Edrophonium
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Also known as Edrophonium cationEdrophonium ionEnlon-plusSID11111143SID90341680SID11111144SID50100235SID50104222EDROPHONIUM CHLORIDE
Summary
Edrophonium (CHEMBL1104) is an approved small-molecule EC 3.1.1.8 (cholinesterase) inhibitor (ATC V04CX07) targeting ACHE; indicated across 2 conditions including orthostatic hypotension and postural orthostatic tachycardia syndrome.
At a glance
- Status: Approved (max clinical phase 4)
- Modality: Small molecule
- ATC class: V04CX07
- Targets: 1 (ACHE)
- Indications: 2 conditions
- Clinical trials: 1
- Chemistry: 166.24 Da · C10H16NO+
Identifiers
Drug identity and classification
| Field | Value |
|---|---|
| ChEMBL ID | CHEMBL1104 |
| Name | Edrophonium |
| Type | Small molecule |
| Max phase | 4 |
| FDA approved | no |
| PubChem CID | 3202 |
| ChEBI | CHEBI:251408 |
| ATC | V04CX07 |
| Molecular formula | C10H16NO+ |
| Molecular weight | 166.24 |
| InChIKey | VWLHWLSRQJQWRG-UHFFFAOYSA-O |
SMILES: CC[N+](C)(C)C1=CC(=CC=C1)O
IUPAC name: ethyl-(3-hydroxyphenyl)-dimethylazanium
ChEBI definition: A quaternary ammonium ion that is N-ethyl-N,N-dimethylanilinium in which one of the meta positions is substituted by a hydroxy group. It is a reversible inhibitor of cholinesterase, with a rapid onset (30-60 seconds after injection) but a short duration of action (5-15 minutes). The chloride salt is used in myasthenia gravis both diagnostically and to distinguish between under- or over-treatment with other anticholinesterases. It has also been used for the reversal of neuromuscular blockade in anaesthesia, and for the management of poisoning due to tetrodotoxin, a neuromuscular blocking toxin found in puffer fish and other marine animals.
Pharmacological roles (ChEBI): EC 3.1.1.8 (cholinesterase) inhibitor, diagnostic agent, antidote.
Also known as: Edrophonium, Edrophonium cation, Edrophonium ion, Enlon-plus, SID11111143, SID90341680, SID11111144, SID50100235, SID50104222, EDROPHONIUM, EDROPHONIUM CHLORIDE, edrophonium
Parent form; salt/anhydrous children: CHEMBL60745, CHEMBL1128
Patent coverage: 6,476 distinct patent families (17,617 SureChEMBL compound mentions), from 2 matched compound structure(s). One matched structure accounts for 17,615 (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 |
|---|---|---|---|---|---|
| ACHE | acetylcholinesterase (Yt blood group) | Inhibition | 6.7 | 9.6% | P22303 |
Broader ChEMBL bioactivity targets: 4 (assay-derived). Sample: Thyrotropin receptor, Acetylcholinesterase, Mu-type opioid receptor, Muscarinic acetylcholine receptor M1.
Bioactivity
ChEMBL activities: 2 potent at pChembl ≥ 5 of 6 total. Top 30 by potency (10 = 0.1 nM, 6 = 1 µM):
| Target | pChembl | Type | Value | Unit | Activity ID |
|---|---|---|---|---|---|
| ACHE | 5.52 | AC50 | 3010 | nM | CHEMBL_ACT_25143010 |
| OPRM1 | 5.14 | AC50 | 7180 | nM | CHEMBL_ACT_25158637 |
Target pathways
Aggregated over 1 target gene(s): ACHE.
Top Reactome pathways
11 total, by targets touching each:
| Pathway | Targets | Genes |
|---|---|---|
| Neurotransmitter clearance | 1 | ACHE |
| Transmission across Chemical Synapses | 1 | ACHE |
| Neuronal System | 1 | ACHE |
| Metabolism | 1 | ACHE |
| Synthesis of PC | 1 | ACHE |
| Glycerophospholipid biosynthesis | 1 | ACHE |
| Phospholipid metabolism | 1 | ACHE |
| Peptide hormone metabolism | 1 | ACHE |
| Metabolism of proteins | 1 | ACHE |
| Synthesis, secretion, and deacylation of Ghrelin | 1 | ACHE |
| Metabolism of lipids | 1 | ACHE |
Dominant GO biological processes
| GO term | Targets |
|---|---|
| acetylcholine catabolic process in synaptic cleft | 1 |
| regulation of receptor recycling | 1 |
| osteoblast development | 1 |
| acetylcholine catabolic process | 1 |
| cell adhesion | 1 |
| nervous system development | 1 |
| synapse assembly | 1 |
| receptor internalization | 1 |
| negative regulation of synaptic transmission, cholinergic | 1 |
| amyloid precursor protein metabolic process | 1 |
| positive regulation of protein secretion | 1 |
| retina development in camera-type eye | 1 |
| acetylcholine receptor signaling pathway | 1 |
| positive regulation of cold-induced thermogenesis | 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 |
|---|---|---|---|
| orthostatic hypotension | 1 | MONDO:0005469 | EFO:0005252 |
| postural orthostatic tachycardia syndrome | 1 | MONDO:0011479 | EFO:1000645 |
Clinical trials
Total trials: 1.
Phase distribution
| Phase | Trials |
|---|---|
| PHASE1 | 1 |
Top trials by phase / activity
| NCT | Phase | Status | Title |
|---|---|---|---|
| NCT00748059 | PHASE1 | COMPLETED | The Pathophysiology of Orthostatic Hypotension |
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.
152 molecules share ≥1 primary target. Top 60 by shared-target count:
| Molecule | Source | Status | Shared targets |
|---|---|---|---|
| GENTIAN VIOLET | ChEMBL + PubChem | Phase 4 (approved) | ACHE |
| PAZOPANIB | ChEMBL + PubChem | Phase 4 (approved) | ACHE |
| TADALAFIL | ChEMBL + PubChem | Phase 4 (approved) | ACHE |
| ALFUZOSIN | ChEMBL | Phase 4 (approved) | ACHE |
| ARIPIPRAZOLE | ChEMBL | Phase 4 (approved) | ACHE |
| BERBERINE | ChEMBL | Phase 4 (approved) | ACHE |
| BOSUTINIB | ChEMBL | Phase 4 (approved) | ACHE |
| BROMOCRIPTINE | ChEMBL | Phase 4 (approved) | ACHE |
| BUTENAFINE | ChEMBL | Phase 4 (approved) | ACHE |
| CABERGOLINE | ChEMBL | Phase 4 (approved) | ACHE |
| CAFFEINE | ChEMBL | Phase 4 (approved) | ACHE |
| CANNABIDIOL | ChEMBL | Phase 4 (approved) | ACHE |
| CITALOPRAM | ChEMBL | Phase 4 (approved) | ACHE |
| CLOTRIMAZOLE | ChEMBL | Phase 4 (approved) | ACHE |
| DECAMETHONIUM | ChEMBL | Phase 4 (approved) | ACHE |
| DECAMETHONIUM BROMIDE | ChEMBL | Phase 4 (approved) | ACHE |
| DEQUALINIUM | ChEMBL | Phase 4 (approved) | ACHE |
| DIETHYLSTILBESTROL | ChEMBL | Phase 4 (approved) | ACHE |
| DISULFIRAM | ChEMBL | Phase 4 (approved) | ACHE |
| DOFETILIDE | ChEMBL | Phase 4 (approved) | ACHE |
| DONEPEZIL | ChEMBL | Phase 4 (approved) | ACHE |
| DYCLONINE | ChEMBL | Phase 4 (approved) | ACHE |
| EBASTINE | ChEMBL | Phase 4 (approved) | ACHE |
| ECONAZOLE | ChEMBL | Phase 4 (approved) | ACHE |
| EPIRUBICIN | ChEMBL | Phase 4 (approved) | ACHE |
| ETHOPROPAZINE | ChEMBL | Phase 4 (approved) | ACHE |
| ETHYLESTRENOL | ChEMBL | Phase 4 (approved) | ACHE |
| FENOFIBRATE | ChEMBL | Phase 4 (approved) | ACHE |
| FLAVOXATE | ChEMBL | Phase 4 (approved) | ACHE |
| FLUOXETINE | ChEMBL | Phase 4 (approved) | ACHE |
| GALANTAMINE | ChEMBL | Phase 4 (approved) | ACHE |
| GALLAMINE | ChEMBL | Phase 4 (approved) | ACHE |
| HEXACHLOROPHENE | ChEMBL | Phase 4 (approved) | ACHE |
| HEXAFLUORENIUM | ChEMBL | Phase 4 (approved) | ACHE |
| ILOPERIDONE | ChEMBL | Phase 4 (approved) | ACHE |
| IRINOTECAN | ChEMBL | Phase 4 (approved) | ACHE |
| ISOFLUROPHATE | ChEMBL | Phase 4 (approved) | ACHE |
| LEVALLORPHAN | ChEMBL | Phase 4 (approved) | ACHE |
| LORLATINIB | ChEMBL | Phase 4 (approved) | ACHE |
| LURASIDONE | ChEMBL | Phase 4 (approved) | ACHE |
| MELPHALAN | ChEMBL | Phase 4 (approved) | ACHE |
| MEMANTINE | ChEMBL | Phase 4 (approved) | ACHE |
| MEPTAZINOL | ChEMBL | Phase 4 (approved) | ACHE |
| METHOXSALEN | ChEMBL | Phase 4 (approved) | ACHE |
| MICONAZOLE | ChEMBL | Phase 4 (approved) | ACHE |
| MINAPRINE | ChEMBL | Phase 4 (approved) | ACHE |
| NAFTOPIDIL | ChEMBL | Phase 4 (approved) | ACHE |
| NEFAZODONE | ChEMBL | Phase 4 (approved) | ACHE |
| NEOSTIGMINE | ChEMBL | Phase 4 (approved) | ACHE |
| NEOSTIGMINE METHYLSULFATE | ChEMBL | Phase 4 (approved) | ACHE |
| NICERGOLINE | ChEMBL | Phase 4 (approved) | ACHE |
| NIZATIDINE | ChEMBL | Phase 4 (approved) | ACHE |
| ORLISTAT | ChEMBL | Phase 4 (approved) | ACHE |
| OXICONAZOLE | ChEMBL | Phase 4 (approved) | ACHE |
| PALBOCICLIB | ChEMBL | Phase 4 (approved) | ACHE |
| PENTAMIDINE | ChEMBL | Phase 4 (approved) | ACHE |
| PENTOXIFYLLINE | ChEMBL | Phase 4 (approved) | ACHE |
| PERICIAZINE | ChEMBL | Phase 4 (approved) | ACHE |
| PHYSOSTIGMINE | ChEMBL | Phase 4 (approved) | ACHE |
| PHYSOSTIGMINE SALICYLATE | ChEMBL | Phase 4 (approved) | ACHE |
Related Atlas pages
- Genes: ACHE
- Drugs: Pazopanib, Tadalafil, Alfuzosin, Aripiprazole, Berberine, Bosutinib, Bromocriptine, Butenafine, Cabergoline, Caffeine, Cannabidiol, Citalopram, Clotrimazole, Decamethonium, Dequalinium, Diethylstilbestrol, Disulfiram, Dofetilide, Donepezil, Dyclonine, Ebastine, Econazole, Epirubicin, Ethopropazine, Ethylestrenol, Fenofibrate, Flavoxate, Fluoxetine, Galantamine, Gallamine, Hexachlorophene, Hexafluorenium, Iloperidone, Irinotecan, Isoflurophate, Levallorphan, Lorlatinib, Lurasidone, Melphalan, Memantine, Meptazinol, Methoxsalen, Miconazole, Minaprine, Naftopidil, Nefazodone, Neostigmine, Nicergoline, Nizatidine, Orlistat, Oxiconazole, Palbociclib, Pentamidine, Pentoxifylline, Periciazine, Physostigmine