Chemical compound
Glycopyrronium bromide
Trade names Robinul, Cuvposa, Seebri, others Other names glycopyrrolate (
USAN
US )
AHFS /
Drugs.com
Monograph
MedlinePlus
a602014
License data
Pregnancy category
Routes of administration
By mouth ,
intravenous ,
inhalation ,
topical ,
injection ,
subcutaneous
Drug class
Antimuscarinic agent
ATC code
Legal status
Elimination half-life 0.6–1.2 hours
Excretion 85% Kidney, unknown amount in the bile
3-[2-Cyclopentyl(hydroxy)phenylacetoxy]-1,1-dimethylpyrrolidinium bromide
CAS Number
PubChem
CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (
EPA )
ECHA InfoCard
100.008.990
Formula C 19 H 28 Br N O 3
Molar mass 398.341 g·mol−1 3D model (
JSmol )
C[N+]1(CCC(C1)OC(=O)C(C2CCCC2)(C3=CC=CC=C3)O)C.[Br-]
as cation: C[N+]1(CCC(C1)OC(=O)C(C2CCCC2)(C3=CC=CC=C3)O)C
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
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
^
a
b
"Robinul- glycopyrrolate tablet Robinul Forte- glycopyrrolate tablet" . DailyMed . 1 June 2021. Retrieved 20 June 2022 .
^
"Dartisla ODT- glycopyrrolate orally disintegrating tablets tablet, orally disintegrating" . DailyMed . 9 December 2021. Retrieved 20 June 2022 .
^
a
b
c
d
"Seebri Breezhaler EPAR" .
European Medicines Agency (EMA) . 17 September 2018.
Archived from the original on 29 February 2020. Retrieved 28 February 2020 .
^
a
b
c
"Tovanor Breezhaler EPAR" .
European Medicines Agency (EMA) . 17 September 2018.
Archived from the original on 29 February 2020. Retrieved 28 February 2020 .
^
a
b
c
"Enurev Breezhaler EPAR" . European Medicines Agency . 17 September 2018. Retrieved 29 January 2023 .
^
a
b
c
d
"Sialanar EPAR" . European Medicines Agency . 17 September 2018. Retrieved 29 January 2023 . Text was copied from this source which is copyright European Medicines Agency. Reproduction is authorized provided the source is acknowledged.
^
"Glycopyrrolate Oral Inhalation" . MedlinePlus .
Archived from the original on 17 August 2021. Retrieved 20 June 2022 .
^
"Glycopyrronium Topical" . MedlinePlus .
Archived from the original on 17 August 2021. Retrieved 20 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. Retrieved 2018-07-02 .
^
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.
^
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.
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 .
^ 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. Retrieved 2008-11-26 .
^ 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. Retrieved 4 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, Barnes PJ (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 from
the original on 2013-04-14.
^ 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 from
the original on 2013-04-14.
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