Glycopyrronium

Glycopyrronium
Names
Trade namesRobinul, Cuvposa, Seebri, others
Other namesGlycopyrrolate, glycopyrronium bromide, glycopyrronium tosylate
IUPAC name
  • 3-[2-Cyclopentyl(hydroxy)phenylacetoxy]-1,1-dimethylpyrrolidinium bromide
Clinical data
Drug classAntimuscarinic[1]
Main usesCOPD, excessive saliva[1]
Side effectsDry mouth, urinary retention, blurry vision, large pupils, headache, confusion, sleepiness, constipation[1]
WHO AWaReUnlinkedWikibase error: ⧼unlinkedwikibase-error-statements-entity-not-set⧽
Pregnancy
category
  • AU: B2
  • US: B (No risk in non-human studies)
    Routes of
    use    		By mouth, intravenous, inhaled, topical
    External links
    AHFS/Drugs.comSystemic: Monograph
    Topical: Monograph
    Legal
    License data
    Legal status
    • AU: S4 (Prescription only)
    • UK: POM (Prescription only)
    • US: ℞-only
    • In general: ℞ (Prescription only)
    Chemical and physical data
    FormulaC19H28BrNO3
    Molar mass398.341 g·mol−1
    3D model (JSmol)
    SMILES
    • C[N+]1(CCC(C1)OC(=O)C(C2CCCC2)(C3=CC=CC=C3)O)C.[Br-]
    InChI
    • InChI=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
    • Key:VPNYRYCIDCJBOM-UHFFFAOYSA-M

    Glycopyrronium, also known as glycopyrrolate, is a medication used to treat COPD, excessive saliva, and excessive sweating.[1][2] It may be taken by mouth, by injection, applied to the skin, or inhaled.[1][2] Effects may last for up to 12 hours.[1] It is also available in combination with a long-acting beta-adrenoceptor agonist (LABA) and inhaled steroid.[2]

    Common side effects include dry mouth, urinary retention, blurry vision, large pupils, headache, confusion, sleepiness, and constipation.[1] Other side effects may include allergic reactions and bronchospasm.[1] Safety in pregnancy is unclear.[1] It is an antimuscarinic.[1] It does not generally cross the blood–brain barrier.[1]

    Glycopyrronium was approved for medical use in the United States in 1961.[1] It is on the World Health Organization's List of Essential Medicines as an alternative to tiotropium.[3] In the United Kingdom a month of inhaled medication costs the NHS about £28 as of 2021.[2] In the United States the tablets are inexpensive.[4]

    Medical uses

    Intravenous glycopyrronium has been used before surgery to reduce salivary, tracheobronchial, and pharyngeal secretions.[5] It is also used in conjunction with neostigmine, a neuromuscular blocking reversal agent, to prevent neostigmine's muscarinic effects such as bradycardia. 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][7][8] and Ménière's disease.[9] In end of life care, it may be used to decrease bronchial secretions in people who are no longer able to clear their own airway through insufficient coughing reflex.

    It has been used topically and orally to treat hyperhidrosis, in particular, gustatory hyperhidrosis.[10][11]

    In inhalable form it is used to treat chronic obstructive pulmonary disease (COPD).[12][13] Doses for inhalation are much lower than oral ones, so that swallowing a dose will not have an effect.[14][15]

    Dosage

    For COPD the inhaled form is used at a dose of 44 micrograms once per day.[2]

    Side effects

    Dry mouth, urinary retention, headaches, vomiting, diarrhea, constipation, blurry vision are possible side effects of the medication.[5] Since glycopyrronium reduces the body's sweating ability, it can even cause hyperthermia and heat stroke in hot environments. The medication also induces drowsiness, an effect exacerbated by the consumption of alcohol.

    Pharmacology

    Mechanism of action

    Glycopyrronium competitively blocks muscarinic receptors,[5][16] 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.[17]

    History

    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.[5]

    Names

    The cation, which is the active moiety, is called "glycopyrronium" (INN)[18] or "glycopyrrolate" (USAN).

    Research

    It has been studied in asthma.[19][20]

    References

    1. 1 2 3 4 5 6 7 8 9 10 11 12 "Glycopyrrolate Monograph for Professionals". Drugs.com. Archived from the original on 16 July 2021. Retrieved 3 December 2021.
    2. 1 2 3 4 5 BNF 81: March-September 2021. BMJ Group and the Pharmaceutical Press. 2021. p. 262. ISBN 978-0857114105.
    3. ↑ World Health Organization (2021). World Health Organization model list of essential medicines: 22nd list (2021). Geneva: World Health Organization. hdl:10665/345533. WHO/MHP/HPS/EML/2021.02.
    4. ↑ "Glycopyrrolate Prices, Coupons & Savings Tips - GoodRx". GoodRx. Retrieved 9 December 2021.
    5. 1 2 3 4 Chabicovsky, Monika; Winkler, Swantje; Soeberdt, Michael; Kilic, Ana; Masur, Clarissa; Abels, Christoph (May 2019). "Pharmacology, toxicology and clinical safety of glycopyrrolate". Toxicology and Applied Pharmacology. 370: 154–169. doi:10.1016/j.taap.2019.03.016. PMID 30905688. S2CID 85498396.
    6. ↑ Mier RJ, Bachrach SJ, Lakin RC, Barker T, Childs J, Moran M (December 2000). "Treatment of sialorrhea with glycopyrrolate: A double-blind, dose-ranging study". Arch Pediatr Adolesc Med. 154 (12): 1214–8. doi:10.1001/archpedi.154.12.1214. PMID 11115305. Archived from the original on 2011-08-10. Retrieved 2021-10-09.
    7. ↑ Tscheng DZ (November 2002). "Sialorrhea - therapeutic drug options". Ann Pharmacother. 36 (11): 1785–90. doi:10.1345/aph.1C019. PMID 12398577. S2CID 45799443.
    8. ↑ Olsen AK, Sjøgren P (October 1999). "Oral glycopyrrolate alleviates drooling in a patient with tongue cancer". J Pain Symptom Manage. 18 (4): 300–2. doi:10.1016/S0885-3924(99)00080-9. PMID 10534970.
    9. ↑ Maria, Sammartano Azia; Claudia, Cassandro; Pamela, Giordano; Andrea, Canale; Roberto, Albera (1 December 2012). "Medical therapy in Ménière's disease". Audiological Medicine. 10 (4): 171–177. doi:10.3109/1651386X.2012.718413. S2CID 72380413.
    10. ↑ Kim WO, Kil HK, Yoon DM, Cho MJ (August 2003). "Treatment of compensatory gustatory hyperhidrosis with topical glycopyrrolate". Yonsei Med. J. 44 (4): 579–82. doi:10.3349/ymj.2003.44.4.579. PMID 12950111.
    11. ↑ Kim WO, Kil HK, Yoon KB, Yoon DM (May 2008). "Topical glycopyrrolate for patients with facial hyperhidrosis". Br. J. Dermatol. 158 (5): 1094–7. doi:10.1111/j.1365-2133.2008.08476.x. PMID 18294315. S2CID 39870296.
    12. ↑ "Seebri Breezhaler EPAR". European Medicines Agency (EMA). 17 September 2018. Archived from the original on 29 February 2020. Retrieved 28 February 2020.
    13. ↑ "Tovanor Breezhaler EPAR". European Medicines Agency (EMA). 17 September 2018. Archived from the original on 29 February 2020. Retrieved 28 February 2020.
    14. ↑ "EPAR – Product information for Seebri Breezhaler" (PDF). European Medicines Agency. 28 September 2012. Archived (PDF) from the original on 30 July 2018. Retrieved 9 October 2021.
    15. ↑ Tzelepis G, Komanapolli S, Tyler D, Vega D, Fulambarker A (January 1996). "Comparison of nebulized glycopyrrolate and metaproterenol in chronic obstructive pulmonary disease". Eur. Respir. J. 9 (1): 100–3. doi:10.1183/09031936.96.09010100. PMID 8834341.
    16. ↑ Haddad EB, Patel H, Keeling JE, Yacoub MH, Barnes PJ, Belvisi MG (May 1999). "Pharmacological characterization of the muscarinic receptor antagonist, glycopyrrolate, in human and guinea-pig airways". Br. J. Pharmacol. 127 (2): 413–20. doi:10.1038/sj.bjp.0702573. PMC 1566042. PMID 10385241.
    17. ↑ Rumpler, M.J.; Colahan, P.; Sams, R.A. (2014). "The pharmacokinetics of glycopyrrolate in Standardbred horses". Journal of Veterinary Pharmacology and Therapeutics. 37 (3): 260–8. doi:10.1111/jvp.12085. PMID 24325462.
    18. ↑ Bajaj V, Langtry JA (July 2007). "Use of oral glycopyrronium bromide in hyperhidrosis". Br. J. Dermatol. 157 (1): 118–21. doi:10.1111/j.1365-2133.2007.07884.x. PMID 17459043. S2CID 29080876.
    19. ↑ Hansel TT, Neighbour H, Erin EM, et al. (October 2005). "Glycopyrrolate causes prolonged bronchoprotection and bronchodilatation in patients with asthma". Chest. 128 (4): 1974–9. doi:10.1378/chest.128.4.1974. PMID 16236844. Archived from the original on 2013-04-14.
    20. ↑ Gilman MJ, Meyer L, Carter J, Slovis C (November 1990). "Comparison of aerosolized glycopyrrolate and metaproterenol in acute asthma". Chest. 98 (5): 1095–8. doi:10.1378/chest.98.5.1095. PMID 2225951. Archived from the original on 2013-04-14.
    Identifiers:
    • "Glycopyrronium bromide". Drug Information Portal. U.S. National Library of Medicine. Archived from the original on 2020-02-29. Retrieved 2021-10-09.
    • "Glycopyrronium". Drug Information Portal. U.S. National Library of Medicine. Archived from the original on 2021-04-26. Retrieved 2021-10-09.
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