tadalafil

Trade name: cialis

Small moleculeapproved

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

Phase 1
48
Phase 2
105
Phase 3
68
Phase 4
50

Earliest trial started Jul 1, 2001 (NCT00707187)

Timeline

2000s

  1. Jan 1, 2001

    Earliest Phase 2 Sponsor(trial)

  2. Jan 1, 2002

    Eli Lilly — Earliest Phase 3 Sponsor(trial)

  3. Jan 1, 2003

    Earliest Phase 1 Sponsor(trial)

  4. Nov 21, 2003

    Earliest FDA Approval

  5. May 22, 2009

    Eli Lilly — First NDA Organization

  6. May 22, 2009

    Eli Lilly — NDA Organization

2010s

  1. May 22, 2018

    Teva — Marketing Organization

  2. Aug 3, 2018

    Mylan — Marketing Organization

  3. Feb 5, 2019

    Ajanta Pharma Ltd — Marketing Organization

  4. Feb 5, 2019

    Aurobindo Pharma — Marketing Organization

  5. Feb 5, 2019

    Cipla — Marketing Organization

  6. Feb 5, 2019

    Dr. Reddy's Laboratories — Marketing Organization

  7. Feb 5, 2019

    Hetero Labs Ltd — Marketing Organization

  8. Feb 5, 2019

    Lupin — Marketing Organization

  9. Mar 26, 2019

    Alembic — Marketing Organization

  10. Mar 26, 2019

    Accord Research — Marketing Organization

  11. Mar 26, 2019

    Amneal Pharmaceuticals — Marketing Organization

  12. Mar 26, 2019

    Qilu Pharmaceutical Co., Ltd. — Marketing Organization

  13. Mar 26, 2019

    Sun Pharmaceuticals — Marketing Organization

  14. Mar 26, 2019

    Sunshine Lake Pharma Co., Ltd. — Marketing Organization

  15. Mar 26, 2019

    Torrent Pharmaceuticals Limited — Marketing Organization

  16. Mar 26, 2019

    Unichem — Marketing Organization

  17. Mar 26, 2019

    Zydus Discovery DMCC — Marketing Organization

  18. Mar 29, 2019

    Watson Pharmaceuticals — Marketing Organization

  19. Mar 29, 2019

    Allergan PLC (2015) — Marketing Organization

  20. Apr 29, 2019

    Rising Pharmaceuticals — Marketing Organization

  21. Oct 7, 2019

    Macleods Pharmaceuticals, Ltd — Marketing Organization

  22. Oct 7, 2019

    Neogen — Marketing Organization

2020s

  1. Oct 23, 2020

    Umedica Labs Pvt Ltd — Marketing Organization

  2. Oct 27, 2020

    Austarpharma — Marketing Organization

  3. Oct 27, 2020

    Shaanxi Buchang Pharmaceutical Co., Ltd — Marketing Organization

  4. Dec 29, 2020

    Chartwell Pharmaceuticals — Marketing Organization

  5. Dec 29, 2020

    Glenmark Pharmaceuticals — Marketing Organization

  6. Nov 4, 2021

    VKT Pharma — Marketing Organization

  7. Dec 9, 2021

    Veru Inc. — NDA Secondary Org

  8. Dec 9, 2021

    BLUE WATER BIOTECH — NDA Secondary Org

  9. Jun 17, 2022

    CMP Therapeutics Ltd — Marketing Organization

  10. Jun 17, 2022

    CMP Therapeutics Ltd — NDA Secondary Org

  11. Aug 11, 2022

    Prinston Inc — Marketing Organization

  12. Mar 3, 2023

    Novitium Pharma — Marketing Organization

  13. Mar 3, 2023

    Ani Pharmaceuticals — Marketing Organization

Indications

Studied for

Mechanism of action

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

Loading structure…

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

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 IDPhaseStart dateSponsor(s)
NCT07245680Phase 3Jan 15, 2026Assistance Publique - Hôpitaux de Paris
NCT07177326Phase 3Oct 1, 2025Assiut University
NCT07172815Phase 2Sep 30, 2025Imperial College London
NCT07117383Phase 1Aug 31, 2025Aspargo Labs, Inc
NCT07312955N/AMay 15, 2025Ain Shams University
NCT06968962N/AMay 14, 2025Huzhou University, Nanchang University, Ningbo Medical Center Lihuili Eastern Hospital, Ningbo No. 2 Hospital, Ningbo University, Shantou University, Wenzhou Medical University, Zhejiang University
NCT06805513Phase 3Jan 30, 2025Sanofi
NCT06543628N/AAug 31, 2024Zhejiang University
NCT06717711Phase 3Aug 31, 2024ISTITUTO REGINA ELENA
NCT06583590Phase 2/Phase 3 (Phase 3)Aug 1, 2024Aswan University, Cairo University
NCT06296212Phase 3Jun 25, 2024Biomedica Foscama S.p.A.
NCT06290713Phase 2Jun 5, 2024National Institute of Arthritis and Musculoskeletal and Skin Diseases (NIAMS), University of Florida
NCT06520839Phase 3May 17, 2024University of Ljubljana
NCT06553924Phase 1May 14, 2024Humanis Saglık Anonim Sirketi
NCT06553937Phase 1May 10, 2024Humanis Saglık Anonim Sirketi
NCT06466369Phase 3Mar 15, 2024Al Azhar University
NCT05844462Phase 3Jan 31, 2024Assistance Publique - Hôpitaux de Paris
NCT05937854Phase 2Jan 15, 2024Department of Veteran Affairs
NCT06947265Phase 4Jan 14, 2024Cairo University
NCT06213077N/ADec 12, 2023OnSite Clinical Solutions, RHA Investments Ltd
Showing 20 of 232 trials
Page 1 / 12

Organizations

Research & Development (168)

OrganizationOrg typeTrialsAs lead sponsorPhasesEarliest year
Eli LillyFor profit575052002
ICOSFor profit22032002
ActelionFor profit7732015
Cedars-Sinai Medical CenterAcademic/Hospital7732010
Cairo UniversityAcademic/Hospital6542020
Johns Hopkins UniversityAcademic/Hospital6522006
Chong Kun Dang PharmaceuticalFor profit5522014
Hanmi PharmaceuticalFor profit5432014
Mansoura UniversityAcademic/Hospital5532020
National Heart, Lung, and Blood Institute (NHLBI)Government5022010
National Institutes of Health (NIH)Government5042006
University of CopenhagenAcademic/Hospital5432008
Beni Suef UniversityAcademic/Hospital4432020
Mayo ClinicAcademic/Hospital4422012
University of Roma La SapienzaAcademic/Hospital4422014
Vanderbilt UniversityAcademic/Hospital4422006
Aswan UniversityAcademic/Hospital3332017
BayerFor profit3322003
Chonbuk National UniversityAcademic/Hospital3012014
Dongkook Pharmaceutical Co., Ltd.For profit3322013
168 organizations
Page 1 / 9

Marketing (47)

OrganizationOrg typeRelationshipDate
Accord ResearchFor profitMKTGMar 26, 2019
Ajanta Pharma LtdFor profitMKTGFeb 5, 2019
AlembicFor profitMKTGMar 26, 2019
AlembicFor profitSYNMar 26, 2019
Allergan PLC (2015)For profitMKTGMar 29, 2019
Amneal PharmaceuticalsFor profitMKTGMar 26, 2019
Ani PharmaceuticalsFor profitMKTGMar 3, 2023
Aurobindo PharmaFor profitMKTGFeb 5, 2019
AustarpharmaFor profitMKTGOct 27, 2020
BLUE WATER BIOTECHFor profitNDA2Dec 9, 2021
CMP Therapeutics LtdFor profitMKTGJun 17, 2022
CMP Therapeutics LtdFor profitNDA2Jun 17, 2022
Chartwell PharmaceuticalsFor profitMKTGDec 29, 2020
CiplaFor profitMKTGFeb 5, 2019
Dr. Reddy's LaboratoriesFor profitSYNFeb 5, 2019
Dr. Reddy's LaboratoriesFor profitMKTGFeb 5, 2019
Eli LillyFor profitSYNNov 21, 2003
Eli LillyFor profitNDAMay 22, 2009
Glenmark PharmaceuticalsFor profitMKTGDec 29, 2020
Hetero Labs LtdFor profitMKTGFeb 5, 2019
LupinFor profitMKTGFeb 5, 2019
Macleods Pharmaceuticals, LtdFor profitMKTGOct 7, 2019
MylanFor profitMKTGAug 3, 2018
MylanFor profitSYNAug 3, 2018
NeogenFor profitMKTGOct 7, 2019
Novitium PharmaFor profitMKTGMar 3, 2023
Prinston IncFor profitMKTGAug 11, 2022
Qilu Pharmaceutical Co., Ltd.For profitMKTGMar 26, 2019
Qilu Pharmaceutical Co., Ltd.For profitMKTGMar 26, 2019
Qilu Pharmaceutical Co., Ltd.For profitSYNMar 26, 2019
Rising PharmaceuticalsFor profitSYNApr 29, 2019
Rising PharmaceuticalsFor profitMKTGApr 29, 2019
Shaanxi Buchang Pharmaceutical Co., LtdFor profitMKTGOct 27, 2020
Sun PharmaceuticalsFor profitMKTGMar 26, 2019
Sun PharmaceuticalsFor profitSYNMar 26, 2019
Sunshine Lake Pharma Co., Ltd.For profitMKTGMar 26, 2019
Sunshine Lake Pharma Co., Ltd.For profitMKTGMar 26, 2019
TevaFor profitMKTGMay 22, 2018
TevaFor profitSYNOct 12, 2022
Torrent Pharmaceuticals LimitedFor profitMKTGMar 26, 2019
Umedica Labs Pvt LtdFor profitMKTGOct 23, 2020
UnichemFor profitMKTGMar 26, 2019
UnichemFor profitMKTGMar 26, 2019
VKT PharmaFor profitMKTGNov 4, 2021
Veru Inc.For profitNDA2Dec 9, 2021
Watson PharmaceuticalsFor profitMKTGMar 29, 2019
Zydus Discovery DMCCFor profitMKTGMar 26, 2019