PIRENZEPINE

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 Search

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

Description
Sources: https://www.boehringer-interaktiv.de/system/files/field_ia_apf_file/20160828T134714/gebrauchsinformation_gastrozepin_50mg_tabletten_2013-07.pdf | https://www.ncbi.nlm.nih.gov/pubmed/6941375

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

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Muscarinic acetylcholine receptor M1 160 Target ID: P11229 Gene ID: 1128.0 Gene Symbol: CHRM1 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/21918262	Antagonist 2577		192.0 nM [IC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Duodenal ulcer 51 Sources: https://www.boehringer-interaktiv.de/system/files/field_ia_apf_file/20160828T134714/gebrauchsinformation_gastrozepin_50mg_tabletten_2013-07.pdf	Primary		Approved 7997	GASTROZEPIN Approved Use GASTROZEPIN is used for a duodenal ulcer and a benign stomach ulcer.
Benign stomach ulcer 4 Sources: https://www.boehringer-interaktiv.de/system/files/field_ia_apf_file/20160828T134714/gebrauchsinformation_gastrozepin_50mg_tabletten_2013-07.pdf	Primary		Approved 7997	GASTROZEPIN Approved Use GASTROZEPIN is used for a duodenal ulcer and a benign stomach ulcer.

PubMed

Title	Date	PubMed
M3 muscarinic receptor activation of a delayed rectifier potassium current in canine atrial myocytes.	1999	10353596
A double-blind placebo-controlled case study of the use of donepezil to improve cognition in a schizoaffective disorder patient: functional MRI correlates.	2001	11320158
Pharmacology, distribution and development of muscarinic acetylcholine receptor subtypes in the optic tectum of Rana pipiens.	2001	11311540
First experiences in combination therapy using olanzapine with SSRIs (citalopram, paroxetine) in delusional depression.	2001	11287796
Weight change and atypical antipsychotic treatment in patients with schizophrenia.	2001	11232752
Cardiac safety parameters of olanzapine: comparison with other atypical and typical antipsychotics.	2001	11232751
Evidence for the effectiveness of olanzapine among patients nonresponsive and/or intolerant to risperidone.	2001	11232749
An efficacy analysis of olanzapine treatment data in schizophrenia patients with catatonic signs and symptoms.	2001	11232748
Rapid tranquilization with olanzapine in acute psychosis: a case series.	2001	11232745
Atypical antipsychotics: new directions and new challenges in the treatment of schizophrenia.	2001	11160792
Manic symptoms induced by olanzapine.	2001 Apr	11313153
Comment: olanzapine-induced acute pancreatitis.	2001 Apr	11302419
Olanzapine overdose.	2001 Apr	11284876
Olanzapine-associated priapism.	2001 Apr	11270930
Acetylcholine increases intracellular Ca2+ in the rat pituitary folliculostellate cells in primary culture.	2001 Apr	11254468
Effects of brucine, a plant alkaloid, on M(1) muscarinic receptors and alpha(1)-adrenoceptors in the rabbit vas deferens preparation.	2001 Apr	11024498
Long-term olanzapine treatment: weight change and weight-related health factors in schizophrenia.	2001 Feb	11247108
Effects of newer atypical antipsychotics on autonomic neurocardiac function: a comparison between amisulpride, olanzapine, sertindole, and clozapine.	2001 Feb	11199953
Olanzapine plasma concentrations and clinical response: acute phase results of the North American Olanzapine Trial.	2001 Feb	11199942
The economic consequences of a drug-drug interaction.	2001 Feb	11199940
Repeated episodes of hypothermia in a subject treated with haloperidol, levomepromazine, olanzapine, and thioridazine.	2001 Feb	11199936
Atypical antipsychotics and cardiovascular risk in schizophrenic patients.	2001 Feb	11199934
Pharmacological characterization of muscarinic receptors in dog isolated ciliary and urinary bladder smooth muscle.	2001 Feb	11181424
Traditional and new antipsychotic drugs differentially alter neurotransmission markers in basal ganglia-thalamocortical neural pathways.	2001 Feb	11180502
Modulation by muscarinic antagonists of the response to carbon dioxide challenge in panic disorder.	2001 Feb	11177112
Rehospitalization rates of chronically ill schizophrenic patients discharged on a regimen of risperidone, olanzapine, or conventional antipsychotics.	2001 Feb	11156809
Muscarinic receptor subtypes and calcium signaling in Fischer rat thyroid cells.	2001 Feb 1	11172738
Characterisation of the prejunctional inhibitory muscarinic receptor on cholinergic nerves in the rat urinary bladder.	2001 Feb 16	11226391
A novel augmentation strategy for treating resistant major depression.	2001 Jan	11136647
Lowered seizure threshold on olanzapine.	2001 Jan	11136221
Consistency of atypical antipsychotic superiority to placebo in recent clinical trials.	2001 Jan 1	11163781
Double-blind comparison of olanzapine versus clozapine in schizophrenic patients clinically eligible for treatment with clozapine.	2001 Jan 1	11163780
Dopamine transporter density in young patients with schizophrenia assessed with [123]FP-CIT SPECT.	2001 Jan 15	11163545
[Olanzapine and pregnancy].	2001 Jan 21	11217163
Interleukin-2 and interleukin-4 increase the survival of retinal ganglion cells in culture.	2001 Jan 22	11201067
[Subjective and objective evaluation of treating schizophrenia with classic or atypical drugs].	2001 Jan-Feb	11324382
[Obsessive-compulsive disorders in adolescents with diagnosed schizophrenia].	2001 Jan-Feb	11324381
Dementia with Lewy bodies in Down's syndrome.	2001 Mar	11288166
Effects of antimanic mood-stabilizing drugs on fetuses, neonates, and nursing infants.	2001 Mar	11284518
Olanzapine-lnduced hyperglycemic nonketonic coma.	2001 Mar	11261526
Autoantibodies against neonatal heart M1 muscarinic acetylcholine receptor in children with congenital heart block.	2001 Mar	11247640
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	11238736
Low blood glucose and olanzapine.	2001 Mar	11230004
Insulin and leptin levels in patients with schizophrenia or related psychoses--a comparison between different antipsychotic agents.	2001 Mar 1	11314683
Quantitative determination of olanzapine in rat brain tissue by high-performance liquid chromatography with electrochemical detection.	2001 Mar 5	11254198
Separation of olanzapine, carbamazepine and their main metabolites by capillary electrophoresis with pseudo-stationary phases.	2001 Mar 5	11254196
The antinociceptive and sedative effects of carbachol and oxycodone administered into brainstem pontine reticular formation and spinal subarachnoid space in rats.	2001 May	11323367
Expression of multiple subtypes of muscarinic receptors and cellular distribution in the human heart.	2001 May	11306684
Long-term effects of olanzapine, risperidone, and quetiapine on dopamine receptor types in regions of rat brain: implications for antipsychotic drug treatment.	2001 May	11303062
Antibodies against human putamen in adolescents with anorexia nervosa.	2001 May	11285584

Patents

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 `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

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Name

Type

Language

PIRENZEPINE

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