◎ Sugi Atlas

Atlas / Drug / Acetylcholine

Acetylcholine

drug
On this page

Also known as NN-trimethylethanaminiumSID26756572SID124883320Acetyl choline

Summary

Acetylcholine (CHEMBL667) is an approved small-molecule vasodilator agent (ATC S01EB09) targeting CHRM1, CHRM2, and CHRM3; indicated across 8 conditions including glaucoma and anemia.

At a glance

  • Status: Approved (max clinical phase 4)
  • Modality: Small molecule
  • ATC class: S01EB09
  • Targets: 5 (CHRM1, CHRM2, CHRM3…)
  • Indications: 8 conditions
  • Clinical trials: 43
  • Chemistry: 146.21 Da · C7H16NO2+

Identifiers

Drug identity and classification

FieldValue
ChEMBL IDCHEMBL667
NameAcetylcholine
TypeSmall molecule
Max phase4
FDA approvedyes
PubChem CID187
ChEBICHEBI:15355
ATCS01EB09
Molecular formulaC7H16NO2+
Molecular weight146.21
InChIKeyOIPILFWXSMYKGL-UHFFFAOYSA-N

SMILES: CC(=O)OCC[N+](C)(C)C

IUPAC name: 2-acetyloxyethyl(trimethyl)azanium

ChEBI definition: Actylcholine is an ester of acetic acid and choline, which acts as a neurotransmitter.

Pharmacological roles (ChEBI): neurotransmitter, vasodilator agent, muscarinic agonist, hormone.

Other ChEBI roles (chemical / environmental): human metabolite, mouse metabolite.

Also known as: Acetylcholine, acetylcholine, N, N-trimethylethanaminium, SID26756572, SID124883320, ACETYLCHOLINE, Acetyl choline

Parent form; salt/anhydrous children: CHEMBL60457, CHEMBL1184, CHEMBL1427664, CHEMBL1736587

Patent coverage: 43,013 distinct patent families (124,626 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).

GeneTargetActionpAffinityCancer dependencyUniProt
CHRM1M1 receptorFull agonist4.90.2%P11229
CHRM2M2 receptorFull agonist6.50%P08172
CHRM3M3 receptorFull agonist5.40%P20309
CHRM4M4 receptorFull agonist5.61.6%P08173
CHRM5M5 receptorFull agonist6.10%P08912

Broader ChEMBL bioactivity targets: 25 (assay-derived). Sample: Survival motor neuron protein, Muscarinic acetylcholine receptor M4, Neuronal acetylcholine receptor subunit alpha-4, Neuronal acetylcholine receptor; alpha3/beta2, Neuronal acetylcholine receptor; alpha4/beta2, Neuronal acetylcholine receptor; alpha2/beta2, Neuronal acetylcholine receptor; alpha3/beta4, Neuronal acetylcholine receptor; alpha3/beta4, Neuronal acetylcholine receptor; alpha4/beta4, Neuronal acetylcholine receptor; alpha4/beta2.

Bioactivity

ChEMBL activities: 109 potent at pChembl ≥ 5 of 144 total. Top 30 by potency (10 = 0.1 nM, 6 = 1 µM):

TargetpChemblTypeValueUnitActivity ID
CHRM18.96EC501.1nMCHEMBL_ACT_10951420
CHRM18.96EC501.1nMCHEMBL_ACT_3439264
CHRM58.92EC501.2nMCHEMBL_ACT_10951421
CHRM58.92EC501.2nMCHEMBL_ACT_3430226
CHRNB28.77EC501.7nMCHEMBL_ACT_15023514
CHRM18.51AC503.1nMCHEMBL_ACT_25209678
CHRM38.49EC503.2nMCHEMBL_ACT_10951435
CHRM38.49EC503.2nMCHEMBL_ACT_3430206
CHRM28.15EC507nMCHEMBL_ACT_15720440
P094838.12Ki7.6nMCHEMBL_ACT_1493416
CHRM48EC5010nMCHEMBL_ACT_10951475
CHRM48EC5010nMCHEMBL_ACT_3430215
P123897.96Ki11nMCHEMBL_ACT_278649
P084827.92IC5012nMCHEMBL_ACT_580903
P084827.92IC5012nMCHEMBL_ACT_614664
P084827.92IC5012nMCHEMBL_ACT_930058
CHRM27.9EC5012.59nMCHEMBL_ACT_18121755
CHRM27.89EC5013nMCHEMBL_ACT_18121756
CHRM57.72EC5019.1nMCHEMBL_ACT_15720521
CHRM27.66AC5022nMCHEMBL_ACT_25215220
CHRM37.64EC5022.91nMCHEMBL_ACT_18121762
CHRM37.64EC5023nMCHEMBL_ACT_18121763
CHRM17.59EC5025.9nMCHEMBL_ACT_15720416
P094837.48Ki33.11nMCHEMBL_ACT_12626952
P094837.48Ki33nMCHEMBL_ACT_12626982
P094837.48Ki33nMCHEMBL_ACT_15712196
P094837.48Ki33.11nMCHEMBL_ACT_15712229
P094837.42Ki37.7nMCHEMBL_ACT_3561637
P094837.41Ki39nMCHEMBL_ACT_2109481
P047577.39Ki41nMCHEMBL_ACT_278651

Target pathways

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

Top Reactome pathways

17 total, by targets touching each:

PathwayTargetsGenes
Signal Transduction5CHRM1, CHRM2, CHRM3, CHRM4, CHRM5
Signaling by GPCR5CHRM1, CHRM2, CHRM3, CHRM4, CHRM5
Class A/1 (Rhodopsin-like receptors)5CHRM1, CHRM2, CHRM3, CHRM4, CHRM5
Amine ligand-binding receptors5CHRM1, CHRM2, CHRM3, CHRM4, CHRM5
GPCR downstream signalling5CHRM1, CHRM2, CHRM3, CHRM4, CHRM5
Muscarinic acetylcholine receptors5CHRM1, CHRM2, CHRM3, CHRM4, CHRM5
GPCR ligand binding5CHRM1, CHRM2, CHRM3, CHRM4, CHRM5
G alpha (q) signalling events3CHRM1, CHRM3, CHRM5
G alpha (i) signalling events2CHRM2, CHRM4
Metabolism1CHRM3
Integration of energy metabolism1CHRM3
Membrane Trafficking1CHRM2
Acetylcholine regulates insulin secretion1CHRM3
Regulation of insulin secretion1CHRM3
Vesicle-mediated transport1CHRM2
Cargo recognition for clathrin-mediated endocytosis1CHRM2
Clathrin-mediated endocytosis1CHRM2

Dominant GO biological processes

GO termTargets
signal transduction5
G protein-coupled receptor signaling pathway5
G protein-coupled receptor signaling pathway, coupled to cyclic nucleotide second messenger5
adenylate cyclase-inhibiting G protein-coupled acetylcholine receptor signaling pathway5
G protein-coupled acetylcholine receptor signaling pathway5
chemical synaptic transmission5
phospholipase C-activating G protein-coupled acetylcholine receptor signaling pathway3
nervous system development3
acetylcholine receptor signaling pathway3
regulation of locomotion2
saliva secretion2
regulation of smooth muscle contraction2
phospholipase C-activating G protein-coupled receptor signaling pathway1
neuromuscular synaptic transmission1
positive regulation of monoatomic ion transport1

Indications & clinical

Indications

8 indications (1 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).

IndicationTrial phaseMONDOEFO
glaucoma4MONDO:0005041MONDO:0005041
anemia2MONDO:0002280EFO:0004272
type 2 diabetes mellitus2MONDO:0005148MONDO:0005148
sickle cell disease2MONDO:0011382MONDO:0011382
ischemic disease1MONDO:0005053EFO:0000556
HIV infectious disease1MONDO:0005109EFO:0000764
coronary artery disorder1MONDO:0005010EFO:0001645

1 further indication record had no mapped disease name (EFO/MeSH-only) or were duplicates, and are omitted.

Clinical trials

Total trials: 43.

Phase distribution

PhaseTrials
Not specified18
PHASE110
EARLY_PHASE18
PHASE25
PHASE1/PHASE22

Top trials by phase / activity

NCTPhaseStatusTitle
NCT00001870PHASE2COMPLETEDStudy of the Effects of Vitamin C on Patients With Type 2 Diabetes
NCT00009581PHASE2COMPLETEDNitric Oxide to Improve Blood Flow in Sickle Cell Disease
NCT00166166PHASE2TERMINATEDEndothelial Hyperpolarization in Humans
NCT00453531PHASE1/PHASE2COMPLETEDModel System for Transient Forearm Blood Vessel Dysfunction
NCT00508989PHASE2COMPLETEDNiacin to Improve Blood Flow in People With Sickle Cell Disease
NCT03446612PHASE2TERMINATEDAnemia Study in Chronic Kidney Disease (CKD) : Erythropoiesis Via a Novel Prolyl Hydroxylase Inhibitor (PHI) Daprodustat -Forearm Blood Flow (ASCEND-FBF)
NCT03953326PHASE1/PHASE2TERMINATEDHeartPhone Cancer Survivors Trial 2019
NCT02966665PHASE1RECRUITING: Vascular Function in Health and Disease
NCT00072826PHASE1COMPLETEDAtorvastatin Therapy to Improve Endothelial Function in Sickle Cell Disease
NCT00076414PHASE1COMPLETEDThe Effect of Lopinavir/Ritonavir on Endothelial Function
NCT00160888PHASE1UNKNOWNVasoreactivity in Carriers of Genetic Polymorphisms
NCT00250185PHASE1COMPLETEDThe Role of Nitrite in Preconditioning Mediated Tolerance to Ischemic Stress
NCT00264186PHASE1COMPLETEDRecombinant Human Superoxide Dismutase (rhSOD) and Vascular Reactivity
NCT00327080PHASE1TERMINATEDSildenafil to Treat HIV-Associated Pulmonary Hypertension
NCT01137656PHASE1COMPLETEDStorage Lesion in Banked Blood Due to Disruption of Nitric Oxide (NO) Homeostasis
NCT01848301PHASE1TERMINATEDEndothelial Injury and Development of Coronary Intimal Thickening After Heart Transplantation
NCT03462017PHASE1COMPLETEDPharmacodynamic Study to Assess the Effects of Repeated Dosing of SAR247799 on Endothelial Function in Patients With Type 2 Diabetes Mellitus
NCT05653973EARLY_PHASE1RECRUITINGPrenatal Aspirin and Postpartum Vascular Function
NCT05946785EARLY_PHASE1RECRUITINGOxidative Stress in Microvascular Dysfunction Following Gestational Diabetes
NCT05946798EARLY_PHASE1RECRUITINGRole of NADPH Oxidase in Microvascular Dysfunction Following GDM
NCT06499844EARLY_PHASE1RECRUITINGComparing Approaches to Assess Nitric Oxide-dependent Cutaneous Vasodilation
NCT06520982EARLY_PHASE1RECRUITINGEarly Neurovascular Adaptations in Aging Women
NCT03738943EARLY_PHASE1COMPLETEDPyridoxine, P2 Receptor Antagonism, and ATP-mediated Vasodilation in Young Adults
NCT03972683EARLY_PHASE1WITHDRAWNRole of Acetylcholine in Blood Flow Regulation in Healthy Adults: Effects of Age and Exercise Training
NCT04001647EARLY_PHASE1TERMINATEDTargeting ER Stress in Vascular Dysfunction
NCT05193968Not specifiedRECRUITINGHot Flashes and Neurovascular Function in Women
NCT06043310Not specifiedACTIVE_NOT_RECRUITINGEstrogen and Microvascular Function
NCT06443151Not specifiedRECRUITINGRole of Endothelial Function in SCI CVD Risk
NCT00152724Not specifiedCOMPLETEDMechanisms of Human Cutaneous Microcirculation in Healthy Volunteers
NCT00184847Not specifiedSUSPENDEDAdenosine Receptors Influence Ischemia-Reperfusion Injury
NCT00901719Not specifiedCOMPLETEDInvestigating Systemic and Local Vascular Responses to Apelin in the Context of Renin-angiotensin Upregulation
NCT01075776Not specifiedWITHDRAWNThe Effects of C-type Natriuretic Peptide on Human Forearm Blood Vessels
NCT01125943Not specifiedCOMPLETEDBevacizumab and Endothelium Dependent Vasodilation
NCT01162824Not specifiedUNKNOWNBlood Markers for Inflammation and Coronary Artery Vasoreactivity Testing in Patients With Chest Pain and Normal Coronary Arteries
NCT02034331Not specifiedCOMPLETEDIR and Microvascular Blood Flow in SCI
NCT02085317Not specifiedCOMPLETEDMicrocirculatory Impairment in Patients With Leprosy
NCT02123069Not specifiedCOMPLETEDVascular Function and Uterine Fibroids
NCT02652065Not specifiedCOMPLETEDCutaneous Microcirculation and Nervous Sensitivity in Psoriasis
NCT02987465Not specifiedCOMPLETEDEvaluating the Effect of Standard-of-care Erythropoiesis-stimulating Agents on Forearm Blood Flow in Nondialysis-dependent Subjects With Anaemia Associated With Chronic Kidney Disease.
NCT04777383Not specifiedTERMINATEDThe Effects of Iontophoresed Vasoactive Drugs on Cutaneus Blood Flow

Clinical evidence (CIViC)

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

Pharmacology

Pharmacogenomics

No CPIC/DPWG dosing guideline, but PharmGKB curates 1 clinical and 1 variant annotation(s) for this drug (gene-keyed; see PharmGKB).

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.

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

MoleculeSourceStatusShared targets
ACLIDINIUM BROMIDEChEMBL + PubChemPhase 4 (approved)CHRM1, CHRM2, CHRM3, CHRM4, CHRM5
CLOZAPINEChEMBL + PubChemPhase 4 (approved)CHRM1, CHRM2, CHRM3, CHRM4, CHRM5
GENTIAN VIOLETChEMBL + PubChemPhase 4 (approved)CHRM1, CHRM2, CHRM3, CHRM4, CHRM5
MavorixaforChEMBL + PubChemPhase 4 (approved)CHRM1, CHRM2, CHRM3, CHRM4, CHRM5
OLANZAPINEChEMBL + PubChemPhase 4 (approved)CHRM1, CHRM2, CHRM3, CHRM4, CHRM5
AMIODARONEChEMBLPhase 4 (approved)CHRM1, CHRM2, CHRM3, CHRM4, CHRM5
AMITRIPTYLINEChEMBLPhase 4 (approved)CHRM1, CHRM2, CHRM3, CHRM4, CHRM5
AMOXAPINEChEMBLPhase 4 (approved)CHRM1, CHRM2, CHRM3, CHRM4, CHRM5
ASTEMIZOLEChEMBLPhase 4 (approved)CHRM1, CHRM2, CHRM3, CHRM4, CHRM5
ATROPINEChEMBLPhase 4 (approved)CHRM1, CHRM2, CHRM3, CHRM4, CHRM5
BENZTROPINEChEMBLPhase 4 (approved)CHRM1, CHRM2, CHRM3, CHRM4, CHRM5
BETHANECHOLChEMBLPhase 4 (approved)CHRM1, CHRM2, CHRM3, CHRM4, CHRM5
CARBACHOLChEMBLPhase 4 (approved)CHRM1, CHRM2, CHRM3, CHRM4, CHRM5
CARBAMOYLCHOLINEChEMBLPhase 4 (approved)CHRM1, CHRM2, CHRM3, CHRM4, CHRM5
CHLOROQUINEChEMBLPhase 4 (approved)CHRM1, CHRM2, CHRM3, CHRM4, CHRM5
CHLORPROMAZINEChEMBLPhase 4 (approved)CHRM1, CHRM2, CHRM3, CHRM4, CHRM5
CINNARIZINEChEMBLPhase 4 (approved)CHRM1, CHRM2, CHRM3, CHRM4, CHRM5
CLEMASTINEChEMBLPhase 4 (approved)CHRM1, CHRM2, CHRM3, CHRM4, CHRM5
CLIDINIUMChEMBLPhase 4 (approved)CHRM1, CHRM2, CHRM3, CHRM4, CHRM5
CLOMIPRAMINEChEMBLPhase 4 (approved)CHRM1, CHRM2, CHRM3, CHRM4, CHRM5
CYCLIZINEChEMBLPhase 4 (approved)CHRM1, CHRM2, CHRM3, CHRM4, CHRM5
CYPROHEPTADINEChEMBLPhase 4 (approved)CHRM1, CHRM2, CHRM3, CHRM4, CHRM5
DARIFENACINChEMBLPhase 4 (approved)CHRM1, CHRM2, CHRM3, CHRM4, CHRM5
DESLORATADINEChEMBLPhase 4 (approved)CHRM1, CHRM2, CHRM3, CHRM4, CHRM5
DEXCHLORPHENIRAMINEChEMBLPhase 4 (approved)CHRM1, CHRM2, CHRM3, CHRM4, CHRM5
DICYCLOMINEChEMBLPhase 4 (approved)CHRM1, CHRM2, CHRM3, CHRM4, CHRM5
DIMENHYDRINATEChEMBLPhase 4 (approved)CHRM1, CHRM2, CHRM3, CHRM4, CHRM5
DIPHENHYDRAMINEChEMBLPhase 4 (approved)CHRM1, CHRM2, CHRM3, CHRM4, CHRM5
DIPHENIDOLChEMBLPhase 4 (approved)CHRM1, CHRM2, CHRM3, CHRM4, CHRM5
DOXEPINChEMBLPhase 4 (approved)CHRM1, CHRM2, CHRM3, CHRM4, CHRM5
EBASTINEChEMBLPhase 4 (approved)CHRM1, CHRM2, CHRM3, CHRM4, CHRM5
GLYCOPYRRONIUM BROMIDEChEMBLPhase 4 (approved)CHRM1, CHRM2, CHRM3, CHRM4, CHRM5
HALOPERIDOLChEMBLPhase 4 (approved)CHRM1, CHRM2, CHRM3, CHRM4, CHRM5
HOMATROPINEChEMBLPhase 4 (approved)CHRM1, CHRM2, CHRM3, CHRM4, CHRM5
HYDROXYCHLOROQUINEChEMBLPhase 4 (approved)CHRM1, CHRM2, CHRM3, CHRM4, CHRM5
IMIPRAMINEChEMBLPhase 4 (approved)CHRM1, CHRM2, CHRM3, CHRM4, CHRM5
IPRATROPIUMChEMBLPhase 4 (approved)CHRM1, CHRM2, CHRM3, CHRM4, CHRM5
KETOTIFENChEMBLPhase 4 (approved)CHRM1, CHRM2, CHRM3, CHRM4, CHRM5
LOXAPINEChEMBLPhase 4 (approved)CHRM1, CHRM2, CHRM3, CHRM4, CHRM5
MAPROTILINEChEMBLPhase 4 (approved)CHRM1, CHRM2, CHRM3, CHRM4, CHRM5
MEPAZINEChEMBLPhase 4 (approved)CHRM1, CHRM2, CHRM3, CHRM4, CHRM5
METHSCOPOLAMINEChEMBLPhase 4 (approved)CHRM1, CHRM2, CHRM3, CHRM4, CHRM5
METHSCOPOLAMINE BROMIDEChEMBLPhase 4 (approved)CHRM1, CHRM2, CHRM3, CHRM4, CHRM5
MIANSERINChEMBLPhase 4 (approved)CHRM1, CHRM2, CHRM3, CHRM4, CHRM5
NORTRIPTYLINEChEMBLPhase 4 (approved)CHRM1, CHRM2, CHRM3, CHRM4, CHRM5
ORPHENADRINEChEMBLPhase 4 (approved)CHRM1, CHRM2, CHRM3, CHRM4, CHRM5
OXYBUTYNINChEMBLPhase 4 (approved)CHRM1, CHRM2, CHRM3, CHRM4, CHRM5
PAROXETINEChEMBLPhase 4 (approved)CHRM1, CHRM2, CHRM3, CHRM4, CHRM5
PERHEXILINEChEMBLPhase 4 (approved)CHRM1, CHRM2, CHRM3, CHRM4, CHRM5
PILOCARPINEChEMBLPhase 4 (approved)CHRM1, CHRM2, CHRM3, CHRM4, CHRM5
PIRENZEPINEChEMBLPhase 4 (approved)CHRM1, CHRM2, CHRM3, CHRM4, CHRM5
PROCHLORPERAZINEChEMBLPhase 4 (approved)CHRM1, CHRM2, CHRM3, CHRM4, CHRM5
PROMAZINEChEMBLPhase 4 (approved)CHRM1, CHRM2, CHRM3, CHRM4, CHRM5
PROMETHAZINEChEMBLPhase 4 (approved)CHRM1, CHRM2, CHRM3, CHRM4, CHRM5
QUETIAPINEChEMBLPhase 4 (approved)CHRM1, CHRM2, CHRM3, CHRM4, CHRM5
QUINACRINEChEMBLPhase 4 (approved)CHRM1, CHRM2, CHRM3, CHRM4, CHRM5
RISPERIDONEChEMBLPhase 4 (approved)CHRM1, CHRM2, CHRM3, CHRM4, CHRM5
SCOPOLAMINEChEMBLPhase 4 (approved)CHRM1, CHRM2, CHRM3, CHRM4, CHRM5
SERTRALINEChEMBLPhase 4 (approved)CHRM1, CHRM2, CHRM3, CHRM4, CHRM5
SOLIFENACINChEMBLPhase 4 (approved)CHRM1, CHRM2, CHRM3, CHRM4, CHRM5

About this page

Generated deterministically by Sugi Atlas from primary biomedical databases via BioBTree. Every record on this page traces to a primary source.

Generated
Atlas version
v1.1.2
BioBTree
v2.0.2

Sources 30

This page pulls from 30 datasets indexed by BioBTree:

chebichembl_activitychembl_moleculechembl_targetcivic_evidenceclingen_dosageclinical_trialsdepmapefoensemblentrezgogoparentgtopdbgtopdb_interactiongtopdb_ligandhgncmeshmondomsigdbpatent_compoundpharmgkbpharmgkb_guidelinepubchempubchem_activityreactomereactomeparentrefseqtranscriptuniprot