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Pyridostigmine

January 01, 1970

Not to be confused with Physostigmine.

Pyridostigmine is a medication used to treat myasthenia gravis[1] and underactive bladder.[2] It is also used together with atropine to end the effects of neuromuscular blocking medication of the non-depolarizing type.[3] It is typically given by mouth but can also be used by injection.[3] The effects generally begin within 45 minutes and last up to 6 hours.[3]

Pyridostigmine
Clinical data
Trade namesMestinon, others
AHFS/Drugs.comMonograph
MedlinePlusa682229
Pregnancy
category
  • AU: C
Routes of
administration		By mouth, intravenous
ATC code
Legal status
Legal status
Pharmacokinetic data
Bioavailability7.6 +/- 2.4%
Elimination half-life1.78 +/- 0.24hrs
Excretionkidney
Identifiers
  • 3-[(dimethylcarbamoyl)oxy]-1-methylpyridinium
CAS Number
  • 155-97-5 Y
PubChem CID
  • 4991
DrugBank
  • DB00545 Y
ChemSpider
  • 4817 Y
UNII
  • 19QM69HH21
KEGG
  • C07410 Y
ChEMBL
  • ChEMBL1115 Y
CompTox Dashboard (EPA)
  • DTXSID20165786
Chemical and physical data
FormulaC9H13N2O2
Molar mass181.215 g·mol−1
3D model (JSmol)
  • Interactive image
  • O=C(Oc1ccc[n+](c1)C)N(C)C
  • InChI=1S/C9H13N2O2/c1-10(2)9(12)13-8-5-4-6-11(3)7-8/h4-7H,1-3H3/q+1 Y
  • Key:RVOLLAQWKVFTGE-UHFFFAOYSA-N Y
  (verify)

Common side effects include nausea, diarrhea, frequent urination, and abdominal pain.[3] More severe side effects include low blood pressure, weakness, and allergic reactions.[3] It is unclear if use in pregnancy is safe for the fetus.[3] Pyridostigmine is an acetylcholinesterase inhibitor in the cholinergic family of medications.[3] It works by blocking the action of acetylcholinesterase and therefore increases the levels of acetylcholine.[3]

Pyridostigmine was patented in 1945 and came into medical use in 1955.[4] It is on the World Health Organization's List of Essential Medicines.[5] Pyridostigmine is available as a generic medication.[3][6]

Medical uses edit

Pyridostigmine is used to treat muscle weakness in people with myasthenia gravis or forms of congenital myasthenic syndrome and to combat the effects of curariform drug toxicity. Pyridostigmine bromide has been FDA approved for military use during combat situations as an agent to be given prior to exposure to the nerve agent Soman in order to increase survival. Used in particular during the first Gulf War, pyridostigmine bromide has been implicated as a causal factor in Gulf War syndrome.[7][8]

With pyridostigmine classified as a type of parasympathomimetic, it can be used to treat underactive bladder.[9]

Pyridostigmine sometimes is used to treat orthostatic hypotension.[10] It may also be of benefit in chronic axonal polyneuropathy.[11]

It is also being prescribed 'off-label' for postural orthostatic tachycardia syndrome as well as complications resulting from Ehlers–Danlos syndrome.[11][12]

Contraindications edit

Pyridostigmine bromide is contraindicated in cases of mechanical intestinal or urinary obstruction and should be used with caution in patients with bronchial asthma.[13][14]

Side effects edit

Common side effects include:[13]

  • Sweating
  • Diarrhea
  • Nausea
  • Vomiting
  • Abdominal cramps
  • Increased salivation
  • Tearing
  • Increased bronchial secretions
  • Constricted pupils
  • Facial flushing due to vasodilation
  • Erectile dysfunction

Additional side effects include:[13]

  • Muscle twitching
  • Muscle cramps and weakness

Mechanism of action edit

Pyridostigmine inhibits acetylcholinesterase in the synaptic cleft, thus slowing down the hydrolysis of acetylcholine. Like its predecessor neostigmine, it is a quaternary carbamate inhibitor of cholinesterase that does not cross the blood–brain barrier. It carbamylates about 30% of peripheral cholinesterase enzyme, and the carbamylated enzyme eventually regenerates by natural hydrolysis and excess acetylcholine (ACh) levels revert to normal.

The ACh diffuses across the synaptic cleft and binds to receptors on the post synaptic membrane, causing an influx of sodium (Na+,) resulting in depolarization. If large enough, this depolarization results in an action potential. To prevent constant stimulation once the ACh is released, an enzyme called acetylcholinesterase is present in the endplate membrane close to the receptors on the post synaptic membrane, and quickly hydrolyses ACh.

Names edit

Pyridostigmine bromide is available under the trade name Mestinon (Valeant Pharmaceuticals), Regonol and Gravitor (SUN Pharma).

References edit

  1. ^ World Health Organization (2009). Stuart MC, Kouimtzi M, Hill SR (eds.). WHO Model Formulary 2008. World Health Organization. p. 429. hdl:10665/44053. ISBN 9789241547659.
  2. ^ Moro C, Phelps C, Veer V, Clark J, Glasziou P, Tikkinen KA, Scott AM (November 2021). "The effectiveness of parasympathomimetics for treating underactive bladder: A systematic review and meta-analysis". Neurourology and Urodynamics. 41 (1): 127–139. doi:10.1002/nau.24839. PMID 34816481. S2CID 244530010.
  3. ^ a b c d e f g h i "Neostigmine Bromide". The American Society of Health-System Pharmacists. from the original on 21 December 2016. Retrieved 8 December 2016.
  4. ^ Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 540. ISBN 9783527607495. from the original on 2016-12-20.
  5. ^ World Health Organization (2019). World Health Organization model list of essential medicines: 21st list 2019. Geneva: World Health Organization. hdl:10665/325771. WHO/MVP/EMP/IAU/2019.06. License: CC BY-NC-SA 3.0 IGO.
  6. ^ "Competitive Generic Therapy Approvals". U.S. Food and Drug Administration (FDA). 3 March 2023. Retrieved 6 March 2023.
  7. ^ Golomb BA (March 2008). "Acetylcholinesterase inhibitors and Gulf War illnesses". Proceedings of the National Academy of Sciences of the United States of America. 105 (11): 4295–4300. Bibcode:2008PNAS..105.4295G. doi:10.1073/pnas.0711986105. JSTOR 25461411. PMC 2393741. PMID 18332428.
  8. ^ Steenhuysen, Julie (March 10, 2008). "Gulf War illness linked to chemical exposure-study". Reuters.
  9. ^ Moro C, Phelps C, Veer V, Clark J, Glasziou P, Tikkinen KA, Scott AM (November 2021). "The effectiveness of parasympathomimetics for treating underactive bladder: A systematic review and meta-analysis". Neurourology and Urodynamics. 41 (1): 127–139. doi:10.1002/nau.24839. PMID 34816481. S2CID 244530010.
  10. ^ Gales BJ, Gales MA (February 2007). "Pyridostigmine in the treatment of orthostatic intolerance". The Annals of Pharmacotherapy. 41 (2): 314–318. doi:10.1345/aph.1H458. PMID 17284509. S2CID 22855759.
  11. ^ a b Gales BJ, Gales MA (February 2007). "Pyridostigmine in the treatment of orthostatic intolerance". The Annals of Pharmacotherapy. 41 (2): 314–318. doi:10.1345/aph.1H458. PMID 17284509. S2CID 22855759.
  12. ^ Kanjwal K, Karabin B, Sheikh M, Elmer L, Kanjwal Y, Saeed B, Grubb BP (June 2011). "Pyridostigmine in the treatment of postural orthostatic tachycardia: a single-center experience". Pacing and Clinical Electrophysiology. 34 (6): 750–755. doi:10.1111/j.1540-8159.2011.03047.x. PMID 21410722. S2CID 20405336.
  13. ^ a b c Mestinon | Home 2008-05-13 at the Wayback Machine
  14. ^ Mestinon Official FDA information, side effects and uses 2008-05-24 at the Wayback Machine

External links edit

  • "Pyridostigmine". Drug Information Portal. U.S. National Library of Medicine.

January 01, 1970
pyridostigmine, confused, with, physostigmine, medication, used, treat, myasthenia, gravis, underactive, bladder, also, used, together, with, atropine, effects, neuromuscular, blocking, medication, depolarizing, type, typically, given, mouth, also, used, injec. Not to be confused with Physostigmine Pyridostigmine is a medication used to treat myasthenia gravis 1 and underactive bladder 2 It is also used together with atropine to end the effects of neuromuscular blocking medication of the non depolarizing type 3 It is typically given by mouth but can also be used by injection 3 The effects generally begin within 45 minutes and last up to 6 hours 3 PyridostigmineClinical dataTrade namesMestinon othersAHFS Drugs comMonographMedlinePlusa682229PregnancycategoryAU CRoutes ofadministrationBy mouth intravenousATC codeN07AA02 WHO Legal statusLegal statusUK POM Prescription only US onlyPharmacokinetic dataBioavailability7 6 2 4 Elimination half life1 78 0 24hrsExcretionkidneyIdentifiersIUPAC name 3 dimethylcarbamoyl oxy 1 methylpyridiniumCAS Number155 97 5 YPubChem CID4991DrugBankDB00545 YChemSpider4817 YUNII19QM69HH21KEGGC07410 YChEMBLChEMBL1115 YCompTox Dashboard EPA DTXSID20165786Chemical and physical dataFormulaC 9H 13N 2O 2Molar mass181 215 g mol 13D model JSmol Interactive imageSMILES O C Oc1ccc n c1 C N C CInChI InChI 1S C9H13N2O2 c1 10 2 9 12 13 8 5 4 6 11 3 7 8 h4 7H 1 3H3 q 1 YKey RVOLLAQWKVFTGE UHFFFAOYSA N Y verify Common side effects include nausea diarrhea frequent urination and abdominal pain 3 More severe side effects include low blood pressure weakness and allergic reactions 3 It is unclear if use in pregnancy is safe for the fetus 3 Pyridostigmine is an acetylcholinesterase inhibitor in the cholinergic family of medications 3 It works by blocking the action of acetylcholinesterase and therefore increases the levels of acetylcholine 3 Pyridostigmine was patented in 1945 and came into medical use in 1955 4 It is on the World Health Organization s List of Essential Medicines 5 Pyridostigmine is available as a generic medication 3 6 Contents 1 Medical uses 2 Contraindications 3 Side effects 4 Mechanism of action 5 Names 6 References 7 External linksMedical uses editPyridostigmine is used to treat muscle weakness in people with myasthenia gravis or forms of congenital myasthenic syndrome and to combat the effects of curariform drug toxicity Pyridostigmine bromide has been FDA approved for military use during combat situations as an agent to be given prior to exposure to the nerve agent Soman in order to increase survival Used in particular during the first Gulf War pyridostigmine bromide has been implicated as a causal factor in Gulf War syndrome 7 8 With pyridostigmine classified as a type of parasympathomimetic it can be used to treat underactive bladder 9 Pyridostigmine sometimes is used to treat orthostatic hypotension 10 It may also be of benefit in chronic axonal polyneuropathy 11 It is also being prescribed off label for postural orthostatic tachycardia syndrome as well as complications resulting from Ehlers Danlos syndrome 11 12 Contraindications editPyridostigmine bromide is contraindicated in cases of mechanical intestinal or urinary obstruction and should be used with caution in patients with bronchial asthma 13 14 Side effects editCommon side effects include 13 Sweating Diarrhea Nausea Vomiting Abdominal cramps Increased salivation Tearing Increased bronchial secretions Constricted pupils Facial flushing due to vasodilation Erectile dysfunction Additional side effects include 13 Muscle twitching Muscle cramps and weaknessMechanism of action editPyridostigmine inhibits acetylcholinesterase in the synaptic cleft thus slowing down the hydrolysis of acetylcholine Like its predecessor neostigmine it is a quaternary carbamate inhibitor of cholinesterase that does not cross the blood brain barrier It carbamylates about 30 of peripheral cholinesterase enzyme and the carbamylated enzyme eventually regenerates by natural hydrolysis and excess acetylcholine ACh levels revert to normal The ACh diffuses across the synaptic cleft and binds to receptors on the post synaptic membrane causing an influx of sodium Na resulting in depolarization If large enough this depolarization results in an action potential To prevent constant stimulation once the ACh is released an enzyme called acetylcholinesterase is present in the endplate membrane close to the receptors on the post synaptic membrane and quickly hydrolyses ACh Names editPyridostigmine bromide is available under the trade name Mestinon Valeant Pharmaceuticals Regonol and Gravitor SUN Pharma References edit World Health Organization 2009 Stuart MC Kouimtzi M Hill SR eds WHO Model Formulary 2008 World Health Organization p 429 hdl 10665 44053 ISBN 9789241547659 Moro C Phelps C Veer V Clark J Glasziou P Tikkinen KA Scott AM November 2021 The effectiveness of parasympathomimetics for treating underactive bladder A systematic review and meta analysis Neurourology and Urodynamics 41 1 127 139 doi 10 1002 nau 24839 PMID 34816481 S2CID 244530010 a b c d e f g h i Neostigmine Bromide The American Society of Health System Pharmacists Archived from the original on 21 December 2016 Retrieved 8 December 2016 Fischer J Ganellin CR 2006 Analogue based Drug Discovery John Wiley amp Sons p 540 ISBN 9783527607495 Archived from the original on 2016 12 20 World Health Organization 2019 World Health Organization model list of essential medicines 21st list 2019 Geneva World Health Organization hdl 10665 325771 WHO MVP EMP IAU 2019 06 License CC BY NC SA 3 0 IGO Competitive Generic Therapy Approvals U S Food and Drug Administration FDA 3 March 2023 Retrieved 6 March 2023 Golomb BA March 2008 Acetylcholinesterase inhibitors and Gulf War illnesses Proceedings of the National Academy of Sciences of the United States of America 105 11 4295 4300 Bibcode 2008PNAS 105 4295G doi 10 1073 pnas 0711986105 JSTOR 25461411 PMC 2393741 PMID 18332428 Steenhuysen Julie March 10 2008 Gulf War illness linked to chemical exposure study Reuters Moro C Phelps C Veer V Clark J Glasziou P Tikkinen KA Scott AM November 2021 The effectiveness of parasympathomimetics for treating underactive bladder A systematic review and meta analysis Neurourology and Urodynamics 41 1 127 139 doi 10 1002 nau 24839 PMID 34816481 S2CID 244530010 Gales BJ Gales MA February 2007 Pyridostigmine in the treatment of orthostatic intolerance The Annals of Pharmacotherapy 41 2 314 318 doi 10 1345 aph 1H458 PMID 17284509 S2CID 22855759 a b Gales BJ Gales MA February 2007 Pyridostigmine in the treatment of orthostatic intolerance The Annals of Pharmacotherapy 41 2 314 318 doi 10 1345 aph 1H458 PMID 17284509 S2CID 22855759 Kanjwal K Karabin B Sheikh M Elmer L Kanjwal Y Saeed B Grubb BP June 2011 Pyridostigmine in the treatment of postural orthostatic tachycardia a single center experience Pacing and Clinical Electrophysiology 34 6 750 755 doi 10 1111 j 1540 8159 2011 03047 x PMID 21410722 S2CID 20405336 a b c Mestinon Home Archived 2008 05 13 at the Wayback Machine Mestinon Official FDA information side effects and uses Archived 2008 05 24 at the Wayback MachineExternal links edit Pyridostigmine Drug Information Portal U S National Library of Medicine Portal nbsp Medicine Retrieved from https en wikipedia org w index php title Pyridostigmine amp oldid 1220339622, wikipedia, wiki, book, books, library,

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