB00670
Created by admin on Sat Jun 26 04:03:26 UTC 2021 , Edited by admin on Sat Jun 26 04:03:26 UTC 2021
PRIMARY
PUBCHEM
4848
Created by admin on Sat Jun 26 04:03:26 UTC 2021 , Edited by admin on Sat Jun 26 04:03:26 UTC 2021
PRIMARY
MERCK INDEX
M8874
Created by admin on Sat Jun 26 04:03:26 UTC 2021 , Edited by admin on Sat Jun 26 04:03:26 UTC 2021
PRIMARY Merck Index
WIKIPEDIA
PIRENZEPINE
Created by admin on Sat Jun 26 04:03:26 UTC 2021 , Edited by admin on Sat Jun 26 04:03:26 UTC 2021
PRIMARY
EPA CompTox
28797-61-7
Created by admin on Sat Jun 26 04:03:26 UTC 2021 , Edited by admin on Sat Jun 26 04:03:26 UTC 2021
PRIMARY
IUPHAR
328
Created by admin on Sat Jun 26 04:03:26 UTC 2021 , Edited by admin on Sat Jun 26 04:03:26 UTC 2021
PRIMARY
FDA UNII
3G0285N20N
Created by admin on Sat Jun 26 04:03:26 UTC 2021 , Edited by admin on Sat Jun 26 04:03:26 UTC 2021
PRIMARY
ChEMBL
CHEMBL9967
Created by admin on Sat Jun 26 04:03:26 UTC 2021 , Edited by admin on Sat Jun 26 04:03:26 UTC 2021
PRIMARY
NCI_THESAURUS
C76002
Created by admin on Sat Jun 26 04:03:26 UTC 2021 , Edited by admin on Sat Jun 26 04:03:26 UTC 2021
PRIMARY
RXCUI
8352
Created by admin on Sat Jun 26 04:03:26 UTC 2021 , Edited by admin on Sat Jun 26 04:03:26 UTC 2021
PRIMARY RxNorm
INN
3476
Created by admin on Sat Jun 26 04:03:26 UTC 2021 , Edited by admin on Sat Jun 26 04:03:26 UTC 2021
PRIMARY
EVMPD
SUB09904MIG
Created by admin on Sat Jun 26 04:03:26 UTC 2021 , Edited by admin on Sat Jun 26 04:03:26 UTC 2021
PRIMARY
ECHA (EC/EINECS)
249-228-4
Created by admin on Sat Jun 26 04:03:26 UTC 2021 , Edited by admin on Sat Jun 26 04:03:26 UTC 2021
PRIMARY
Related Record Type Details
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
Related Record Type Details
ACTIVE MOIETY