tadalafil

Also known as Adcirca®, Cialis®, IC-351, IC351, (6R,12aR)-2,3,6,7,12,12a-Hexahydro-2-methyl-6-(3,4-(methylenedioxy)phenyl) pyrazino(1',2':1,6)pyrido(3,4-b)indole-1,4-dione, (6R-trans)-6-(1,3-Benzodioxol-5-yl)-2,3,6,7,12,12a-hexahydro-2-methyl-pyrazino(1',2':1,6)pyrido(3,4-b)indole-1,4-dione, (6R,12AR)-2,3,6,7,12,12a-hexahydro-2-methyl-6-(3,4-(methylenedioxy)phenyl) pyrazino(1',2':1,6)pyrido(3,4-b)indole-1,4-dione, Tadanafil

thumb|Tadalafil - STADA T20 - 20 Milligram

Key facts

Drug.Watchedfields: changed
Drug.verifiedrevid: 635551343
Drug.image: Tadalafil.svg
Drug.image_class: skin-invert-image
Drug.width: 180
Drug.image2: Tadalafil 3D 1XOZ.png
Drug.image_class2: bg-transparent
Drug.tradename: Cialis, others
Drug.MedlinePlus: a604008
Drug.DailyMedID: Tadalafil
Drug.pregnancy_AU: B1
Drug.routes_of_administration: By mouth
Drug.class: PDE5 inhibitor
Drug.ATC_prefix: G04
Drug.ATC_suffix: BE08
Drug.legal_AU: S4
Drug.legal_UK: POM
Drug.legal_US: Rx-only

via Wikipedia infobox

Chemical data

Formula: C22H19N3O4
Molecular weight: 389.4 g/mol
IUPAC name: (2R,8R)-2-(1,3-benzodioxol-5-yl)-6-methyl-3,6,17-triazatetracyclo[8.7.0.03,8.011,16]heptadeca-1(10),11,13,15-tetraene-4,7-dione
SMILES: CN1CC(=O)N2[C@@H](C1=O)CC3=C([C@H]2C4=CC5=C(C=C4)OCO5)NC6=CC=CC=C36
InChIKey: WOXKDUGGOYFFRN-IIBYNOLFSA-N
XLogP: 2.3
Polar surface area: 74.9 Å²
H-bond donors: 1
H-bond acceptors: 4
Formal charge: 0

via PubChem

Research

3,161 papers

Direct comparison of tadalafil with sildenafil for the treatment of erectile dysfunction: a systematic review and meta-analysis.International urology and nephrology · 2017
Tadalafil for the treatment of benign prostatic hyperplasia.Expert opinion on pharmacotherapy · 2019
Benefits of Tadalafil and Sildenafil on Mortality, Cardiovascular Disease, and Dementia.The American journal of medicine · 2025
Tadalafil Alone or in Combination with Tamsulosin for the Management for LUTS/BPH and ED.Current urology reports · 2020
Efficacy and safety of long-term tadalafil 5 mg once daily combined with sildenafil 50 mg as needed at the early stage of treatment for patients with erectile dysfunction.Andrologia · 2015

via PubMed

Wikidata facts

Subclass of: chemical compound
Mass: 389.138
Image: Tadalafil von STADA - T20 - 20 Milligramm - Potenzmittel - Bild 005.jpg
Has use: medication

Show 10 more facts

isomeric SMILES: CN1CC(=O)N2[C@@H](C1=O)CC3=C([C@H]2C4=CC5=C(C=C4)OCO5)NC6=CC=CC=C36
chemical formula: C₂₂H₁₉N₃O₄
defined daily dose: 10
Commons category: Tadalafil
canonical SMILES: CN1CC(=O)N2C(C1=O)CC3=C(C2C4=CC5=C(C=C4)OCO5)NC6=CC=CC=C36
World Health Organisation international non-proprietary name: tadalafil
medical condition treated: erectile dysfunction
physically interacts with: Phosphodiesterase 5A
legal status (medicine): boxed warning
significant drug interaction: alfuzosin

Sources (9)

via Wikidata · CC0

~13 min read

Encyclopedic overview

17 sections

Contents

Medical uses
Benign prostatic hyperplasia
Pulmonary arterial hypertension
Adverse effects
Vision
Hearing
Metabolism
Mechanism of action
Duration of action
Comparison with actions of other PDE5 inhibitors
Chemistry
History
Society and culture
Marketing
Economics
Research
References

thumb|Tadalafil - STADA T20 - 20 Milligram

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

Excerpted from Wikipedia’s “tadalafil” article, available under the CC BY-SA 4.0 licence.