Anticholinergic
Pharmaceutical compound
Glycopyrronium bromideINN: Clinical data Trade names Robinul, Cuvposa, Seebri, others Other names glycopyrrolate (USAN US AHFS /Drugs.com Monograph MedlinePlus a602014 License data Pregnancy Routes of By mouth ,intravenous ,inhalation ,topical ,injection ,subcutaneous Drug class Antimuscarinic (peripherally-selective )ATC code Legal status Legal status Pharmacokinetic dataEliminationhalf-life 0.6–1.2 hours Excretion 85% Kidney, unknown amount in the bile Identifiers CAS Number PubChem CID IUPHAR/BPS DrugBank ChemSpider UNII KEGG ChEBI ChEMBL CompTox Dashboard (EPA) ECHA InfoCard 100.008.990 Chemical and physical data Formula C 19 H 28 Br N O 3 Molar mass −1 3D model (JSmol ) 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
as cation: InChI=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
Key:ANGKOCUUWGHLCE-UHFFFAOYSA-N
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Glycopyrronium bromide is amedication of themuscarinic anticholinergic group.[ 7] blood–brain barrier and consequently has few to no central effects. It is givenby mouth ,[ 8] on the skin ,[ 9] inhalation .[ 4] [ 5] [ 6] quaternary ammonium compound .[ 2] cation , which is the activemoiety , is calledglycopyrronium (INN )[ 10] glycopyrrolate (USAN ).
The most common side effects includeirritability ,flushing ,nasal congestion , reduced secretions in the airways,dry mouth ,constipation ,diarrhea ,nausea andvomiting , andurinary retention .[ 7]
In September 2012, glycopyrronium was approved for medical use in the European Union.[ 4] Food and Drug Administration (FDA) to treat excessive underarm sweating, becoming the first drug developed specifically to reduce excessive sweating.[ 11] World Health Organization's List of Essential Medicines .[ 12]
Glycopyrronium was first used in 1961 to treatpeptic ulcers . Since 1975,intravenous glycopyrronium has been used before surgery to reducesalivary ,tracheobronchial , andpharyngeal secretions.[ 13] neostigmine , aneuromuscular blocking reversal agent , to prevent neostigmine's muscarinic effects such asbradycardia .[ 14] heart rate inreflex bradycardia as a result of avasovagal reaction, which often will also increase the blood pressure.[ 15]
It is also used to reduce excessive saliva (sialorrhea ),[ 7] [ 16] [ 17] [ 18] Ménière's disease .[ 19]
It has been used topically and orally to treathyperhidrosis , in particular,gustatory hyperhidrosis andgeneralized hyperhidrosis .[ 20] [ 21]
When inhaled, it is used to treatchronic obstructive pulmonary disease (COPD).[ 4] [ 5] [ 6] [ 22] [ 23]
Dry mouth ,urinary retention ,headaches ,vomiting ,diarrhea ,constipation , andblurry vision are possible side effects of the medication.[ 13]
Mechanism of action [ edit ] Glycopyrronium competitively blocksmuscarinic receptors ,[ 13] [ 24] cholinergic transmission.
Glycopyrronium bromide affects the gastrointestinal tracts, liver and kidney but has a very limited effect on the brain and thecentral 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 toatropine , is more resistant to penetration through the blood-brain barrier andplacenta .[ 25]
It has been studied inasthma .[ 26] [ 27]
^ "Neurological therapies" .Health Canada . Retrieved13 April 2024 .^a b "Robinul- glycopyrrolate tablet Robinul Forte- glycopyrrolate tablet" .DailyMed . 1 June 2021. Retrieved20 June 2022 .^ "Dartisla ODT- glycopyrrolate orally disintegrating tablets tablet, orally disintegrating" .DailyMed . 9 December 2021. Retrieved20 June 2022 .^a b c d "Seebri Breezhaler EPAR" .European Medicines Agency (EMA)Archived from the original on 29 February 2020. Retrieved28 February 2020 .^a b c "Tovanor Breezhaler EPAR" .European Medicines Agency (EMA)Archived from the original on 29 February 2020. Retrieved28 February 2020 .^a b c "Enurev Breezhaler EPAR" .European Medicines Agency . 17 September 2018. Retrieved29 January 2023 .^a b c d "Sialanar EPAR" .European Medicines Agency . 17 September 2018. Retrieved29 January 2023 .^ "Glycopyrrolate Oral Inhalation" .MedlinePlus .Archived from the original on 17 August 2021. Retrieved20 June 2022 .^ "Glycopyrronium Topical" .MedlinePlus .Archived from the original on 17 August 2021. Retrieved20 June 2022 .^ Bajaj V, Langtry JA (July 2007). "Use of oral glycopyrronium bromide in hyperhidrosis".The British Journal of Dermatology .157 (1):118– 121.doi :10.1111/j.1365-2133.2007.07884.x .PMID 17459043 .S2CID 29080876 . ^ "FDA OKs first drug made to reduce excessive sweating" .AP News .Archived from the original on 2018-07-02. Retrieved2018-07-02 .^ World Health Organization (2021).World Health Organization model list of essential medicines: 22nd list (2021) . Geneva: World Health Organization.hdl :10665/345533 ^a b c Chabicovsky M, Winkler S, Soeberdt M, Kilic A, Masur C, Abels C (May 2019). "Pharmacology, toxicology and clinical safety of glycopyrrolate".Toxicology and Applied Pharmacology .370 :154– 169.Bibcode :2019ToxAP.370..154C .doi :10.1016/j.taap.2019.03.016 .PMID 30905688 .S2CID 85498396 . ^ Howard J, Wigley J, Rosen G, D'mello J (February 2017). "Glycopyrrolate: It's time to review".Journal of Clinical Anesthesia .36 :51– 53.doi :10.1016/j.jclinane.2016.09.013 .PMID 28183573 . ^ Gallanosa A, Stevens JB, Quick J (June 2023)."Glycopyrrolate" .StatPearls [Internet] . Treasure Island (FL): StatPearls Publishing.PMID 30252291 . RetrievedSeptember 13, 2024 . ^ 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" Archives of Pediatrics & Adolescent Medicine .154 (12):1214– 1218.doi :10.1001/archpedi.154.12.1214 PMID 11115305 .Archived from the original on 2011-08-10. Retrieved2008-11-26 . ^ Tscheng DZ (November 2002). "Sialorrhea - therapeutic drug options".The Annals of Pharmacotherapy .36 (11):1785– 1790.doi :10.1345/aph.1C019 .PMID 12398577 .S2CID 45799443 . [permanent dead link ^ Olsen AK, Sjøgren P (October 1999)."Oral glycopyrrolate alleviates drooling in a patient with tongue cancer" .Journal of Pain and Symptom Management .18 (4):300– 302.doi :10.1016/S0885-3924(99)00080-9 PMID 10534970 . ^ Maria SA, Claudia C, Pamela G, Andrea C, Roberto A (1 December 2012). "Medical therapy in Ménière's disease".Audiological Medicine .10 (4):171– 177.doi :10.3109/1651386X.2012.718413 .S2CID 72380413 . ^ Kim WO, Kil HK, Yoon DM, Cho MJ (August 2003)."Treatment of compensatory gustatory hyperhidrosis with topical glycopyrrolate" .Yonsei Medical Journal .44 (4):579– 582.doi :10.3349/ymj.2003.44.4.579 PMID 12950111 . ^ Kim WO, Kil HK, Yoon KB, Yoon DM (May 2008). "Topical glycopyrrolate for patients with facial hyperhidrosis".The British Journal of Dermatology .158 (5):1094– 1097.doi :10.1111/j.1365-2133.2008.08476.x .PMID 18294315 .S2CID 39870296 . ^ "EPAR – Product information for Seebri Breezhaler" (PDF) .European Medicines Agency . 28 September 2012.Archived (PDF) from the original on 30 July 2018. Retrieved4 February 2017 .^ Tzelepis G, Komanapolli S, Tyler D, Vega D, Fulambarker A (January 1996)."Comparison of nebulized glycopyrrolate and metaproterenol in chronic obstructive pulmonary disease" .The European Respiratory Journal .9 (1):100– 103.doi :10.1183/09031936.96.09010100 PMID 8834341 . ^ 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" .British Journal of Pharmacology .127 (2):413– 420.doi :10.1038/sj.bjp.0702573 .PMC 1566042 PMID 10385241 . ^ Rumpler MJ, Colahan P, Sams RA (June 2014). "The pharmacokinetics of glycopyrrolate in Standardbred horses".Journal of Veterinary Pharmacology and Therapeutics .37 (3):260– 268.doi :10.1111/jvp.12085 .PMID 24325462 . ^ Hansel TT, Neighbour H, Erin EM, Tan AJ, Tennant RC, Maus JG, et al. (October 2005)."Glycopyrrolate causes prolonged bronchoprotection and bronchodilatation in patients with asthma" .Chest .128 (4):1974– 1979.doi :10.1378/chest.128.4.1974 .PMID 16236844 . Archived fromthe original ^ Gilman MJ, Meyer L, Carter J, Slovis C (November 1990)."Comparison of aerosolized glycopyrrolate and metaproterenol in acute asthma" .Chest .98 (5):1095– 1098.doi :10.1378/chest.98.5.1095 .PMID 2225951 . Archived fromthe original
mAChRs Tooltip Muscarinic acetylcholine receptors
Agonists Antagonists 3-Quinuclidinyl benzilate 4-DAMP Aclidinium bromide (+formoterol )Abediterol AF-DX 250 AF-DX 384 Ambutonium bromide Anisodamine Anisodine Antihistamines (first-generation) (e.g.,brompheniramine ,buclizine ,captodiame ,chlorphenamine (chlorpheniramine) ,cinnarizine ,clemastine ,cyproheptadine ,dimenhydrinate ,dimetindene ,diphenhydramine ,doxylamine ,meclizine ,mequitazine ,perlapine ,phenindamine ,pheniramine ,phenyltoloxamine ,promethazine ,propiomazine ,triprolidine )AQ-RA 741 Atropine Atropine methonitrate Atypical antipsychotics (e.g.,clozapine ,fluperlapine ,olanzapine (+fluoxetine ),rilapine ,quetiapine ,tenilapine ,zotepine )Benactyzine Benzatropine (benztropine) Benzilone Benzilylcholine mustard Benzydamine Bevonium BIBN 99 Biperiden Bornaprine Camylofin CAR-226,086 CAR-301,060 CAR-302,196 CAR-302,282 CAR-302,368 CAR-302,537 CAR-302,668 Caramiphen Cimetropium bromide Clidinium bromide Cloperastine CS-27349 Cyclobenzaprine Cyclopentolate Darifenacin DAU-5884 Desfesoterodine Dexetimide DIBD Dicycloverine (dicyclomine) Dihexyverine Difemerine Diphemanil metilsulfate Ditran Drofenine EA-3167 EA-3443 EA-3580 EA-3834 Emepronium bromide Etanautine Etybenzatropine (ethybenztropine) Fenpiverinium Fentonium bromide Fesoterodine Flavoxate Glycopyrronium bromide (+beclometasone/formoterol ,+indacaterol ,+neostigmine )Hexahydrodifenidol Hexahydrosiladifenidol Hexbutinol Hexocyclium Himbacine HL-031,120 Homatropine Imidafenacin Ipratropium bromide (+salbutamol )Isopropamide J-104,129 Hyoscyamine Mamba toxin 3 Mamba toxin 7 Mazaticol Mebeverine Meladrazine Mepenzolate Methantheline Methoctramine Methylatropine Methylhomatropine Methylscopolamine Metixene Muscarinic toxin 7 N-Ethyl-3-piperidyl benzilate N-Methyl-3-piperidyl benzilate Nefopam Octatropine methylbromide (anisotropine methylbromide) Orphenadrine Otenzepad (AF-DX 116) Otilonium bromide Oxapium iodide Oxitropium bromide Oxybutynin Oxyphencyclimine Oxyphenonium bromide PBID PD-102,807 PD-0298029 Penthienate Pethidine pFHHSiD Phenglutarimide Phenyltoloxamine Pipenzolate bromide Piperidolate Pirenzepine Piroheptine Pizotifen Poldine Pridinol Prifinium bromide Procyclidine Profenamine (ethopropazine) Propantheline bromide Propiverine Quinidine 3-Quinuclidinyl thiochromane-4-carboxylate Revefenacin Rociverine RU-47,213 SCH-57,790 SCH-72,788 SCH-217,443 Scopolamine (hyoscine) Scopolamine butylbromide (hyoscine butylbromide) Silahexacyclium Sofpironium bromide Solifenacin SSRIs Tooltip Selective serotonin reuptake inhibitors (e.g.,femoxetine ,paroxetine )Telenzepine Terodiline Tetracyclic antidepressants (e.g.,amoxapine ,maprotiline ,mianserin ,mirtazapine )Tiemonium iodide Timepidium bromide Tiotropium bromide Tiquizium bromide Tofenacin Tolterodine Tricyclic antidepressants (e.g.,amitriptyline (+perphenazine ),amitriptylinoxide ,butriptyline ,cidoxepin ,clomipramine ,desipramine ,desmethyldesipramine ,dibenzepin ,dosulepin (dothiepin) ,doxepin ,imipramine ,lofepramine ,nitroxazepine ,northiaden (desmethyldosulepin) ,nortriptyline ,protriptyline ,quinupramine ,trimipramine )Tridihexethyl Trihexyphenidyl Trimebutine Tripitamine (tripitramine) Tropacine Tropatepine Tropicamide Tropine benzilate Trospium chloride Typical antipsychotics (e.g.,chlorpromazine ,chlorprothixene ,cyamemazine (cyamepromazine) ,loxapine ,mesoridazine ,thioridazine )Umeclidinium bromide (+vilanterol )WIN-2299 Xanomeline Zamifenacin
Precursors (andprodrugs )
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