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Details

Stereochemistry ACHIRAL
Molecular Formula C19H21N5O2.2ClH
Molecular Weight 424.324
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of PIRENZEPINE HYDROCHLORIDE

SMILES

Cl.Cl.CN1CCN(CC(=O)N2C3=C(C=CC=C3)C(=O)NC4=C2N=CC=C4)CC1

InChI

InChIKey=FFNMBRCFFADNAO-UHFFFAOYSA-N
InChI=1S/C19H21N5O2.2ClH/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

HIDE SMILES / InChI
Molecular Formula ClH
Molecular Weight 36.461
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE
Molecular Formula C19H21N5O2
Molecular Weight 351.4023
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description

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

CNS Penetrant
2554
Curator's Comment: Pirenzepine passes the blood-brain barrier, but only to a small extent.

Originator

Approval Year

Unknown
139594
Targets

Targets

Primary TargetPharmacologyConditionPotency
Muscarinic acetylcholine receptor M1
169
Target ID: P11229
Gene ID: 1128.0
Gene Symbol: CHRM1
Target Organism: Homo sapiens (Human)
Antagonist
2778
 192.0 nM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Approved
8429
GASTROZEPIN

Approved Use

GASTROZEPIN is used for a duodenal ulcer and a benign stomach ulcer.
Primary
Approved
8429
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
Weight change and atypical antipsychotic treatment in patients with schizophrenia.
2001
Cardiac safety parameters of olanzapine: comparison with other atypical and typical antipsychotics.
2001
Olanzapine: an updated review of its use in the management of schizophrenia.
2001
Manic symptoms induced by olanzapine.
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
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
Functional characterization of rat submaxillary gland muscarinic receptors using microphysiometry.
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
Supersensitivity psychosis in patients with schizophrenia after sudden olanzapine withdrawal.
2001 Feb
A case report of olanzapine-induced hypersensitivity syndrome.
2001 Feb
Olanzapine and hypertriglyceridemia.
2001 Feb
Fully automated on-line determination of olanzapine in serum for routine therapeutic drug monitoring.
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
Traditional and new antipsychotic drugs differentially alter neurotransmission markers in basal ganglia-thalamocortical neural pathways.
2001 Feb
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
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
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
[Viewpoint of schizophrenic patients: a European survey].
2001 Jan-Feb
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
Atypical antipsychotics and hyperglycaemia.
2001 Mar
Dose-dependent olanzapine-associated leukopenia: three case reports.
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
Effects of olanzapine and other antipsychotics on cognitive function in chronic schizophrenia: a longitudinal study.
2001 Mar 1
Quantitative determination of olanzapine in rat brain tissue by high-performance liquid chromatography with electrochemical detection.
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
Agonist activation of cytosolic Ca2+ in subfornical organ cells projecting to the supraoptic nucleus.
2001 May
Patents

Patents

US3660380A
4

Sample Use Guides

In Vivo Use Guide
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 Dec 15 15:24:27 GMT 2023
Edited
by admin
on Fri Dec 15 15:24:27 GMT 2023
Record UNII
10YM403FLS
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
PIRENZEPINE HYDROCHLORIDE
MART.   USAN   VANDF  
USAN  
Official Name English
PIRENZEPINE HCL
Common Name English
6H-PYRIDO(2,3-B)(1,4)BENZODIAZEPIN-6-ONE, 5,11-DIHYDRO-11-((4-METHYL-1-PIPERAZINYL)ACETYL)-, DIHYDROCHLORIDE
Common Name English
LS-519CL2
Code English
LS 519 CL2
Code English
PIRENZEPINE HYDROCHLORIDE [MART.]
Common Name English
5,11-Dihydro-11-[(4-methyl-1-piperazinyl)acetyl]-6H-pyrido[2,3-b][1,4]benzodiazepin-6-one dihydrochloride
Systematic Name English
LS-519 CL2
Code English
PIRENZEPINE DIHYDROCHLORIDE [MI]
Common Name English
PIRENZEPINE HYDROCHLORIDE [USAN]
Common Name English
PIRENZEPINE HYDROCHLORIDE [VANDF]
Common Name English
PIRENZEPINE DIHYDROCHLORIDE
MI   WHO-DD  
Common Name English
NSC-757846
Code English
Pirenzepine dihydrochloride [WHO-DD]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C29704
Created by admin on Fri Dec 15 15:24:27 GMT 2023 , Edited by admin on Fri Dec 15 15:24:27 GMT 2023
Code System Code Type Description
NCI_THESAURUS
C76003
Created by admin on Fri Dec 15 15:24:27 GMT 2023 , Edited by admin on Fri Dec 15 15:24:27 GMT 2023
PRIMARY
SMS_ID
100000086497
Created by admin on Fri Dec 15 15:24:27 GMT 2023 , Edited by admin on Fri Dec 15 15:24:27 GMT 2023
PRIMARY
PUBCHEM
71405
Created by admin on Fri Dec 15 15:24:27 GMT 2023 , Edited by admin on Fri Dec 15 15:24:27 GMT 2023
PRIMARY
MERCK INDEX
m8874
Created by admin on Fri Dec 15 15:24:27 GMT 2023 , Edited by admin on Fri Dec 15 15:24:27 GMT 2023
PRIMARY Merck Index
NSC
757846
Created by admin on Fri Dec 15 15:24:27 GMT 2023 , Edited by admin on Fri Dec 15 15:24:27 GMT 2023
PRIMARY
RXCUI
235775
Created by admin on Fri Dec 15 15:24:27 GMT 2023 , Edited by admin on Fri Dec 15 15:24:27 GMT 2023
PRIMARY RxNorm
FDA UNII
10YM403FLS
Created by admin on Fri Dec 15 15:24:27 GMT 2023 , Edited by admin on Fri Dec 15 15:24:27 GMT 2023
PRIMARY
USAN
X-89
Created by admin on Fri Dec 15 15:24:27 GMT 2023 , Edited by admin on Fri Dec 15 15:24:27 GMT 2023
PRIMARY
DRUG BANK
DBSALT001002
Created by admin on Fri Dec 15 15:24:27 GMT 2023 , Edited by admin on Fri Dec 15 15:24:27 GMT 2023
PRIMARY
EVMPD
SUB20712
Created by admin on Fri Dec 15 15:24:27 GMT 2023 , Edited by admin on Fri Dec 15 15:24:27 GMT 2023
PRIMARY
CAS
29868-97-1
Created by admin on Fri Dec 15 15:24:27 GMT 2023 , Edited by admin on Fri Dec 15 15:24:27 GMT 2023
PRIMARY
ECHA (EC/EINECS)
249-907-5
Created by admin on Fri Dec 15 15:24:27 GMT 2023 , Edited by admin on Fri Dec 15 15:24:27 GMT 2023
PRIMARY
EPA CompTox
DTXSID50952328
Created by admin on Fri Dec 15 15:24:27 GMT 2023 , Edited by admin on Fri Dec 15 15:24:27 GMT 2023
PRIMARY
ChEMBL
CHEMBL9967
Created by admin on Fri Dec 15 15:24:27 GMT 2023 , Edited by admin on Fri Dec 15 15:24:27 GMT 2023
PRIMARY
Related Record Type Details
Structure of PIRENZEPINE HYDROCHLORIDE MONOHYDRATE
SOLVATE->ANHYDROUS
Structure of PIRENZEPINE
PARENT -> SALT/SOLVATE
Related Record Type Details
Structure of PIRENZEPINE
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