Ipratropium

Summary

Ipratropium (CHEMBL1621597) is an approved small molecule targeting CHRM1, CHRM2, and CHRM3; indicated across 2 conditions including chronic obstructive pulmonary disease and status asthmaticus.

At a glance

• Status: Approved (max clinical phase 4)
• Modality: Small molecule
• Targets: 5 (CHRM1, CHRM2, CHRM3…)
• Indications: 2 conditions
• Clinical trials: 21
• Chemistry: 332.5 Da · C20H30NO3+

Identifiers

Drug identity and classification

Field	Value
ChEMBL ID	CHEMBL1621597
Name	Ipratropium
Type	Small molecule
Max phase	4
FDA approved	no
PubChem CID	657309
Molecular formula	C20H30NO3+
Molecular weight	332.5
InChIKey	OEXHQOGQTVQTAT-BZQJJPTISA-N

SMILES: CC(C)[N+]1([C@@H]2CC[C@H]1CC(C2)OC(=O)C(CO)C3=CC=CC=C3)C

IUPAC name: [(1R,5S)-8-methyl-8-propan-2-yl-8-azoniabicyclo[3.2.1]octan-3-yl] 3-hydroxy-2-phenylpropanoate

Also known as: Ipratropium, Ipratropium cation, Ipratropium ion, rel-Ipratropium, ipratropium, IPRATROPIUM

Parent form; salt/anhydrous children: CHEMBL2134724, CHEMBL3085123

Patent coverage: 17 distinct patent families (35 SureChEMBL compound mentions), from 1 matched compound structure(s). 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	9.8	0.2%	P11229
CHRM2	M2 receptor	Antagonist	9.8	0%	P08172
CHRM3	M3 receptor	Antagonist	9.8	0%	P20309
CHRM4	M4 receptor	Antagonist	9.2	1.6%	P08173
CHRM5	M5 receptor	Antagonist	8.8	0%	P08912

Broader ChEMBL bioactivity targets: 5 (assay-derived). Sample: Muscarinic acetylcholine receptor M4, Muscarinic acetylcholine receptor M5, Muscarinic acetylcholine receptor M2, Muscarinic acetylcholine receptor M1, Muscarinic acetylcholine receptor M3.

Bioactivity

ChEMBL activities: 11 potent at pChembl ≥ 5 of 11 total. Top 30 by potency (10 = 0.1 nM, 6 = 1 µM):

Target	pChembl	Type	Value	Unit	Activity ID
CHRM3	9.1	Ki	0.79	nM	CHEMBL_ACT_24360619
CHRM2	9.1	Ki	0.79	nM	CHEMBL_ACT_24360764
CHRM2	9.05	AC50	0.9	nM	CHEMBL_ACT_25196396
CHRM2	8.92	AC50	1.2	nM	CHEMBL_ACT_25195361
CHRM4	8.89	AC50	1.3	nM	CHEMBL_ACT_25144458
CHRM3	8.77	AC50	1.7	nM	CHEMBL_ACT_25137066
CHRM1	8.68	Ki	2.11	nM	CHEMBL_ACT_25617999
CHRM1	8.55	AC50	2.8	nM	CHEMBL_ACT_25135854
CHRM5	8.52	AC50	3	nM	CHEMBL_ACT_25137467
CHRM2	8.52	AC50	3	nM	CHEMBL_ACT_25196147
CHRM1	8.39	AC50	4.1	nM	CHEMBL_ACT_25210562

Target pathways

Aggregated over 5 target gene(s): CHRM1, CHRM2, CHRM3, CHRM4, CHRM5.

Top Reactome pathways

17 total, by targets touching each:

Pathway	Targets	Genes
Signal Transduction	5	CHRM1, CHRM2, CHRM3, CHRM4, CHRM5
Signaling by GPCR	5	CHRM1, CHRM2, CHRM3, CHRM4, CHRM5
Class A/1 (Rhodopsin-like receptors)	5	CHRM1, CHRM2, CHRM3, CHRM4, CHRM5
Amine ligand-binding receptors	5	CHRM1, CHRM2, CHRM3, CHRM4, CHRM5
GPCR downstream signalling	5	CHRM1, CHRM2, CHRM3, CHRM4, CHRM5
Muscarinic acetylcholine receptors	5	CHRM1, CHRM2, CHRM3, CHRM4, CHRM5
GPCR ligand binding	5	CHRM1, CHRM2, CHRM3, CHRM4, CHRM5
G alpha (q) signalling events	3	CHRM1, CHRM3, CHRM5
G alpha (i) signalling events	2	CHRM2, CHRM4
Metabolism	1	CHRM3
Integration of energy metabolism	1	CHRM3
Membrane Trafficking	1	CHRM2
Acetylcholine regulates insulin secretion	1	CHRM3
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	5
G protein-coupled receptor signaling pathway	5
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

2 indications (0 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
chronic obstructive pulmonary disease	3	MONDO:0005002	EFO:0000341
status asthmaticus	1	MONDO:0004766	EFO:0008590

Clinical trials

Total trials: 21.

Phase distribution

Phase	Trials
PHASE3	6
Not specified	5
PHASE4	4
PHASE1	3
PHASE2	2
PHASE2/PHASE3	1

Top trials by phase / activity

NCT	Phase	Status	Title
NCT01253473	PHASE4	COMPLETED	Symbicort in Airway Predominant Chronic Obstructive Pulmonary Disease (COPD)
NCT01691482	PHASE4	COMPLETED	A Study to Look at Day to Day Changes in Lung Function in COPD Subjects Taking Albuterol/Salbutamol and Ipratropium
NCT01696214	PHASE4	COMPLETED	A Pilot Study to Determine the Feasibility and Utility of Implementing of the Full Scale TOM Trial
NCT02182856	PHASE4	COMPLETED	Ipratropium or Salbutamol Sulphate Alone or Combination Therapy Salbutamol and Ipratropium in Patients With COPD
NCT00000568	PHASE3	COMPLETED	Lung Health Study (LHS) I and III
NCT00274040	PHASE3	COMPLETED	Comparison of Tiotropium and Ipratropium in a Double-Blind, Double-dummy, Efficacy and Safety Study in Adults With COPD
NCT00274066	PHASE3	COMPLETED	Acute Bronchodilator Response of a Single Dose of Atrovent or Berotec on Top of Pharmacodynamic Steady State of Spiriva
NCT04446637	PHASE3	WITHDRAWN	Acute Bronchodilator Effects of Ipratropium/Levosalbutamol 20/50 mcg Fixed Dose Combination vs Salbutamol 100 mcg Inhaler Plus Ipratropium 20 mcg Inhalation Aerosol Free Combination in Patients With Stable COPD
NCT05890638	PHASE3	UNKNOWN	Comparison of Ipratropium / Levosalbutamol Fixed Dose Combination and Ipratropium and Levosalbutamol Free Dose Combination Nebuliser Solutions in Stable Chronic Obstructive Pulmonary Disease (COPD) Patients
NCT06040424	PHASE3	UNKNOWN	Comparison of Ipratropium / Levosalbutamol Fixed Dose Combination and Ipratropium and Levosalbutamol Free Dose Combination in pMDI Form in Stable Chronic Obstructive Pulmonary Disease (COPD) Patients
NCT06376942	PHASE2/PHASE3	UNKNOWN	A RCT to Compare the Effectiveness of Nebulized Anticholinergics for Cough Suppression During Flexible Bronchoscopy
NCT02542254	PHASE2	COMPLETED	The Effects of RPL554 on Top of Standard COPD Reliever Medications
NCT03064113	PHASE2	COMPLETED	Effects of TD-4208 on FEV1 in Subjects With Chronic Obstructive Pulmonary Disease (COPD)
NCT00549120	PHASE1	COMPLETED	Optimising the Propranolol Block Model
NCT02207452	PHASE1	COMPLETED	Helium-3 MRI Imaging Study in COPD
NCT02872597	PHASE1	COMPLETED	Phase I, Placebo-Controlled, Blinded Pilot Study of Ipratropium in Children Admitted to the ICU With Status Asthmaticus
NCT00371527	Not specified	COMPLETED	Effect of Ipratropium on Acute Bronchitis in Subjects Without Underlying Lung Disease
NCT00498251	Not specified	COMPLETED	Prevention of Lung Edema After Thoracic Surgery
NCT00583778	Not specified	COMPLETED	A Comparison of Levalbuterol Plus Ipratropium With Levalbuterol Alone in the Treatment of Acute Asthma Exacerbation
NCT00904436	Not specified	COMPLETED	Evaluation of Breathing Pattern and Dyspnea in Subjects With Tetraplegia
NCT03296579	Not specified	UNKNOWN	Non-invasive Ventilation vs. Standard Therapy for Children Hospitalized With an Acute Exacerbation of Asthma

Clinical evidence (CIViC)

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

Pharmacology

Pharmacogenomics

No PharmGKB pharmacogenomic data curated for this drug.

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.

576 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
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
PIRENZEPINE	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