Echothiophate
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Also known as Echothiophate cationEchothiophate ionEcothiopateEcothiopate cation
Summary
Echothiophate (CHEMBL1201341) is an approved small-molecule EC 3.1.1.8 (cholinesterase) inhibitor (ATC S01EB03) targeting ACHE; indicated across 1 condition including glaucoma.
At a glance
- Status: Approved (max clinical phase 4)
- Modality: Small molecule
- ATC class: S01EB03
- Targets: 1 (ACHE)
- Indications: 1 condition
- Chemistry: 256.33 Da · C9H23NO3PS+
Identifiers
Drug identity and classification
| Field | Value |
|---|---|
| ChEMBL ID | CHEMBL1201341 |
| Name | Echothiophate |
| Type | Small molecule |
| Max phase | 4 |
| FDA approved | yes |
| PubChem CID | 10548 |
| ChEBI | CHEBI:4753 |
| ATC | S01EB03 |
| Molecular formula | C9H23NO3PS+ |
| Molecular weight | 256.33 |
| InChIKey | BJOLKYGKSZKIGU-UHFFFAOYSA-N |
SMILES: CCOP(=O)(OCC)SCC[N+](C)(C)C
IUPAC name: 2-diethoxyphosphorylsulfanylethyl(trimethyl)azanium
ChEBI definition: The phosphorothioate obtained by formal condensation of diethyl phosphate with N,N,N-trimethyl-2-sulfanylethanaminium. An irreversible acetylcholinesterase inhibitor, its iodide salt is used an ocular antihypertensive in the treatment of open-angle glaucoma, particularly when other drugs have proved inadequate.
Pharmacological roles (ChEBI): EC 3.1.1.8 (cholinesterase) inhibitor, miotic.
Also known as: Echothiophate cation, Echothiophate ion, Ecothiopate, Ecothiopate cation, echothiophate, ECHOTHIOPHATE
Parent form; salt/anhydrous children: CHEMBL1200367
Patent coverage: 144 distinct patent families (260 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 |
|---|---|---|---|---|---|
| ACHE | acetylcholinesterase (Yt blood group) | Inhibition | 9.6% | P22303 |
Bioactivity
No ChEMBL bioactivity rows at pChembl ≥ 5 (expected for biologics / antibodies).
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
1 indication (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).
| Indication | Trial phase | MONDO | EFO |
|---|---|---|---|
| glaucoma | 4 | MONDO:0005041 | MONDO:0005041 |
Clinical trials
Total trials: 0.
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.
153 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 |
| EDROPHONIUM | ChEMBL | Phase 4 (approved) | ACHE |
| EDROPHONIUM CHLORIDE | 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 |
Related Atlas pages
- Genes: ACHE
- Diseases: glaucoma
- Drugs: Pazopanib, Tadalafil, Alfuzosin, Aripiprazole, Berberine, Bosutinib, Bromocriptine, Butenafine, Cabergoline, Caffeine, Cannabidiol, Citalopram, Clotrimazole, Decamethonium, Dequalinium, Diethylstilbestrol, Disulfiram, Dofetilide, Donepezil, Dyclonine, Ebastine, Econazole, Edrophonium, 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