alprostadil

Trade name: prostin

Small moleculeapproved

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

Phase 1
7
Phase 2
23
Phase 3
9
Phase 4
13

Earliest trial started Apr 1, 2001 (NCT01263925)

Timeline

1980s

  1. Oct 16, 1981

    Upjohn — Earliest FDA Approval

  2. Oct 16, 1981

    Pharmacia & Upjohn — NDA Secondary Org

  3. Oct 16, 1981

    Upjohn — NDA Organization

1990s

  1. Nov 19, 1996

    Mylan — NDA Secondary Org

  2. Nov 19, 1996

    Viatris — Marketing Organization

  3. Jun 12, 1997

    Auxillium — NDA Secondary Org

  4. Jun 12, 1997

    Endo Pharmaceuticals — Marketing Organization

  5. Oct 31, 1997

    Pfizer — NDA Secondary Org

  6. Jan 20, 1998

    West-Ward Pharmaceutical — Marketing Organization

  7. Jan 20, 1998

    Hikma — Marketing Organization

  8. Apr 30, 1999

    Teva — Marketing Organization

  9. Apr 30, 1999

    Eu Yan Sang — Marketing Organization

  10. Apr 30, 1999

    Meitheal — Marketing Organization

2000s

  1. Jan 1, 2001

    Earliest Phase 2 Sponsor(trial)

  2. Jan 1, 2001

    Earliest Phase 3 Sponsor(trial)

  3. Jan 1, 2007

    Earliest Phase 1 Sponsor(trial)

Indications

Studied for

Mechanism of action

Approval history

  • approvedPriority reviewOct 16, 1981

Chemistry & pharmacology

Loading structure…

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

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 IDPhaseStart dateSponsor(s)
NCT06768177N/AApr 1, 2023ASL Bari
NCT05475717Phase 2Oct 20, 2022Shijiazhuang Pharma Group (CSPC)
NCT04536363Phase 2Oct 1, 2020Fundación Santa Fe de Bogota
NCT04312555Phase 4Apr 1, 2020Al Azhar University, Assiut University
NCT04197323Phase 2Oct 1, 2019Shijiazhuang Pharma Group (CSPC)
NCT03892447Phase 4Aug 1, 2019Shengjing Hospital
NCT04054115Phase 1Jul 23, 2019University of Toronto
NCT04172558Phase 2/Phase 3 (Phase 3)Mar 10, 2019Benha University
NCT03788083Phase 1Nov 12, 2018eTheRNA, Free University of Brussels
NCT03669562Phase 1Aug 7, 2018Shijiazhuang Pharma Group (CSPC)
NCT03851562Phase 2Jun 13, 2018Fundacion para la Formacion e Investigacion Sanitarias de la Region de Murcia
NCT03682952Phase 4Feb 1, 2018Xuzhou Medical University
NCT03252665Phase 4Sep 1, 2017Huazhong University of Science and Technology, Jiao Tong University
NCT03252626Phase 4Aug 18, 2017Jilin University
NCT02888756Phase 2Apr 4, 2017Asphalion, 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
NCT02877173Phase 2Aug 1, 2016Capital 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
NCT02895373Phase 2Jul 1, 2016Medical University of Vienna, University of Vienna
NCT02628106Phase 4Dec 1, 2015Sichuan University
NCT02620215Phase 4Nov 1, 2015KK Women's and Children's Hospital, University of Malaya
NCT02574338N/ASep 1, 2015Federal Teaching Hospital Abakaliki
Showing 20 of 51 trials
Page 1 / 3

Organizations

Research & Development (82)

OrganizationOrg typeTrialsAs lead sponsorPhasesEarliest year
Free University of BrusselsAcademic/Hospital3122009
Hoosier Cancer Research NetworkAcademic/Hospital3322001
Jiao Tong UniversityAcademic/Hospital3222015
Shijiazhuang Pharma Group (CSPC)For profit3322018
Duke UniversityAcademic/Hospital2012008
eTheRNAFor profit2022017
Guangzhou Yipinhong Pharmaceutical CO.,LTDFor profit2222010
Huazhong University of Science and TechnologyAcademic/Hospital2112012
Jilin UniversityAcademic/Hospital2122016
Mitsubishi TanabeFor profit2212001
National Institute of Child Health and Human Development (NICHD)Government2212008
National Institutes of Health (NIH)Government2012008
Sichuan UniversityAcademic/Hospital2122015
Stanford UniversityAcademic/Hospital2012008
Sun Yat-Sen UniversityAcademic/Hospital2122011
The University of Texas, DallasAcademic/Hospital2012008
University of Alabama, BirminghamAcademic/Hospital2012008
University of BarcelonaAcademic/Hospital2122015
University of IowaAcademic/Hospital2012008
University of New MexicoAcademic/Hospital2012008
82 organizations
Page 1 / 5

Marketing (12)

OrganizationOrg typeRelationshipDate
AuxilliumFor profitNDA2Jun 12, 1997
Endo PharmaceuticalsFor profitMKTGJun 12, 1997
Eu Yan SangFor profitMKTGApr 30, 1999
HikmaFor profitMKTGJan 20, 1998
MeithealFor profitMKTGApr 30, 1999
MylanFor profitNDA2Nov 19, 1996
PfizerFor profitNDA2Oct 31, 1997
Pharmacia & UpjohnFor profitNDA2Oct 16, 1981
TevaFor profitMKTGApr 30, 1999
UpjohnFor profitNDAOct 16, 1981
ViatrisFor profitMKTGNov 19, 1996
West-Ward PharmaceuticalFor profitMKTGJan 20, 1998