Structure via PubChem · Public domain (PubChem)
pirenzepine
Sign in to saveAlso known as PIR335, 11-[(4-methyl-1-piperazinyl)acetyl]-5,11-dihydro-6H-pyrido(2,3-b)(1,4)benzodiazepin-6-one
Pirenzepine (Gastrozepin), an M1 selective antagonist, is used in the treatment of peptic ulcers, as it reduces gastric acid secretion and reduces muscle spasm. It is in a class of drugs known as muscarinic receptor antagonists; acetylcholine is the neurotransmitter of the parasympathetic nervous system which initiates the rest-and-digest state (as opposed to fight-or-flight), resulting in an increase in gastric motility and digestion; whereas pirenzepine would inhibit these actions and cause decreased gastric motility leading to delayed gastric emptying and constipation. It has no effects on
Chemical data
- Formula
- C19H21N5O2
- Molecular weight
- 351.4 g/mol
- IUPAC name
- 11-[2-(4-methylpiperazin-1-yl)acetyl]-5H-pyrido[2,3-b][1,4]benzodiazepin-6-one
- SMILES
- CN1CCN(CC1)CC(=O)N2C3=CC=CC=C3C(=O)NC4=C2N=CC=C4
- InChIKey
- RMHMFHUVIITRHF-UHFFFAOYSA-N
- XLogP
- 0.1
- Polar surface area
- 68.8 Ų
- H-bond donors
- 1
- H-bond acceptors
- 5
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Max clinical phase
- Approved
- Molecule type
- Small molecule
- Admin. routes
- oral
- Indications
- Peptic ulcer, gastroesophageal reflux disease, peripheral neuropathy, gastric ulcer
via ChEMBL · EBI
Research
5,229 papers- [A selective antimuscarinic agent: pirenzepine. Review of its pharmacologic and clinical properties].Minerva dietologica e gastroenterologica · 1989
- Unexpected scaffold rearrangement product of pirenzepine found in commercial samples.Scientific reports · 2021
- Olanzapine: another psychotropic?The American journal of hospice & palliative care · 2001
- Pirenzepine prevents form deprivation myopia in a dose dependent manner.Ophthalmic & physiological optics : the journal of the British College of Ophthalmic Opticians (Optometrists) · 1995
- Olanzapine.British journal of hospital medicine · 1997
via PubMed
Wikidata facts
- Subclass of
- chemical compound
- Mass
- 351.169525
- Has use
- medication
Show 7 more facts
- subject has role
- muscarinic antagonist
- chemical formula
- C₁₉H₂₁N₅O₂
- Commons category
- Pirenzepine
- canonical SMILES
- CN1CCN(CC1)CC(=O)N2C3=CC=CC=C3C(=O)NC4=C2N=CC=C4
- World Health Organisation international non-proprietary name
- pirenzepine
- has characteristic
- bitterness
- defined daily dose
- 20
via Wikidata · CC0
~1 min read
Encyclopedic overview
2 sectionsContents
- See also
- References
Pirenzepine (Gastrozepin), an M1 selective antagonist, is used in the treatment of peptic ulcers, as it reduces gastric acid secretion and reduces muscle spasm. It is in a class of drugs known as muscarinic receptor antagonists; acetylcholine is the neurotransmitter of the parasympathetic nervous system which initiates the rest-and-digest state (as opposed to fight-or-flight), resulting in an increase in gastric motility and digestion; whereas pirenzepine would inhibit these actions and cause decreased gastric motility leading to delayed gastric emptying and constipation. It has no effects on the brain and spinal cord as it cannot diffuse through the blood–brain barrier.
Pirenzepine has been investigated for use in myopia control.
Excerpted from Wikipedia’s “pirenzepine” article, available under the CC BY-SA 4.0 licence.