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Tadalafil information


Tadalafil
Clinical data
Pronunciation/təˈdæləfɪl/ tə-DAL-ə-fil
Trade namesCialis, Adcirca, others
AHFS/Drugs.comMonograph
MedlinePlusa604008
License data
  • US DailyMed: Tadalafil
Pregnancy
category
  • AU: B1[1]
Routes of
administration
By mouth
ATC code
  • G04BE08 (WHO)
Legal status
Legal status
  • AU: S4 (Prescription only)[3]
  • UK: POM (Prescription only)[4]
  • US: WARNING[2]Rx-only[5][6]
  • EU: Rx-only[7]
  • In general: ℞ (Prescription only)
Pharmacokinetic data
BioavailabilityVaries
Protein binding94%
MetabolismLiver (predominantly CYP3A4)
MetabolitesCatechol metabolite
Onset of action30 minutes
Elimination half-life17.5 hours
ExcretionFeces (~61%), urine (~36%)[5]
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
  • 171596-29-5 checkY
PubChem CID
  • 110635
IUPHAR/BPS
  • 7299
DrugBank
  • DB00820 checkY
ChemSpider
  • 99301 checkY
UNII
  • 742SXX0ICT
KEGG
  • D02008 checkY
ChEBI
  • CHEBI:71940 checkY
ChEMBL
  • ChEMBL779 checkY
PDB ligand
  • CIA (PDBe, RCSB PDB)
CompTox Dashboard (EPA)
  • DTXSID9046786 Edit this at Wikidata
ECHA InfoCard100.214.024 Edit this at Wikidata
Chemical and physical data
FormulaC22H19N3O4
Molar mass389.411 g·mol−1
3D model (JSmol)
  • Interactive image
SMILES
  • CN1CC(=O)N2[C@H](Cc3c([nH]c4ccccc34)[C@H]2c2ccc3c(c2)OCO3)C1=O
InChI
  • 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 checkY
  • Key:WOXKDUGGOYFFRN-IIBYNOLFSA-N checkY
  (verify)
Tadalafil - STADA T20 - 20 Milligramm

Tadalafil, sold under the brand name Cialis among others, is a medication used to treat erectile dysfunction, benign prostatic hyperplasia, and pulmonary arterial hypertension.[5][6][8] It is taken by mouth.[8] Onset is typically within half an hour and the duration is up to 36 hours.[8]

Common side effects include headache, muscle pain, flushed skin, and nausea.[8] Caution is advised in those with cardiovascular disease.[8] Rare but serious side effects include a prolonged erection that can lead to damage to the penis, vision problems, and hearing loss.[8] Tadalafil is not recommended in people taking nitrovasodilators such as nitroglycerin, as this may result in a serious drop in blood pressure.[8] Tadalafil is a PDE5 inhibitor which increases blood flow to the penis.[8] It also dilates blood vessels in the lungs, which lowers the pulmonary artery pressure.[8]

Tadalafil was approved for medical use in the United States in 2003.[8] It is available as a generic medication.[9] In 2021, it was the 171st most commonly prescribed medication in the United States, with more than 3 million prescriptions.[10][11]

  1. ^ "Tadalafil Use During Pregnancy". Drugs.com. 14 March 2019. Archived from the original on 1 December 2020. Retrieved 20 August 2020.
  2. ^ "FDA-sourced list of all drugs with black box warnings (Use Download Full Results and View Query links.)". nctr-crs.fda.gov. FDA. Retrieved 22 October 2023.
  3. ^ Cite error: The named reference Cialis tadalafil PI was invoked but never defined (see the help page).
  4. ^ "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.
  5. ^ a b c "Cialis- tadalafil tablet, film coated". DailyMed. 12 June 2020. Archived from the original on 21 September 2019. Retrieved 20 August 2020.
  6. ^ a b "Adcirca- tadalafil tablet". DailyMed. 23 June 2022. Archived from the original on 6 March 2023. Retrieved 10 April 2023.
  7. ^ "Cialis EPAR". European Medicines Agency (EMA). 17 September 2018. Archived from the original on 7 January 2021. Retrieved 20 August 2020.
  8. ^ 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.
  9. ^ British national formulary : BNF 76 (76 ed.). Pharmaceutical Press. 2018. p. 796. ISBN 978-0-85711-338-2.
  10. ^ "The Top 300 of 2021". ClinCalc. Archived from the original on 15 January 2024. Retrieved 14 January 2024.
  11. ^ "Tadalafil - Drug Usage Statistics". ClinCalc. Retrieved 14 January 2024.

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Tadalafil

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Tadalafil, sold under the brand name Cialis among others, is a medication used to treat erectile dysfunction, benign prostatic hyperplasia, and pulmonary...

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PDE5 inhibitor

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dysfunction. Sildenafil and tadalafil are also indicated for the treatment of some subtypes of pulmonary hypertension, while tadalafil is also licensed for the...

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Pulmonary hypertension

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treprostinil, iloprost, bosentan, ambrisentan, macitentan, and sildenafil, tadalafil, selexipag, riociguat. Lung transplantation may be an option in severe...

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Vardenafil

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it is closely related in function to sildenafil citrate (Viagra) and tadalafil (Cialis). The difference between the vardenafil molecule and sildenafil...

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Piperonal

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Piperonal can be used in the synthesis of some pharmaceutical drugs including tadalafil, L-DOPA, and atrasentan. Piperonal has a floral odor which is commonly...

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Dapoxetine

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drug–drug interaction between dapoxetine and PDE5 inhibitors such as tadalafil (Cialis) or sildenafil (Viagra). In Dresser study (2006), plasma concentration...

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Cyanopsia

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Cyanopsia also sometimes occurs as a side effect of taking sildenafil, tadalafil, or vardenafil. Cyanopsia is a medical symptom and not a sign. It is a...

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Epimedium

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there is little clinical evidence to date, as sildenafil, vardenafil, and tadalafil – sold under the brand names Viagra, Levitra and Cialis – are all based...

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ATC code G04

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Yohimbin G04BE05 Phentolamine G04BE06 Moxisylyte G04BE07 Apomorphine G04BE08 Tadalafil G04BE09 Vardenafil G04BE10 Avanafil G04BE11 Udenafil G04BE30 Combinations...

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Cyclic guanosine monophosphate

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threshold. This effect is largely avoided by other PDE5 inhibitors, such as tadalafil. cGMP is involved in the regulation of some protein-dependent kinases...

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Avanafil

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primarily in the corpus cavernosum penis. Other similar drugs are sildenafil, tadalafil and vardenafil. The advantage of avanafil is that it has very fast onset...

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Icos

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other biotechnology companies. Icos is best known for the development of tadalafil (Cialis), a drug used to treat erectile dysfunction. This drug was discovered...

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Udenafil

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within the PDE5 inhibitor class (which also includes avanafil, sildenafil, tadalafil, and vardenafil). Like other PDE5 inhibitors, it is used to treat erectile...

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Sildenafil

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cause an erection. Other drugs that operate by the same mechanism include tadalafil (Cialis) and vardenafil (Levitra). Sildenafil is broken down in the liver...

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Adam4Adam

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companies offering erection enhancement drugs like sildenafil, vardenafil, tadalafil and their generic drug equivalents through mail order. The site offers...

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Benign prostatic hyperplasia

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but may require multiple doses daily to maintain adequate urine flow. Tadalafil, a phosphodiesterase-5 inhibitor, was considered then rejected by NICE...

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Isosorbide mononitrate

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mononitrate and sildenafil (Viagra) or other phosphodiesterase inhibitors (Tadalafil and Udenafil) can potentiate the vasodilatory effect of isosorbide mononitrate...

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Vasodilation

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agents indirectly increase the effects of nitric oxide sildenafil (Viagra) tadalafil (Cialis) vardenafil (Levitra) tetrahydrocannabinol (THC), the principal...

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ATC code C02

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Macitentan C02KX05 Riociguat C02KX52 Ambrisentan and tadalafil C02KX54 Macitentan and tadalafil C02LA01 Reserpine and diuretics C02LA02 Rescinnamine and...

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Raynaud syndrome

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symptoms, but the data is weak. PDE5 inhibitors, such as sildenafil and tadalafil, are used off-label to treat severe ischemia and ulcers in fingers and...

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Methylenedioxy

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natural products, including safrole, and drugs and chemicals such as tadalafil, MDMA, paroxetine and piperonyl butoxide. Enzymes within the cytochrome...

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Discovery and development of phosphodiesterase 5 inhibitors

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inhibitors (a subset of the phosphodiesterase inhibitors) are sildenafil, tadalafil, vardenafil, and avanafil, and although all share the same mechanism of...

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Nitrate

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paraxanthine) cGMP preferring PDE inhibitors (e.g., sildenafil, paraxanthine, tadalafil) Statins (e.g., simvastatin) See also: Receptor/signaling modulators...

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