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Details

Stereochemistry ACHIRAL
Molecular Formula C19H21N5O2.2ClH
Molecular Weight 424.3248
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of PIRENZEPINE HYDROCHLORIDE

SMILES

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

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 C19H21N5O2
Molecular Weight 351.4031
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

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

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
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
Atypical antipsychotics: new directions and new challenges in the treatment of schizophrenia.
2001
One further case of pancytopenia induced by olanzapine in a Parkinson's disease patient.
2001
Neuroleptic malignant syndrome after addition of haloperidol to atypical antipsychotic.
2001 Apr
Olanzapine-associated priapism.
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
Long-term olanzapine treatment: weight change and weight-related health factors in schizophrenia.
2001 Feb
Priapism associated with polypharmacy.
2001 Feb
Effects of newer atypical antipsychotics on autonomic neurocardiac function: a comparison between amisulpride, olanzapine, sertindole, and clozapine.
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
Bodyweight gain with atypical antipsychotics. A comparative review.
2001 Jan
Consistency of atypical antipsychotic superiority to placebo in recent clinical trials.
2001 Jan 1
[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
Treatment of posttraumatic stress disorder with olanzapine.
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
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
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
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 22:10:54 UTC 2021
Edited
by admin
on Fri Jun 25 22:10:54 UTC 2021
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 DIHYDROCHLORIDE [WHO-DD]
Common Name 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
Classification Tree Code System Code
NCI_THESAURUS C29704
Created by admin on Fri Jun 25 22:10:54 UTC 2021 , Edited by admin on Fri Jun 25 22:10:54 UTC 2021
Code System Code Type Description
NCI_THESAURUS
C76003
Created by admin on Fri Jun 25 22:10:54 UTC 2021 , Edited by admin on Fri Jun 25 22:10:54 UTC 2021
PRIMARY
PUBCHEM
71405
Created by admin on Fri Jun 25 22:10:54 UTC 2021 , Edited by admin on Fri Jun 25 22:10:54 UTC 2021
PRIMARY
MERCK INDEX
M8874
Created by admin on Fri Jun 25 22:10:54 UTC 2021 , Edited by admin on Fri Jun 25 22:10:54 UTC 2021
PRIMARY Merck Index
RXCUI
235775
Created by admin on Fri Jun 25 22:10:54 UTC 2021 , Edited by admin on Fri Jun 25 22:10:54 UTC 2021
PRIMARY RxNorm
FDA UNII
10YM403FLS
Created by admin on Fri Jun 25 22:10:54 UTC 2021 , Edited by admin on Fri Jun 25 22:10:54 UTC 2021
PRIMARY
DRUG BANK
DBSALT001002
Created by admin on Fri Jun 25 22:10:54 UTC 2021 , Edited by admin on Fri Jun 25 22:10:54 UTC 2021
PRIMARY
EVMPD
SUB20712
Created by admin on Fri Jun 25 22:10:54 UTC 2021 , Edited by admin on Fri Jun 25 22:10:54 UTC 2021
PRIMARY
CAS
29868-97-1
Created by admin on Fri Jun 25 22:10:54 UTC 2021 , Edited by admin on Fri Jun 25 22:10:54 UTC 2021
PRIMARY
ECHA (EC/EINECS)
249-907-5
Created by admin on Fri Jun 25 22:10:54 UTC 2021 , Edited by admin on Fri Jun 25 22:10:54 UTC 2021
PRIMARY
ChEMBL
CHEMBL9967
Created by admin on Fri Jun 25 22:10:54 UTC 2021 , Edited by admin on Fri Jun 25 22:10:54 UTC 2021
PRIMARY
Related Record Type Details
PARENT -> SALT/SOLVATE
Related Record Type Details
ACTIVE MOIETY