Glycopyrronium bromide

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Glycopyrronium bromide
Glycopyrroniumbromide Structural Formulae.png
Systematic (IUPAC) name
3-[2-Cyclopentyl(hydroxy)phenylacetoxy]-1,1-dimethylpyrrolidinium bromide
Clinical data
Pregnancy cat. B (US)
Legal status -only (US)
Identifiers
ATC code A03AB02 R03BB06
PubChem CID 11693
ChemSpider 11201
Chemical data
Formula C19H28BrNO3 
Mol. mass 398.335 g/mol
Glycopyrronium
Glycopyrrolate.svg
Systematic (IUPAC) name
3-(2-Cyclopentyl-2-hydroxy-2-phenylacetoxy)-1,1-dimethylpyrrolidinium
Clinical data
AHFS/Drugs.com monograph
MedlinePlus a602014
Pregnancy cat. B (US)
Legal status -only (US)
Routes oral, IV
Pharmacokinetic data
Half-life 0.6–1.2 hours
Excretion 85% renal, unknown amount in the bile
Identifiers
CAS number 596-51-0 YesY
ATC code A03AB02 R03BB06
PubChem CID 3494
DrugBank DB00986
ChemSpider 3374
UNII V92SO9WP2I YesY
KEGG D00540 YesY
ChEMBL CHEMBL1201335 N
Chemical data
Formula C19H28NO3+
Mol. mass 318.431 g/mol
 N (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[edit]

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

Medical uses[edit]

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[edit]

Since glycopyronium 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.

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

References[edit]

  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. 
  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. 
  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. 
  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. 
  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. 
  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. 
  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.