Basic information
- CAS
28797-61-7- Standard SMILES
CN1CCN(CC(=O)N2c3ccccc3C(=O)Nc3cccnc32)CC1- InChIKey
RMHMFHUVIITRHF-UHFFFAOYSA-N- Molecular formula
- C19H21N5O2
- Average molar mass
- 351.4 g/mol
- Monoisotopic mass
- 351.16952493
Overview
Pirenzepine is a pyridobenzodiazepine. It has a role as a muscarinic antagonist, an anti-ulcer drug and an antispasmodic drug.
Names & identifiers
- Preferred name
- Pirenzepine
- IUPAC
- 11-[2-(4-methylpiperazin-1-yl)acetyl]-5H-pyrido[2,3-b][1,4]benzodiazepin-6-one
- English name
- Pirenzepine
- Molecular formula
- C19H21N5O2
- Molecular weight
- 351.4
Names & synonyms
pirenzepine28797-61-7PirenzepinPirenzepinaPirenzepinum11-[2-(4-methylpiperazin-1-yl)acetyl]-5H-pyrido[2,3-b][1,4]benzodiazepin-6-oneDTXSID7023487ACI-9111-((4-Methyl-1-piperazinyl)acetyl)-5,11-dihydro-6H-pyrido(2,3-b)(1,4)benzodiazepin-6-oneWST-05711-[(4-methylpiperazin-1-yl)acetyl]-5,11-dihydro-6H-pyrido[2,3-b][1,4]benzodiazepin-6-oneLS-519
Show more names
LS-519-C12Gastrozepinnyl)acetyl)-Tabe：UlcufortonPirenzepineBasePirenzepine dihydrocPirenzepine USP/EP/BPOmbitasvir Impurity 2
3G0285N20NCHEBI:8247DTXCID3034876H-Pyrido(2,3-b)(1,4)benzodiazepin-6-one, 5,11-dihydro-11-((4-methyl-1-piperazinyl)acetyl)-Pyrenzepine6H-Pyrido[2,3-b][1,4]benzodiazepin-6-one, 5,11-dihydro-11-[(4-methyl-1-piperazinyl)acetyl]-LS 519Piren basan
Database identifiers
- CAS
Properties
Computed structural properties
- XLogP
- 0.1
- Topological polar surface area
- 68.8 Ų
- Hydrogen bond donors
- 1
- Hydrogen bond acceptors
- 5
- Rotatable bonds
- 2
- Heavy atoms
- 26
- Formal charge
- 0
- Complexity
- 534
Experimental & physicochemical properties
Drugs
Pharmaceuticals -> Listed in ZINC15
Pharmaceuticals
LogP
0.6
0.1
Solubility6.82e-01 g/L
Physical DescriptionSolid
Collision Cross Section187.76 Ų [M+K]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
Physicochemical properties
- Boiling point
- 541.7 · 541.7±50.0 °C(Predicted)
- Density
- 1.271 · 1.271±0.06 g/cm3(Predicted)
- storage temp.
- Store at RT
- solubility
- soluble in No data available
- pka
- 11.29 · 11.29±0.20(Predicted)
- form
- solid
- color
- white
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS ClassificationNot Classified
Hazard information
Regulatory InformationREACH registered substance: Pirenzepine (EC: 249-228-4)
Other Safety InformationIMAP assessments - 6H-Pyrido[2,3-b][1,4]benzodiazepin-6-one, 5,11-dihydro-11-[(4-methyl-1-piperazinyl)acetyl]-: Environment tier I assessment
Hazard Classes and CategoriesNot Classified
Safety data
- wgk
- WGK 2
- Storage Class
- 11 - Combustible Solids
- REACH Registrations
- Active
Chemistry & industry
Pharmacology
ATC Code
A - Alimentary tract and metabolism
QA - Alimentary tract and metabolism
Pharmacodynamics
Pirenzepine belongs to a group of medications called antispasmodics/anticholinergics. These medications are used to relieve cramps or spasms of the stomach, intestines, and bladder. Pirenzepine is used to treat duodenal or stomach ulcers or intestine problems. It can be used together with antacids or other medicine in the treatment of peptic ulcer. It may also be used to prevent nausea, vomiting, and motion sickness.
Mechanism of Action
Pirenzepine is a muscarinic receptor antagonist and binds to the muscarinic acetylcholine receptor. The muscarinic acetylcholine receptor mediates various cellular responses, including inhibition of adenylate cyclase, breakdown of phosphoinositides and modulation of potassium channels through the action of G proteins.
MeSH Pharmacological Classification
Various agents with different action mechanisms used to treat or ameliorate PEPTIC ULCER or irritation of the gastrointestinal tract. This has included ANTIBIOTICS to treat HELICOBACTER INFECTIONS; HISTAMINE H2 ANTAGONISTS to reduce GASTRIC ACID secretion; and ANTACIDS for symptomatic relief.
Drugs that bind to but do not activate MUSCARINIC RECEPTORS, thereby blocking the actions of endogenous ACETYLCHOLINE or exogenous agonists. Muscarinic antagonists have widespread effects including actions on the iris and ciliary muscle of the eye, the heart and blood vessels, secretions of the respiratory tract, GI system, and salivary glands, GI motility, urinary bladder tone, and the central nervous system.
Cellular LocationsMembrane
Metabolite PathwaysPirenzepine Action Pathway
Uses & manufacturing
Related reactions
1 records
Compound notes
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