Ipratropium bromide

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Ipratropium bromide
Ipratropiumbromid.svg
Systematic (IUPAC) name
[8-methyl-8-(1-methylethyl)- 8-azoniabicyclo[3.2.1] oct-3-yl] 3-hydroxy-2-phenyl-propanoate
Clinical data
Trade names Atrovent, Apovent, Ipraxa, Aerovent, Rinatec
AHFS/Drugs.com monograph
Pregnancy cat. B (US)
Legal status POM (UK) -only (US)
Routes Inhalation
Pharmacokinetic data
Protein binding 0 to 9% in vitro
Metabolism Hepatic
Half-life 2 hours
Identifiers
CAS number 22254-24-6
60205-81-4 (cation)
ATC code R01AX03 R03BB01
PubChem CID 657308
IUPHAR ligand 325
DrugBank DB00332
ChemSpider 10481997
UNII GR88G0I6UL YesY
ChEMBL CHEMBL1464005 N
Chemical data
Formula C20H30BrNO3 
Mol. mass 412.37 g/mol
 N (what is this?)  (verify)

Ipratropium bromide (INN, trade names Atrovent, Apovent, Ipraxa, Aerovent and Rinatec) is a drug that relieves bronchial spasms. It is an anticholinergic drug used for the treatment of chronic obstructive pulmonary disease and acute asthma. It blocks the muscarinic acetylcholine receptors in the smooth muscles of the bronchi in the lungs, opening the bronchi.[1]

It is on the World Health Organization's List of Essential Medicines, a list of the most important medication needed in a basic health system.[2]

Medical uses[edit]

Ipratropium is administered by inhalation for the treatment of chronic obstructive pulmonary disease (COPD). For that purpose it is supplied in a canister for use in an inhaler or in single dose vials for use in a nebulizer.[3]

It is aso used to treat and prevent minor and moderate bronchial asthma, especially asthma that is accompanied by cardiovascular system diseases.[citation needed]

It is also combined with salbutamol (albuterol, USA) under the trade names Combivent (metered-dose inhaler or MDI) and Duoneb (nebulizer) for the management of COPD and asthma, and with fenoterol (trade names Duovent and Berodual N) for the management of asthma.

Ipratropium as a .03% nasal solution sprayed into the nostrils can reduce rhinorrhea but will not help nasal congestion.[4]

Contraindications[edit]

There are no contraindications for inhaled ipratropium, apart from hypersensitivity to atropine and related substances. For oral administration, contraindications are similar to other anticholinergics; they include narrow angle glaucoma and obstructions in the gastrointestinal tract and urinary system.[5][6]

Peanut allergy[edit]

Previously atrovent inhalers used chlorofluorocarbon (CFC) as a propellant and contained soy lecithin in the propellant ingredients. In 2008 all CFC inhalers were phased out and hydrofluoroalkane (HFA) inhalers replaced them. Allergy to peanuts was noted for the inhaler as a contraindication but now is not. It has never been a contraindication when administered as a nebulized solution.[7]

Side effects[edit]

If ipratropium is inhaled, side effects resembling those of other anticholinergics are minimal. However, dry mouth and sedation have been reported. Also, effects such as skin flushing, tachycardia, acute angle-closure glaucoma, nausea, palpitations and headache have been observed. Inhaled ipratropium does not decrease mucociliary clearance.[6] The inhalation itself can cause headache and irritation of the throat in a few percent of patients.[5]

Urinary retention has been reported in patients receiving doses by nebulizer. As a result, caution may be warranted, especially by men with prostatic hypertrophy.[8]

Interactions[edit]

Combination with beta-adrenergic agonists, as well as theophylline and other xanthine derivatives, increases the dilating effect on the bronchi. Interactions with other anticholinergics like tricyclic antidepressants, antiparkinson drugs and quinidine, which theoretically increase side effects, are clinically irrelevant when ipratropium is administered as an inhalant.[5][6]

Pharmacology[edit]

Ipratropium exhibits broncholytic action by reducing cholinergic influence on the bronchial musculature. It blocks muscarinic acetylcholine receptors, without specificity for subtypes, and therefore promotes the degradation of cyclic guanosine monophosphate (cGMP), resulting in a decreased intracellular concentration of cGMP.[9] Most likely due to actions of cGMP on intracellular calcium, this results in decreased contractility of smooth muscle in the lung, inhibiting bronchoconstriction and mucus secretion. It is a nonselective muscarinic antagonist,[5] and does not diffuse into the blood, which prevents systemic side effects. Ipratropium is a derivative of atropine[10] but is a quaternary amine and therefore does not cross the blood–brain barrier, which prevents central side effects (anticholinergic syndrome). Ipratropium is not considered a short-acting bronchodilator and should never be used in place of albuterol (salbutamol) as a rescue medication.

Synthesis[edit]

Ipratropium bromide, 3α-hydroxy-8-isopropyl-1αH,5αH-tropanium bromide, is synthesized by reacting N-isopropylnoratropine with methyl bromide

  • K. Zeile, W. Schulz, R. Bonholzer, H. Wick, U.S. Patent 3,505,337 (1967).
  • K. Zeile, W. Schulz, R. Bonholzer, H. Wick, S. Afr. Pat., 67 07.766 (1968).
  • W. Schulz, R. Banholzer, K.H. Pook, Arznei.-Forsch., 26, 960 (1976).

See also[edit]

References[edit]

  1. ^ Baigelman W, Chodosh S (March 1977). "Bronchodilator action of the anticholinergic drug, ipratropium bromide (Sch 1000), as an aerosol in chronic bronchitis and asthma". Chest 71 (3): 324–8. doi:10.1378/chest.71.3.324. PMID 138578. 
  2. ^ "WHO Model List of EssentialMedicines". World Health Organization. October 2013. Retrieved 22 April 2014. 
  3. ^ Ipratropium Oral Inhalation PubMed Health Retrieved May 28, 2012
  4. ^ Atrovent Nasal Spray Drugs.com Retrieved May 28, 2012
  5. ^ a b c d Haberfeld, H, ed. (2009). Austria-Codex (in German) (2009/2010 ed.). Vienna: Österreichischer Apothekerverlag. ISBN 3-85200-196-X. 
  6. ^ a b c Dinnendahl, V, Fricke, U, ed. (2010). Arzneistoff-Profile (in German) 2 (23 ed.). Eschborn, Germany: Govi Pharmazeutischer Verlag. ISBN 978-3-7741-9846-3. 
  7. ^ Ipratropium Soybean and Nuts Allergy EMSMedRx Retrieved April 6, 2013
  8. ^ Afonso, A. S. M.; Verhamme, K. M. C.; Stricker, B. H. C.; Sturkenboom, M. C. J. M.; Brusselle, G. G. O. (2011). "Inhaled anticholinergic drugs and risk of acute urinary retention". BJU International 107 (8): 1265–1272. doi:10.1111/j.1464-410X.2010.09600.x. PMID 20880196.  edit
  9. ^ Ipratropium Drugs.com
  10. ^ Yamatake Y, Sasagawa S, Yanaura S, Okamiya Y (1977). "[Antiallergic asthma effect of ipratropium bromide (Sch 1000) in dogs (author's transl)]". Nippon Yakurigaku Zasshi (in Japanese) 73 (7): 785–91. doi:10.1254/fpj.73.785. PMID 145994.