Pyridostigmine

Identification

Summary

Pyridostigmine is a cholinesterase inhibitor used for symptomatic treatment of myasthenia gravis and congenital myasthenic syndromes and to reverse neuromuscular blockade by nondepolarizing muscle relaxants.

Brand Names
Mestinon, Regonol
Generic Name
Pyridostigmine
DrugBank Accession Number
DB00545
Background

Myasthenia gravis is an autoimmune disease involving dysfunction at the neuromuscular junction, most commonly due to autoantibodies directed against the acetylcholine receptor (AChR), which results in muscle tone loss, muscle weakness, and fatigue.2 Acetylcholinesterase inhibitors have been the symptomatic treatment of choice in myasthenia gravis since the 1930s with the early use of physostigmine and neostigmine. By inhibiting the breakdown of acetylcholine in the neuromuscular junction, they increase signalling and relieve symptoms.2,10,11 Pyridostigmine is the current drug of choice, with superior pharmacokinetics and reduced side effects compared to neostigmine.10,11 In addition to treating myasthenia gravis, pyridostigmine is used to reverse neuromuscular blocks, relieve symptoms in congenital myasthenic syndromes, and protect against certain nerve agents, notably during the Gulf War.3,4,11,12

Pyridostigmine was granted initial FDA approval on April 6, 1955, as an oral tablet. Possible dose forms have been expanded to include extended-release tablets, syrups, and injections, marketed under various brand and generic names.10,11

Type
Small Molecule
Groups
Approved, Investigational
Structure
Thumb
Weight
Average: 181.2117
Monoisotopic: 181.09770267
Chemical Formula
C9H13N2O2
Synonyms
  • Piridostigmina
  • Pyridostigmine cation

Pharmacology

Indication

Pyridostigmine is indicated for the treatment of myasthenia gravis.10 When administered intravenously, it is indicated for the reversal or antagonism of the neuromuscular blocking effects of nondepolarizing muscle relaxants.11

Pyridostigmine has also been used as a prophylactic agent against irreversible organophosphorus acetylcholinesterase inhibitors, primarily in a military capacity.12

Pharmacology
Reduce drug development failure rates
Build, train, & validate machine-learning models
with evidence-based and structured datasets.
See how
Build, train, & validate predictive machine-learning models with structured datasets.
See how
Associated Conditions
Contraindications & Blackbox Warnings
Contraindications
Avoid life-threatening adverse drug events
Improve clinical decision support with information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.
Learn more
Avoid life-threatening adverse drug events & improve clinical decision support.
Learn more
Pharmacodynamics

Pyridostigmine bromide, designated as 3-hydroxy-1-methyl-pyridinium bromide dimethyl-carbamate, is an orally active reversible cholinesterase inhibitor similar to neostigmine but with a milder adverse effect profile and a longer duration of action. Pyridostigmine may, specifically in the case of excessive administration, result in a cholinergic crisis, with symptoms mimicking a myasthenic crisis. Administration of atropine is recommended in the case of a true cholinergic crisis or to counteract muscarinic/nicotinic effects such as bradycardia and excessive bronchial secretions.10,11

Mechanism of action

Myasthenia gravis is an autoimmune disease involving dysfunction at the neuromuscular junction most commonly due to autoantibodies directed against the acetylcholine receptor (AChR), but also against other targets such as the muscle-specific kinase (MUSK), lipoprotein-related protein 4 (LRP4), or agrin.2 In the case of AChR antibodies, AChRs are directly bound and cross-linked, impairing acetylcholine binding and contributing through various mechanisms to receptor degradation.2 The lack of acetylcholine signalling leads to muscle tone loss, muscle weakness, and fatigue.2

Pyridostigmine is a reversible acetylcholinesterase inhibitor that increases extracellular acetylcholine levels in the neuromuscular junction by impairing its breakdown by acetylcholinesterase.10,11 The increased acetylcholine leads to increased neural transmission across the junction, which drastically improves myasthenia gravis symptoms.2

In addition to its use in myasthenia gravis and in reversing neuromuscular blocks, pyridostigmine is also a common first-line treatment in congenital myasthenic syndromes (CMS), of which there are multiple subtypes caused by mutations in more than 30 distinct genes.3,4 CMS present similarly to myasthenia gravis, albeit due to distinct underlying causes, and often benefit from pyridostigmine. However, in some subgroups, treatment with pyridostigmine is detrimental; detailed genetic testing is required before starting therapy.3,4

TargetActionsOrganism
AAcetylcholinesterase
inhibitor
Humans
ACholinesterase
inhibitor
Humans
Absorption

Pyridostigmine administered orally is poorly absorbed in the GI tract, with an oral bioavailability of only 10-20%. However, this may in part be due to some metabolism by both the blood and liver.5,12 Approximately 1-2 hours following a single oral dose of 60 mg, the Cmax was determined to be 40-60 μg/L.5 Pyridostigmine follows approximately linear kinetics, with a direct correlation between the dose and plasma AUC.5 Pyridostigmine taken orally with food results in a flatter peak to the plasma concentration vs. time curve. The peak plasma concentrations are reached ~90 minutes later than in fasted subjects but with no change in bioavailability or AUC.6

Volume of distribution

Pyridostigmine administered intravenously in healthy, myasthenic, and surgical patients has a range of distribution volumes, between 0.53 and 1.76 L/kg.5

Protein binding

Neither pyridostigmine nor any of its detectable plasma metabolites are appreciably protein-bound.5,12

Metabolism

Pyridostigmine is hydrolyzed by cholinesterases systemically, including in the blood, and by microsomal enzymes in the liver, though this remains poorly defined. The primary hydrolysis product is 3-hydroxy-N-methyl-pyridinium (HNM), which can be glucuronidated.5,12 One study suggested the existence of as many as eight metabolites in the urine of patients receiving radiolabeled pyridostigmine intravenously, including various glucuronidated, demethylated, and oxidized (quinone) metabolites.7,12 Another study confirmed that HNM is the main metabolite, and suggested additional possible metabolites such as a 3,4- or 3,6-dihydroxy-N-methyl-pyridinium or a methoxy- or acetoxy-N-methyl-pyridinium.8 The exact products formed, apart from HNM, require further validation.

Hover over products below to view reaction partners

Route of elimination

Pyridostigmine is primarily renally eliminated.11 Roughly 90% of an intravenous dose is recovered in the urine within 24 hours, with unchanged pyridostigmine and its main metabolite HNM recovered in an approximately 4:1 ratio.5,8,12

Half-life

Pyridostigmine administered intravenously in healthy, myasthenic, and surgical patients has a range of elimination half-lives, between 0.38 and 1.86 hours.5

Clearance

Pyridostigmine administered intravenously in healthy, myasthenic, and surgical patients has a range of clearance values, between 0.29 and 1.0 L/h/kg.5

Adverse Effects
Adverseeffects
Improve decision support & research outcomes
With structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates.
Learn more
Improve decision support & research outcomes with our structured adverse effects data.
Learn more
Toxicity

Toxicity information regarding pyridostigmine is not readily available. Patients experiencing an overdose are at an increased risk of severe adverse effects such as bradycardia, excessive bronchial secretions, and cholinergic crisis. Symptomatic and supportive measures are recommended.10,11

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
AcebutololPyridostigmine may increase the bradycardic activities of Acebutolol.
AcetylcholineThe risk or severity of adverse effects can be increased when Pyridostigmine is combined with Acetylcholine.
AclidiniumPyridostigmine may increase the neuromuscular blocking activities of Aclidinium.
AmantadineThe therapeutic efficacy of Amantadine can be decreased when used in combination with Pyridostigmine.
AmifampridineThe risk or severity of adverse effects can be increased when Pyridostigmine is combined with Amifampridine.
AmitriptylineThe therapeutic efficacy of Amitriptyline can be decreased when used in combination with Pyridostigmine.
AmobarbitalThe therapeutic efficacy of Amobarbital can be decreased when used in combination with Pyridostigmine.
AmoxapineThe therapeutic efficacy of Amoxapine can be decreased when used in combination with Pyridostigmine.
Anisotropine methylbromideThe therapeutic efficacy of Anisotropine methylbromide can be decreased when used in combination with Pyridostigmine.
AripiprazoleThe therapeutic efficacy of Aripiprazole can be decreased when used in combination with Pyridostigmine.
Interactions
Identify potential medication risks
Easily compare up to 40 drugs with our drug interaction checker.
Get severity rating, description, and management advice.
Learn more
Food Interactions
  • Take with food. Food decreases irritation.

Products

Products2
Drug product information from 10+ global regions
Our datasets provide approved product information including:
dosage, form, labeller, route of administration, and marketing period.
Access now
Access drug product information from over 10 global regions.
Access now
Product Ingredients
IngredientUNIICASInChI Key
Pyridostigmine bromideKVI301NA53101-26-8VNYBTNPBYXSMOO-UHFFFAOYSA-M
Pyridostigmine chloride45X1P9AO697681-22-3TYXYRYORUZYJDX-UHFFFAOYSA-M
Product Images
International/Other Brands
Amiasten (AC Farma) / Amygra (Tabros) / Antilon (Yuan Chou) / Astinon (Samarth) / Kalymin (Arzneimittelwerk Dresden) / Kalymin forte (Temmler) / Kalymin N (Temmler) / Kalymin retard (Temmler) / Meshanon60 (Hasan) / Mestinon retard (Meda) / Myestin (VHB) / Pyrimine (Sriprasit Dispensary)
Brand Name Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
MestinonSolution60 mg/5mLOralBausch Health US, LLC1965-01-25Not applicableUS flag
MestinonTablet, extended release180 mg/1OralBausch Health US, LLC1959-01-12Not applicableUS flag
MestinonTablet60 mg/1OralBausch Health US, LLC1955-04-06Not applicableUS flag
MestinonTablet60 mgOralBausch Health, Canada Inc.1990-12-31Not applicableCanada flag
Mestinon-SRTablet, extended release180 mgOralBausch Health, Canada Inc.1991-12-31Not applicableCanada flag
Pyridostigmine bromideTablet30 mg/1OralValeant Pharmaceuticals2008-10-27Not applicableUS flag
Pyridostigmine BromideTablet30 mg/1OralSurgeon General-Department of the Army (TSG-DA)1990-12-05Not applicableUS flag
RegonolInjection, solution5 mg/1mLIntravenous; ParenteralSandoz Inc2005-05-10Not applicableUS flag
Regonol Inj 5mg/mlLiquid5 mg / mLIntramuscular; IntravenousOrganon Canada Ltd Ltee1977-12-311999-08-11Canada flag
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
Jamp Pyridostigmine BromideTablet60 mgOralJamp Pharma CorporationNot applicableNot applicableCanada flag
Pryidostigmine BromideSolution60 mg/5mLOralAthem LLC2021-02-25Not applicableUS flag
Pryidostigmine BromideSolution60 mg/5mLOralTrigen Laboratories LLC2020-01-302021-01-31US flag
PyridostigmineSolution60 mg/5mLOralNovitium Pharma Llc2019-03-11Not applicableUS flag
Pyridostigmine BromideSolution60 mg/5mLOralVistapharm, Inc.2020-01-06Not applicableUS flag
Pyridostigmine BromideTablet60 mg/1OralKaiser Foundations Hospitals2010-08-022012-07-31US flag
Pyridostigmine BromideTablet180 mg/1OralRising Pharmaceuticals, Inc.2017-08-15Not applicableUS flag
Pyridostigmine BromideTablet30 mg/1OralMethod Pharmaceuticals, LLC2019-06-01Not applicableUS flag
Pyridostigmine BromideSolution60 mg/5mLOralOceanside Pharmaceuticals2019-07-01Not applicableUS flag
Pyridostigmine BromideTablet, extended release180 mg/1OralOceanside Pharmaceuticals1959-01-12Not applicableUS flag

Categories

ATC Codes
N07AA02 — Pyridostigmine
Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as n-methylpyridinium compounds. These are methylpyridines that carry a methyl group at the 1-position.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Pyridines and derivatives
Sub Class
Methylpyridines
Direct Parent
N-methylpyridinium compounds
Alternative Parents
Pyridinium derivatives / Heteroaromatic compounds / Carbamate esters / Organic carbonic acids and derivatives / Azacyclic compounds / Organopnictogen compounds / Organonitrogen compounds / Organic oxides / Hydrocarbon derivatives / Carbonyl compounds
show 1 more
Substituents
Aromatic heteromonocyclic compound / Azacycle / Carbamic acid ester / Carbonic acid derivative / Carbonyl group / Heteroaromatic compound / Hydrocarbon derivative / N-methylpyridinium / Organic cation / Organic nitrogen compound
show 6 more
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
pyridinium ion (CHEBI:8665)
Affected organisms
  • Humans and other mammals

Chemical Identifiers

UNII
19QM69HH21
CAS number
155-97-5
InChI Key
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
IUPAC Name
3-[(dimethylcarbamoyl)oxy]-1-methylpyridin-1-ium
SMILES
CN(C)C(=O)OC1=C[N+](C)=CC=C1

References

Synthesis Reference

Gennaro, A.R., ed. (1990) Remington's Pharmaceutical Sciences, 18th ed., Easton, PA, Mack Publishing Co., p. 898.

US20040063957
General References
  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. [Article]
  2. Gilhus NE, Verschuuren JJ: Myasthenia gravis: subgroup classification and therapeutic strategies. Lancet Neurol. 2015 Oct;14(10):1023-36. doi: 10.1016/S1474-4422(15)00145-3. [Article]
  3. Rodriguez Cruz PM, Palace J, Beeson D: The Neuromuscular Junction and Wide Heterogeneity of Congenital Myasthenic Syndromes. Int J Mol Sci. 2018 Jun 5;19(6). pii: ijms19061677. doi: 10.3390/ijms19061677. [Article]
  4. Lee M, Beeson D, Palace J: Therapeutic strategies for congenital myasthenic syndromes. Ann N Y Acad Sci. 2018 Jan;1412(1):129-136. doi: 10.1111/nyas.13538. [Article]
  5. Aquilonius SM, Hartvig P: Clinical pharmacokinetics of cholinesterase inhibitors. Clin Pharmacokinet. 1986 May-Jun;11(3):236-49. doi: 10.2165/00003088-198611030-00005. [Article]
  6. Aquilonius SM, Eckernas SA, Hartvig P, Lindstrom B, Osterman PO: Pharmacokinetics and oral bioavailability of pyridostigmine in man. Eur J Clin Pharmacol. 1980 Nov;18(5):423-8. doi: 10.1007/BF00636797. [Article]
  7. Kornfeld P, Samuels AJ, Wolf RL, Osserman KE: Metabolism of 14C-labeled pyridostigmine in myasthenia gravis. Evidence for multiple metabolites. Neurology. 1970 Jul;20(7):634-41. doi: 10.1212/wnl.20.7.634. [Article]
  8. Somani SM, Roberts JB, Wilson A: Pyridostigmine metabolism in man. Clin Pharmacol Ther. 1972 May-Jun;13(3):393-9. doi: 10.1002/cpt1972133393. [Article]
  9. Katz NK, Barohn RJ: The history of acetylcholinesterase inhibitors in the treatment of myasthenia gravis. Neuropharmacology. 2021 Jan;182:108303. doi: 10.1016/j.neuropharm.2020.108303. Epub 2020 Sep 9. [Article]
  10. FDA Approved Drug Products: Mestinon (pyridostigmine bromide) syrup and tablets [Link]
  11. FDA Approved Drug Products: REGONOL (pyridostigmine bromide) injection [Link]
  12. NIH: pyridostigmine bromide CSWG report [Link]
  13. Cayman Chemical: pyridostigmine MSDS [Link]
Human Metabolome Database
HMDB0014685
KEGG Drug
D00487
KEGG Compound
C07410
PubChem Compound
4991
PubChem Substance
46506129
ChemSpider
4817
BindingDB
50313079
RxNav
9000
ChEBI
8665
ChEMBL
CHEMBL1115
ZINC
ZINC000000002009
Therapeutic Targets Database
DNC001171
PharmGKB
PA451185
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
Wikipedia
Pyridostigmine
FDA label
Download (120 KB)
MSDS
Download (74.6 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
4CompletedTreatmentNeurogenic Orthostatic Hypotension (nOH)1
4CompletedTreatmentPostural Orthostatic Tachycardia Syndrome (POTS)1
4RecruitingTreatmentMyasthenia Gravis1
4Unknown StatusSupportive CareMuscle Relaxation1
3CompletedTreatmentLeukemias1
3TerminatedTreatmentOcular Myasthenia Gravis1
2CompletedOtherHuman Immunodeficiency Virus (HIV) Infections1
2CompletedTreatmentAutonomic Disturbances in Parkinson's Disease1
2CompletedTreatmentFibromyalgia (FM)1
2CompletedTreatmentHeart Failure1

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
  • Barr Pharmaceuticals
  • Corepharma LLC
  • DSM Corp.
  • Global Pharmaceuticals
  • Heartland Repack Services LLC
  • Impax Laboratories Inc.
  • Kaiser Foundation Hospital
  • Legacy Pharmaceuticals Packaging LLC
  • Murfreesboro Pharmaceutical Nursing Supply
  • Oceanside Pharmaceuticals Incorporated
  • Professional Co.
  • Sandoz
  • Southcoast Pharmaceuticals Inc.
  • Valeant Ltd.
Dosage Forms
FormRouteStrength
Tablet, coatedOral500 mg
TabletOral60 mg
Tablet, extended releaseOral180 MG
Tablet, sugar coatedOral
Tablet, coatedOral
Tablet, coatedOral60 mg
Tablet, sugar coatedOral10 mg
TabletOral
Tablet, sugar coatedOral60 mg
Tablet, extended releaseOral
SolutionOral60 mg/5mL
TabletOral180 mg/1
TabletOral30 mg/1
TabletOral60 mg/1
Tablet, extended releaseOral180 mg/1
Injection, solutionIntravenous; Parenteral5 mg/1mL
LiquidIntramuscular; Intravenous5 mg / mL
SolutionOral
Prices
Unit descriptionCostUnit
Mestinon 30 180 mg Controlled Release Tabs Bottle129.42USD bottle
Pyridostigmine bromide powder87.6USD g
Regonol 5 mg/ml ampul13.64USD ml
Mestinon 180 mg timespan3.59USD each
Mestinon 60 mg tablet2.46USD tablet
Mestinon-Sr 180 mg Sustained-Release Tablet1.06USD tablet
Pyridostigmine Bromide 60 mg tablet0.62USD tablet
Pyridostigmine br 60 mg tablet0.6USD tablet
Mestinon 60 mg Tablet0.48USD tablet
Mestinon 60 mg/5ml Syrup0.43USD ml
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)152-154https://ntp.niehs.nih.gov/ntp/htdocs/chem_background/exsumpdf/pyridostbromide_508.pdf
water solubility100 mg/mlMSDS
Predicted Properties
PropertyValueSource
Water Solubility1.04 mg/mLALOGPS
logP-3.1ALOGPS
logP-3.5ChemAxon
logS-2.3ALOGPS
pKa (Strongest Acidic)19.53ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area33.42 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity49.66 m3·mol-1ChemAxon
Polarizability19.38 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.9441
Blood Brain Barrier+0.9818
Caco-2 permeable+0.6465
P-glycoprotein substrateNon-substrate0.737
P-glycoprotein inhibitor INon-inhibitor0.915
P-glycoprotein inhibitor IINon-inhibitor0.8654
Renal organic cation transporterNon-inhibitor0.8863
CYP450 2C9 substrateNon-substrate0.7541
CYP450 2D6 substrateNon-substrate0.7082
CYP450 3A4 substrateSubstrate0.586
CYP450 1A2 substrateNon-inhibitor0.9045
CYP450 2C9 inhibitorNon-inhibitor0.9341
CYP450 2D6 inhibitorNon-inhibitor0.9274
CYP450 2C19 inhibitorNon-inhibitor0.9025
CYP450 3A4 inhibitorNon-inhibitor0.9782
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.8422
Ames testNon AMES toxic0.9133
CarcinogenicityNon-carcinogens0.9193
BiodegradationReady biodegradable0.5528
Rat acute toxicity3.1468 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9248
hERG inhibition (predictor II)Non-inhibitor0.8484
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Targets

Drugtargets2
Build, predict & validate machine-learning models
Use our structured and evidence-based datasets to unlock new
insights and accelerate drug research.
Learn more
Use our structured and evidence-based datasets to unlock new insights and accelerate drug research.
Learn more
Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Inhibitor
General Function
Serine hydrolase 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
Uniprot Name
Acetylcholinesterase
Molecular Weight
67795.525 Da
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. [Article]
  2. Ricordel I, Meunier J: [Chemical weapons: antidotes. View about the real means, perspectives]. Ann Pharm Fr. 2000 Jan;58(1):5-12. [Article]
  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. [Article]
  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. [Article]
  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. [Article]
  6. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [Article]
  7. FDA Approved Drug Products: Mestinon (pyridostigmine bromide) syrup and tablets [Link]
  8. FDA Approved Drug Products: REGONOL (pyridostigmine bromide) injection [Link]
Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Inhibitor
General Function
Identical protein binding
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
Uniprot Name
Cholinesterase
Molecular Weight
68417.575 Da
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. [Article]
  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. [Article]
  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. [Article]
  4. FDA Approved Drug Products: Mestinon (pyridostigmine bromide) syrup and tablets [Link]
  5. FDA Approved Drug Products: REGONOL (pyridostigmine bromide) injection [Link]

Enzymes

Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
Substrate
General Function
Serine hydrolase 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
Uniprot Name
Acetylcholinesterase
Molecular Weight
67795.525 Da
References
  1. Aquilonius SM, Hartvig P: Clinical pharmacokinetics of cholinesterase inhibitors. Clin Pharmacokinet. 1986 May-Jun;11(3):236-49. doi: 10.2165/00003088-198611030-00005. [Article]
  2. NIH: pyridostigmine bromide CSWG report [Link]
Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
Substrate
General Function
Identical protein binding
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
Uniprot Name
Cholinesterase
Molecular Weight
68417.575 Da
References
  1. Aquilonius SM, Hartvig P: Clinical pharmacokinetics of cholinesterase inhibitors. Clin Pharmacokinet. 1986 May-Jun;11(3):236-49. doi: 10.2165/00003088-198611030-00005. [Article]
  2. NIH: pyridostigmine bromide CSWG report [Link]
Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
Inducer
Curator comments
A single study has suggested weak induction of CYP3A4 by pyridostigmine bromide.
General Function
Vitamin d3 25-hydroxylase activity
Specific Function
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 react...
Gene Name
CYP3A4
Uniprot ID
P08684
Uniprot Name
Cytochrome P450 3A4
Molecular Weight
57342.67 Da
References
  1. Usmani KA, Rose RL, Hodgson E: Inhibition and activation of the human liver microsomal and human cytochrome P450 3A4 metabolism of testosterone by deployment-related chemicals. Drug Metab Dispos. 2003 Apr;31(4):384-91. doi: 10.1124/dmd.31.4.384. [Article]

Drug created on June 13, 2005 13:24 / Updated on October 20, 2021 19:48