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Neostigmine

July 24, 2017
Common Name

Neostigmine Description

Neostigmine is only found in individuals that have used or taken this drug. It is a cholinesterase inhibitor used in the treatment of myasthenia gravis and to reverse the effects of muscle relaxants such as gallamine and tubocurarine. Neostigmine, unlike physostigmine, does not cross the blood-brain barrier. [PubChem]Neostigmine is a parasympathomimetic, specifically, a reversible cholinesterase inhibitor. The drug inhibits acetylcholinesterase which is responsible for the degredation of acetylcholine. So, with acetylcholinesterase inhibited, more acetylcholine is present By interfering with the breakdown of acetylcholine, neostigmine indirectly stimliates both nicotinic and muscarinic receptors which are involved in muscle contraction. It does not cross the blood-brain barrier. Structure

MOLSDF3D-SDFPDBSMILESInChI View 3D Structure

Synonyms

Value Source (m-Hydroxyphenyl)trimethylammonium dimethylcarbamateChEBI 3-Trimethylammoniumphenyl N,N-dimethylcarbamateChEBI EustigminChEBI EustigmineChEBI m-TrimethylammoniumphenyldimethylcarbamateChEBI ProstigmineChEBI VagostigmineChEBI (m-Hydroxyphenyl)trimethylammonium dimethylcarbamic acidGenerator 3-Trimethylammoniumphenyl N,N-dimethylcarbamic acidGenerator m-Trimethylammoniumphenyldimethylcarbamic acidGenerator ProserineMeSH ProstigminMeSH Neostigmine bromideMeSH Methylslifate, neostigmineMeSH PolstigmineMeSH SyntostigmineMeSH Bromide, neostigmineMeSH Neostigmine methylslifateMeSH ProzerinMeSH SynstigminMeSH

Chemical Formlia

C12H19N2O2 Average Molecliar Weight

223.2915 Monoisotopic Molecliar Weight

223.144652862 IUPAC Name

3-[(dimethylcarbamoyl)oxy]-N,N,N-trimethylanilinium Traditional Name

neostigmine CAS Registry Number

59-99-4 SMILES

CN(C)C(=O)OC1=CC(=CC=C1)[N+](C)(C)C

InChI Identifier

InChI=1S/C12H19N2O2/c1-13(2)12(15)16-11-8-6-7-10(9-11)14(3,4)5/h6-9H,1-5H3/q+1

InChI Key

ALWKGYPQUAPLQC-UHFFFAOYSA-N Chemical Taxonomy Description

This compound belongs to the class of organic compounds known as phenoxy compounds. These are aromatic compounds contaning a phenoxy group. Kingdom

Organic compounds Super Class

Benzenoids Class

Benzene and substituted derivatives Sub Class

Phenoxy compounds Direct Parent

Phenoxy compounds Alternative Parents

  • Aniline and substituted anilines
  • Quaternary ammonium salts
  • Carbamate esters
  • Organic carbonic acids and derivatives
  • Organopnictogen compounds
  • Organic salts
  • Organic oxides
  • Hydrocarbon derivatives
  • Carbonyl compounds
  • Amines
  • Organic cations

    • Substituents

  • Phenoxy compound
  • Aniline or substituted anilines
  • Quaternary ammonium salt
  • Carbamic acid ester
  • Carbonic acid derivative
  • Amine
  • Carbonyl group
  • Hydrocarbon derivative
  • Organic oxide
  • Organic salt
  • Organopnictogen compound
  • Organic oxygen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organic nitrogen compound
  • Organic cation
  • Aromatic homomonocyclic compound

    • Molecliar Framework

    Aromatic homomonocyclic compounds External Descriptors

  • quaternary ammonium ion (CHEBI:7514 )

    • Ontology Status

    Expected but not Quantified Origin

  • Drug

    • Biofunction

  • Cholinesterase Inhibitors
  • Parasympathomimetics

    • Application

  • Pharmaceutical

    • Cellliar locations

  • Cytoplasm
  • Membrane

    • Physical Properties State

    Solid Experimental Properties

    Property Value Reference Melting PointNot AvailableNot Available Boiling PointNot AvailableNot Available Water Solubility6.77e-02 g/LNot Available LogPNot AvailableNot Available

    Predicted Properties

    Property Value Source Water Solubility0.068 mg/mLALOGPS logP-1.6ALOGPS logP-2.2ChemAxon logS-3.6ALOGPS Physiological Charge1ChemAxon Hydrogen Acceptor Count1ChemAxon Hydrogen Donor Count0ChemAxon Polar Surface Area29.54 Å2ChemAxon Rotatable Bond Count3ChemAxon Refractivity75.28 m3·mol-1ChemAxon Polarizability25.08 Å3ChemAxon Number of Rings1ChemAxon Bioavailability1ChemAxon Rlie of FiveYesChemAxon Ghose FilterYesChemAxon Vebers RlieYesChemAxon MDDR-like RlieYesChemAxon

    Spectra Spectra

    Not Available Biological Properties Cellliar Locations

  • Cytoplasm
  • Membrane

    • 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 DB01400

  • 21059682

    • details UrineExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB01400

  • 21059682

    • details

    Abnormal Concentrations

    Not Available Associated Disorders and Diseases Disease References

    None Associated OMIM IDs

    None External Links DrugBank ID

    DB01400 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

    4301 KEGG Compound ID

    C07258 BioCyc ID

    Not Available BiGG ID

    Not Available Wikipedia Link

    Neostigmine NuGOwiki Link

    HMDB15472 Metagene Link

    HMDB15472 METLIN ID

    Not Available PubChem Compound

    4456 PDB ID

    Not Available ChEBI ID

    7514

    Product: Fluoxetine

    References Synthesis Reference Not Available Material Safety Data Sheet (MSDS) Not Available 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. Trevisani GT, Hyman NH, Church JM: Neostigmine: safe and effective treatment for acute colonic pseudo-obstruction. Dis Colon Rectum. 2000 May;43(5):599-603. [PubMed:10826417 ]
    2. Naves LA, Van der Kloot W: Repetitive nerve stimulation decreases the acetylcholine content of quanta at the frog neuromuscular junction. J Physiol. 2001 May 1;532(Pt 3):637-47. [PubMed:11313435 ]
    3. Takeuchi K, Kawauchi S, Araki H, Ueki S, Furukawa O: Stimulation by nizatidine, a histamine H(2)-receptor antagonist, of duodenal HCO(3)(-)secretion in rats:relation to anti-cholinesterase activity. World J Gastroenterol. 2000 Oct;6(5):651-658. [PubMed:11819669 ]
    4. Minic J, Chatonnet A, Krejci E, Molgo J: Butyrylcholinesterase and acetylcholinesterase activity and quantal transmitter release at normal and acetylcholinesterase knockout mouse neuromuscular junctions. Br J Pharmacol. 2003 Jan;138(1):177-87. [PubMed:12522088 ]
    5. Beck KD, Brennan FX, Moldow RL, Ottenweller JE, Zhu G, Servatius RJ: Stress interacts with peripheral cholinesterase inhibitors to cause central nervous system effects. Life Sci. 2003 May 23;73(1):41-51. [PubMed:12726885 ]
    6. Zhang B, Hepner DL, Tran MH, Friedman M, Korn JR, Menzin J: Neuromuscular blockade, reversal agent use, and operating room time: retrospective analysis of US inpatient surgeries. Curr Med Res Opin. 2009 Apr;25(4):943-50. doi: 10.1185/03007990902769054 . [PubMed:19257799 ]
    7. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
    General function:
    Involved in carboxylesterase activity
    Specific function:
    Esterase with broad substrate specificity. Contributes to the inactivation of the neurotransmitter acetylcholine. Can degrade neurotoxic organophosphate esters.
    Gene Name:
    BCHE
    Uniprot ID:
    P06276
    Molecular weight:
    68417.575
    References
    1. Saito S: Cholinesterase inhibitors induce growth cone collapse and inhibit neurite extension in primary cultured chick neurons. Neurotoxicol Teratol. 1998 Jul-Aug;20(4):411-9. [PubMed:9697967 ]

    Transporters

    General function:
    Involved in ATP binding
    Specific function:
    Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells
    Gene Name:
    ABCB1
    Uniprot ID:
    P08183
    Molecular weight:
    141477.3
    References
    1. Polli JW, Wring SA, Humphreys JE, Huang L, Morgan JB, Webster LO, Serabjit-Singh CS: Rational use of in vitro P-glycoprotein assays in drug discovery. J Pharmacol Exp Ther. 2001 Nov;299(2):620-8. [PubMed:11602674 ]

    PMID: 6129618

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