فیزوستیگمین

Also known as Antilirium®, eserine, physostigmine salicylate, Physostol, Antilirium, Physostigmine, Eserine, esromiotin

Physostigmine (also known as eserine from éséré, the West African name for the Calabar bean) is a highly toxic parasympathomimetic alkaloid, specifically, a reversible cholinesterase inhibitor. It occurs naturally in the Calabar bean and the fruit of the Manchineel tree.

Key facts

Drug.Watchedfields: changed
Drug.class: Cholinesterase inhibitor
Drug.verifiedrevid: 464206065
Drug.IUPAC_name: (3aS,8aR)-1,3a,8-Trimethyl-1,2,3,3a,8,8a-hexahydropyrrolo[2,3-b]indol-5-yl methylcarbamate
Drug.image: Physostigmin.svg
Drug.image_class: skin-invert-image
Drug.image2: Physostigmine ball-and-stick model from xtal 2002.png
Drug.image_class2: bg-transparent
Drug.tradename: Antilirium
Drug.pregnancy_AU: C
Drug.pregnancy_US: C
Drug.legal_US: Rx-only
Drug.routes_of_administration: Intravenous, intramuscular, ophthalmic
Drug.metabolism: Major metabolite: Eseroline
Drug.IUPHAR_ligand: 6598
Drug.CAS_number: 57-47-6
Drug.ATC_prefix: S01
Drug.ATC_suffix: EB05

via Wikipedia infobox

Chemical data

Formula: C15H21N3O2
Molecular weight: 275.35 g/mol
IUPAC name: [(3aR,8bS)-3,4,8b-trimethyl-2,3a-dihydro-1H-pyrrolo[2,3-b]indol-7-yl] N-methylcarbamate
SMILES: C[C@@]12CCN([C@@H]1N(C3=C2C=C(C=C3)OC(=O)NC)C)C
InChIKey: PIJVFDBKTWXHHD-HIFRSBDPSA-N
XLogP: 0.7
Polar surface area: 44.8 Å²
H-bond donors: 1
H-bond acceptors: 4
Formal charge: 0

via PubChem

Drug data · ChEMBL

Max clinical phase: Approved
Molecule type: Small molecule
Admin. routes: parenteral
Indications: pain, insulin resistance, delirium, glaucoma

via ChEMBL · EBI

Research

7,478 papers

Adverse Effects of Physostigmine.Journal of medical toxicology : official journal of the American College of Medical Toxicology · 2019
Physostigmine: is there a role for this antidote in pediatric poisonings?Current opinion in pediatrics · 2007
Physostigmine as a treatment for gamma-hydroxybutyrate toxicity: a review.Journal of toxicology. Clinical toxicology · 2002
Physostigmine antagonizes ketamine.Anesthesia and analgesia · 1980
Assessing physostigmine's contraindication in cyclic antidepressant ingestions.The Journal of emergency medicine · 2003

via PubMed

Wikidata facts

Has part: carbon
Mass: 275.163377
Has use: medication

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medical condition treated: glaucoma
described by source: Granat Encyclopedic Dictionary
chemical formula: C₁₅H₂₁N₃O₂
subject has role: acetylcholinesterase inhibitor
isomeric SMILES: C[C@@]12CCN([C@@H]1N(C3=C2C=C(C=C3)OC(=O)NC)C)C
canonical SMILES: CC12CCN(C1N(C3=C2C=C(C=C3)OC(=O)NC)C)C
Commons category: Physostigmine
defined daily dose: 0.4
found in taxon: Penicillium
physically interacts with: butyrylcholinesterase

Sources (4)

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Gallery (5)

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