Neostigmine
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Also known as MiostinNeostigmine (cation)Neostigmine cationNeostigmine hydroxideNeostigmine ionSID11111527SID26756597SID90340848SID11111528Neostigmine (methyl sulfate)NEOSTIGMINE BROMIDE
Summary
Neostigmine (CHEMBL278020) is an approved small-molecule EC 3.1.1.7 (acetylcholinesterase) inhibitor (ATC S01EB06) targeting ACHE; indicated across 11 conditions including glaucoma and burn.
At a glance
- Status: Approved (max clinical phase 4)
- Modality: Small molecule
- ATC class: S01EB06 (+2 more)
- Targets: 1 (ACHE)
- Indications: 11 conditions
- Clinical trials: 161
- Chemistry: 223.29 Da · C12H19N2O2+
Identifiers
Drug identity and classification
| Field | Value |
|---|---|
| ChEMBL ID | CHEMBL278020 |
| Name | Neostigmine |
| Type | Small molecule |
| Max phase | 4 |
| FDA approved | yes |
| PubChem CID | 4456 |
| ChEBI | CHEBI:7514 |
| ATC | S01EB06, N07AA01, N07AA51 |
| Molecular formula | C12H19N2O2+ |
| Molecular weight | 223.29 |
| InChIKey | ALWKGYPQUAPLQC-UHFFFAOYSA-N |
SMILES: CN(C)C(=O)OC1=CC=CC(=C1)[N+](C)(C)C
IUPAC name: [3-(dimethylcarbamoyloxy)phenyl]-trimethylazanium
ChEBI definition: A quaternary ammonium ion comprising an anilinium ion core having three methyl substituents on the aniline nitrogen, and a 3-[(dimethylcarbamoyl)oxy] substituent at position 3. It is a parasympathomimetic which acts as a reversible acetylcholinesterase inhibitor.
Pharmacological roles (ChEBI): EC 3.1.1.7 (acetylcholinesterase) inhibitor, antidote to curare poisoning.
Also known as: Miostin, Neostigmine, Neostigmine (cation), Neostigmine cation, Neostigmine hydroxide, Neostigmine ion, SID11111527, SID26756597, SID90340848, SID11111528, NEOSTIGMINE, Neostigmine (methyl sulfate)
Parent form; salt/anhydrous children: CHEMBL54126, CHEMBL211471
Patent coverage: 2,921 distinct patent families (9,463 SureChEMBL compound mentions), from 2 matched compound structure(s). One matched structure accounts for 9,453 (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 | 7.35 | 9.6% | P22303 |
Broader ChEMBL bioactivity targets: 7 (assay-derived). Sample: Prelamin-A/C, Cholinesterase, Acetylcholinesterase, Muscarinic acetylcholine receptor M1, Acetylcholinesterase, Acetylcholinesterase, Cholinesterase.
Bioactivity
ChEMBL activities: 12 potent at pChembl ≥ 5 of 21 total. Top 30 by potency (10 = 0.1 nM, 6 = 1 µM):
| Target | pChembl | Type | Value | Unit | Activity ID |
|---|---|---|---|---|---|
| P04058 | 8.34 | IC50 | 4.6 | nM | CHEMBL_ACT_14530643 |
| O42275 | 7.72 | IC50 | 19 | nM | CHEMBL_ACT_25879992 |
| ACHE | 7.06 | AC50 | 87.3 | nM | CHEMBL_ACT_25142419 |
| ACHE | 7.02 | AC50 | 94.9 | nM | CHEMBL_ACT_25142182 |
| P81908 | 6.8 | IC50 | 160 | nM | CHEMBL_ACT_25025801 |
| ACHE | 5.62 | IC50 | 2400 | nM | CHEMBL_ACT_15044953 |
| P81908 | 5.53 | IC50 | 2930 | nM | CHEMBL_ACT_22402428 |
| LMNA | 5.3 | Potency | 5012 | nM | CHEMBL_ACT_3621834 |
| P08482 | 5.25 | Potency | 5623 | nM | CHEMBL_ACT_4857878 |
| O42275 | 5.12 | IC50 | 7500 | nM | CHEMBL_ACT_22402421 |
| P08482 | 5.1 | Potency | 7943 | nM | CHEMBL_ACT_4807582 |
| P81908 | 5.08 | IC50 | 8410 | nM | CHEMBL_ACT_25879995 |
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
11 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).
| Indication | Trial phase | MONDO | EFO |
|---|---|---|---|
| glaucoma | 4 | MONDO:0005041 | MONDO:0005041 |
| burn | 3 | MONDO:0043519 | EFO:0009516 |
| morbid obesity | 2 | MONDO:0005139 | EFO:0001074 |
| hypospadias | 2 | MONDO:0005345 | EFO:0004209 |
| breast neoplasm | 2 | MONDO:0021100 | MONDO:0007254 |
| gastroparesis | 2 | MONDO:0006769 | EFO:1000948 |
| kidney disorder | 2 | MONDO:0005240 | EFO:0003086 |
4 further indication records had no mapped disease name (EFO/MeSH-only) or were duplicates, and are omitted.
Clinical trials
Total trials: 161.
Phase distribution
| Phase | Trials |
|---|---|
| PHASE4 | 73 |
| Not specified | 46 |
| PHASE3 | 17 |
| PHASE2 | 8 |
| PHASE2/PHASE3 | 7 |
| PHASE1 | 5 |
| EARLY_PHASE1 | 3 |
| PHASE1/PHASE2 | 2 |
Top trials by phase / activity
| NCT | Phase | Status | Title |
|---|---|---|---|
| NCT06493838 | PHASE4 | NOT_YET_RECRUITING | Clinical Efficacy of Prophylactic Intravenous Neostigmine and Atropine in Preventing Post-Dural Puncture Headache Among Parturient Undergoing Spinal Anesthesia for Cesarean Section: A Double-blind Randomized Placebo-controlled Trial |
| NCT06685705 | PHASE4 | NOT_YET_RECRUITING | Comparative Study Between Intrathecal Magnesium Sulfate, Neostigmine and Fentanyl as Adjuvant for Bubivacaine in Postoperative Analgesia in Lower Abdominal Surgeries |
| NCT07203287 | PHASE4 | RECRUITING | Risk of Acute Complications With Rocuronium vs Cisatracurium in Patients With Chronic Kidney Disease |
| NCT00001520 | PHASE4 | COMPLETED | The Early Reversibility of Rocuronium After Different Doses of Neostigmine |
| NCT00676377 | PHASE4 | COMPLETED | A New Approach of Neostigmine in Unavoidable Post Operative Ileus |
| NCT00745095 | PHASE4 | COMPLETED | Efficacy and Safety of Standard Oral Colonoscopic Preparations With or Without Neostigmine Compared to Pulse-Irrigation Colonic Lavage |
| NCT00895609 | PHASE4 | COMPLETED | Sugammadex and Neostigmine at Shallow Neuromuscular Blockade |
| NCT01134848 | PHASE4 | COMPLETED | A Study of Serial Magnetic Resonance Cholangiopancreatography (MRCP) Following Morphine-neostigmine and Secretin Provocation in Healthy Volunteers |
| NCT01142648 | PHASE4 | COMPLETED | Sugammadex and Brain Waves |
| NCT01199237 | PHASE4 | COMPLETED | Impact of Anesthetic Choice (Sevoflurane Versus Desflurane) on Airway Reflex Recovery in the Context of Antagonized Neuromuscular Block |
| NCT01453530 | PHASE4 | UNKNOWN | Street Fitness in Surgical Patients Undergoing General Anesthesia After Reversal of Neuromuscular Blockade |
| NCT01539044 | PHASE4 | COMPLETED | Optimal Relaxation Technique for Laparotomies With Rocuronium Infusion Followed by Sugammadex Reversal |
| NCT01718236 | PHASE4 | COMPLETED | Modern Myorelaxation Procedure and Reversal of Neuromuscular Blockade With General Anesthesia for Caesarean Section |
| NCT01761552 | PHASE4 | UNKNOWN | A Prospective, Randomized Controlled Trial Comparing Traditional Methods of Neuromuscular Block Reversal to Sugammadex for Extubation in the Operating Room in ASA 4 and 4E Patients |
| NCT02160223 | PHASE4 | COMPLETED | Sugammadex Compared With Neostigmin/Atropin for Neuromuscular Block Reversal in Patients With Obstructive Sleep Apnea |
| NCT02215382 | PHASE4 | COMPLETED | Intraocular Pressure Changes Associated With Tracheal Extubation: Comparison of Sugammadex With Conventional Reversal of Neuromuscular Blockade |
| NCT02243943 | PHASE4 | COMPLETED | Effect of Neuromuscular Reversal With Sugammadex on Postoperative Recovery Profile |
| NCT02256280 | PHASE4 | TERMINATED | A Randomized Double Blind Controlled Trial Comparing Sugammadex and Neostigmine After Thoracic Anesthesia |
| NCT02284412 | PHASE4 | COMPLETED | Functional Respiratory Imaging After Neostigmine or Sugammadex |
| NCT02286752 | PHASE4 | COMPLETED | Comparison of the Effects of Neostigmine With Sugammadex on Postoperative Nausea and Vomiting. |
| NCT02327923 | PHASE4 | COMPLETED | Intraoperative Lidocaine Infusion vs. Esmolol Infusion for Postoperative Analgesia in Laparoscopic Cholecystectomy |
| NCT02329964 | PHASE4 | UNKNOWN | Effectiveness of Sugammadex in LMS Surgery |
| NCT02361060 | PHASE4 | COMPLETED | Effects of Neuromuscular Block Reversal With Sugammadex vs Neostigmine on Postoperative Respiratory Outcomes After Major Abdominal Surgery |
| NCT02375217 | PHASE4 | COMPLETED | Low Dose Sugammadex Combined With Neostigmine and Glycopyrrolate Versus Full Dose Sugammadex for Reversal of Rocuronium-induced Neuromuscular Blockade: a Cost Saving Strategy |
| NCT02390817 | PHASE4 | COMPLETED | Effect of Sugammadex for Muscle Motor Response and Awareness in Intraoperative Wakeup |
| NCT02403063 | PHASE4 | COMPLETED | Electromyographic Activity of the Respiratory Muscles During Neostigmine or Sugammadex Enhanced Recovery After Neuromuscular Blockade |
| NCT02410590 | PHASE4 | WITHDRAWN | Rocuronium + Sugammadex vs. Succinylcholine + Cisatracurium + Neostigmine/Atropine in Obese Participants (MK-8616-104) |
| NCT02414880 | PHASE4 | COMPLETED | Sugammadex Versus Neostigmine in Patients With Liver Cirrhosis Undergoing Liver Resection |
| NCT02433808 | PHASE4 | COMPLETED | Neostigmine Reversal And Neuromuscular Recovery |
| NCT02698969 | PHASE4 | UNKNOWN | Recovery of Muscle Function After Deep Neuromuscular Block by Means of Diaphragm Ultrasonography |
| NCT02825576 | PHASE4 | TERMINATED | Prevention of Postoperative Events Following Reversal With Sugammadex or Neostigmine |
| NCT02845375 | PHASE4 | COMPLETED | Effect of Neuromuscular Blockade and Reversal on Breathing |
| NCT02860507 | PHASE4 | COMPLETED | Study to Determine if Administration of Sugammadex Impacts Hospital Efficiency |
| NCT02861131 | PHASE4 | COMPLETED | The Effect of Sugammadex Versus Neostigmine on Postoperative Pulmonary Complications |
| NCT02909439 | PHASE4 | COMPLETED | Quality of Recovery After Reversal With Neostigmine or Sugammadex. |
| NCT03034577 | PHASE4 | COMPLETED | Deep Neuromuscular Block for Laparoscopic Surgery |
| NCT03111121 | PHASE4 | COMPLETED | Use of Sugammadex for Reversal of Paralysis in Microlaryngoscopy |
| NCT03112993 | PHASE4 | COMPLETED | Speed of Recovery of Reversal of Neuromuscular Blockade in Geriatric Patients Undergoing Spine Surgery |
| NCT03138967 | PHASE4 | COMPLETED | Investigation of Sugammadex in Outpatient Urological Procedures |
| NCT03144453 | PHASE4 | UNKNOWN | Recovery From Anesthesia After Robotic Assisted Radical Cystectomy |
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.
151 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 |
| 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
- Diseases: glaucoma, burn
- 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, Nicergoline, Nizatidine, Orlistat, Oxiconazole, Palbociclib, Pentamidine, Pentoxifylline, Periciazine, Physostigmine