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Revision as of 12:05, 6 December 2011 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Saving copy of the {{drugbox}} taken from revid 457062639 of page Pyridostigmine for the Chem/Drugbox validation project (updated: 'DrugBank').  Latest revision as of 05:16, 2 October 2024 edit 2603:90d8:700:bb64:7d05:1bec:1a91:5e3f (talk)No edit summary 
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{{Short description|Medication used to treat myasthenia gravis}}
{{ambox | text = This page contains a copy of the infobox ({{tl|drugbox}}) taken from revid of page ] with values updated to verified values.}}
{{Distinguish|Physostigmine}}
{{Drugbox {{Drugbox
⚫ | verifiedrevid = 464377022
| Verifiedfields = changed
⚫ | verifiedrevid = 441620411
| IUPAC_name = 3--1-methylpyridinium | IUPAC_name = 3--1-methylpyridinium
| image = Pyridostigmine.svg | image = Pyridostigmine.svg
| image2 = Pyridostigmine ball-and-stick.png


<!--Clinical data--> <!-- Clinical data -->
| tradename = Mestinon | tradename = Mestinon, others
| Drugs.com = {{drugs.com|monograph|pyridostigmine-bromide}} | Drugs.com = {{drugs.com|monograph|pyridostigmine-bromide}}
| MedlinePlus = a682229 | MedlinePlus = a682229
| pregnancy_AU = C | pregnancy_AU = C
| pregnancy_US = C
| legal_UK = POM | legal_UK = POM
| legal_US = Rx-only | legal_US = Rx-only
| routes_of_administration = Oral, ] | routes_of_administration = ], ]
| class = ]; ]


<!--Pharmacokinetic data--> <!-- Pharmacokinetic data -->
| bioavailability = 7.6 +/- 2.4% | bioavailability = 7.6 ± 2.4%
| protein_bound = | protein_bound =
| metabolism = | metabolism =
| elimination_half-life = 1.78 +/- 0.24hrs | elimination_half-life = 1.78 ± 0.24 hours
| excretion = ] | excretion = ]


<!--Identifiers--> <!-- Identifiers -->
| CASNo_Ref = {{cascite|correct|CAS}}
| CAS_number_Ref = {{cascite|correct|??}} | CAS_number_Ref = {{cascite|correct|??}}
| CAS_number = 155-97-5 | CAS_number = 155-97-5
| ATC_prefix = N07 | ATC_prefix = N07
| ATC_suffix = AA02 | ATC_suffix = AA02
| ATC_supplemental = | ATC_supplemental =
| PubChem = 4991 | PubChem = 4991
| DrugBank_Ref = {{drugbankcite|correct|drugbank}} | DrugBank_Ref = {{drugbankcite|correct|drugbank}}
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 4817 | ChemSpiderID = 4817
| UNII_Ref = {{fdacite|changed|FDA}} | UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 19QM69HH21 | UNII = 19QM69HH21
| KEGG_Ref = {{keggcite|changed|kegg}} | KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = D00487 | KEGG = C07410
| ChEMBL_Ref = {{ebicite|correct|EBI}} | ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 1115 | ChEMBL = 1115


<!--Chemical data--> <!-- Chemical data -->
| C=9 | H=13 | N=2 | O=2 | C=9 | H=13 | N=2 | O=2
⚫ | SMILES = O=C(Oc1ccc(c1)C)N(C)C
| molecular_weight = 181.212 g/mol
⚫ | smiles = O=C(Oc1ccc(c1)C)N(C)C
| InChI = 1/C9H13N2O2/c1-10(2)9(12)13-8-5-4-6-11(3)7-8/h4-7H,1-3H3/q+1
| InChIKey = RVOLLAQWKVFTGE-UHFFFAOYAK
| StdInChI_Ref = {{stdinchicite|correct|chemspider}} | StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C9H13N2O2/c1-10(2)9(12)13-8-5-4-6-11(3)7-8/h4-7H,1-3H3/q+1 | StdInChI = 1S/C9H13N2O2/c1-10(2)9(12)13-8-5-4-6-11(3)7-8/h4-7H,1-3H3/q+1
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| StdInChIKey = RVOLLAQWKVFTGE-UHFFFAOYSA-N | StdInChIKey = RVOLLAQWKVFTGE-UHFFFAOYSA-N
}} }}
<!-- Definition and medical uses -->
'''Pyridostigmine''' is a medication used to treat ]<ref name=WHO2008>{{cite book | title = WHO Model Formulary 2008 | year = 2009 | isbn = 9789241547659 | vauthors = ((World Health Organization)) | veditors = Stuart MC, Kouimtzi M, Hill SR | hdl = 10665/44053 | author-link = World Health Organization | publisher = World Health Organization |page=429 }}</ref> and underactive bladder.<ref>{{cite journal | vauthors = Moro C, Phelps C, Veer V, Clark J, Glasziou P, Tikkinen KA, Scott AM | title = The effectiveness of parasympathomimetics for treating underactive bladder: A systematic review and meta-analysis | journal = Neurourology and Urodynamics | date = November 2021 | volume = 41 | issue = 1 | pages = 127–139 | pmid = 34816481 | doi = 10.1002/nau.24839 | s2cid = 244530010 | url = https://research.bond.edu.au/en/publications/62295e6a-d035-4557-bb8d-12380be96c0c }}</ref> It is also used together with ] to end the effects of ] of the ] type.<ref name=AHFS2016/> It is also used off-label to treat some forms of ]. It is typically given ] but can also be used by injection.<ref name=AHFS2016/> The effects generally begin within 45 minutes and last up to 4 hours.<ref name=AHFS2016>{{cite web|title=Neostigmine Bromide|url=https://www.drugs.com/monograph/neostigmine-bromide.html|publisher=The American Society of Health-System Pharmacists|access-date=8 December 2016|url-status=live|archive-url=https://web.archive.org/web/20161221012812/https://www.drugs.com/monograph/neostigmine-bromide.html|archive-date=21 December 2016}}</ref>

<!-- Side effects and mechanisms -->
Common side effects include nausea, diarrhea, frequent urination, and abdominal pain.<ref name=AHFS2016/> More severe side effects include ], weakness, and ].<ref name=AHFS2016/> It is unclear if use in ] is safe for the fetus.<ref name=AHFS2016/> Pyridostigmine is an ] in the ] family of medications.<ref name=AHFS2016/> It works by blocking the action of ] and therefore increases the levels of ].<ref name=AHFS2016/>

<!-- History and culture -->
Pyridostigmine was patented in 1945 and came into medical use in 1955.<ref name=Fis2006>{{cite book| vauthors = Fischer J, Ganellin CR |title=Analogue-based Drug Discovery|date=2006|publisher=John Wiley & Sons|isbn=9783527607495|page=540|url=https://books.google.com/books?id=FjKfqkaKkAAC&pg=PA540|language=en|url-status=live|archive-url=https://web.archive.org/web/20161220143859/https://books.google.ca/books?id=FjKfqkaKkAAC&pg=PA540|archive-date=2016-12-20}}</ref> It is on the ].<ref name="WHO21st">{{cite book | vauthors = ((World Health Organization)) | title = World Health Organization model list of essential medicines: 21st list 2019 | year = 2019 | hdl = 10665/325771 | author-link = World Health Organization | publisher = World Health Organization | location = Geneva | id = WHO/MVP/EMP/IAU/2019.06. License: CC BY-NC-SA 3.0 IGO | hdl-access=free }}</ref> Pyridostigmine is available as a ].<ref name=AHFS2016/><ref>{{cite web | title=Competitive Generic Therapy Approvals | website=U.S. ] (FDA) | date=3 March 2023 | url=https://www.fda.gov/drugs/generic-drugs/competitive-generic-therapy-approvals | access-date=6 March 2023}}</ref>

==Medical uses==
Pyridostigmine is used to treat muscle weakness in people with ] or forms of ] and to combat the effects of ] 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 ] in order to increase survival. Used in particular during the first ], pyridostigmine bromide has been implicated as a causal factor in ].<ref name=Golomb>{{cite journal | vauthors = Golomb BA | title = Acetylcholinesterase inhibitors and Gulf War illnesses | journal = Proceedings of the National Academy of Sciences of the United States of America | volume = 105 | issue = 11 | pages = 4295–4300 | date = March 2008 | pmid = 18332428 | pmc = 2393741 | doi = 10.1073/pnas.0711986105 | doi-access = free | bibcode = 2008PNAS..105.4295G | jstor = 25461411}}</ref><ref name="Steenhuysen 2008">{{cite web | last=Steenhuysen | first=Julie | title=Gulf War illness linked to chemical exposure-study | work=] | date=March 10, 2008 | url=https://www.reuters.com/article/idUSN10593482}}</ref>

With pyridostigmine classified as a type of ], it can be used to treat underactive bladder.<ref>{{cite journal | vauthors = Moro C, Phelps C, Veer V, Clark J, Glasziou P, Tikkinen KA, Scott AM | title = The effectiveness of parasympathomimetics for treating underactive bladder: A systematic review and meta-analysis | journal = Neurourology and Urodynamics | date = November 2021 | volume = 41 | issue = 1 | pages = 127–139 | pmid = 34816481 | doi = 10.1002/nau.24839 | s2cid = 244530010 | url = https://research.bond.edu.au/en/publications/62295e6a-d035-4557-bb8d-12380be96c0c }}</ref>

Pyridostigmine sometimes is used to treat ].<ref name="Gales-2007">{{cite journal | vauthors = Gales BJ, Gales MA | title = Pyridostigmine in the treatment of orthostatic intolerance | journal = The Annals of Pharmacotherapy | volume = 41 | issue = 2 | pages = 314–318 | date = February 2007 | pmid = 17284509 | doi = 10.1345/aph.1H458 | s2cid = 22855759 }}</ref> It may also be of benefit in chronic axonal ].<ref name="Galassi-2011">{{cite journal | vauthors = Gales BJ, Gales MA | title = Pyridostigmine in the treatment of orthostatic intolerance | journal = The Annals of Pharmacotherapy | volume = 41 | issue = 2 | pages = 314–318 | date = February 2007 | pmid = 17284509 | doi = 10.1345/aph.1H458 | s2cid = 22855759 }}</ref>

It is also being prescribed ] for ] (POTS) as well as complications resulting from ].<ref name="Galassi-2011"/><ref>{{cite journal | vauthors = Kanjwal K, Karabin B, Sheikh M, Elmer L, Kanjwal Y, Saeed B, Grubb BP | title = Pyridostigmine in the treatment of postural orthostatic tachycardia: a single-center experience | journal = Pacing and Clinical Electrophysiology | volume = 34 | issue = 6 | pages = 750–755 | date = June 2011 | pmid = 21410722 | doi = 10.1111/j.1540-8159.2011.03047.x | s2cid = 20405336 }}</ref>

==Contraindications==
Pyridostigmine bromide is contraindicated in cases of mechanical intestinal or urinary obstruction and should be used with caution in patients with bronchial asthma.<ref name=autogenerated1> {{webarchive|url=https://web.archive.org/web/20080513104925/http://www.mestinon.com/ |date=2008-05-13 }}</ref><ref> {{webarchive|url=https://web.archive.org/web/20080524034654/http://www.drugs.com/pro/mestinon.html |date=2008-05-24 }}</ref>

==Side effects==
Common side effects include:<ref name=autogenerated1 />

* 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:<ref name=autogenerated1 />

* Muscle twitching
* Muscle cramps and weakness

==Mechanism of action==
Pyridostigmine is an ]. It ]s ] in the ], thus slowing down the ] of ]. Like its predecessor ], it is a quaternary ] inhibitor of cholinesterase that does not cross the ]. 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 ] (Na<sup>+</sup>,) 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 ] is present in the endplate membrane close to the receptors on the post synaptic membrane, and quickly hydrolyses ACh.

==Names==
Pyridostigmine bromide is available under the trade name Mestinon (]), Regonol and Gravitor (SUN Pharma).

==References==
{{Reflist}}

==External links==
* {{cite web | url = https://druginfo.nlm.nih.gov/drugportal/name/pyridostigmine | publisher = U.S. National Library of Medicine | work = Drug Information Portal | title = Pyridostigmine }}

{{Acetylcholine metabolism and transport modulators}}
{{Portal bar|Medicine}}

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