Aclidinium bromide

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Aclidinium
)
Not to be confused with
Acridinium bromide or Clidinium bromide
.
Aclidinium bromide
Clinical data
Trade namesBretaris Genuair, Eklira Genuair, Tudorza Pressair
AHFS/Drugs.comMonograph
License data
Routes of
administration		Inhalation
ATC code
Legal status
Legal status
Pharmacokinetic data
Bioavailability<5% (in system)
30% (in lung)
MetabolismEster hydrolysis
Elimination half-life2–3 hrs
Duration of action>24 hrs
Excretion65% urine, 33% feces
Identifiers
  • [(8R)-1-(3-Phenoxypropyl)-1-azoniabicyclo[2.2.2]octan-8-yl] 2-hydroxy-2,2-dithiophen-2-ylacetate bromide
JSmol)
  • [Br-].O=C(O[C@@H]3C2CC[N+](CCCOc1ccccc1)(CC2)C3)C(O)(c4sccc4)c5sccc5
  • InChI=1S/C26H30NO4S2.BrH/c28-25(26(29,23-9-4-17-32-23)24-10-5-18-33-24)31-22-19-27(14-11-20(22)12-15-27)13-6-16-30-21-7-2-1-3-8-21;/h1-5,7-10,17-18,20,22,29H,6,11-16,19H2;1H/q+1;/p-1/t20?,22-,27?;/m0./s1 ☒N
  • Key:XLAKJQPTOJHYDR-QTQXQZBYSA-M ☒N
 ☒NcheckY (what is this?)  (verify)

Aclidinium bromide (

INN) is a long-acting, inhaled muscarinic antagonist (LAMA) approved in the United States on July 24, 2012[2] as a maintenance treatment for chronic obstructive pulmonary disease (COPD).[3]

Evidence shows that it can improve

tiotropium or other commonly used medications from the class of LAMAs.[4]

Aclidinium is delivered via a multidose

dry powder inhaler, the Genuair inhaler. It is on the World Health Organization's List of Essential Medicines.[5]

Adverse effects

The substance is generally well tolerated. Common side effects (in more than 1% of patients) are

diarrhoea and nausea. The latter is less common under the drug than under placebo. Skin reactions such as rash, as well as side effects that are typical of muscarinic antagonists (fast heart rate, palpitations, and urinary retention), occur in less than 1% of patients.[6][7]

A small increase of

cardiovascular risk cannot be excluded from available data. Patients with relevant cardiovascular diseases were excluded from studies.[8]

Interactions

No systematic interaction studies have been performed. It is expected that adverse effects of aclidinium increase if it is combined with other muscarinic antagonists. In clinical practice, no interactions with other COPD medications such as

metabolized as soon as it reaches the bloodstream, it is considered to have a very low potential for interactions.[6][8]

Pharmacology

Mechanism of action

Further information: Muscarinic antagonist

Aclidinium is a long-acting,

tiotropium are 0.47 hours and 62.2 hours, respectively.[8]

Its action at subtype M3 at the smooth muscle of the bronchioles is responsible for its desired effect: it reduces contraction of these muscles and improves the airflow.[6][7] M2 affinity is the main reason for adverse effects at the heart.[8]

Pharmacokinetics

About 30% of inhaled aclidinium are deposited in the lung.

hydrolysed to the carboxylic acid and the alcohol, so that less than 5% of the inhaled dose are found unchanged in the plasma. Hydrolysis is both non-enzymatic and enzymatic, the latter mainly by butyrylcholinesterase.[6][8]

The acid metabolite has a plasma protein binding of 87%, and the alcohol of 15%. These

metabolites are found to 65% in the urine and to 33% in the faeces. Elimination half-life is two to three hours. Unchanged aclidinium accounts for only 0.1% of the excreted dose.[6]

Chemistry

Aclidinium is a quaternary ammonium cation with an asymmetric carbon atom. It is used as the pure R-enantiomer. The salt, aclidinium bromide, is a crystalline powder that is hardly soluble in water or ethanol.

Society and culture

Brand names

It is marketed under the brand name Tudorza Pressair in the US, Eklira Genuair in the UK, and Tudorza Genuair in Canada; licensed to Menarini under the brand name Bretaris Genuair for majority of EU member states.[9]

An inhalable combination with formoterol is marketed as Brimica Genuair[10] and Duaklir Genuair[11] in the European Union.

References

  1. ^ "Prescription medicines: registration of new chemical entities in Australia, 2014". Therapeutic Goods Administration (TGA). 21 June 2022. Retrieved 10 April 2023.
  2. ^ "Forest Laboratories and Almirall Announce FDA Approval of Tudorza Pressair for the Long-Term Maintenance Treatment of COPD" (Press release). Forest Laboratories. Retrieved 2012-07-24.
  3. S2CID 10533142
    .
  4. ^
    PMID 25234126
    .
  5. hdl:10665/345533
    . WHO/MHP/HPS/EML/2021.02.
  6. ^ a b c d e Haberfeld H, ed. (2015). Austria-Codex (in German). Vienna: Österreichischer Apothekerverlag.
  7. ^ a b c FDA Professional Drug Information on Tudorza Pressair.
  8. ^
    ISBN 978-3-7741-9846-3
    .
  9. ^ "Almirall and Menarini sign a licence agreement and commercial alliance for Aclidinium in the majority of European member states and a number of non-EU countries" (Press release). Menarini. Retrieved 2012-03-26.
  10. ^ "Brimica Genuair: Uses, Side Effects, Benefits/Risks". Drugs.com. 19 November 2014. Retrieved 26 July 2020.
  11. ^ "Duaklir Genuair: Uses, Side Effects, Benefits/Risks". Drugs.com. 19 November 2014. Retrieved 26 July 2020.
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