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Ipratropium bromide

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Ipratropium bromide
Clinical data
Trade namesAtrovent, Apovent, Ipraxa, Rinatec, other
AHFS/Drugs.comMonograph
Routes of
administration		Inhalation
ATC code
Legal status
Legal status
Pharmacokinetic data
Protein binding0 to 9% in vitro
MetabolismHepatic
Elimination half-life2 hours
Identifiers
  • [8-methyl-8-(1-methylethyl)- 8-azoniabicyclo[3.2.1] oct-3-yl] 3-hydroxy-2-phenyl-propanoate
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.040.779 Edit this at Wikidata
Chemical and physical data
FormulaC20H30BrNO3
Molar mass412.37 g/mol g·mol−1
3D model (JSmol)
  • CC(C)[N+]1([C@@H]2CC[C@H]1C[C@H](C2)OC(=O)C(CO)C3=CC=CC=C3)C.[Br-]
  • InChI=1S/C20H30NO3.BrH/c1-14(2)21(3)16-9-10-17(21)12-18(11-16)24-20(23)19(13-22)15-7-5-4-6-8-15;/h4-8,14,16-19,22H,9-13H2,1-3H3;1H/q+1;/p-1/t16-,17+,18+,19?,21?;
  • Key:LHLMOSXCXGLMMN-WDTICOSOSA-M
 ☒NcheckY (what is this?)  (verify)

Ipratropium bromide, sold under the trade name Atrovent among others, is a medication which opens up the medium and large airways in the lungs.[1] It is used to treat the symptoms of chronic obstructive pulmonary disease and asthma.[1] It is used by inhaler or nebulizer.[1] Onset of action is typically within 15 to 30 minutes and lasts for three to five hours.[1]

Common side effects include dry mouth, cough, and inflammation of the airways.[1] Potentially serious side effects include urinary retention, worsening spasms of the airways, and a severe allergic reaction.[1] It appears to be safe in pregnancy and breastfeeding.[1][2] Ipratropium is a muscarinic antagonist, a type of anticholinergic, which works by causing smooth muscles to relax.[1]

Ipratropium bromide was developed in Germany in 1976.[3] It was approved for medical use in the United States in 1986.[1] It is on the World Health Organization's List of Essential Medicines, the most effective and safe medicines needed in a health system.[4] Ipratropium is available as a generic medication.[1] The wholesale price in the developing world is about 6.60 USD for a 200 dose inhaler.[5] In the United States, a month worth of medication costs 100 to 200 USD.[6]

Medical uses

Ipratropium is administered by inhalation for the treatment of chronic obstructive pulmonary disease (COPD) and asthma exacerbation. For that purpose, it is supplied in a canister for use in an inhaler or in single dose vials for use in a nebulizer.[7]

It is also 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 — USAN) under the trade names Combivent (a non-aerosol 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 nasal solution sprayed into the nostrils can reduce rhinorrhea but will not help nasal congestion.[8]

Combination with beta-adrenergic agonists increases the dilating effect on the bronchi.

Contraindications

The main contraindication for inhaled ipratropium is 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.[9][10]

Peanut allergy

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.[11]

Side effects

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.[10] The inhalation itself can cause headache and irritation of the throat in a few percent of patients.[9]

Urinary retention has been reported in patients receiving doses by nebulizer. As a result, caution may be warranted, especially by men with prostatic hypertrophy.[12]

Interactions

Interactions with other anticholinergics like tricyclic antidepressants, anti-Parkinson drugs and quinidine, which theoretically increase side effects, are clinically irrelevant when ipratropium is administered as an inhalant.[9][10]

Pharmacology

Chemically, ipratropium bromide is a quaternary ammonium compound (which is indicated by the -ium per the BAN and the USAN) [13] obtained by treating atropine with isopropyl bromide, thus the name: isopropyl + atropine.[citation needed]

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.[14] 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,[9] and does not diffuse into the blood, which prevents systemic side effects. Ipratropium is a derivative of atropine[15] 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 salbutamol (albuterol) as a rescue medication.

References

  1. ^ a b c d e f g h i j "Ipratropium Bromide". The American Society of Health-System Pharmacists. Archived from the original on 2015-12-08. Retrieved Dec 2, 2015. {{cite web}}: Unknown parameter |deadurl= ignored (|url-status= suggested) (help)
  2. ^ Yaffe, Gerald G. Briggs, Roger K. Freeman, Sumner J. (2011). Drugs in pregnancy and lactation : a reference guide to fetal and neonatal risk (9th ed.). Philadelphia: Wolters Kluwer Health/Lippincott Williams & Wilkins. p. 763. ISBN 9781608317080. Archived from the original on 2016-03-05. {{cite book}}: Unknown parameter |deadurl= ignored (|url-status= suggested) (help)CS1 maint: multiple names: authors list (link)
  3. ^ Ravina, Enrique (2011). The evolution of drug discovery : from traditional medicines to modern drugs (1. Aufl. ed.). Weinheim: Wiley-VCH. p. 144. ISBN 9783527326693. Archived from the original on 2015-12-08. {{cite book}}: Unknown parameter |deadurl= ignored (|url-status= suggested) (help)
  4. ^ "WHO Model List of Essential Medicines (19th List)" (PDF). World Health Organization. April 2015. Archived from the original (PDF) on 13 December 2016. Retrieved 8 December 2016. {{cite web}}: Unknown parameter |deadurl= ignored (|url-status= suggested) (help)
  5. ^ "Ipratropium Bromide". International Drug Price Indicator Guide. Retrieved 5 December 2015.[permanent dead link]
  6. ^ Hamilton, Richart (2015). Tarascon Pocket Pharmacopoeia 2015 Deluxe Lab-Coat Edition. Jones & Bartlett Learning. p. 455. ISBN 9781284057560.
  7. ^ Ipratropium Oral Inhalation Archived 2012-09-02 at the Wayback Machine PubMed Health Retrieved May 28, 2012
  8. ^ Atrovent Nasal Spray Archived 2012-01-11 at the Wayback Machine Drugs.com Retrieved May 28, 2012
  9. ^ a b c d Haberfeld, H, ed. (2009). Austria-Codex (in German) (2009/2010 ed.). Vienna: Österreichischer Apothekerverlag. ISBN 3-85200-196-X.
  10. ^ a b c Dinnendahl, V; Fricke, U, eds. (2010). Arzneistoff-Profile (in German). Vol. 2 (23 ed.). Eschborn, Germany: Govi Pharmazeutischer Verlag. ISBN 978-3-7741-9846-3.
  11. ^ Ipratropium Soybean and Nuts Allergy Archived 2012-05-13 at the Wayback Machine EMSMedRx Retrieved April 6, 2013
  12. ^ 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.
  13. ^ "The Use of Common Stems in the Selection of International Nonproprietary Names (INN) for Pharmaceutical Substances". who.int. World Health Organization. 2000. Retrieved July 18, 2018.
  14. ^ Ipratropium Archived 2012-05-19 at the Wayback Machine Drugs.com
  15. ^ 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.
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