Ipratropium bromide

Ipratropium bromide

Systematic (IUPAC) name
[8-methyl-8-(1-methylethyl)- 8-azoniabicyclo[3.2.1] oct-3-yl] 3-hydroxy-2-phenyl-propanoate
Clinical data
AHFS/Drugs.com	monograph
Pregnancy cat.	B(US)
Legal status	POM (UK)
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	APRD00537
ChemSpider	19962157 Y
UNII	GR88G0I6UL Y
ChEMBL	CHEMBL541165 N
Chemical data
Formula	C20H30BrNO3
Mol. mass	412.37 g/mol
SMILES	eMolecules & PubChem
InChI InChI=1S/C20H30NO3/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/q+1/t16-,17+,18+,19?,21? Y Key:OEXHQOGQTVQTAT-BHIXFJMTSA-N Y
N(what is this?)  bromide (verify)

Ipratropium bromide (INN, trade names Atrovent, Apovent, and Aerovent) 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]

Uses

It is administered by inhalation for the treatment of chronic obstructive pulmonary disease (COPD).

Ipratropium 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 can reduce rhinorrhea but will not help nasal congestion.

Contraindications

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.^[2][3]

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 ocular dislocure, nausea, palpitations and headache have been observed. Inhaled ipratropium does not decrease mucociliary clearance.^[2] The inhalation itself can cause headache and irritation of the throat in a few percent of patients.^[3] Some studies suggest that patients with peanut allergies may have a anaphylactic response to atrovent.^{[citation needed]}

Pharmacology

It blocks muscarinic acetylcholine receptors, without specificity for subtypes, and therefore inhibits degradation of cyclic guanosine monophosphate (cGMP), resulting in an increase of cGMP concentration. 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, and does not diffuse into the blood, which prevents systemic side effects. Ipratropium is a derivative of atropine^[4] but is a quaternary amine and therefore does not cross the blood-brain barrier, which prevents central side effects (anticholinergic syndrome). Ipratropium is considered a short-acting bronchodilator.^[5][6]

Interactions

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.^[2][3]

See also

• Epinephrine
• Beclometasone dipropionate
• Salbutamol
• Ipratropium/salbutamol

References

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. http://www.chestjournal.org/cgi/pmidlookup?view=long&pmid=138578. 
2. ^ ^{a b c} Dinnendahl, V, Fricke, U, ed (2010) (in German). Arzneistoff-Profile. 2 (23 ed.). Eschborn, Germany: Govi Pharmazeutischer Verlag. ISBN 978-3-7741-98-46-3. 
3. ^ ^{a b c} Haberfeld, H, ed (2009) (in German). Austria-Codex (2009/2010 ed.). Vienna: Österreichischer Apothekerverlag. ISBN 3-85200-196-X. 
4. ^ Yamatake Y, Sasagawa S, Yanaura S, Okamiya Y (1977). "[Antiallergic asthma effect of ipratropium bromide (Sch 1000) in dogs (author's transl)]" (in Japanese). Nippon Yakurigaku Zasshi 73 (7): 785–91. PMID 145994. 
5. ^ Kerstjens HA, Bantje TA, Luursema PB, et al. (2007). "Effects of short-acting bronchodilators added to maintenance tiotropium therapy". Chest 132 (5): 1493–9. doi:10.1378/chest.06-3059. PMID 17890476. 
6. ^ Knott L (November 20, 2007). "Antimuscarinic Bronchodilators". PatientUK. EMIS. http://www.patient.co.uk/showdoc/40025112/. Retrieved 2008-06-16.