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Details

Stereochemistry ACHIRAL
Molecular Formula C19H21N5O2.2ClH.H2O
Molecular Weight 442.3401
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of PIRENZEPINE HYDROCHLORIDE MONOHYDRATE

SMILES

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

InChI

InChIKey=ZOAVUHCVXFVQOA-UHFFFAOYSA-N
InChI=1S/C19H21N5O2.2ClH.H2O/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);2*1H;1H2

HIDE SMILES / InChI

Molecular Formula ClH
Molecular Weight 36.4609
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula H2O
Molecular Weight 18.0153
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

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
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
An efficacy analysis of olanzapine treatment data in schizophrenia patients with catatonic signs and symptoms.
2001
Effective resolution with olanzapine of acute presentation of behavioral agitation and positive psychotic symptoms in schizophrenia.
2001
Manic symptoms induced by olanzapine.
2001 Apr
Neuroleptic malignant syndrome after addition of haloperidol to atypical antipsychotic.
2001 Apr
Six-month outcomes for patients who switched to olanzapine treatment.
2001 Apr
Acetylcholine increases the free intracellular calcium concentration in podocytes in intact rat glomeruli via muscarinic M(5) receptors.
2001 Apr
Olanzapine-associated priapism.
2001 Apr
Olanzapine and Huntington's disease.
2001 Apr
Acetylcholine increases intracellular Ca2+ in the rat pituitary folliculostellate cells in primary culture.
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
Priapism associated with polypharmacy.
2001 Feb
Tolerability and effectiveness of atypical antipsychotics in male geriatric inpatients.
2001 Feb
Fully automated on-line determination of olanzapine in serum for routine therapeutic drug monitoring.
2001 Feb
Effects of newer atypical antipsychotics on autonomic neurocardiac function: a comparison between amisulpride, olanzapine, sertindole, and clozapine.
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
Characterisation of the prejunctional inhibitory muscarinic receptor on cholinergic nerves in the rat urinary bladder.
2001 Feb 16
The effects of olanzapine in reducing the emergence of psychosis among nursing home patients with Alzheimer's disease.
2001 Jan
Bodyweight gain with atypical antipsychotics. A comparative review.
2001 Jan
Allelic variation in the 5-HT2C receptor (HT2RC) and the increase in slow wave sleep produced by olanzapine.
2001 Jan 1
A sensitive high-performance liquid chromatographic method using electrochemical detection for the analysis of olanzapine and desmethylolanzapine in plasma of schizophrenic patients using a new solid-phase extraction procedure.
2001 Jan 5
[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
Olanzapine may be an effective adjunctive therapy in the management of acne excoriée: a case report.
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
Effects of antimanic mood-stabilizing drugs on fetuses, neonates, and nursing infants.
2001 Mar
Treatment of posttraumatic stress disorder with olanzapine.
2001 Mar
Olanzapine-lnduced hyperglycemic nonketonic coma.
2001 Mar
Serine/threonine protein phosphatases and synaptic inhibition regulate the expression of cholinergic-dependent plateau potentials.
2001 Mar
Autoantibodies against neonatal heart M1 muscarinic acetylcholine receptor in children with congenital heart block.
2001 Mar
Atypical antipsychotics and hyperglycaemia.
2001 Mar
Low blood glucose and olanzapine.
2001 Mar
Does fast dissociation from the dopamine d(2) receptor explain the action of atypical antipsychotics?: A new hypothesis.
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
Haloperidol-stomach lesions attenuation by pentadecapeptide BPC 157, omeprazole, bromocriptine, but not atropine, lansoprazole, pantoprazole, ranitidine, cimetidine and misoprostol in mice.
2001 Mar 9
Reversal of pathologic cardiac parameters after transition from clozapine to olanzapine treatment: a case report.
2001 Mar-Apr
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
Long-term effects of olanzapine, risperidone, and quetiapine on dopamine receptor types in regions of rat brain: implications for antipsychotic drug treatment.
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 Fri Jun 25 20:42:20 UTC 2021
Edited
by admin
on Fri Jun 25 20:42:20 UTC 2021
Record UNII
TR66JMA2FS
Record Status Validated (UNII)
Record Version
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Name Type Language
PIRENZEPINE HYDROCHLORIDE MONOHYDRATE
Common Name English
PIRENZEPINE HYDROCHLORIDE HYDRATE
JAN  
Common Name English
PIRENZEPINE HYDROCHLORIDE HYDRATE [JAN]
Common Name English
PIRENZEPINE DIHYDROCHLORIDE MONOHYDRATE [EP MONOGRAPH]
Common Name English
PIRENZEPINE DIHYDROCHLORIDE MONOHYDRATE
Common Name English
11-((4-METHYLPIPERAZIN-1-YL)ACETYL)-5,11-DIHYDRO-6H-PYRIDO(2,3-B)(1,4)BENZODIAZEPIN-6-ONE DIHYDROCHLORIDE MONOHYDRATE
Systematic Name English
Code System Code Type Description
PUBCHEM
11954384
Created by admin on Fri Jun 25 20:42:20 UTC 2021 , Edited by admin on Fri Jun 25 20:42:20 UTC 2021
PRIMARY
EVMPD
SUB12219MIG
Created by admin on Fri Jun 25 20:42:20 UTC 2021 , Edited by admin on Fri Jun 25 20:42:20 UTC 2021
PRIMARY
FDA UNII
TR66JMA2FS
Created by admin on Fri Jun 25 20:42:20 UTC 2021 , Edited by admin on Fri Jun 25 20:42:20 UTC 2021
PRIMARY
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PARENT -> SALT/SOLVATE
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ACTIVE MOIETY