Tadalafil

Tadalafil
Clinical data
Pronunciation/təˈdæləfɪl/ tə-DAL-ə-fil
Trade namesCialis, others
AHFS/Drugs.comMonograph
MedlinePlusa604008
License data
Pregnancy
category
Routes of
administration		By mouth
Drug classPDE5 inhibitor
ATC code
Legal status
Legal status
  • AU: S4 (Prescription only)[2]
  • UK: POM (Prescription only)[3]
  • US: ℞-only[4][5]
  • EU: Rx-only[6]
  • In general: ℞ (Prescription only)
Pharmacokinetic data
BioavailabilityVaries
Protein binding94%
MetabolismLiver (predominantly CYP3A4)
MetabolitesCatechol metabolite
Onset of action30 minutes
Elimination half-life17.5 hours
Duration of action≤ 36 hours
ExcretionFeces (~61%), urine (~36%)[4]
Identifiers
IUPAC name
  • (6R,12aR)-6-(1,3-benzodioxol-5-yl)-2-methyl-2,3,6,7,12,12a-hexahydropyrazino[1',2':1,6]
    pyrido[3,4-b]indole-1,4-dione
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
PDB ligand
CompTox Dashboard (EPA)
ECHA InfoCard100.214.024
Chemical and physical data
FormulaC22H19N3O4
Molar mass389.411 g·mol−1
3D model (JSmol)
SMILES
  • CN1CC(=O)N2[C@H](Cc3c([nH]c4ccccc34)[C@H]2c2ccc3c(c2)OCO3)C1=O
  • InChI=1S/C22H19N3O4/c1-24-10-19(26)25-16(22(24)27)9-14-13-4-2-3-5-15(13)23-20(14)21(25)12-6-7-17-18(8-12)29-11-28-17/h2-8,16,21,23H,9-11H2,1H3/t16-,21-/m1/s1 Y
  • Key:WOXKDUGGOYFFRN-IIBYNOLFSA-N Y
  (verify)

Tadalafil, sold under the brand name Cialis among others, is a medication used to treat erectile dysfunction, benign prostatic hyperplasia, and pulmonary arterial hypertension.[4][5][7] It is taken by mouth.[7] Onset is typically within half an hour and the duration is up to 36 hours.[7]

Common side effects include headache, muscle pain, flushing, and nausea.[7] Caution is advised in those with cardiovascular disease.[7] Rare but serious side effects include a prolonged erection that can lead to damage to the penis, vision problems, and hearing loss.[7] Tadalafil is not recommended in people taking nitrovasodilators such as nitroglycerin, as this may result in a serious drop in blood pressure.[7] Tadalafil is a PDE5 inhibitor which increases blood flow to the penis.[7] It also dilates blood vessels in the lungs, which lowers the pulmonary artery pressure.[7]

Tadalafil was approved for medical use in the United States in 2003.[7] It is available as a generic medication.[8] In 2022, it was the 172nd most commonly prescribed medication in the United States, with more than 3 million prescriptions.[9][10]

  1. ^ "Tadalafil Use During Pregnancy". Drugs.com. 14 March 2019. Archived from the original on 1 December 2020. Retrieved 20 August 2020.
  2. ^ Cite error: The named reference Cialis tadalafil PI was invoked but never defined (see the help page).
  3. ^ "Cialis 10mg film-coated tablets - Summary of Product Characteristics (SmPC)". (emc). 26 April 2017. Archived from the original on 1 December 2020. Retrieved 20 August 2020.
  4. ^ a b c "Cialis- tadalafil tablet, film coated". DailyMed. 12 June 2020. Archived from the original on 21 September 2019. Retrieved 20 August 2020.
  5. ^ a b "Adcirca- tadalafil tablet". DailyMed. 23 June 2022. Archived from the original on 6 March 2023. Retrieved 10 April 2023.
  6. ^ "Cialis EPAR". European Medicines Agency (EMA). 17 September 2018. Archived from the original on 7 January 2021. Retrieved 20 August 2020.
  7. ^ a b c d e f g h i j "Tadalafil Monograph for Professionals". Drugs.com. American Society of Health-System Pharmacists. Archived from the original on 20 September 2020. Retrieved 8 April 2019.
  8. ^ British national formulary: BNF 76 (76 ed.). Pharmaceutical Press. 2018. p. 796. ISBN 978-0-85711-338-2.
  9. ^ "The Top 300 of 2022". ClinCalc. Archived from the original on 30 August 2024. Retrieved 30 August 2024.
  10. ^ "Tadalafil Drug Usage Statistics, United States, 2013 - 2022". ClinCalc. Retrieved 30 August 2024.
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