pirenzepine Indications/Contra | FAERs-F | FAERs-M | Orange Bk | BioActivity |

Stem definitionDrug idCAS RN
tricyclic compounds 2200 28797-61-7

Description:

MoleculeDescription

Molfile Inchi Smiles

Synonyms:

  • pirenzepine hydrochloride hydrate
  • pirenzepine
  • pirenzepin
  • pirenzepine dihydrochloride
  • pirenzepine hydrochloride
  • pirenzepine HCl
An antimuscarinic agent that inhibits gastric secretion at lower doses than are required to affect gastrointestinal motility, salivary, central nervous system, cardiovascular, ocular, and urinary function. It promotes the healing of duodenal ulcers and due to its cytoprotective action is beneficial in the prevention of duodenal ulcer recurrence. It also potentiates the effect of other antiulcer agents such as CIMETIDINE and RANITIDINE. It is generally well tolerated by patients.
  • Molecular weight: 351.41
  • Formula: C19H21N5O2
  • CLOGP: -0.35
  • LIPINSKI: 0
  • HAC: 7
  • HDO: 1
  • TPSA: 68.78
  • ALOGS: -2.71
  • ROTB: 2

Drug dosage:

DoseUnitRoute
0.10 g O
20 mg P

ADMET properties:

PropertyValueReference
BDDCS (Biopharmaceutical Drug Disposition Classification System) 3 Benet LZ, Broccatelli F, Oprea TI
S (Water solubility) 50 mg/mL Benet LZ, Broccatelli F, Oprea TI
EoM (Fraction excreted unchanged in urine) 43 % Benet LZ, Broccatelli F, Oprea TI
MRTD (Maximum Recommended Therapeutic Daily Dose) 7.11 ┬ÁM/kg/day Contrera JF, Matthews EJ, Kruhlak NL, Benz RD
BA (Bioavailability) 14 % Kim MT, Sedykh A, Chakravarti SK, Saiakhov RD, Zhu H
Vd (Volume of distribution) 1.71 L/kg Lombardo F, Berellini G, Obach RS
CL (Clearance) 2.77 mL/min/kg Lombardo F, Berellini G, Obach RS
t_half (Half-life) 11.10 hours Lombardo F, Berellini G, Obach RS

Approvals:

None

FDA Adverse Event Reporting System (Female)

None

FDA Adverse Event Reporting System (Male)

None

Pharmacologic Action:

SourceCodeDescription
ATC A02BX03 ALIMENTARY TRACT AND METABOLISM
DRUGS FOR ACID RELATED DISORDERS
DRUGS FOR PEPTIC ULCER AND GASTRO-OESOPHAGEAL REFLUX DISEASE (GORD)
Other drugs for peptic ulcer and gastro-oesophageal reflux disease (GORD)
MeSH PA D000897 Anti-Ulcer Agents
MeSH PA D018678 Cholinergic Agents
MeSH PA D018680 Cholinergic Antagonists
MeSH PA D005765 Gastrointestinal Agents
MeSH PA D018727 Muscarinic Antagonists
MeSH PA D018377 Neurotransmitter Agents
CHEBI has role CHEBI:49201 anti-ulcer drug
CHEBI has role CHEBI:48876 muscarinic antagonist
CHEBI has role CHEBI:53784 antispasmodic drug

Drug Use (View source of the data)

DiseaseRelationSNOMED_IDDOID
Peptic ulcer indication 13200003 DOID:750

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation levelDissociation constantType (acidic/basic)
pKa1 8.89 acidic
pKa2 7.77 Basic
pKa3 2.58 Basic
pKa4 1.96 Basic

Orange Book patent data (new drug applications)

None

Orange Book exclusivity data (new drug applications)

None

Bioactivity Summary:

TargetClassPharosUniProtActionTypeActivity value
(-log[M])
Mechanism
action
Bioact sourceMoA source
Muscarinic acetylcholine receptor M1 GPCR ANTAGONIST Ki 7.68 WOMBAT-PK IUPHAR
Muscarinic acetylcholine receptor M4 GPCR Ki 7.12 WOMBAT-PK
Muscarinic acetylcholine receptor M3 GPCR Ki 6.61 WOMBAT-PK
Adenosine receptor A3 GPCR IC50 7.66 CHEMBL
Muscarinic acetylcholine receptor M2 GPCR Ki 6.76 CHEMBL
Muscarinic acetylcholine receptor M5 GPCR Ki 6.55 WOMBAT-PK
Muscarinic acetylcholine receptor GPCR IC50 6.12 CHEMBL
Muscarinic acetylcholine receptor DM1 GPCR Ki 6.41 CHEMBL
Muscarinic acetylcholine receptor GPCR Ki 7.22 CHEMBL
Muscarinic receptor M1 GPCR Ki 8.44 CHEMBL
Muscarinic acetylcholine receptor M1 GPCR Ki 8.28 CHEMBL
Muscarinic acetylcholine receptor M3 GPCR Ki 7.55 CHEMBL
Muscarinic acetylcholine receptor M2 GPCR Ki 6.92 CHEMBL
Muscarinic acetylcholine receptor GPCR Ki 6.96 CHEMBL
Muscarinic acetylcholine receptor M4 GPCR Ki 6.48 CHEMBL

External reference:

IDSource
4025257 VUID
N0000171787 NUI
C0031978 UMLSCUI
D01297 KEGG_DRUG
10YM403FLS UNII
29868-97-1 SECONDARY_CAS_RN
3476 INN_ID
349802000 SNOMEDCT_US
4025257 VANDF
8352 RXNORM
398669004 SNOMEDCT_US
003754 NDDF
CHEMBL9967 ChEMBL_ID
DB00670 DRUGBANK_ID
CHEBI:8247 CHEBI
CHEMBL1257024 ChEMBL_ID
CHEMBL1531864 ChEMBL_ID
D010890 MESH_DESCRIPTOR_UI
4848 PUBCHEM_CID
328 IUPHAR_LIGAND_ID

Pharmaceutical products:

None