Chemistry:Glycopyrronium bromide

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Short description: Chemical compound
Glycopyrronium bromide
Glycopyrronium bromide.svg
Clinical data
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 agent
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)
 ☒N☑Y (what is this?)  (verify)

Glycopyrronium bromide is a medication of the muscarinic anticholinergic group.[6] It does not cross the blood–brain barrier and consequently has few to no central effects. It is given by mouth,[7] via intravenous injection, on the skin,[8] and via inhalation.[3][4][5] It is a synthetic quaternary ammonium compound.[1] The cation, which is the active moiety, is called glycopyrronium (INN)[9] 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).[6]

In September 2012, glycopyrronium was approved for medical use in the European Union.[3] 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.[10] It is on the World Health Organization's List of Essential Medicines.[11]

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.[12] It is also used in conjunction with neostigmine, a neuromuscular blocking reversal agent, to prevent neostigmine's muscarinic effects such as bradycardia.[13] 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),[6][14][15][16] and to treat Ménière's disease.[17]

It has been used topically and orally to treat hyperhidrosis, in particular, gustatory hyperhidrosis.[18][19]

In inhalable form it is used to treat chronic obstructive pulmonary disease (COPD).[3][4][5] 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.[12]

Pharmacology

Mechanism of action

Glycopyrronium competitively blocks muscarinic receptors,[12][22] 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.[23]

Research

It has been studied in asthma.[24][25]

References

  1. ↑ 1.0 1.1 "Robinul- glycopyrrolate tablet Robinul Forte- glycopyrrolate tablet". 1 June 2021. https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=94fb029a-6371-4b1c-89de-35e8209c7cab. 
  2. ↑ "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. 
  3. ↑ 3.0 3.1 3.2 3.3 "Seebri Breezhaler EPAR". 17 September 2018. https://www.ema.europa.eu/en/medicines/human/EPAR/seebri-breezhaler. 
  4. ↑ 4.0 4.1 4.2 "Tovanor Breezhaler EPAR". 17 September 2018. https://www.ema.europa.eu/en/medicines/human/EPAR/tovanor-breezhaler. 
  5. ↑ 5.0 5.1 5.2 "Enurev Breezhaler EPAR". 17 September 2018. https://www.ema.europa.eu/en/medicines/human/EPAR/enurev-breezhaler. 
  6. ↑ 6.0 6.1 6.2 6.3 "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.
  7. ↑ "Glycopyrrolate Oral Inhalation". https://medlineplus.gov/druginfo/meds/a618016.html. 
  8. ↑ "Glycopyrronium Topical". https://medlineplus.gov/druginfo/meds/a618046.html. 
  9. ↑ "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. 
  10. ↑ "FDA OKs first drug made to reduce excessive sweating". AP News. https://apnews.com/21f28f1327ca4f9497cf878cc0229444. 
  11. ↑ World Health Organization model list of essential medicines: 22nd list (2021). Geneva: World Health Organization. 2021. WHO/MHP/HPS/EML/2021.02. 
  12. ↑ 12.0 12.1 12.2 "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. 
  13. ↑ "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. 
  14. ↑ "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. 
  15. ↑ "Sialorrhea - therapeutic drug options". The Annals of Pharmacotherapy 36 (11): 1785–1790. November 2002. doi:10.1345/aph.1C019. PMID 12398577. [yes|permanent dead link|dead link}}]
  16. ↑ "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. 
  17. ↑ "Medical therapy in Ménière's disease". Audiological Medicine 10 (4): 171–177. 1 December 2012. doi:10.3109/1651386X.2012.718413. 
  18. ↑ "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. 
  19. ↑ "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. 
  20. ↑ "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. 
  21. ↑ "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. 
  22. ↑ "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. 
  23. ↑ "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. 
  24. ↑ "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. 
  25. ↑ "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. 

External links



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