Pirenzepine

Possibly Marketed Outside US

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

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	MOL RATIO 1 MOL RATIO (average)

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

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Muscarinic acetylcholine receptor M1 168	Antagonist 2,849		192.0 nM [IC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Duodenal ulcer 49	Primary		Approved 8,583	GASTROZEPIN
Benign stomach ulcer 4	Primary		Approved 8,583	GASTROZEPIN

C_max

Value	Dose	Co-administered	Analyte	Population
57.2 ng/mL	50 mg single, oral		PIRENZEPINE plasma	Homo sapiens
48 ng/mL	50 mg single, oral		PIRENZEPINE plasma	Homo sapiens

AUC

Value	Dose	Analyte	Population
1213 ng × h/mL	50 mg single, oral	PIRENZEPINE plasma	Homo sapiens
1462 ng × h/mL	50 mg single, oral	PIRENZEPINE plasma	Homo sapiens
1013 ng × h/mL	50 mg single, oral	PIRENZEPINE plasma	Homo sapiens
844 ng × h/mL	50 mg single, oral	PIRENZEPINE plasma	Homo sapiens
663 ng × h/mL	50 mg single, oral	PIRENZEPINE plasma	Homo sapiens

T_1/2

Value	Dose	Analyte	Population
17.3 h	50 mg single, oral	PIRENZEPINE plasma	Homo sapiens
18 h	50 mg single, oral	PIRENZEPINE plasma	Homo sapiens
14.7 h	50 mg single, oral	PIRENZEPINE plasma	Homo sapiens
13.9 h	50 mg single, oral	PIRENZEPINE plasma	Homo sapiens
17.9 h	50 mg single, oral	PIRENZEPINE plasma	Homo sapiens

Doses

Show entries

Dose	Population	Adverse events
50 mg 2 times / day multiple, oral Recommended	unhealthy, ADULT	Other AEs: Dry mouth, Visual disturbances...
2 % 2 times / day multiple, ophthalmic Recommended	unhealthy, CHILD	Disc. AE: Drug intolerance, Giant papillary conjunctivitis...

Showing 1 to 2 of 2 entries

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AEs

Show entries

AE	Significance	Dose	Population
Visual disturbances	10.3%	50 mg 2 times / day multiple, oral Recommended	unhealthy, ADULT
Dry mouth	35.9%	50 mg 2 times / day multiple, oral Recommended	unhealthy, ADULT
Eye redness	0.35% Disc. AE	2 % 2 times / day multiple, ophthalmic Recommended	unhealthy, CHILD
Headache	0.35% Disc. AE	2 % 2 times / day multiple, ophthalmic Recommended	unhealthy, CHILD
Lens opacity	0.35% Disc. AE	2 % 2 times / day multiple, ophthalmic Recommended	unhealthy, CHILD

Showing 1 to 5 of 13 entries

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PubMed

Show entries

Title	Date	PubMed
Pharmacology, distribution and development of muscarinic acetylcholine receptor subtypes in the optic tectum of Rana pipiens.	2001	11311540
Evidence for the effectiveness of olanzapine among patients nonresponsive and/or intolerant to risperidone.	2001	11232749
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
Olanzapine-associated priapism.	2001 Apr	11270930

Showing 1 to 5 of 37 entries

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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.