Tadalafil powder

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Tadalafil powder is a medication used to treat erectile dysfunction (ED), benign prostatic hyperplasia (BPH), and pulmonary arterial hypertension.[1] It is a tablet taken by mouth.[1] Onset is typically within half an hour and the duration is up to 36 hours.[1]

Tadalafil was approved for medical use in the United States in 2003.[1] It is available as a generic medication in the United States and United Kingdom.[2] In 2017, it was the 282nd most commonly prescribed medication in the United States, with more than one million prescriptions.[3][4]

Chemistry

Tadalafil is an annulated 2,5-diketopiperazine.[5] It is also a 1,2,3,4-tetrahydro-β-carboline.

Tadalafil can be synthesized starting from (D)-tryptophan methyl ester and piperonal via a Pictet–Spengler reaction. This is followed by condensations with chloroacetyl chloride and methylamine to complete the diketopiperazine ring:[6]

Tadalafil synthesis

References

  1. 1.0 1.1 1.2 1.3 "Tadalafil Monograph for Professionals". American Society of Health-System Pharmacists. https://www.drugs.com/monograph/tadalafil.html. 
  2. British national formulary : BNF 76 (76 ed.). Pharmaceutical Press. 2018. pp. 796. ISBN 9780857113382. 
  3. "The Top 300 of 2020". https://clincalc.com/DrugStats/Top300Drugs.aspx. 
  4. "Tadalafil - Drug Usage Statistics". https://clincalc.com/DrugStats/Drugs/Tadalafil. 
  5. Borthwick AD (May 2012). "2,5-Diketopiperazines: Synthesis, Reactions, Medicinal Chemistry, and Bioactive Natural Products". Chemical Reviews 112 (7): 3641–3716. doi:10.1021/cr200398y. PMID 22575049. 
  6. Baumann M (May 2011). "An overview of the key routes to the best selling 5-membered ring heterocyclic pharmaceuticals". Beilstein Journal of Organic Chemistry 7: 442–495. doi:10.3762/BJOC.7.57. PMC 3107522. PMID 21647262.