Chemistry:Glycopyrronium bromide

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Short description: Anticholinergic

Glycopyrronium bromide
INN: Glycopyrronium
Molecular structure of glycopyrronium bromide
3D representation of a glycopyrronium bromide molecule
Clinical data
Pronunciation/ˌɡlaɪkoʊpaɪˈroʊniʌmˈbroʊmaɪd/ gly-koh-py-ROH-nee-um BROH-myd
Trade namesRobinul, Cuvposa, Seebri, others
Other namesglycopyrrolate (USAN US)
AHFS/Drugs.comMonograph
MedlinePlusa602014
License data
Pregnancy
category
  • AU: B2
Routes of
administration		By mouth, intravenous, inhalation, topical, injection, subcutaneous
Drug classAntimuscarinic (peripherally-selective)
ATC code
Legal status
Legal status
Pharmacokinetic data
Elimination half-life0.6–1.2 hours
Excretion85% Kidney, unknown amount in the bile
Identifiers
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
Chemical and physical data
FormulaC19H28BrNO3
Molar mass398.341 g·mol−1
3D model (JSmol)
 ☒NcheckY (what is this?)  (verify)

Glycopyrronium bromide is a medication of the muscarinic anticholinergic group.[7] It does not cross the blood–brain barrier and consequently has few to no central effects. It can be administered orally,[8] intravenously, topically,[9] or via inhalation.[4][5][6] It is a synthetic quaternary ammonium compound.[2] The cation, which is the active moiety, is called glycopyrronium (INN)[10] or glycopyrrolate (USAN).

The most common side effects include irritability, flushing, nasal congestion, reduced secretions in the airways, dry mouth, constipation, diarrhea, nausea and vomiting, and urinary retention.[7]

In September 2012, glycopyrronium was approved for medical use in the European Union.[4] In June 2018, glycopyrronium was approved by the U.S. Food and Drug Administration (FDA) to treat excessive underarm sweating, becoming the first drug developed specifically to reduce excessive sweating.[11] It is on the World Health Organization's List of Essential Medicines.[12]

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.[13] It is also used in conjunction with neostigmine, a neuromuscular blocking reversal agent, to prevent neostigmine's muscarinic effects such as bradycardia.[14] It can be administered to raise the heart rate in reflex bradycardia as a result of a vasovagal reaction, which often will also increase the blood pressure.[15]

It is also used to reduce excessive saliva (sialorrhea),[7][16][17][18] and to treat Ménière's disease.[19]

It has been used topically and orally to treat hyperhidrosis, in particular, gustatory hyperhidrosis and generalized hyperhidrosis.[20][21]

When inhaled, it is used to treat chronic obstructive pulmonary disease (COPD).[4][5][6] Doses for inhalation are much lower than oral ones, so that swallowing a dose will not have an effect.[22][23]

Side effects

Dry mouth, urinary retention, headaches, vomiting, diarrhea, constipation, and blurry vision are possible side effects of the medication.[13]

Pharmacology

Mechanism of action

Glycopyrronium competitively blocks muscarinic receptors,[13][24] 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.[25]

Research

It has been studied in asthma.[26][27]

References

  1. ↑ "Neurological therapies". 9 May 2018. https://www.canada.ca/en/services/health/drug-health-products/drug-medical-device-highlights-2017/approved-drugs/neurological-therapies.html. 
  2. ↑ 2.0 2.1 "Robinul- glycopyrrolate tablet Robinul Forte- glycopyrrolate tablet". 1 June 2021. https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=94fb029a-6371-4b1c-89de-35e8209c7cab. 
  3. ↑ "Dartisla ODT- glycopyrrolate orally disintegrating tablets tablet, orally disintegrating". 9 December 2021. https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=52daf47e-7ba3-4105-be7f-27001a87e16e. 
  4. ↑ 4.0 4.1 4.2 4.3 "Seebri Breezhaler EPAR". 17 September 2018. https://www.ema.europa.eu/en/medicines/human/EPAR/seebri-breezhaler. 
  5. ↑ 5.0 5.1 5.2 "Tovanor Breezhaler EPAR". 17 September 2018. https://www.ema.europa.eu/en/medicines/human/EPAR/tovanor-breezhaler. 
  6. ↑ 6.0 6.1 6.2 "Enurev Breezhaler EPAR". 17 September 2018. https://www.ema.europa.eu/en/medicines/human/EPAR/enurev-breezhaler. 
  7. ↑ 7.0 7.1 7.2 7.3 "Sialanar EPAR". 17 September 2018. https://www.ema.europa.eu/en/medicines/human/EPAR/sialanar.  Text was copied from this source which is copyright European Medicines Agency. Reproduction is authorized provided the source is acknowledged.
  8. ↑ "Glycopyrrolate Oral Inhalation". https://medlineplus.gov/druginfo/meds/a618016.html. 
  9. ↑ "Glycopyrronium Topical". https://medlineplus.gov/druginfo/meds/a618046.html. 
  10. ↑ "Use of oral glycopyrronium bromide in hyperhidrosis". The British Journal of Dermatology 157 (1): 118–121. July 2007. doi:10.1111/j.1365-2133.2007.07884.x. PMID 17459043. 
  11. ↑ "FDA OKs first drug made to reduce excessive sweating". AP News. https://apnews.com/21f28f1327ca4f9497cf878cc0229444. 
  12. ↑ World Health Organization model list of essential medicines: 22nd list (2021). Geneva: World Health Organization. 2021. WHO/MHP/HPS/EML/2021.02. 
  13. ↑ 13.0 13.1 13.2 "Pharmacology, toxicology and clinical safety of glycopyrrolate". Toxicology and Applied Pharmacology 370: 154–169. May 2019. doi:10.1016/j.taap.2019.03.016. PMID 30905688. Bibcode: 2019ToxAP.370..154C. 
  14. ↑ "Glycopyrrolate: It's time to review". Journal of Clinical Anesthesia 36: 51–53. February 2017. doi:10.1016/j.jclinane.2016.09.013. PMID 28183573. 
  15. ↑ "Glycopyrrolate". StatPearls [Internet]. Treasure Island (FL): StatPearls Publishing. June 2023. https://www.ncbi.nlm.nih.gov/books/NBK526035/. Retrieved September 13, 2024. 
  16. ↑ "Treatment of sialorrhea with glycopyrrolate: A double-blind, dose-ranging study". Archives of Pediatrics & Adolescent Medicine 154 (12): 1214–1218. December 2000. doi:10.1001/archpedi.154.12.1214. PMID 11115305. http://archpedi.ama-assn.org/cgi/pmidlookup?view=long&pmid=11115305. Retrieved 2008-11-26. 
  17. ↑ "Sialorrhea - therapeutic drug options". The Annals of Pharmacotherapy 36 (11): 1785–1790. November 2002. doi:10.1345/aph.1C019. PMID 12398577. 
  18. ↑ "Oral glycopyrrolate alleviates drooling in a patient with tongue cancer". Journal of Pain and Symptom Management 18 (4): 300–302. October 1999. doi:10.1016/S0885-3924(99)00080-9. PMID 10534970. 
  19. ↑ "Medical therapy in Ménière's disease". Audiological Medicine 10 (4): 171–177. 1 December 2012. doi:10.3109/1651386X.2012.718413. 
  20. ↑ "Treatment of compensatory gustatory hyperhidrosis with topical glycopyrrolate". Yonsei Medical Journal 44 (4): 579–582. August 2003. doi:10.3349/ymj.2003.44.4.579. PMID 12950111. 
  21. ↑ "Topical glycopyrrolate for patients with facial hyperhidrosis". The British Journal of Dermatology 158 (5): 1094–1097. May 2008. doi:10.1111/j.1365-2133.2008.08476.x. PMID 18294315. 
  22. ↑ "EPAR – Product information for Seebri Breezhaler". European Medicines Agency. 28 September 2012. http://www.ema.europa.eu/docs/en_GB/document_library/EPAR_-_Product_Information/human/002430/WC500133769.pdf. 
  23. ↑ "Comparison of nebulized glycopyrrolate and metaproterenol in chronic obstructive pulmonary disease". The European Respiratory Journal 9 (1): 100–103. January 1996. doi:10.1183/09031936.96.09010100. PMID 8834341. 
  24. ↑ "Pharmacological characterization of the muscarinic receptor antagonist, glycopyrrolate, in human and guinea-pig airways". British Journal of Pharmacology 127 (2): 413–420. May 1999. doi:10.1038/sj.bjp.0702573. PMID 10385241. 
  25. ↑ "The pharmacokinetics of glycopyrrolate in Standardbred horses". Journal of Veterinary Pharmacology and Therapeutics 37 (3): 260–268. June 2014. doi:10.1111/jvp.12085. PMID 24325462. 
  26. ↑ "Glycopyrrolate causes prolonged bronchoprotection and bronchodilatation in patients with asthma". Chest 128 (4): 1974–1979. October 2005. doi:10.1378/chest.128.4.1974. PMID 16236844. http://www.chestjournal.org/cgi/pmidlookup?view=long&pmid=16236844. 
  27. ↑ "Comparison of aerosolized glycopyrrolate and metaproterenol in acute asthma". Chest 98 (5): 1095–1098. November 1990. doi:10.1378/chest.98.5.1095. PMID 2225951. http://www.chestjournal.org/cgi/pmidlookup?view=long&pmid=2225951. 



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