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=CC=CN=C24)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 2849		192.0 nM [IC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Duodenal ulcer 49 Sources: https://www.boehringer-interaktiv.de/system/files/field_ia_apf_file/20160828T134714/gebrauchsinformation_gastrozepin_50mg_tabletten_2013-07.pdf	Primary		Approved 8583	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 8583	GASTROZEPIN Approved Use GASTROZEPIN is used for a duodenal ulcer and a benign stomach ulcer.

C_max

Value	Dose	Co-administered	Analyte	Population
57.2 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3675700/	50 mg single, oral dose: 50 mg route of administration: Oral experiment type: SINGLE co-administered:		PIRENZEPINE plasma	Homo sapiens population: UNHEALTHY age: UNKNOWN sex: UNKNOWN food status: UNKNOWN
48 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3675700/	50 mg single, oral dose: 50 mg route of administration: Oral experiment type: SINGLE co-administered:		PIRENZEPINE plasma	Homo sapiens population: UNHEALTHY age: UNKNOWN sex: UNKNOWN food status: UNKNOWN

AUC

Value	Dose	Analyte	Population
1213 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/2344866/	50 mg single, oral dose: 50 mg route of administration: Oral experiment type: SINGLE co-administered:	PIRENZEPINE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
1462 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/2344866/	50 mg single, oral dose: 50 mg route of administration: Oral experiment type: SINGLE co-administered:	PIRENZEPINE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
1013 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/2344866/	50 mg single, oral dose: 50 mg route of administration: Oral experiment type: SINGLE co-administered:	PIRENZEPINE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: MALE food status: FASTED
844 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3675700/	50 mg single, oral dose: 50 mg route of administration: Oral experiment type: SINGLE co-administered:	PIRENZEPINE plasma	Homo sapiens population: UNHEALTHY age: UNKNOWN sex: UNKNOWN food status: UNKNOWN
663 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3675700/	50 mg single, oral dose: 50 mg route of administration: Oral experiment type: SINGLE co-administered:	PIRENZEPINE plasma	Homo sapiens population: UNHEALTHY age: UNKNOWN sex: UNKNOWN food status: UNKNOWN

T_1/2

Value	Dose	Analyte	Population
17.3 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/2344866/	50 mg single, oral dose: 50 mg route of administration: Oral experiment type: SINGLE co-administered:	PIRENZEPINE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
18 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/2344866/	50 mg single, oral dose: 50 mg route of administration: Oral experiment type: SINGLE co-administered:	PIRENZEPINE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
14.7 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/2344866/	50 mg single, oral dose: 50 mg route of administration: Oral experiment type: SINGLE co-administered:	PIRENZEPINE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: MALE food status: FASTED
13.9 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3675700/	50 mg single, oral dose: 50 mg route of administration: Oral experiment type: SINGLE co-administered:	PIRENZEPINE plasma	Homo sapiens population: UNHEALTHY age: UNKNOWN sex: UNKNOWN food status: UNKNOWN
17.9 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3675700/	50 mg single, oral dose: 50 mg route of administration: Oral experiment type: SINGLE co-administered:	PIRENZEPINE plasma	Homo sapiens population: UNHEALTHY age: UNKNOWN sex: UNKNOWN food status: UNKNOWN

Doses

Dose	Population	Adverse events
50 mg 2 times / day multiple, oral Recommended Dose: 50 mg, 2 times / day Route: oral Route: multiple Dose: 50 mg, 2 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/3302005/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/3302005/	Other AEs: Dry mouth, Visual disturbances... Other AEs: Dry mouth (35.9%) Visual disturbances (10.3%) Sources: https://pubmed.ncbi.nlm.nih.gov/3302005/
2 % 2 times / day multiple, ophthalmic Recommended Dose: 2 %, 2 times / day Route: ophthalmic Route: multiple Dose: 2 %, 2 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/15629825/	unhealthy, CHILD Health Status: unhealthy Age Group: CHILD Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/15629825/	Disc. AE: Drug intolerance, Giant papillary conjunctivitis... AEs leading to discontinuation/dose reduction: Drug intolerance (7.8%) Giant papillary conjunctivitis Allergy Hypersensitivity Follicles conjunctivia Near vision disturbance (1%) Rash (0.7%) Headache (0.35%) Dyschromatopsia (grade 1, 0.35%) Lens opacity (0.35%) Eye redness (0.35%) Sources: https://pubmed.ncbi.nlm.nih.gov/15629825/

AEs

AE	Significance	Dose	Population
Visual disturbances	10.3%	50 mg 2 times / day multiple, oral Recommended Dose: 50 mg, 2 times / day Route: oral Route: multiple Dose: 50 mg, 2 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/3302005/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/3302005/
Dry mouth	35.9%	50 mg 2 times / day multiple, oral Recommended Dose: 50 mg, 2 times / day Route: oral Route: multiple Dose: 50 mg, 2 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/3302005/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/3302005/
Eye redness	0.35% Disc. AE	2 % 2 times / day multiple, ophthalmic Recommended Dose: 2 %, 2 times / day Route: ophthalmic Route: multiple Dose: 2 %, 2 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/15629825/	unhealthy, CHILD Health Status: unhealthy Age Group: CHILD Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/15629825/
Headache	0.35% Disc. AE	2 % 2 times / day multiple, ophthalmic Recommended Dose: 2 %, 2 times / day Route: ophthalmic Route: multiple Dose: 2 %, 2 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/15629825/	unhealthy, CHILD Health Status: unhealthy Age Group: CHILD Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/15629825/
Lens opacity	0.35% Disc. AE	2 % 2 times / day multiple, ophthalmic Recommended Dose: 2 %, 2 times / day Route: ophthalmic Route: multiple Dose: 2 %, 2 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/15629825/	unhealthy, CHILD Health Status: unhealthy Age Group: CHILD Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/15629825/
Rash	0.7% Disc. AE	2 % 2 times / day multiple, ophthalmic Recommended Dose: 2 %, 2 times / day Route: ophthalmic Route: multiple Dose: 2 %, 2 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/15629825/	unhealthy, CHILD Health Status: unhealthy Age Group: CHILD Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/15629825/
Near vision disturbance	1% Disc. AE	2 % 2 times / day multiple, ophthalmic Recommended Dose: 2 %, 2 times / day Route: ophthalmic Route: multiple Dose: 2 %, 2 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/15629825/	unhealthy, CHILD Health Status: unhealthy Age Group: CHILD Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/15629825/
Drug intolerance	7.8% Disc. AE	2 % 2 times / day multiple, ophthalmic Recommended Dose: 2 %, 2 times / day Route: ophthalmic Route: multiple Dose: 2 %, 2 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/15629825/	unhealthy, CHILD Health Status: unhealthy Age Group: CHILD Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/15629825/
Allergy	Disc. AE	2 % 2 times / day multiple, ophthalmic Recommended Dose: 2 %, 2 times / day Route: ophthalmic Route: multiple Dose: 2 %, 2 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/15629825/	unhealthy, CHILD Health Status: unhealthy Age Group: CHILD Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/15629825/
Follicles conjunctivia	Disc. AE	2 % 2 times / day multiple, ophthalmic Recommended Dose: 2 %, 2 times / day Route: ophthalmic Route: multiple Dose: 2 %, 2 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/15629825/	unhealthy, CHILD Health Status: unhealthy Age Group: CHILD Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/15629825/
Giant papillary conjunctivitis	Disc. AE	2 % 2 times / day multiple, ophthalmic Recommended Dose: 2 %, 2 times / day Route: ophthalmic Route: multiple Dose: 2 %, 2 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/15629825/	unhealthy, CHILD Health Status: unhealthy Age Group: CHILD Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/15629825/
Hypersensitivity	Disc. AE	2 % 2 times / day multiple, ophthalmic Recommended Dose: 2 %, 2 times / day Route: ophthalmic Route: multiple Dose: 2 %, 2 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/15629825/	unhealthy, CHILD Health Status: unhealthy Age Group: CHILD Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/15629825/
Dyschromatopsia	grade 1, 0.35% Disc. AE	2 % 2 times / day multiple, ophthalmic Recommended Dose: 2 %, 2 times / day Route: ophthalmic Route: multiple Dose: 2 %, 2 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/15629825/	unhealthy, CHILD Health Status: unhealthy Age Group: CHILD Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/15629825/

PubMed

Title	Date	PubMed
The antinociceptive and sedative effects of carbachol and oxycodone administered into brainstem pontine reticular formation and spinal subarachnoid space in rats.	2001-05	11323367
Nitric oxide modulates cardiac performance in the heart of Anguilla anguilla.	2001-05	11316492
Expression of multiple subtypes of muscarinic receptors and cellular distribution in the human heart.	2001-05	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.	2001-05	11303071
Molecular and pharmacological characterization of muscarinic receptor subtypes in a rat parotid gland cell line: comparison with native parotid gland.	2001-05	11303063
Long-term effects of olanzapine, risperidone, and quetiapine on dopamine receptor types in regions of rat brain: implications for antipsychotic drug treatment.	2001-05	11303062
Agonist activation of cytosolic Ca2+ in subfornical organ cells projecting to the supraoptic nucleus.	2001-05	11294785
Antibodies against human putamen in adolescents with anorexia nervosa.	2001-05	11285584
[Subjective and objective evaluation of treating schizophrenia with classic or atypical drugs].	2001-04-28	11324382
[Obsessive-compulsive disorders in adolescents with diagnosed schizophrenia].	2001-04-28	11324381
Reversal of pathologic cardiac parameters after transition from clozapine to olanzapine treatment: a case report.	2001-04-18	11307047
[Viewpoint of schizophrenic patients: a European survey].	2001-04-11	11294036
Olanzapine may be an effective adjunctive therapy in the management of acne excoriée: a case report.	2001-04-03	11281430
Effect of amantadine on weight gain during olanzapine treatment.	2001-04	11313165
Manic symptoms induced by olanzapine.	2001-04	11313153
Regulation of phospholipase Cbeta activity by muscarinic acetylcholine and 5-HT(2) receptors in crude and synaptosomal membranes from human cerebral cortex.	2001-04	11311896
Comment: olanzapine-induced acute pancreatitis.	2001-04	11302419
Olanzapine overdose.	2001-04	11284876
Ondansetron for tardive dyskinesia.	2001-04	11282718
Neuroleptic malignant syndrome after addition of haloperidol to atypical antipsychotic.	2001-04	11282706
Six-month outcomes for patients who switched to olanzapine treatment.	2001-04	11274497
Acetylcholine increases the free intracellular calcium concentration in podocytes in intact rat glomeruli via muscarinic M(5) receptors.	2001-04	11274228
Olanzapine-associated priapism.	2001-04	11270930
Reply to comments on "Olanzapine treatment of children, adolescents, and adults with pervasive developmental disorders: an open-label pilot study".	2001-04	11270929
Olanzapine and Huntington's disease.	2001-04	11270928
Functional characterization of rat submaxillary gland muscarinic receptors using microphysiometry.	2001-04	11264256
Ca(2+) signaling in porcine duodenal glands by muscarinic receptor activation.	2001-04	11254500
Acetylcholine increases intracellular Ca2+ in the rat pituitary folliculostellate cells in primary culture.	2001-04	11254468
The allosteric interaction of otenzepad (AF-DX 116) at muscarinic M2 receptors in guinea pig atria.	2001-03-30	11290374
Haloperidol-stomach lesions attenuation by pentadecapeptide BPC 157, omeprazole, bromocriptine, but not atropine, lansoprazole, pantoprazole, ranitidine, cimetidine and misoprostol in mice.	2001-03-09	11292068
Quantitative determination of olanzapine in rat brain tissue by high-performance liquid chromatography with electrochemical detection.	2001-03-05	11254198
Separation of olanzapine, carbamazepine and their main metabolites by capillary electrophoresis with pseudo-stationary phases.	2001-03-05	11254196
Insulin and leptin levels in patients with schizophrenia or related psychoses--a comparison between different antipsychotic agents.	2001-03-01	11314683
Effects of olanzapine and other antipsychotics on cognitive function in chronic schizophrenia: a longitudinal study.	2001-03-01	11278151
Analysis of the QTc interval during olanzapine treatment of patients with schizophrenia and related psychosis.	2001-03	11305706
Dementia with Lewy bodies in Down's syndrome.	2001-03	11288166
Effects of antimanic mood-stabilizing drugs on fetuses, neonates, and nursing infants.	2001-03	11284518
Treatment of posttraumatic stress disorder with olanzapine.	2001-03	11280089
Olanzapine-lnduced hyperglycemic nonketonic coma.	2001-03	11261526
Serine/threonine protein phosphatases and synaptic inhibition regulate the expression of cholinergic-dependent plateau potentials.	2001-03	11247989
Autoantibodies against neonatal heart M1 muscarinic acetylcholine receptor in children with congenital heart block.	2001-03	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.	2001-03	11238736
Treatment of psychogenic polydipsia: comparison of risperidone and olanzapine, and the effects of an adjunctive angiotensin-II receptor blocking drug (irbesartan).	2001-02	11270459
[Anti-ulcer drug pirenzepin: new use as an aid for prevention of myopia?].	2001-02	11258134
Long-term olanzapine treatment: weight change and weight-related health factors in schizophrenia.	2001-02	11247108
Priapism associated with polypharmacy.	2001-02	11247100
Tolerability and effectiveness of atypical antipsychotics in male geriatric inpatients.	2001-02	11241729
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

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 `Wed Apr 02 08:46:55 GMT 2025` Edited by `admin` on `Wed Apr 02 08:46:55 GMT 2025`
Record UNII	3G0285N20N
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

11-[(4-methylpiperazin-1-yl)acetyl]-5,11-dihydro-6H-pyrido[2,3-b][1,4]benzodiazepin-6-one

Preferred Name

English

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-[2-(4-methyl-1-piperazinyl)acetyl]-

Systematic Name

English

ACI-91

Code

English

PIRENZEPINE [VANDF]

Common Name

English

Pirenzepine [WHO-DD]

Common Name

English

5,11-Dihydro-11-[2-(4-methyl-1-piperazinyl)acetyl]-6H-pyrido[2,3-b][1,4]benzodiazepin-6-one

Systematic Name

English

PIRENZEPINE [USAN]

Common Name

English

WST-057

Code

English

Classification Tree Code System Code

WHO-ATC

A02BX03