Pirenzepine

Summary

Pirenzepine (CHEMBL9967) is an approved small-molecule anti-ulcer drug (ATC A02BX03) targeting CHRM1, CHRM2, and CHRM3; indicated across 5 conditions including peptic ulcer disease and gastroesophageal reflux disease.

At a glance

• Status: Approved (max clinical phase 4)
• Modality: Small molecule
• ATC class: A02BX03
• Targets: 6 (CHRM1, CHRM2, CHRM3…)
• Indications: 5 conditions
• Clinical trials: 3
• Chemistry: 351.4 Da · C19H21N5O2

Identifiers

Drug identity and classification

Field	Value
ChEMBL ID	CHEMBL9967
Name	Pirenzepine
Type	Small molecule
Max phase	4
FDA approved	no
PubChem CID	4848
ChEBI	CHEBI:8247
ATC	A02BX03
Molecular formula	C19H21N5O2
Molecular weight	351.4
InChIKey	RMHMFHUVIITRHF-UHFFFAOYSA-N

SMILES: CN1CCN(CC1)CC(=O)N2C3=CC=CC=C3C(=O)NC4=C2N=CC=C4

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

Pharmacological roles (ChEBI): anti-ulcer drug, muscarinic antagonist, antispasmodic drug.

Also known as: ACI-91, Gastri p, Gastrozepin, Pirenzepina, Pirenzepine, Wst-057, SID11111661, SID11111662, SID11113363, SID26751604, SID90341394, Pirenzipine

Parent form; salt/anhydrous children: CHEMBL1531864

Patent coverage: 3,512 distinct patent families (11,458 SureChEMBL compound mentions), from 3 matched compound structure(s). One matched structure accounts for 11,445 (100%) of the total. Mentions count patents naming the compound (not distinct inventions), so promiscuous / reference molecules inflate the mention figure — families are the dedup metric.

Targets

Targets

Primary targets (GtoPdb curated mechanism): the Cancer dependency column is the DepMap CRISPR fitness signal (% of screened cell lines dependent on the target).

Gene	Target	Action	pAffinity	Cancer dependency	UniProt
CHRM1	M1 receptor	Antagonist	8.3	0.2%	P11229
CHRM2	M2 receptor	Antagonist	6.7	0%	P08172
CHRM3	M3 receptor	Antagonist	6.8	0%	P20309
CHRM4	M4 receptor	Antagonist	7.6	1.6%	P08173
CHRM5	M5 receptor	Antagonist	7.1	0%	P08912
TAS2R9	TAS2R9	Agonist	2.74	0%	Q9NYW1

Broader ChEMBL bioactivity targets: 19 (assay-derived). Sample: Ubiquitin carboxyl-terminal hydrolase 2, Prelamin-A/C, Inositol monophosphatase 1, Muscarinic acetylcholine receptor M4, Muscarinic acetylcholine receptor, Muscarinic acetylcholine receptor M5, Muscarinic acetylcholine receptor, Muscarinic acetylcholine receptor, Muscarinic acetylcholine receptor M2, Muscarinic acetylcholine receptor M1.

Bioactivity

ChEMBL activities: 164 potent at pChembl ≥ 5 of 170 total. Top 30 by potency (10 = 0.1 nM, 6 = 1 µM):

Target	pChembl	Type	Value	Unit	Activity ID
CHRM4	8.94	IC50	1.15	nM	CHEMBL_ACT_15087525
CHRM1	8.83	IC50	1.48	nM	CHEMBL_ACT_15087416
CHRM1	8.55	Ki	2.82	nM	CHEMBL_ACT_2557037
P08482	8.42	IC50	3.8	nM	CHEMBL_ACT_748984
CHRM1	8.34	Ki	4.6	nM	CHEMBL_ACT_937738
P08482	8.28	Ki	5.21	nM	CHEMBL_ACT_226180
P08482	8.28	Ki	5.21	nM	CHEMBL_ACT_250723
P08482	8.28	Ki	5.2	nM	CHEMBL_ACT_477288
P08482	8.19	Ki	6.46	nM	CHEMBL_ACT_387108
P08482	8.19	Ki	6.46	nM	CHEMBL_ACT_804748
P08482	8.19	Ki	6.46	nM	CHEMBL_ACT_853860
P08482	8.19	Ki	6.46	nM	CHEMBL_ACT_974968
CHRM1	8.04	Ki	9.1	nM	CHEMBL_ACT_12629843
CHRM1	8	Ki	10	nM	CHEMBL_ACT_13342024
CHRM1	7.92	IC50	12	nM	CHEMBL_ACT_13342096
CHRM1	7.92	IC50	12	nM	CHEMBL_ACT_2573331
CHRM4	7.86	Ki	13.8	nM	CHEMBL_ACT_2557079
CHRM1	7.85	Ki	14	nM	CHEMBL_ACT_880781
CHRM1	7.82	Ki	15	nM	CHEMBL_ACT_14738662
CHRM1	7.82	Ki	15	nM	CHEMBL_ACT_15187896
CHRM1	7.8	Ki	16	nM	CHEMBL_ACT_15186973
CHRM1	7.72	Ki	19	nM	CHEMBL_ACT_26333265
CHRM1	7.72	IC50	19	nM	CHEMBL_ACT_5166002
CHRM1	7.7	Kd	20	nM	CHEMBL_ACT_1464249
CHRM1	7.7	Ki	20	nM	CHEMBL_ACT_18188253
CHRM1	7.69	IC50	20.42	nM	CHEMBL_ACT_15087377
CHRM1	7.68	IC50	21	nM	CHEMBL_ACT_16501816
CHRM1	7.68	IC50	21	nM	CHEMBL_ACT_16838428
CHRM1	7.67	Ki	21.38	nM	CHEMBL_ACT_1989702
CHRM1	7.66	IC50	22	nM	CHEMBL_ACT_1611126

Target pathways

Aggregated over 6 target gene(s): CHRM1, CHRM2, CHRM3, CHRM4, CHRM5, TAS2R9.

Top Reactome pathways

18 total, by targets touching each:

Pathway	Targets	Genes
Signal Transduction	6	CHRM1, CHRM2, CHRM3, CHRM4, CHRM5, TAS2R9
Signaling by GPCR	6	CHRM1, CHRM2, CHRM3, CHRM4, CHRM5, TAS2R9
GPCR downstream signalling	6	CHRM1, CHRM2, CHRM3, CHRM4, CHRM5, TAS2R9
GPCR ligand binding	6	CHRM1, CHRM2, CHRM3, CHRM4, CHRM5, TAS2R9
Class A/1 (Rhodopsin-like receptors)	5	CHRM1, CHRM2, CHRM3, CHRM4, CHRM5
Amine ligand-binding receptors	5	CHRM1, CHRM2, CHRM3, CHRM4, CHRM5
Muscarinic acetylcholine receptors	5	CHRM1, CHRM2, CHRM3, CHRM4, CHRM5
G alpha (q) signalling events	3	CHRM1, CHRM3, CHRM5
G alpha (i) signalling events	3	CHRM2, CHRM4, TAS2R9
Metabolism	1	CHRM3
Integration of energy metabolism	1	CHRM3
Membrane Trafficking	1	CHRM2
Acetylcholine regulates insulin secretion	1	CHRM3
Class C/3 (Metabotropic glutamate/pheromone receptors)	1	TAS2R9
Regulation of insulin secretion	1	CHRM3
Vesicle-mediated transport	1	CHRM2
Cargo recognition for clathrin-mediated endocytosis	1	CHRM2
Clathrin-mediated endocytosis	1	CHRM2

Dominant GO biological processes

GO term	Targets
signal transduction	6
G protein-coupled receptor signaling pathway	6
G protein-coupled receptor signaling pathway, coupled to cyclic nucleotide second messenger	5
adenylate cyclase-inhibiting G protein-coupled acetylcholine receptor signaling pathway	5
G protein-coupled acetylcholine receptor signaling pathway	5
chemical synaptic transmission	5
phospholipase C-activating G protein-coupled acetylcholine receptor signaling pathway	3
nervous system development	3
acetylcholine receptor signaling pathway	3
regulation of locomotion	2
saliva secretion	2
regulation of smooth muscle contraction	2
phospholipase C-activating G protein-coupled receptor signaling pathway	1
neuromuscular synaptic transmission	1
positive regulation of monoatomic ion transport	1

Indications & clinical

Indications

5 indications (2 at ChEMBL trial phase 4). Phase below is the highest clinical-trial phase recorded for this drug against each disease — not the molecule’s overall approval status (that is in the Summary).

Indication	Trial phase	MONDO	EFO
peptic ulcer disease	4	MONDO:0004247	HP:0004398
gastroesophageal reflux disease	4	MONDO:0007186	EFO:0003948
peripheral neuropathy	2	MONDO:0005244	EFO:0003100
diabetic neuropathy	2	MONDO:0006626	EFO:1000783
gastric ulcer	1	MONDO:0001126	EFO:0009454

Clinical trials

Total trials: 3.

Phase distribution

Phase	Trials
PHASE2	3

Top trials by phase / activity

NCT	Phase	Status	Title
NCT05488873	PHASE2	ACTIVE_NOT_RECRUITING	A Study of Topical Pirenzepine or Placebo in Oncology Patients With Chemotherapy Induced Peripheral Neuropathy
NCT04005287	PHASE2	COMPLETED	A 24-Week Study of Topical Pirenzepine or Placebo in Type 2 Diabetic Patients (T2DM) With Peripheral Neuropathy
NCT05005078	PHASE2	COMPLETED	A 16-Week Study of Pirenzepine or Placebo to Treat HIV-Associated Distal Sensory Polyneuropathy in Patients With HIV

Clinical evidence (CIViC)

No CIViC predictive evidence (expected for non-precision-medicine drugs).

Pharmacology

Pharmacogenomics

No CPIC/DPWG dosing guideline or drug-level clinical/variant annotations in PharmGKB for this molecule.

Related molecules

Related molecules

Molecules sharing ≥1 of this drug’s curated primary targets, merged from two biobtree sources and ranked by shared-target count, then clinical phase: ChEMBL clinical-stage candidates (development phase ≥2) and PubChem drug-class bioactivity (approved / known drugs acting on the target). Deduplicated by drug name; the drug’s own salt forms are excluded. Note: for a drug with few primary targets a shared-target match can reflect off-target / promiscuous binding rather than the same therapeutic mechanism — the phase ordering surfaces bona-fide therapeutics first.

577 molecules share ≥1 primary target. Top 60 by shared-target count:

Molecule	Source	Status	Shared targets
ACLIDINIUM BROMIDE	ChEMBL + PubChem	Phase 4 (approved)	CHRM1, CHRM2, CHRM3, CHRM4, CHRM5
CLOZAPINE	ChEMBL + PubChem	Phase 4 (approved)	CHRM1, CHRM2, CHRM3, CHRM4, CHRM5
GENTIAN VIOLET	ChEMBL + PubChem	Phase 4 (approved)	CHRM1, CHRM2, CHRM3, CHRM4, CHRM5
Mavorixafor	ChEMBL + PubChem	Phase 4 (approved)	CHRM1, CHRM2, CHRM3, CHRM4, CHRM5
OLANZAPINE	ChEMBL + PubChem	Phase 4 (approved)	CHRM1, CHRM2, CHRM3, CHRM4, CHRM5
ACETYLCHOLINE	ChEMBL	Phase 4 (approved)	CHRM1, CHRM2, CHRM3, CHRM4, CHRM5
AMIODARONE	ChEMBL	Phase 4 (approved)	CHRM1, CHRM2, CHRM3, CHRM4, CHRM5
AMITRIPTYLINE	ChEMBL	Phase 4 (approved)	CHRM1, CHRM2, CHRM3, CHRM4, CHRM5
AMOXAPINE	ChEMBL	Phase 4 (approved)	CHRM1, CHRM2, CHRM3, CHRM4, CHRM5
ASTEMIZOLE	ChEMBL	Phase 4 (approved)	CHRM1, CHRM2, CHRM3, CHRM4, CHRM5
ATROPINE	ChEMBL	Phase 4 (approved)	CHRM1, CHRM2, CHRM3, CHRM4, CHRM5
BENZTROPINE	ChEMBL	Phase 4 (approved)	CHRM1, CHRM2, CHRM3, CHRM4, CHRM5
BETHANECHOL	ChEMBL	Phase 4 (approved)	CHRM1, CHRM2, CHRM3, CHRM4, CHRM5
CARBACHOL	ChEMBL	Phase 4 (approved)	CHRM1, CHRM2, CHRM3, CHRM4, CHRM5
CARBAMOYLCHOLINE	ChEMBL	Phase 4 (approved)	CHRM1, CHRM2, CHRM3, CHRM4, CHRM5
CHLOROQUINE	ChEMBL	Phase 4 (approved)	CHRM1, CHRM2, CHRM3, CHRM4, CHRM5
CHLORPROMAZINE	ChEMBL	Phase 4 (approved)	CHRM1, CHRM2, CHRM3, CHRM4, CHRM5
CINNARIZINE	ChEMBL	Phase 4 (approved)	CHRM1, CHRM2, CHRM3, CHRM4, CHRM5
CLEMASTINE	ChEMBL	Phase 4 (approved)	CHRM1, CHRM2, CHRM3, CHRM4, CHRM5
CLIDINIUM	ChEMBL	Phase 4 (approved)	CHRM1, CHRM2, CHRM3, CHRM4, CHRM5
CLOMIPRAMINE	ChEMBL	Phase 4 (approved)	CHRM1, CHRM2, CHRM3, CHRM4, CHRM5
CYCLIZINE	ChEMBL	Phase 4 (approved)	CHRM1, CHRM2, CHRM3, CHRM4, CHRM5
CYPROHEPTADINE	ChEMBL	Phase 4 (approved)	CHRM1, CHRM2, CHRM3, CHRM4, CHRM5
DARIFENACIN	ChEMBL	Phase 4 (approved)	CHRM1, CHRM2, CHRM3, CHRM4, CHRM5
DESLORATADINE	ChEMBL	Phase 4 (approved)	CHRM1, CHRM2, CHRM3, CHRM4, CHRM5
DEXCHLORPHENIRAMINE	ChEMBL	Phase 4 (approved)	CHRM1, CHRM2, CHRM3, CHRM4, CHRM5
DICYCLOMINE	ChEMBL	Phase 4 (approved)	CHRM1, CHRM2, CHRM3, CHRM4, CHRM5
DIMENHYDRINATE	ChEMBL	Phase 4 (approved)	CHRM1, CHRM2, CHRM3, CHRM4, CHRM5
DIPHENHYDRAMINE	ChEMBL	Phase 4 (approved)	CHRM1, CHRM2, CHRM3, CHRM4, CHRM5
DIPHENIDOL	ChEMBL	Phase 4 (approved)	CHRM1, CHRM2, CHRM3, CHRM4, CHRM5
DOXEPIN	ChEMBL	Phase 4 (approved)	CHRM1, CHRM2, CHRM3, CHRM4, CHRM5
EBASTINE	ChEMBL	Phase 4 (approved)	CHRM1, CHRM2, CHRM3, CHRM4, CHRM5
GLYCOPYRRONIUM BROMIDE	ChEMBL	Phase 4 (approved)	CHRM1, CHRM2, CHRM3, CHRM4, CHRM5
HALOPERIDOL	ChEMBL	Phase 4 (approved)	CHRM1, CHRM2, CHRM3, CHRM4, CHRM5
HOMATROPINE	ChEMBL	Phase 4 (approved)	CHRM1, CHRM2, CHRM3, CHRM4, CHRM5
HYDROXYCHLOROQUINE	ChEMBL	Phase 4 (approved)	CHRM1, CHRM2, CHRM3, CHRM4, CHRM5
IMIPRAMINE	ChEMBL	Phase 4 (approved)	CHRM1, CHRM2, CHRM3, CHRM4, CHRM5
IPRATROPIUM	ChEMBL	Phase 4 (approved)	CHRM1, CHRM2, CHRM3, CHRM4, CHRM5
KETOTIFEN	ChEMBL	Phase 4 (approved)	CHRM1, CHRM2, CHRM3, CHRM4, CHRM5
LOXAPINE	ChEMBL	Phase 4 (approved)	CHRM1, CHRM2, CHRM3, CHRM4, CHRM5
MAPROTILINE	ChEMBL	Phase 4 (approved)	CHRM1, CHRM2, CHRM3, CHRM4, CHRM5
MEPAZINE	ChEMBL	Phase 4 (approved)	CHRM1, CHRM2, CHRM3, CHRM4, CHRM5
METHSCOPOLAMINE	ChEMBL	Phase 4 (approved)	CHRM1, CHRM2, CHRM3, CHRM4, CHRM5
METHSCOPOLAMINE BROMIDE	ChEMBL	Phase 4 (approved)	CHRM1, CHRM2, CHRM3, CHRM4, CHRM5
MIANSERIN	ChEMBL	Phase 4 (approved)	CHRM1, CHRM2, CHRM3, CHRM4, CHRM5
NORTRIPTYLINE	ChEMBL	Phase 4 (approved)	CHRM1, CHRM2, CHRM3, CHRM4, CHRM5
ORPHENADRINE	ChEMBL	Phase 4 (approved)	CHRM1, CHRM2, CHRM3, CHRM4, CHRM5
OXYBUTYNIN	ChEMBL	Phase 4 (approved)	CHRM1, CHRM2, CHRM3, CHRM4, CHRM5
PAROXETINE	ChEMBL	Phase 4 (approved)	CHRM1, CHRM2, CHRM3, CHRM4, CHRM5
PERHEXILINE	ChEMBL	Phase 4 (approved)	CHRM1, CHRM2, CHRM3, CHRM4, CHRM5
PILOCARPINE	ChEMBL	Phase 4 (approved)	CHRM1, CHRM2, CHRM3, CHRM4, CHRM5
PROCHLORPERAZINE	ChEMBL	Phase 4 (approved)	CHRM1, CHRM2, CHRM3, CHRM4, CHRM5
PROMAZINE	ChEMBL	Phase 4 (approved)	CHRM1, CHRM2, CHRM3, CHRM4, CHRM5
PROMETHAZINE	ChEMBL	Phase 4 (approved)	CHRM1, CHRM2, CHRM3, CHRM4, CHRM5
QUETIAPINE	ChEMBL	Phase 4 (approved)	CHRM1, CHRM2, CHRM3, CHRM4, CHRM5
QUINACRINE	ChEMBL	Phase 4 (approved)	CHRM1, CHRM2, CHRM3, CHRM4, CHRM5
RISPERIDONE	ChEMBL	Phase 4 (approved)	CHRM1, CHRM2, CHRM3, CHRM4, CHRM5
SCOPOLAMINE	ChEMBL	Phase 4 (approved)	CHRM1, CHRM2, CHRM3, CHRM4, CHRM5
SERTRALINE	ChEMBL	Phase 4 (approved)	CHRM1, CHRM2, CHRM3, CHRM4, CHRM5
SOLIFENACIN	ChEMBL	Phase 4 (approved)	CHRM1, CHRM2, CHRM3, CHRM4, CHRM5