PIRENZEPINE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C19H21N5O2
Molecular Weight	351.4023
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CN1CCN(CC(=O)N2C3=CC=CC=C3C(=O)NC4=C2N=CC=C4)CC1

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	351.4023
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 168 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 2737		192.0 nM [IC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Duodenal ulcer 41 Sources: https://www.boehringer-interaktiv.de/system/files/field_ia_apf_file/20160828T134714/gebrauchsinformation_gastrozepin_50mg_tabletten_2013-07.pdf	Primary		Approved 8307	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 8307	GASTROZEPIN Approved Use GASTROZEPIN is used for a duodenal ulcer and a benign stomach ulcer.

PubMed

Title	Date	PubMed
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
Superior efficacy of olanzapine over haloperidol: analysis of patients with schizophrenia from a multicenter international trial.	2001	11232753
Olanzapine: an updated review of its use in the management of schizophrenia.	2001	11217867
Effect of amantadine on weight gain during olanzapine treatment.	2001 Apr	11313165
Manic symptoms induced by olanzapine.	2001 Apr	11313153
Regulation of phospholipase Cbeta activity by muscarinic acetylcholine and 5-HT(2) receptors in crude and synaptosomal membranes from human cerebral cortex.	2001 Apr	11311896
Comment: olanzapine-induced acute pancreatitis.	2001 Apr	11302419
Olanzapine overdose.	2001 Apr	11284876
Ondansetron for tardive dyskinesia.	2001 Apr	11282718
Neuroleptic malignant syndrome after addition of haloperidol to atypical antipsychotic.	2001 Apr	11282706
Six-month outcomes for patients who switched to olanzapine treatment.	2001 Apr	11274497
Acetylcholine increases the free intracellular calcium concentration in podocytes in intact rat glomeruli via muscarinic M(5) receptors.	2001 Apr	11274228
Olanzapine-associated priapism.	2001 Apr	11270930
Reply to comments on "Olanzapine treatment of children, adolescents, and adults with pervasive developmental disorders: an open-label pilot study".	2001 Apr	11270929
Olanzapine and Huntington's disease.	2001 Apr	11270928
Functional characterization of rat submaxillary gland muscarinic receptors using microphysiometry.	2001 Apr	11264256
Ca(2+) signaling in porcine duodenal glands by muscarinic receptor activation.	2001 Apr	11254500
Acetylcholine increases intracellular Ca2+ in the rat pituitary folliculostellate cells in primary culture.	2001 Apr	11254468
Treatment of psychogenic polydipsia: comparison of risperidone and olanzapine, and the effects of an adjunctive angiotensin-II receptor blocking drug (irbesartan).	2001 Feb	11270459
[Anti-ulcer drug pirenzepin: new use as an aid for prevention of myopia?].	2001 Feb	11258134
Priapism associated with polypharmacy.	2001 Feb	11247100
Tolerability and effectiveness of atypical antipsychotics in male geriatric inpatients.	2001 Feb	11241729
Mechanisms of acetylcholine-induced vasorelaxation in high K+-stimulated rabbit renal arteries.	2001 Jan	11217061
[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
[Viewpoint of schizophrenic patients: a European survey].	2001 Jan-Feb	11294036
Olanzapine may be an effective adjunctive therapy in the management of acne excoriée: a case report.	2001 Jan-Feb	11281430
Analysis of the QTc interval during olanzapine treatment of patients with schizophrenia and related psychosis.	2001 Mar	11305706
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
Treatment of posttraumatic stress disorder with olanzapine.	2001 Mar	11280089
Olanzapine-lnduced hyperglycemic nonketonic coma.	2001 Mar	11261526
Serine/threonine protein phosphatases and synaptic inhibition regulate the expression of cholinergic-dependent plateau potentials.	2001 Mar	11247989
Does fast dissociation from the dopamine d(2) receptor explain the action of atypical antipsychotics?: A new hypothesis.	2001 Mar	11229973
Insulin and leptin levels in patients with schizophrenia or related psychoses--a comparison between different antipsychotic agents.	2001 Mar 1	11314683
Effects of olanzapine and other antipsychotics on cognitive function in chronic schizophrenia: a longitudinal study.	2001 Mar 1	11278151
The allosteric interaction of otenzepad (AF-DX 116) at muscarinic M2 receptors in guinea pig atria.	2001 Mar 30	11290374
Quantitative determination of olanzapine in rat brain tissue by high-performance liquid chromatography with electrochemical detection.	2001 Mar 5	11254198
Haloperidol-stomach lesions attenuation by pentadecapeptide BPC 157, omeprazole, bromocriptine, but not atropine, lansoprazole, pantoprazole, ranitidine, cimetidine and misoprostol in mice.	2001 Mar 9	11292068
Reversal of pathologic cardiac parameters after transition from clozapine to olanzapine treatment: a case report.	2001 Mar-Apr	11307047
The antinociceptive and sedative effects of carbachol and oxycodone administered into brainstem pontine reticular formation and spinal subarachnoid space in rats.	2001 May	11323367
Nitric oxide modulates cardiac performance in the heart of Anguilla anguilla.	2001 May	11316492
Expression of multiple subtypes of muscarinic receptors and cellular distribution in the human heart.	2001 May	11306684
Pharmacological properties of (2R)-N-[1-(6-aminopyridin-2-ylmethyl)piperidin-4-yl]-2-[(1R)-3,3-difluorocyclopentyl]-2-hydroxy-2-phenylacetamide: a novel mucarinic antagonist with M(2)-sparing antagonistic activity.	2001 May	11303071
Molecular and pharmacological characterization of muscarinic receptor subtypes in a rat parotid gland cell line: comparison with native parotid gland.	2001 May	11303063
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
Agonist activation of cytosolic Ca2+ in subfornical organ cells projecting to the supraoptic nucleus.	2001 May	11294785
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 `Sun Dec 18 19:52:39 UTC 2022` Edited by `admin` on `Sun Dec 18 19:52:39 UTC 2022`
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

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

Pirenzepine [WHO-DD]

Common 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