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Physostigmine

July 24, 2017
Common Name

Physostigmine 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

MOLSDF3D-SDFPDBSMILESInChI View 3D Structure

Synonyms

Value Source AntiliriumChEBI EserineChEBI PhysostolChEBI ErserineHMDB Eserine slifateHMDB Eserolein, methylcarbamateHMDB

Chemical Formlia

C15H21N3O2 Average Molecliar Weight

275.3461 Monoisotopic Molecliar Weight

275.163376931 IUPAC Name

(3aS,8aR)-1,3a,8-trimethyl-1H,2H,3H,3aH,8H,8aH-pyrrolo[2,3-b]indol-5-yl N-methylcarbamate Traditional Name

physostigmine CAS Registry Number

57-47-6 SMILES

[H][C@]12N(C)CC[C@@]1(C)C1=C(C=CC(OC(=O)NC)=C1)N2C

InChI Identifier

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

InChI Key

PIJVFDBKTWXHHD-HIFRSBDPSA-N Chemical Taxonomy Description

This compound belongs to the class of chemical entities known as pyrroloindoles. These are compounds containing a pyrroloindole moiety, which is a tricyclic heterocycle which consists of a pyrrole ring fused to an indole. Pyrrole is 5-membered ring consisting of four carbon atoms and one nitrogen atom. Indole is a bicyclic compound consisting of a six-membered benzene ring fused to a five-membered nitrogen-containing pyrrole ring. Kingdom

Chemical entities Super Class

Organic compounds Class

Organoheterocyclic compounds Sub Class

Indoles and derivatives Direct Parent

Pyrroloindoles Alternative Parents

  • Indoles
  • Dialkylarylamines
  • N-alkylpyrrolidines
  • Benzenoids
  • Pyrroles
  • Carbamate esters
  • Azacyclic compounds
  • Organopnictogen compounds
  • Organic oxides
  • Hydrocarbon derivatives
  • Carbonyl compounds

    • Substituents

  • Pyrroloindole
  • Indole
  • Dialkylarylamine
  • Benzenoid
  • N-alkylpyrrolidine
  • Pyrrole
  • Pyrrolidine
  • Carbamic acid ester
  • Azacycle
  • Carbonyl group
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organic nitrogen compound
  • Aromatic heteropolycyclic compound

    • Molecliar Framework

    Aromatic heteropolycyclic compounds External Descriptors

  • carbamate ester (CHEBI:27953 )
  • indole alkaloid (CHEBI:27953 )
  • Alkaloids (C06535 )
  • Pyrroloindole alkaloids (C06535 )

    • Ontology Status

    Expected but not Quantified Origin

  • Drug

    • Biofunction

  • Cholinesterase Inhibitors
  • Miotics

    • Application

  • Pharmaceutical

    • Cellliar locations

  • Cytoplasm

    • Physical Properties State

    Solid Experimental Properties

    Property Value Reference Melting Point105.5 °CNot Available Boiling PointNot AvailableNot Available Water Solubility9.92e-01 g/LNot Available LogP1.7Not Available

    Predicted Properties

    Property Value Source Water Solubility0.99 mg/mLALOGPS logP1.8ALOGPS logP2.23ChemAxon logS-2.4ALOGPS pKa (Strongest Acidic)14.77ChemAxon pKa (Strongest Basic)6.59ChemAxon Physiological Charge0ChemAxon Hydrogen Acceptor Count3ChemAxon Hydrogen Donor Count1ChemAxon Polar Surface Area44.81 Å2ChemAxon Rotatable Bond Count2ChemAxon Refractivity78.4 m3·mol-1ChemAxon Polarizability30.62 Å3ChemAxon Number of Rings3ChemAxon Bioavailability1ChemAxon Rlie of FiveYesChemAxon Ghose FilterYesChemAxon Vebers RlieYesChemAxon MDDR-like RlieYesChemAxon

    Spectra Spectra

    Spectrum Type Description Splash Key LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-QQ , positivesplash10-00or-0090000000-1f322550abc600bd72a9View in MoNA LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-QQ , positivesplash10-014i-0490000000-e4a06a93b3b18d738157View in MoNA LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-QQ , positivesplash10-03di-0900000000-d9ddac609ada184032acView in MoNA LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-QQ , positivesplash10-03di-0900000000-ef8f7c2ddbdba70fe1d3View in MoNA LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-QQ , positivesplash10-01ot-0900000000-daf3030c2c85de1db72eView in MoNA LC-MS/MS

    LC-MS/MS Spectrum – LC-ESI-IT , positivesplash10-014i-0090000000-8a9155530ad88f483e2eView in MoNA LC-MS/MS

    LC-MS/MS Spectrum – , positivesplash10-03dj-2900000000-b9d164a9a3afaf8a17cfView in MoNA Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 10V, PositiveNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 20V, PositiveNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 40V, PositiveNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 10V, NegativeNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 20V, NegativeNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 40V, NegativeNot Available

    Biological Properties Cellliar Locations

  • Cytoplasm

    • Biofluid Locations

  • Blood
  • Urine

    • Tissue Location

    Not Available Pathways

    Not Available Normal Concentrations

    Biofluid Status Value Age Sex Condition Reference Details BloodExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB00981

  • 21059682

    • details UrineExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB00981

  • 21059682

    • details

    Abnormal Concentrations

    Not Available Associated Disorders and Diseases Disease References

    None Associated OMIM IDs

    None External Links DrugBank ID

    DB00981 DrugBank Metabolite ID

    Not Available Phenol Explorer Compound ID

    Not Available Phenol Explorer Metabolite ID

    Not Available FoodDB ID

    Not Available KNApSAcK ID

    Not Available Chemspider ID

    5763 KEGG Compound ID

    C06535 BioCyc ID

    Not Available BiGG ID

    Not Available Wikipedia Link

    Physostigmine NuGOwiki Link

    HMDB15116 Metagene Link

    HMDB15116 METLIN ID

    Not Available PubChem Compound

    5983 PDB ID

    Not Available ChEBI ID

    27953

    Product: Helioxanthin 8-2

    References Synthesis Reference Not Available Material Safety Data Sheet (MSDS) Download (PDF) General References Not Available

    Enzymes

    General function:
    Involved in carboxylesterase activity
    Specific function:
    Terminates signal transduction at the neuromuscular junction by rapid hydrolysis of the acetylcholine released into the synaptic cleft. Role in neuronal apoptosis.
    Gene Name:
    ACHE
    Uniprot ID:
    P22303
    Molecular weight:
    67795.525
    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:10368402 ]
    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:10403635 ]
    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:10741458 ]
    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:10873710 ]
    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:11141093 ]
    6. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]

    PMID: 10578125

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