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Identification
Name Physostigmine
Accession Number DB00981 (APRD00406)
Type small molecule
Groups approved
Description

A cholinesterase inhibitor that is rapidly absorbed through membranes. It can be applied topically to the conjunctiva. It also can cross the blood-brain barrier and is used when central nervous system effects are desired, as in the treatment of severe anticholinergic toxicity. [PubChem]
Structure Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  • Erserine
  • Eserine
  • Eserine Sulfate
  • Eserolein, Methylcarbamate
Synonyms
Erserine
Eserine
Eserine Sulfate
Eserolein, Methylcarbamate
Salts Not Available
Brand names
Name Company
Antilirium
Esromiotin
Ezerin
Fysostigmin
Physostol
Brand mixtures Not Available
Categories
  • Cholinesterase Inhibitors
  • Miotics
CAS number 57-47-6
Weight Average: 275.3461
Monoisotopic: 275.163376931
Chemical Formula C15H21N3O2
InChI Key InChIKey=PIJVFDBKTWXHHD-HIFRSBDPSA-N
InChI
InChI=1S/C15H21N3O2/c1-15-7-8-17(3)13(15)18(4)12-6-5-10(9-11(12)15)20-14(19)16-2/h5-6,9,13H,7-8H2,1-4H3,(H,16,19)/t13-,15+/m1/s1
Plain Text
IUPAC Name
(3aS,8aR)-1,3a,8-trimethyl-1H,2H,3H,3aH,8H,8aH-pyrrolo[2,3-b]indol-5-yl N-methylcarbamate
SMILES
CNC(=O)OC1=CC2=C(C=C1)N(C)[C@H]1N(C)CC[C@@]21C
Plain Text
Mass Spec show (9.24 KB)
Taxonomy
Kingdom Organic
Classes
  • Indoles and Indole Derivatives
  • Phenethylamines
  • Phenylpropylamines
Substructures
  • Indoles and Indole Derivatives
  • Carbamates and Derivatives
  • Phenols and Derivatives
  • Pyrrolidines
  • Ethers
  • Benzene and Derivatives
  • Aminals and Derivatives
  • Phenethylamines
  • Heterocyclic compounds
  • Aromatic compounds
  • Anisoles
  • Phenylpropylamines
  • Phenyl Esters
  • Anilines
  • Pyrrolines
Pharmacology
Indication For the treatment of glaucoma, and in the treatment of severe anticholinergic toxicity.
Pharmacodynamics Physostigmine is a parasympathomimetic, specifically, a reversible cholinesterase inhibitor which effectively increases the concentration of acetylcholine at the sites of cholinergic transmission. Physostigmine is used to treat glaucoma. Because it crosses the blood-brain barrier, it is also used to treat the central nervous system effects of atropine overdose and other anticholinergic drug overdoses. Physostigmine can reverse both central and peripheral anticholinergia.
Mechanism of action Physostigmine inhibits acetylcholinesterase, the enzyme responsible for the breakdown of used acetylcholine. By interfering with the metabolism of acetylcholine, physostigmine indirectly stimulates both nicotinic and muscarinic receptors due to the consequential increase in available acetylcholine at the synapse.
Absorption Not Available
Volume of distribution Not Available
Protein binding Not Available
Metabolism Quickly hydrolyzed by cholinesterases
Route of elimination Not Available
Half life Not Available
Clearance Not Available
Toxicity Side effects include increased sweating, loss of bladder control, muscle weakness, nausea, vomiting, diarrhea, or stomach cramps or pain, shortness of breath, tightness in chest, or wheezing, slow or irregular heartbeat, unusual tiredness or weakness, watering of mouth, blurred vision or change in near or distant vision, and eye pain.
Affected organisms
  • Humans and other mammals
Pathways Not Available
Pharmacoeconomics
Manufacturers Not Available
Packagers
Dosage forms
Form Route Strength
Injection, solution Intramuscular
Injection, solution Intravenous
Prices
Unit description Cost Unit
Physostigmine salicyl cryst 39.48 USD g
Physostigmine 1 mg/ml ampul 2.43 USD ml
Patents Not Available
Properties
State solid
Melting point 105.5 oC
Experimental Properties
Property Value Source
water solubility 7760 mg/L PhysProp
logP 1.7 PhysProp
pKa 6.12 Various sources
Predicted Properties
Property Value Source
water solubility 9.92e-01 g/l ALOGPS
logP 1.65 ALOGPS
logP 2.23 ChemAxon Molconvert
logS -2.4 ALOGPS
pKa 0 ChemAxon Molconvert
hydrogen acceptor count 3 ChemAxon Molconvert
hydrogen donor count 1 ChemAxon Molconvert
polar surface area 44.81 ChemAxon Molconvert
rotatable bond count 2 ChemAxon Molconvert
refractivity 78.4 ChemAxon Molconvert
polarizability 30.62 ChemAxon Molconvert
References
Synthesis Reference Not Available
General Reference Not Available
External Links
Resource Link
KEGG Drug D00196 Link_out
KEGG Compound C06535 Link_out
PubChem Compound 5983 Link_out
PubChem Substance 46506998 Link_out
ChemSpider 5763 Link_out
ChEBI 27953 Link_out
ChEMBL 27953 Link_out
Therapeutic Targets Database DAP000561 Link_out
PharmGKB PA450957 Link_out
Drug Product Database 344931 Link_out
RxList http://www.rxlist.com/cgi/generic/physostigmine.htm Link_out
Drugs.com http://www.drugs.com/mtm/physostigmine-ophthalmic.html Link_out
Wikipedia http://en.wikipedia.org/wiki/Physostigmine Link_out
ATC Codes
  • S01EB05
  • V03AB19
AHFS Codes Not Available
PDB Entries
FDA label Not Available
MSDS show (73.3 KB)
Interactions
Drug Interactions Not Available
Food Interactions Not Available
Targets

1. Acetylcholinesterase

Pharmacological action: yes
Actions: inhibitor

Rapidly hydrolyzes choline released into the synapse

Organism class: human
UniProt ID: P22303 Link_out
Gene: ACHE Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Nguyen PV, Aniksztejn L, Catarsi S, Drapeau P: Maturation of neuromuscular transmission during early development in zebrafish. J Neurophysiol. 1999 Jun;81(6):2852-61. Pubmed
  2. Tuovinen K, Kaliste-Korhonen E, Raushel FM, Hanninen O: Success of pyridostigmine, physostigmine, eptastigmine and phosphotriesterase treatments in acute sarin intoxication. Toxicology. 1999 Jun 15;134(2-3):169-78. Pubmed
  3. Blasina MF, Faria AC, Gardino PF, Hokoc JN, Almeida OM, de Mello FG, Arruti C, Dajas F: Evidence for a noncholinergic function of acetylcholinesterase during development of chicken retina as shown by fasciculin. Cell Tissue Res. 2000 Feb;299(2):173-84. Pubmed
  4. Monnet-Tschudi F, Zurich MG, Schilter B, Costa LG, Honegger P: Maturation-dependent effects of chlorpyrifos and parathion and their oxygen analogs on acetylcholinesterase and neuronal and glial markers in aggregating brain cell cultures. Toxicol Appl Pharmacol. 2000 Jun 15;165(3):175-83. Pubmed
  5. Bolognesi ML, Andrisano V, Bartolini M, Minarini A, Rosini M, Tumiatti V, Melchiorre C: Hexahydrochromeno[4,3-b]pyrrole derivatives as acetylcholinesterase inhibitors. J Med Chem. 2001 Jan 4;44(1):105-9. Pubmed
  6. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. Pubmed
Comments
Drug created on June 13, 2005 07:24 / Updated on February 14, 2012 11:45