Glycopyrronium bromide

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Glycopyrronium bromide
INN: Glycopyrronium
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 (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
  • 3-[2-Cyclopentyl(hydroxy)phenylacetoxy]-1,1-dimethylpyrrolidinium bromide
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
E number{{#property:P628}}
CompTox Dashboard (EPA)
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Chemical and physical data
FormulaC19H28BrNO3
Molar mass398.341 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
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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 is given by mouth,[8] via intravenous injection, on the skin,[9] and 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

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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

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

Pharmacology

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Mechanism of action

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Glycopyrronium competitively blocks muscarinic receptors,[13][24] thus inhibiting cholinergic transmission.

Pharmacokinetics

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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

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

References

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