tadalafil
Trade name: cialis
Approved
Nov 21, 2003
Tadalafil is used to treat male erectile dysfunction (impotence) and pulmonary arterial hypertension (PAH). Part of the physiological process of erection involves the release of nitric oxide (NO) in the corpus cavernosum. This then activates the enzyme guanylate cyclase which results in increased levels of cyclic guanosine monophosphate (cGMP), leading to smooth muscle relaxation in the corpus cavernosum, resulting in increased inflow of blood and an erection. Tadalafil is a potent and selective inhibitor of cGMP specific phosphodiesterase type 5 (PDE5) which is responsible for degradation of cGMP in the corpus cavernosum. This means that, with tadalafil on board, normal sexual stimulation leads to increased levels of cGMP in the corpus cavernosum which leads to better erections. Without sexual stimulation and no activation of the NO/cGMP system, tadalafil should not cause an erection.Tadalafil inhibits the cGMP specific phosphodiesterase type 5 (PDE5) which is responsible for degradation of cGMP in the corpus cavernosum located around the penis. Penile erection during sexual stimulation is caused by increased penile blood flow resulting from the relaxation of penile arteries and corpus cavernosal smooth muscle. This response is mediated by the release of nitric oxide (NO) from nerve terminals and endothelial cells, which stimulates the synthesis of cGMP in smooth muscle cells. Cyclic GMP causes smooth muscle relaxation and increased blood flow into the corpus cavernosum. The inhibition of phosphodiesterase type 5 (PDE5) by tadalafil enhances erectile function by increasing the amount of cGMP. Tadalafil is used for the treatment of erectile dysfunction. — NCATS
Clinical trial activity
232 trials · 168 clinical orgs · 35 marketing orgs
Earliest trial started Jul 1, 2001 (NCT00707187)
Timeline
2000s
2010s
- May 22, 2018
Teva — Marketing Organization
- Aug 3, 2018
Mylan — Marketing Organization
- Feb 5, 2019
Ajanta Pharma Ltd — Marketing Organization
- Feb 5, 2019
Aurobindo Pharma — Marketing Organization
- Feb 5, 2019
Cipla — Marketing Organization
- Feb 5, 2019
Dr. Reddy's Laboratories — Marketing Organization
- Feb 5, 2019
Hetero Labs Ltd — Marketing Organization
- Feb 5, 2019
Lupin — Marketing Organization
- Mar 26, 2019
Alembic — Marketing Organization
- Mar 26, 2019
Accord Research — Marketing Organization
- Mar 26, 2019
Amneal Pharmaceuticals — Marketing Organization
- Mar 26, 2019
Qilu Pharmaceutical Co., Ltd. — Marketing Organization
- Mar 26, 2019
Sun Pharmaceuticals — Marketing Organization
- Mar 26, 2019
Sunshine Lake Pharma Co., Ltd. — Marketing Organization
- Mar 26, 2019
Torrent Pharmaceuticals Limited — Marketing Organization
- Mar 26, 2019
Unichem — Marketing Organization
- Mar 26, 2019
Zydus Discovery DMCC — Marketing Organization
- Mar 29, 2019
Watson Pharmaceuticals — Marketing Organization
- Mar 29, 2019
Allergan PLC (2015) — Marketing Organization
- Apr 29, 2019
Rising Pharmaceuticals — Marketing Organization
- Oct 7, 2019
Macleods Pharmaceuticals, Ltd — Marketing Organization
- Oct 7, 2019
Neogen — Marketing Organization
2020s
- Oct 23, 2020
Umedica Labs Pvt Ltd — Marketing Organization
- Oct 27, 2020
Austarpharma — Marketing Organization
- Oct 27, 2020
Shaanxi Buchang Pharmaceutical Co., Ltd — Marketing Organization
- Dec 29, 2020
Chartwell Pharmaceuticals — Marketing Organization
- Dec 29, 2020
Glenmark Pharmaceuticals — Marketing Organization
- Nov 4, 2021
VKT Pharma — Marketing Organization
- Dec 9, 2021
Veru Inc. — NDA Secondary Org
- Dec 9, 2021
BLUE WATER BIOTECH — NDA Secondary Org
- Jun 17, 2022
CMP Therapeutics Ltd — Marketing Organization
- Jun 17, 2022
CMP Therapeutics Ltd — NDA Secondary Org
- Aug 11, 2022
Prinston Inc — Marketing Organization
- Mar 3, 2023
Novitium Pharma — Marketing Organization
- Mar 3, 2023
Ani Pharmaceuticals — Marketing Organization
Indications
Studied for
- Abdominal Neoplasms · Phase 1
- Altitude Sickness · Phase 1/Phase 2
- Alzheimer Disease · Phase 2
- Andropause · Phase 4
- Anemia, Sickle Cell · Phase 2
- Aortic Valve Stenosis · Phase 4
- Astrocytoma · Phase 1
- Carcinoma, Hepatocellular · Phase 2
- Cardiomyopathies · Phase 2
- Cardiovascular Diseases · Phase 3
- Cerebral Small Vessel Diseases · Phase 2
- Colorectal Neoplasms · Phase 2
- Connective Tissue Diseases · Phase 4
- COVID-19 · Phase 4
- Dementia, Vascular · Phase 2
- Diabetes Mellitus · Phase 4
- Diabetes Mellitus, Type 2 · Phase 4
- Diabetic Cardiomyopathies · Phase 4
- Dyspnea · Phase 2
- Eisenmenger Complex · Phase 2
- Emphysema · Phase 4
- Endothelial Cells · Phase 1
- Esophageal Neoplasms · Phase 2
- Exercise · Phase 2
- Fecal Incontinence · Phase 1
- Fertilization in Vitro · Phase 2/Phase 3
- Fontan Procedure · Phase 3
- Gastroparesis · Phase 4
- Glioblastoma · Phase 1
- Glucose Intolerance · Phase 3
- Head and Neck Neoplasms · Phase 2
- Healthy Volunteers · Phase 2
- Heart Defects, Congenital · Phase 3
- Heart Diseases · Phase 3
- Heart Failure · Phase 3
- Heart Ventricles · Phase 1
- Hypertension · Phase 2
- Hypertension, Pulmonary · Phase 4
- Hypertrophy, Left Ventricular · Phase 4
- Hypotension · Phase 4
- Insulin Resistance · Phase 3
- Ischemic Stroke · Phase 2
- Kidney Failure, Chronic · Phase 1/Phase 2
- Larynx · Early Phase 1
- Lip Diseases · Early Phase 1
- Liver Cirrhosis · Phase 4
- Liver Neoplasms · Phase 2
- Lower Urinary Tract Symptoms · Phase 4
- Lung Diseases, Interstitial · Phase 3
- Major Depressive Disorder · Phase 1/Phase 2
- Mouth Neoplasms · Phase 2
- Multiple Myeloma · Phase 2
- Muscular Dystrophies · Phase 2
- Muscular Dystrophy, Duchenne · Phase 4
- Myocardium · Phase 3
- Nausea · Phase 4
- Neoplasm Metastasis · Phase 2
- Neoplasms · Phase 2
- Nephrolithiasis · Phase 4
- Obesity · Phase 4
- Pain · Phase 4
- Pancreatic Neoplasms · Phase 2
- Parkinson Disease · Phase 4
- Pneumonia · Phase 3
- Prediabetic State · Phase 4
- Premature Ejaculation · Phase 4
- Priapism · Phase 2
- Prostate · Phase 2
- Prostatic Neoplasms · Phase 3
- Pulmonary Arterial Hypertension · Phase 4
- Pulmonary Disease, Chronic Obstructive · Phase 3
- Quality of Life · Phase 4
- Raynaud Disease · Phase 3
- Respiratory Distress Syndrome · Phase 4
- Scleroderma, Systemic · Phase 4
- Sexual Dysfunction, Physiological · Phase 4
- Sexual Dysfunctions, Psychological · Phase 3
- Smoking · Phase 1
- Spinal Cord Injuries · Phase 4
- Squamous Cell Carcinoma of Head and Neck · Phase 2
- Stomach Neoplasms · Phase 2
- Stroke, Lacunar · Phase 2
- Ulcer · Phase 3
- Ureteral Calculi · Phase 3
- Ureteral Diseases · Phase 4
- Urinary Bladder, Overactive · Phase 4
- Urinary Incontinence, Stress · Phase 1
- Urination Disorders · Phase 4
- Urogenital Neoplasms · Phase 3
- Vasodilation · Phase 2
- Vomiting · Phase 4
Mechanism of action
- Phosphodiesterase 5AINHIBITOR
PDE5A inhibitor
Selective
Combination products
entadfi
with finasteride
opsynvi
with macitentan
Also known as fdc of macitentan/tadalafil (10 mg/20 mg), propsynvi
Approval history
- approvedNov 21, 2003
Chemistry & pharmacology
SMILES
CN1CC(=O)N2[C@H](CC3=C(NC4=C3C=CC=C4)[C@H]2C5=CC=C6OCOC6=C5)C1=O- Mol. weight
- 389.404 g/mol
- Lipinski Ro5
- Pass
- Rule of 3
- No
- Chirality
- Single Stereoisomer
- Inorganic
- No
- Polymer
- No
- Delivery
- Oral
- Availability
- Prescription Only
Oral
Yes
Parenteral
No
Topical
No
Sources
- WikipediaTadalafil ↗
- NCATS742SXX0ICT ↗
- ChEMBLCHEMBL779 ↗
Also known as
- 6-benzo[1,3]dioxol-5-yl-2-methyl-2,3,6,7,12,12a-hexahydro-pyrazino[1',2':1,6]pyrido[3,4-b]indole-1,4-dione
- 6-benzo[1,3]dioxol-5-yl-2-methyl-2,3,6,7,12,12a-hexahydro-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
- (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-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
- adcirca
- adcirca
- cialis
- cialis
- cialis
- cialis
- ic351
- ic351
- ic351
- ic-351
- ic-351
- icos 351
- icos 351
- tadalafil
- tadalafil
- tadalafil
- tadalafil
- tadalafil
- tadalafil
- tadalafil
- tadalafil
- tadalafil
- tadalafil
- tadalafil, cialis
- tadanafil
- tadanafil
- tardenafil
- tildenafil
- zalutia
- zalutia
- zalutia
- zalutia
- zalutia
- zalutia
Clinical trials
| NCT ID | Phase | Start date | Sponsor(s) |
|---|---|---|---|
| NCT07245680 | Phase 3 | Jan 15, 2026 | Assistance Publique - Hôpitaux de Paris |
| NCT07177326 | Phase 3 | Oct 1, 2025 | Assiut University |
| NCT07172815 | Phase 2 | Sep 30, 2025 | Imperial College London |
| NCT07117383 | Phase 1 | Aug 31, 2025 | Aspargo Labs, Inc |
| NCT07312955 | N/A | May 15, 2025 | Ain Shams University |
| NCT06968962 | N/A | May 14, 2025 | Huzhou University, Nanchang University, Ningbo Medical Center Lihuili Eastern Hospital, Ningbo No. 2 Hospital, Ningbo University, Shantou University, Wenzhou Medical University, Zhejiang University |
| NCT06805513 | Phase 3 | Jan 30, 2025 | Sanofi |
| NCT06543628 | N/A | Aug 31, 2024 | Zhejiang University |
| NCT06717711 | Phase 3 | Aug 31, 2024 | ISTITUTO REGINA ELENA |
| NCT06583590 | Phase 2/Phase 3 (Phase 3) | Aug 1, 2024 | Aswan University, Cairo University |
| NCT06296212 | Phase 3 | Jun 25, 2024 | Biomedica Foscama S.p.A. |
| NCT06290713 | Phase 2 | Jun 5, 2024 | National Institute of Arthritis and Musculoskeletal and Skin Diseases (NIAMS), University of Florida |
| NCT06520839 | Phase 3 | May 17, 2024 | University of Ljubljana |
| NCT06553924 | Phase 1 | May 14, 2024 | Humanis Saglık Anonim Sirketi |
| NCT06553937 | Phase 1 | May 10, 2024 | Humanis Saglık Anonim Sirketi |
| NCT06466369 | Phase 3 | Mar 15, 2024 | Al Azhar University |
| NCT05844462 | Phase 3 | Jan 31, 2024 | Assistance Publique - Hôpitaux de Paris |
| NCT05937854 | Phase 2 | Jan 15, 2024 | Department of Veteran Affairs |
| NCT06947265 | Phase 4 | Jan 14, 2024 | Cairo University |
| NCT06213077 | N/A | Dec 12, 2023 | OnSite Clinical Solutions, RHA Investments Ltd |
Organizations
Research & Development (168)
| Organization | Org type | Trials | As lead sponsor | Phases | Earliest year |
|---|---|---|---|---|---|
| Eli Lilly | For profit | 57 | 50 | 5 | 2002 |
| ICOS | For profit | 22 | 0 | 3 | 2002 |
| Actelion | For profit | 7 | 7 | 3 | 2015 |
| Cedars-Sinai Medical Center | Academic/Hospital | 7 | 7 | 3 | 2010 |
| Cairo University | Academic/Hospital | 6 | 5 | 4 | 2020 |
| Johns Hopkins University | Academic/Hospital | 6 | 5 | 2 | 2006 |
| Chong Kun Dang Pharmaceutical | For profit | 5 | 5 | 2 | 2014 |
| Hanmi Pharmaceutical | For profit | 5 | 4 | 3 | 2014 |
| Mansoura University | Academic/Hospital | 5 | 5 | 3 | 2020 |
| National Heart, Lung, and Blood Institute (NHLBI) | Government | 5 | 0 | 2 | 2010 |
| National Institutes of Health (NIH) | Government | 5 | 0 | 4 | 2006 |
| University of Copenhagen | Academic/Hospital | 5 | 4 | 3 | 2008 |
| Beni Suef University | Academic/Hospital | 4 | 4 | 3 | 2020 |
| Mayo Clinic | Academic/Hospital | 4 | 4 | 2 | 2012 |
| University of Roma La Sapienza | Academic/Hospital | 4 | 4 | 2 | 2014 |
| Vanderbilt University | Academic/Hospital | 4 | 4 | 2 | 2006 |
| Aswan University | Academic/Hospital | 3 | 3 | 3 | 2017 |
| Bayer | For profit | 3 | 3 | 2 | 2003 |
| Chonbuk National University | Academic/Hospital | 3 | 0 | 1 | 2014 |
| Dongkook Pharmaceutical Co., Ltd. | For profit | 3 | 3 | 2 | 2013 |
Marketing (47)
| Organization | Org type | Relationship | Date |
|---|---|---|---|
| Accord Research | For profit | MKTG | Mar 26, 2019 |
| Ajanta Pharma Ltd | For profit | MKTG | Feb 5, 2019 |
| Alembic | For profit | MKTG | Mar 26, 2019 |
| Alembic | For profit | SYN | Mar 26, 2019 |
| Allergan PLC (2015) | For profit | MKTG | Mar 29, 2019 |
| Amneal Pharmaceuticals | For profit | MKTG | Mar 26, 2019 |
| Ani Pharmaceuticals | For profit | MKTG | Mar 3, 2023 |
| Aurobindo Pharma | For profit | MKTG | Feb 5, 2019 |
| Austarpharma | For profit | MKTG | Oct 27, 2020 |
| BLUE WATER BIOTECH | For profit | NDA2 | Dec 9, 2021 |
| CMP Therapeutics Ltd | For profit | MKTG | Jun 17, 2022 |
| CMP Therapeutics Ltd | For profit | NDA2 | Jun 17, 2022 |
| Chartwell Pharmaceuticals | For profit | MKTG | Dec 29, 2020 |
| Cipla | For profit | MKTG | Feb 5, 2019 |
| Dr. Reddy's Laboratories | For profit | SYN | Feb 5, 2019 |
| Dr. Reddy's Laboratories | For profit | MKTG | Feb 5, 2019 |
| Eli Lilly | For profit | SYN | Nov 21, 2003 |
| Eli Lilly | For profit | NDA | May 22, 2009 |
| Glenmark Pharmaceuticals | For profit | MKTG | Dec 29, 2020 |
| Hetero Labs Ltd | For profit | MKTG | Feb 5, 2019 |
| Lupin | For profit | MKTG | Feb 5, 2019 |
| Macleods Pharmaceuticals, Ltd | For profit | MKTG | Oct 7, 2019 |
| Mylan | For profit | MKTG | Aug 3, 2018 |
| Mylan | For profit | SYN | Aug 3, 2018 |
| Neogen | For profit | MKTG | Oct 7, 2019 |
| Novitium Pharma | For profit | MKTG | Mar 3, 2023 |
| Prinston Inc | For profit | MKTG | Aug 11, 2022 |
| Qilu Pharmaceutical Co., Ltd. | For profit | MKTG | Mar 26, 2019 |
| Qilu Pharmaceutical Co., Ltd. | For profit | MKTG | Mar 26, 2019 |
| Qilu Pharmaceutical Co., Ltd. | For profit | SYN | Mar 26, 2019 |
| Rising Pharmaceuticals | For profit | SYN | Apr 29, 2019 |
| Rising Pharmaceuticals | For profit | MKTG | Apr 29, 2019 |
| Shaanxi Buchang Pharmaceutical Co., Ltd | For profit | MKTG | Oct 27, 2020 |
| Sun Pharmaceuticals | For profit | MKTG | Mar 26, 2019 |
| Sun Pharmaceuticals | For profit | SYN | Mar 26, 2019 |
| Sunshine Lake Pharma Co., Ltd. | For profit | MKTG | Mar 26, 2019 |
| Sunshine Lake Pharma Co., Ltd. | For profit | MKTG | Mar 26, 2019 |
| Teva | For profit | MKTG | May 22, 2018 |
| Teva | For profit | SYN | Oct 12, 2022 |
| Torrent Pharmaceuticals Limited | For profit | MKTG | Mar 26, 2019 |
| Umedica Labs Pvt Ltd | For profit | MKTG | Oct 23, 2020 |
| Unichem | For profit | MKTG | Mar 26, 2019 |
| Unichem | For profit | MKTG | Mar 26, 2019 |
| VKT Pharma | For profit | MKTG | Nov 4, 2021 |
| Veru Inc. | For profit | NDA2 | Dec 9, 2021 |
| Watson Pharmaceuticals | For profit | MKTG | Mar 29, 2019 |
| Zydus Discovery DMCC | For profit | MKTG | Mar 26, 2019 |