Glycopyrronium bromide explained

Verifiedfields:changed
Verifiedrevid:461122867
Usan:glycopyrrolate
Tradename:Robinul, Cuvposa, Seebri, others
Dailymedid:Glycopyrrolate
Pregnancy Au:B2
Routes Of Administration:By mouth, intravenous, inhalation, topical, injection, subcutaneous
Class:Antimuscarinic agent
Atc Prefix:A03
Atc Suffix:AB02
Legal Au:S3 / S4
Legal Ca:Rx-only
Legal Ca Comment:[1]
Legal Uk:POM
Legal Us:Rx-only
Legal Us Comment:[2] [3]
Legal Eu:Rx-only
Legal Eu Comment:[4]
Legal Status:Rx-only
Elimination Half-Life:0.6–1.2 hours
Excretion:85% Kidney, unknown amount in the bile
Index2 Label:as cation
Cas Number:51186-83-5
Cas Number2:596-51-0
Pubchem:3494
Pubchem2:11693
Iuphar Ligand:7459
Drugbank:DBSALT001183
Drugbank2:DB00986
Chemspiderid:11201
Chemspiderid2:3374
Unii:V92SO9WP2I
Unii2:A14FB57V1D
Kegg:D00540
Kegg2:D10938
Chebi:90972
Chembl:1201027
Chembl2:1201335
Iupac Name:3-[2-Cyclopentyl(hydroxy)phenylacetoxy]-1,1-dimethylpyrrolidinium bromide
C:19
H:28
Br:1
N:1
O:3
Smiles:C[N+]1(CCC(C1)OC(=O)C(C2CCCC2)(C3=CC=CC=C3)O)C.[Br-]
Smiles2:C[N+]1(CCC(C1)OC(=O)C(C2CCCC2)(C3=CC=CC=C3)O)C
Stdinchi:1S/C19H28NO3.BrH/c1-20(2)13-12-17(14-20)23-18(21)19(22,16-10-6-7-11-16)15-8-4-3-5-9-15;/h3-5,8-9,16-17,22H,6-7,10-14H2,1-2H3;1H/q+1;/p-1
Stdinchi2:1S/C19H28NO3/c1-20(2)13-12-17(14-20)23-18(21)19(22,16-10-6-7-11-16)15-8-4-3-5-9-15/h3-5,8-9,16-17,22H,6-7,10-14H2,1-2H3/q+1
Stdinchikey:VPNYRYCIDCJBOM-UHFFFAOYSA-M
Stdinchikey2:ANGKOCUUWGHLCE-UHFFFAOYSA-N

Glycopyrronium bromide is a medication of the muscarinic anticholinergic group. It does not cross the blood–brain barrier and consequently has few to no central effects. It is given by mouth,[5] via intravenous injection, on the skin,[6] and via inhalation. It is a synthetic quaternary ammonium compound. The cation, which is the active moiety, is called glycopyrronium (INN)[7] or glycopyrrolate (USAN).

The most common side effects include irritability, flushing, blocked nose, reduced secretions in the airways, dry mouth, constipation, diarrhea, vomiting and inability to completely empty the bladder (urinary retention).

In September 2012, glycopyrronium was approved for medical use in the European Union. In June 2018, glycopyrronium was approved by the US Food and Drug Administration (FDA) to treat excessive underarm sweating, becoming the first drug developed specifically to reduce excessive sweating.[8] It is on the World Health Organization's List of Essential Medicines.[9]

Medical uses

Glycopyrronium was first used in 1961 to treat peptic ulcers. Since 1975, intravenous glycopyrronium has been used before surgery to reduce salivary, tracheobronchial, and pharyngeal secretions. It is also used in conjunction with neostigmine, a neuromuscular blocking reversal agent, to prevent neostigmine's muscarinic effects such as bradycardia.[10] It can be administered to raise the heart rate in bradycardia, which often will also increase the blood pressure.

It is also used to reduce excessive saliva (sialorrhea),[11] [12] [13] and to treat Ménière's disease.[14]

It has been used topically and orally to treat hyperhidrosis, in particular, gustatory hyperhidrosis.[15] [16]

In inhalable form it is used to treat chronic obstructive pulmonary disease (COPD).[17] [18] [19] Doses for inhalation are much lower than oral ones, so that swallowing a dose will not have an effect.[20] [21]

Side effects

Dry mouth, urinary retention, headaches, vomiting, diarrhea, constipation, blurry vision are possible side effects of the medication.

Pharmacology

Mechanism of action

Glycopyrronium competitively blocks muscarinic receptors,[22] [23] thus inhibiting cholinergic transmission.

Pharmacokinetics

Glycopyrronium bromide affects the gastrointestinal tracts, liver and kidney but has a very limited effect on the brain and the central nervous system. In horse studies, after a single intravenous infusion, the observed tendencies of glycopyrronium followed a tri-exponential equation, by rapid disappearance from the blood followed by a prolonged terminal phase. Excretion was mainly in urine and in the form of an unchanged drug. Glycopyrronium has a relatively slow diffusion rate, and in a standard comparison to atropine, is more resistant to penetration through the blood-brain barrier and placenta.[24]

Research

It has been studied in asthma.[25] [26]

Notes and References

  1. Web site: Neurological therapies . . 9 May 2018 . 13 April 2024.
  2. Web site: Robinul- glycopyrrolate tablet Robinul Forte- glycopyrrolate tablet . DailyMed . 1 June 2021 . 20 June 2022.
  3. Web site: Dartisla ODT- glycopyrrolate orally disintegrating tablets tablet, orally disintegrating . DailyMed . 9 December 2021 . 20 June 2022.
  4. Web site: Sialanar EPAR . European Medicines Agency . 17 September 2018 . 29 January 2023. Text was copied from this source which is copyright European Medicines Agency. Reproduction is authorized provided the source is acknowledged.
  5. Web site: Glycopyrrolate Oral Inhalation . MedlinePlus . 20 June 2022 . 17 August 2021 . https://web.archive.org/web/20210817020822/https://medlineplus.gov/druginfo/meds/a618016.html . live .
  6. Web site: Glycopyrronium Topical . MedlinePlus . 20 June 2022 . 17 August 2021 . https://web.archive.org/web/20210817175947/https://medlineplus.gov/druginfo/meds/a618046.html . live .
  7. Bajaj V, Langtry JA . Use of oral glycopyrronium bromide in hyperhidrosis . The British Journal of Dermatology . 157 . 1 . 118–121 . July 2007 . 17459043 . 10.1111/j.1365-2133.2007.07884.x . 29080876 .
  8. News: FDA OKs first drug made to reduce excessive sweating. AP News. 2018-07-02. 2018-07-02. https://web.archive.org/web/20180702233319/https://apnews.com/21f28f1327ca4f9497cf878cc0229444. live.
  9. Book: ((World Health Organization)) . World Health Organization model list of essential medicines: 22nd list (2021) . 2021 . 10665/345533 . World Health Organization . World Health Organization . Geneva . WHO/MHP/HPS/EML/2021.02 . free .
  10. Howard J, Wigley J, Rosen G, D'mello J . Glycopyrrolate: It's time to review . Journal of Clinical Anesthesia . 36 . 51–53 . February 2017 . 28183573 . 10.1016/j.jclinane.2016.09.013 .
  11. Mier RJ, Bachrach SJ, Lakin RC, Barker T, Childs J, Moran M . Treatment of sialorrhea with glycopyrrolate: A double-blind, dose-ranging study . Archives of Pediatrics & Adolescent Medicine . 154 . 12 . 1214–1218 . December 2000 . 11115305 . 10.1001/archpedi.154.12.1214 . 2008-11-26 . live . free . https://archive.today/20110810032036/http://archpedi.ama-assn.org/cgi/pmidlookup?view=long&pmid=11115305 . 2011-08-10 .
  12. Tscheng DZ . Sialorrhea - therapeutic drug options . The Annals of Pharmacotherapy . 36 . 11 . 1785–1790 . November 2002 . 12398577 . 10.1345/aph.1C019 . 45799443 .
  13. Olsen AK, Sjøgren P . Oral glycopyrrolate alleviates drooling in a patient with tongue cancer . Journal of Pain and Symptom Management . 18 . 4 . 300–302 . October 1999 . 10534970 . 10.1016/S0885-3924(99)00080-9 . free .
  14. Medical therapy in Ménière's disease. Audiological Medicine. Maria SA, Claudia C, Pamela G, Andrea C, Roberto A . 1 December 2012. 10. 4. 171–177. 10.3109/1651386X.2012.718413. 72380413.
  15. Kim WO, Kil HK, Yoon DM, Cho MJ . Treatment of compensatory gustatory hyperhidrosis with topical glycopyrrolate . Yonsei Medical Journal . 44 . 4 . 579–582 . August 2003 . 12950111 . 10.3349/ymj.2003.44.4.579 . free .
  16. Kim WO, Kil HK, Yoon KB, Yoon DM . Topical glycopyrrolate for patients with facial hyperhidrosis . The British Journal of Dermatology . 158 . 5 . 1094–1097 . May 2008 . 18294315 . 10.1111/j.1365-2133.2008.08476.x . 39870296 .
  17. Web site: Seebri Breezhaler EPAR . European Medicines Agency (EMA) . 17 September 2018 . 28 February 2020 . 29 February 2020 . https://web.archive.org/web/20200229101656/https://www.ema.europa.eu/en/medicines/human/EPAR/seebri-breezhaler . live .
  18. Web site: Tovanor Breezhaler EPAR . European Medicines Agency (EMA) . 17 September 2018 . 28 February 2020 . 29 February 2020 . https://web.archive.org/web/20200229101658/https://www.ema.europa.eu/en/medicines/human/EPAR/tovanor-breezhaler . live .
  19. Web site: Enurev Breezhaler EPAR . European Medicines Agency . 17 September 2018 . 29 January 2023.
  20. Web site: EPAR – Product information for Seebri Breezhaler. European Medicines Agency. 28 September 2012. 4 February 2017. 30 July 2018. https://web.archive.org/web/20180730210441/http://www.ema.europa.eu/docs/en_GB/document_library/EPAR_-_Product_Information/human/002430/WC500133769.pdf. live.
  21. Tzelepis G, Komanapolli S, Tyler D, Vega D, Fulambarker A . Comparison of nebulized glycopyrrolate and metaproterenol in chronic obstructive pulmonary disease . The European Respiratory Journal . 9 . 1 . 100–103 . January 1996 . 8834341 . 10.1183/09031936.96.09010100 . free .
  22. Chabicovsky M, Winkler S, Soeberdt M, Kilic A, Masur C, Abels C . Pharmacology, toxicology and clinical safety of glycopyrrolate . Toxicology and Applied Pharmacology . 370 . 154–169 . May 2019 . 30905688 . 10.1016/j.taap.2019.03.016 . 85498396 .
  23. Haddad EB, Patel H, Keeling JE, Yacoub MH, Barnes PJ, Belvisi MG . Pharmacological characterization of the muscarinic receptor antagonist, glycopyrrolate, in human and guinea-pig airways . British Journal of Pharmacology . 127 . 2 . 413–420 . May 1999 . 10385241 . 1566042 . 10.1038/sj.bjp.0702573 .
  24. Rumpler MJ, Colahan P, Sams RA . The pharmacokinetics of glycopyrrolate in Standardbred horses . Journal of Veterinary Pharmacology and Therapeutics . 37 . 3 . 260–268 . June 2014 . 24325462 . 10.1111/jvp.12085 .
  25. Hansel TT, Neighbour H, Erin EM, Tan AJ, Tennant RC, Maus JG, Barnes PJ . Glycopyrrolate causes prolonged bronchoprotection and bronchodilatation in patients with asthma . Chest . 128 . 4 . 1974–1979 . October 2005 . 16236844 . 10.1378/chest.128.4.1974 . dead . https://archive.today/20130414111933/http://www.chestjournal.org/cgi/pmidlookup?view=long&pmid=16236844 . 2013-04-14 .
  26. Gilman MJ, Meyer L, Carter J, Slovis C . Comparison of aerosolized glycopyrrolate and metaproterenol in acute asthma . Chest . 98 . 5 . 1095–1098 . November 1990 . 2225951 . 10.1378/chest.98.5.1095 . dead . https://archive.today/20130414121303/http://www.chestjournal.org/cgi/pmidlookup?view=long&pmid=2225951 . 2013-04-14 .

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