Jump to content

Glycopyrronium bromide

From Wikipedia, the free encyclopedia

This is an old revision of this page, as edited by Hydra Rain (talk | contribs) at 22:49, 12 March 2015. The present address (URL) is a permanent link to this revision, which may differ significantly from the current revision.

Glycopyrronium bromide
Clinical data
ATC code
Legal status
Legal status
Identifiers
  • 3-[2-Cyclopentyl(hydroxy)phenylacetoxy]-1,1-dimethylpyrrolidinium bromide
PubChem CID
ChemSpider
CompTox Dashboard (EPA)
ECHA InfoCard100.008.990 Edit this at Wikidata
Chemical and physical data
FormulaC19H28BrNO3
Molar mass398.335 g/mol g·mol−1
3D model (JSmol)
  • C[N+]1(CCC(C1)OC(=O)C(C2CCCC2)(C3=CC=CC=C3)O)C.[Br-]
  • 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
Clinical data
AHFS/Drugs.comMonograph
MedlinePlusa602014
Routes of
administration		oral, IV
ATC code
Legal status
Legal status
Pharmacokinetic data
Elimination half-life0.6–1.2 hours
Excretion85% renal, unknown amount in the bile
Identifiers
  • 3-(2-Cyclopentyl-2-hydroxy-2-phenylacetoxy)-1,1-dimethylpyrrolidinium
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.008.990 Edit this at Wikidata
Chemical and physical data
FormulaC19H28NO3+
Molar mass318.431 g/mol g·mol−1
3D model (JSmol)
  • C[N+]1(CCC(C1)OC(=O)C(C2CCCC2)(C3=CC=CC=C3)O)C
  • 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
 ☒NcheckY (what is this?)  (verify)

Glycopyrronium bromide is a medication of the muscarinic anticholinergic group. It does not cross the blood–brain barrier and consequently has no to few central effects. A synthetic quaternary amine, it is available in oral and intravenous (i.v.) forms. It was developed by Sosei and licensed to Novartis in 2005. The cation, which is the active moiety, is also known as glycopyrrolate.[1]

Pharmacology

Glycopyrronium blocks muscarinic receptors,[2] thus inhibiting cholinergic transmission.

Medical uses

In anesthesia, glycopyrronium injection can be used as a preoperative medication in order to reduce salivary, tracheobronchial, and pharyngeal secretions, as well as decreasing the acidity of gastric secretion. It is also used in conjunction with neostigmine, a neuromuscular blocking reversal agent, to prevent neostigmine's muscarinic effects such as bradycardia.

It is also used to reduce excessive saliva (sialorrhea).[3][4][5]

It decreases acid secretion in the stomach and so may be used for treating stomach ulcers, in combination with other medications.

Use in treating asthma[6][7] and COPD[8] has been described.

It has been used topically and orally to treat hyperhidrosis.[9][10]

Side effects

Since glycopyrronium reduces the body's sweating ability, it can even cause fever and heat stroke in hot environments. Dry mouth, difficulty urinating, headaches, diarrhea and constipation are also observed side effects of the medication.

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 tendency of glycopyrronium followed a tri-exponential equation, followed by rapid disappearance from the blood followed by a prolonger 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 ro atropine, is more resistant to penetration through the blood-brain barrier and placenta.

The medication also induces drowsiness or blurred vision, an effect exacerbated by the consumption of alcohol.

References

  1. ^ 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.
  2. ^ 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.{{cite journal}}: CS1 maint: multiple names: authors list (link)
  3. ^ 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.{{cite journal}}: CS1 maint: multiple names: authors list (link)
  4. ^ Tscheng DZ (November 2002). "Sialorrhea - therapeutic drug options". Ann Pharmacother. 36 (11): 1785–90. doi:10.1345/aph.1C019. PMID 12398577.
  5. ^ 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.
  6. ^ 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. {{cite journal}}: Explicit use of et al. in: |author= (help)CS1 maint: multiple names: authors list (link)
  7. ^ 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.{{cite journal}}: CS1 maint: multiple names: authors list (link)
  8. ^ 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.{{cite journal}}: CS1 maint: multiple names: authors list (link)
  9. ^ Kim WO, Kil HK, Yoon DM, Cho MJ (August 2003). "Treatment of compensatory gustatory hyperhidrosis with topical glycopyrrolate" ([dead link]). Yonsei Med. J. 44 (4): 579–82. PMID 12950111.{{cite journal}}: CS1 maint: multiple names: authors list (link)
  10. ^ 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.{{cite journal}}: CS1 maint: multiple names: authors list (link)
Retrieved from "https://en.wikipedia.org/w/index.php?title=Glycopyrronium_bromide&oldid=651114500"