alprostadil
Trade name: prostin
Approved
Oct 16, 1981
Ecraprost [AS 013, Circulase] is a prodrug of prostaglandin E(1) within lipid microspheres that is being developed in Japan by Mitsubishi Pharma Corporation and Asahi Glass. It was originally in development with Welfide Corporation. On 1 October 2001, Welfide Corporation (formerly Yoshitomi) merged with Mitsubishi-Tokyo Pharmaceuticals to form Mitsubishi Pharma Corporation. The new company is a subsidiary of Mitsubishi Chemical. Taisho and Seikagaku Corporation had been involved in the development of ecraprost but discontinued their licences to do so. The effects of ecraprost on reperfusion injury, in preclinical studies, had been reported by Taisho. Ecraprost is in phase II in Japan and was in phase II in Europe for the treatment of peripheral arterial disease. It was also in a phase II study in the treatment of diabetic neuropathies. However, this is no longer an active indication. A phase III trial using a lipid emulsion of ecraprost [Circulase] is underway with Mitsubishi Pharma Corporation in the US, using ecraprost for the treatment of patients with severe peripheral arterial disease, which, because of decreased blood flow to the extremities, can lead to painful ulcers on the legs and feet and subsequent amputation. Alpha Therapeutic Corporation (a former subsidiary of Mitsubishi Pharma) was initially involved in trials of ecraprost in the US, but this responsibility has been taken over by the parent company. — NCATS
Clinical trial activity
51 trials · 82 clinical orgs · 12 marketing orgs
Earliest trial started Apr 1, 2001 (NCT01263925)
Timeline
1980s
- Oct 16, 1981
Upjohn — Earliest FDA Approval
- Oct 16, 1981
Pharmacia & Upjohn — NDA Secondary Org
- Oct 16, 1981
Upjohn — NDA Organization
1990s
- Nov 19, 1996
Mylan — NDA Secondary Org
- Nov 19, 1996
Viatris — Marketing Organization
- Jun 12, 1997
Auxillium — NDA Secondary Org
- Jun 12, 1997
Endo Pharmaceuticals — Marketing Organization
- Oct 31, 1997
Pfizer — NDA Secondary Org
- Jan 20, 1998
West-Ward Pharmaceutical — Marketing Organization
- Jan 20, 1998
Hikma — Marketing Organization
- Apr 30, 1999
Teva — Marketing Organization
- Apr 30, 1999
Eu Yan Sang — Marketing Organization
- Apr 30, 1999
Meitheal — Marketing Organization
Indications
Studied for
- Acute Kidney Injury · Phase 4
- Alprostadil · Phase 4
- Arterial Occlusive Diseases · Phase 4
- Arteriosclerosis Obliterans · Phase 2
- Breast Neoplasms · Phase 1
- Child · Phase 2/Phase 3
- Chronic Limb-Threatening Ischemia · Phase 4
- Coronary Disease · Phase 4
- COVID-19 · Phase 2
- Diabetes Mellitus · Phase 4
- Diabetic Nephropathies · Phase 4
- Extracorporeal Membrane Oxygenation · Phase 2
- Heart Defects, Congenital · Phase 1
- Heart Failure · Phase 3
- HIV Infections · Phase 2
- Hypertension, Pulmonary · Phase 2
- Infant, Newborn · Phase 2
- Infant, Premature, Diseases · Phase 2
- Infertility · Phase 2
- Intermittent Claudication · Phase 3
- Kidney Diseases · Phase 4
- Kidney Failure, Chronic · Phase 4
- Labor, Induced · Phase 4
- Labor Pain · Phase 3
- Liver Transplantation · Phase 2
- Macular Degeneration · Phase 3
- Melanoma · Phase 1
- Microsurgery · Phase 4
- Optic Neuropathy, Ischemic · Phase 2
- Pediatrics · Phase 4
- Percutaneous Coronary Intervention · Phase 3
- Peripheral Arterial Disease · Phase 2
- Peripheral Vascular Diseases · Phase 3
- Pregnancy · Phase 4
- Prostatic Neoplasms · Phase 2
- Renal Insufficiency · Phase 4
- Renal Insufficiency, Chronic · Phase 4
- Respiratory Distress Syndrome · Phase 2
- Respiratory Distress Syndrome, Newborn · Phase 2
- Respiratory Insufficiency · Phase 2
- Sclerosis · Phase 2
- Sexual Dysfunction, Physiological · Phase 2
- Sexual Health · Phase 1
- Squamous Cell Carcinoma of Head and Neck · Phase 4
- ST Elevation Myocardial Infarction · Phase 4
- Streptococcal Infections · Phase 2
- Stroke · Phase 4
- Thrombosis · Phase 4
Mechanism of action
- Prostanoid EP1 receptorAGONIST
PTGER1 agonist
- Prostanoid EP2 receptorAGONIST
PTGER2 agonist
Approval history
- approvedPriority reviewOct 16, 1981
Chemistry & pharmacology
SMILES
CCCCC[C@H](O)\C=C\[C@H]1[C@H](O)CC(=O)[C@@H]1CCCCCCC(O)=O- Mol. weight
- 354.481 g/mol
- Lipinski Ro5
- 1 violation(s)
- Rule of 3
- No
- Chirality
- Single Stereoisomer
- Inorganic
- No
- Polymer
- No
- Availability
- Prescription Only
Oral
No
Parenteral
No
Topical
No
Sources
- WikipediaProstaglandin E1 ↗
- NCATSF5TD010360 ↗
- ChEMBLCHEMBL495 ↗
- ChEMBLCHEMBL2104574 ↗
Also known as
- (11alpha,13e,15s)-11,15-dihydroxy-9-oxoprost-13-en-1-oic acid
- (11alpha,13e,15s)-11,15-dihydroxy-9-oxoprost-13-en-1-oic acid
- 11alpha,15alpha-dihydroxy-9-oxo-13-trans-prostenoic acid
- 11alpha,15alpha-dihydroxy-9-oxo-13-trans-prostenoic acid
- (13e)-(15s)-11alpha,15-dihydroxy-9-oxoprost-13-enoate
- (13e)-(15s)-11alpha,15-dihydroxy-9-oxoprost-13-enoate
- alprostadil
- alprostadil
- alprostadil
- alprostadil
- alprostadil
- alprostadil
- alprostadil
- alprostadil
- alprostadil
- alprostadil
- alprostadil
- alprostadil liposomes
- alprostadilum
- alprostadilum
- as-013
- as-013
- as-013
- befar
- befar
- butyryl prostaglandin f1 butyl ester
- caverject
- caverject
- caverject impulse
- caverject impulse
- circulase
- ecraprost
- ecraprost
- ecraprost
- ecraprost
- edex
- edex
- eglandin
- lipo as-013
- lipoprostaglandin e1
- liposomal prostaglandin e1
- liposomal prostaglandin e1
- pge₁
- pge₁
- pge1
- pge1
- pge1
- pge1
- pge-1
- pge-1
- pge1 α-cd
- pge1 α-cd
- prostaglandin e1
- prostaglandin e1
- prostaglandin e1
- prostaglandin e1
- prostaglandin e1
- prostavasin
- prostin vr
- prostin vr
- prostin vr pediatric
- prostin vr pediatric
- trimix
- trimix
- u-10136
- u-10136
- vasaprostan
- viridal 10
- viridal 20
- viridal 5
- viridal duo
- vitaros
- vitaros
Clinical trials
| NCT ID | Phase | Start date | Sponsor(s) |
|---|---|---|---|
| NCT06768177 | N/A | Apr 1, 2023 | ASL Bari |
| NCT05475717 | Phase 2 | Oct 20, 2022 | Shijiazhuang Pharma Group (CSPC) |
| NCT04536363 | Phase 2 | Oct 1, 2020 | Fundación Santa Fe de Bogota |
| NCT04312555 | Phase 4 | Apr 1, 2020 | Al Azhar University, Assiut University |
| NCT04197323 | Phase 2 | Oct 1, 2019 | Shijiazhuang Pharma Group (CSPC) |
| NCT03892447 | Phase 4 | Aug 1, 2019 | Shengjing Hospital |
| NCT04054115 | Phase 1 | Jul 23, 2019 | University of Toronto |
| NCT04172558 | Phase 2/Phase 3 (Phase 3) | Mar 10, 2019 | Benha University |
| NCT03788083 | Phase 1 | Nov 12, 2018 | eTheRNA, Free University of Brussels |
| NCT03669562 | Phase 1 | Aug 7, 2018 | Shijiazhuang Pharma Group (CSPC) |
| NCT03851562 | Phase 2 | Jun 13, 2018 | Fundacion para la Formacion e Investigacion Sanitarias de la Region de Murcia |
| NCT03682952 | Phase 4 | Feb 1, 2018 | Xuzhou Medical University |
| NCT03252665 | Phase 4 | Sep 1, 2017 | Huazhong University of Science and Technology, Jiao Tong University |
| NCT03252626 | Phase 4 | Aug 18, 2017 | Jilin University |
| NCT02888756 | Phase 2 | Apr 4, 2017 | Asphalion, Badalona Hospital Germans Trias i Pujol, CR2O, Erasmus University Rotterdam, eTheRNA, Free University of Brussels, Institute of Tropical Medicine, Belgium, IrsiCaixa, Synapse bv, University of Barcelona |
| NCT02877173 | Phase 2 | Aug 1, 2016 | Capital Medical University, Guangzhou Yipinhong Pharmaceutical CO.,LTD, Hebei University, Heilongjiang University of Traditional Chinese Medicine, Jiao Tong University, Jilin University, Nanjing Medical University, Qingdao University, Sichuan University, Sun Yat-Sen University, Tianjin Medical University |
| NCT02895373 | Phase 2 | Jul 1, 2016 | Medical University of Vienna, University of Vienna |
| NCT02628106 | Phase 4 | Dec 1, 2015 | Sichuan University |
| NCT02620215 | Phase 4 | Nov 1, 2015 | KK Women's and Children's Hospital, University of Malaya |
| NCT02574338 | N/A | Sep 1, 2015 | Federal Teaching Hospital Abakaliki |
Organizations
Research & Development (82)
Marketing (12)
| Organization | Org type | Relationship | Date |
|---|---|---|---|
| Auxillium | For profit | NDA2 | Jun 12, 1997 |
| Endo Pharmaceuticals | For profit | MKTG | Jun 12, 1997 |
| Eu Yan Sang | For profit | MKTG | Apr 30, 1999 |
| Hikma | For profit | MKTG | Jan 20, 1998 |
| Meitheal | For profit | MKTG | Apr 30, 1999 |
| Mylan | For profit | NDA2 | Nov 19, 1996 |
| Pfizer | For profit | NDA2 | Oct 31, 1997 |
| Pharmacia & Upjohn | For profit | NDA2 | Oct 16, 1981 |
| Teva | For profit | MKTG | Apr 30, 1999 |
| Upjohn | For profit | NDA | Oct 16, 1981 |
| Viatris | For profit | MKTG | Nov 19, 1996 |
| West-Ward Pharmaceutical | For profit | MKTG | Jan 20, 1998 |