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Identification
Name Pyridostigmine
Accession Number DB00545 (APRD00380)
Type small molecule
Groups approved
Description

A cholinesterase inhibitor with a slightly longer duration of action than neostigmine. It is used in the treatment of myasthenia gravis and to reverse the actions of muscle relaxants. [PubChem]
Structure Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
Pyridine N-Oxide
Pyridostigmine Bromide
Pyridostigmine Bromine
Pyridostigminum
Salts Not Available
Brand names
Name Company
Mestinon
Mestinon-SR
Regonol
Brand mixtures Not Available
Categories
  • Parasympathomimetics
  • Cholinesterase Inhibitors
  • Antimyasthenics
CAS number 155-97-5
Weight Average: 181.2117
Monoisotopic: 181.09770267
Chemical Formula C9H13N2O2
InChI Key InChIKey=RVOLLAQWKVFTGE-UHFFFAOYSA-N
InChI
InChI=1S/C9H13N2O2/c1-10(2)9(12)13-8-5-4-6-11(3)7-8/h4-7H,1-3H3/q+1
Plain Text
IUPAC Name
3-[(dimethylcarbamoyl)oxy]-1-methylpyridin-1-ium
SMILES
CN(C)C(=O)OC1=C[N+](C)=CC=C1
Plain Text
Mass Spec Not Available
Taxonomy
Kingdom Organic
Classes
  • Carbamates and Derivatives
  • Pyridines and Derivatives
Substructures
  • Carbamates and Derivatives
  • Pyridines and Derivatives
  • Ethers
  • Heterocyclic compounds
  • Aromatic compounds
  • Cations
Pharmacology
Indication For the treatment of myasthenia gravis.
Pharmacodynamics Pyridostigmine is a parasympathomimetic and a reversible cholinesterase inhibitor. Since it is a quaternary amine, it is poorly absorbed in the gut and doesn't cross the blood-brain barrier. Pyridostigmine has a slightly longer duration of action than NEOSTIGMINE. It is used in the treatment of myasthenia gravis and to reverse the actions of muscle relaxants.
Mechanism of action Pyridostigmine inhibits acetylcholinesterase in the synaptic cleft by competing with acetylcholine for attachment to acetylcholinesterase, thus slowing down the hydrolysis of acetylcholine, and thereby increases efficiency of cholinergic transmission in the neuromuscular junction and prolonges the effects of acetylcholine.
Absorption Poorly absorbed from the GI tract with an oral bioavailability of 7.6 +/- 2.4%.
Volume of distribution Not Available
Protein binding Not Available
Metabolism
Hydrolysis by cholinesterases and by liver.
Route of elimination Not Available
Half life 3 hours following oral administration.
Clearance Not Available
Toxicity Not Available
Affected organisms
  • Humans and other mammals
Pathways Not Available
Pharmacoeconomics
Manufacturers
  • Valeant pharmaceuticals international
  • Sandoz canada inc
  • Barr laboratories inc
  • Corepharma llc
  • Impax laboratories inc
  • Solvay pharmaceuticals
  • United states army office surgeon general
Packagers
Dosage forms
Form Route Strength
Tablet Oral
Tablet, extended release Oral
Prices
Unit description Cost Unit
Mestinon 30 180 mg Controlled Release Tabs Bottle 129.42 USD bottle
Pyridostigmine bromide powder 87.6 USD g
Regonol 5 mg/ml ampul 13.64 USD ml
Mestinon 180 mg timespan 3.59 USD each
Mestinon 60 mg tablet 2.46 USD tablet
Mestinon-Sr 180 mg Sustained-Release Tablet 1.06 USD tablet
Pyridostigmine Bromide 60 mg tablet 0.62 USD tablet
Pyridostigmine br 60 mg tablet 0.6 USD tablet
Mestinon 60 mg Tablet 0.48 USD tablet
Mestinon 60 mg/5ml Syrup 0.43 USD ml
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents Not Available
Properties
State solid
Experimental Properties
Property Value Source
melting point 153 °C Not Available
logP 1.554 Not Available
Predicted Properties
Property Value Source
water solubility 1.04e+00 g/l ALOGPS
logP -3.1 ALOGPS
logP -3.5 ChemAxon
logS -2.3 ALOGPS
pKa (strongest acidic) 19.53 ChemAxon
physiological charge 1 ChemAxon
hydrogen acceptor count 1 ChemAxon
hydrogen donor count 0 ChemAxon
polar surface area 33.42 ChemAxon
rotatable bond count 2 ChemAxon
refractivity 49.66 ChemAxon
polarizability 19.38 ChemAxon
References
Synthesis Reference Not Available
General Reference
  1. Singer W, Opfer-Gehrking TL, McPhee BR, Hilz MJ, Bharucha AE, Low PA: Acetylcholinesterase inhibition: a novel approach in the treatment of neurogenic orthostatic hypotension. J Neurol Neurosurg Psychiatry. 2003 Sep;74(9):1294-8. Pubmed
External Links
Resource Link
KEGG Drug D00487 Link_out
KEGG Compound C07410 Link_out
PubChem Compound 4991 Link_out
PubChem Substance 46506129 Link_out
ChemSpider 4817 Link_out
BindingDB 50018231 Link_out
Therapeutic Targets Database DNC001171 Link_out
PharmGKB PA451185 Link_out
Drug Product Database 869953 Link_out
RxList http://www.rxlist.com/cgi/generic2/pyridostigmine.htm Link_out
Drugs.com http://www.drugs.com/cdi/pyridostigmine.html Link_out
Wikipedia http://en.wikipedia.org/wiki/Pyridostigmine Link_out
ATC Codes
  • N07AA02
AHFS Codes
  • 12:04.00
PDB Entries
FDA label show (120 KB)
MSDS show (74.6 KB)
Interactions
Drug Interactions
Drug Interaction
Betamethasone The corticosteroid, betamethasone, may decrease the effect of the anticholinesterase, pyridostigmine.
Corticotropin The corticosteroid, corticotropin, may decrease the effect of the anticholinesterase, pyridostigmine.
Cortisone acetate The corticosteroid, cortisone acetate, may decrease the effect of the anticholinesterase, pyridostigmine.
Dexamethasone The corticosteroid, dexamethasone, may decrease the effect of the anticholinesterase, pyridostigmine.
Fludrocortisone The corticosteroid, fludrocortisone, may decrease the effect of the anticholinesterase, pyridostigmine.
Hydrocortisone The corticosteroid, hydrocortisone, may decrease the effect of the anticholinesterase, pyridostigmine.
Methylprednisolone The corticosteroid, methylprednisolone, may decrease the effect of the anticholinesterase, pyridostigmine.
Paramethasone The corticosteroid, paramethasone, may decrease the effect of the anticholinesterase, pyridostigmine.
Prednisolone The corticosteroid, prednisolone, may decrease the effect of the anticholinesterase, pyridostigmine.
Prednisone The corticosteroid, prednisone, may decrease the effect of the anticholinesterase, pyridostigmine.
Triamcinolone The corticosteroid, triamcinolone, may decrease the effect of the anticholinesterase, pyridostigmine.
Food Interactions
  • Take with food to decrease adverse effects.
Targets

1. Acetylcholinesterase

Pharmacological action: yes
Actions: antagonist, 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. Drake-Baumann R, Seil FJ: Effects of exposure to low-dose pyridostigmine on neuromuscular junctions in vitro. Muscle Nerve. 1999 Jun;22(6):696-703. Pubmed
  2. Ricordel I, Meunier J: [Chemical weapons: antidotes. View about the real means, perspectives] Ann Pharm Fr. 2000 Jan;58(1):5-12. Pubmed
  3. Prasad V, Scotch R, Chaudhuri AR, Walss C, Fathy DB, Miller C, Luduena RF: Interactions of bovine brain tubulin with pyridostigmine bromide and N,N’-diethyl-m-toluamide. Neurochem Res. 2000 Jan;25(1):19-25. Pubmed
  4. Sinton CM, Fitch TE, Petty F, Haley RW: Stressful manipulations that elevate corticosterone reduce blood-brain barrier permeability to pyridostigmine in the Rat. Toxicol Appl Pharmacol. 2000 May 15;165(1):99-105. Pubmed
  5. Servatius RJ, Ottenweller JE, Guo W, Beldowicz D, Zhu G, Natelson BH: Effects of inescapable stress and treatment with pyridostigmine bromide on plasma butyrylcholinesterase and the acoustic startle response in rats. Physiol Behav. 2000 May;69(3):239-46. Pubmed
  6. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. Pubmed

2. Cholinesterase

Pharmacological action: yes
Actions: antagonist

An acylcholine + H(2)O = choline + a carboxylate

Organism class: human
UniProt ID: P06276 Link_out
Gene: BCHE Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Somani SM, Husain K, Asha T, Helfert R: Interactive and delayed effects of pyridostigmine and physical stress on biochemical and histological changes in peripheral tissues of mice. J Appl Toxicol. 2000 Jul-Aug;20(4):327-34. Pubmed
  2. Servatius RJ, Ottenweller JE, Guo W, Beldowicz D, Zhu G, Natelson BH: Effects of inescapable stress and treatment with pyridostigmine bromide on plasma butyrylcholinesterase and the acoustic startle response in rats. Physiol Behav. 2000 May;69(3):239-46. Pubmed
  3. Abou-Donia MB, Wilmarth KR, Abdel-Rahman AA, Jensen KF, Oehme FW, Kurt TL: Increased neurotoxicity following concurrent exposure to pyridostigmine bromide, DEET, and chlorpyrifos. Fundam Appl Toxicol. 1996 Dec;34(2):201-22. Pubmed
Enzymes

1. Cytochrome P450 3A4

Actions: inducer

Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4- hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. The enzyme also hydroxylates etoposide

UniProt ID: P08684 Link_out
Gene: CYP3A4
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. Epub 2009 Nov 24. Pubmed
Comments
Drug created on June 13, 2005 07:24 / Updated on February 08, 2013 16:19