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Details

Stereochemistry ABSOLUTE
Molecular Formula C20H33O5.Na
Molecular Weight 376.4628
Optical Activity UNSPECIFIED
Defined Stereocenters 4 / 4
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of ALPROSTADIL SODIUM

SMILES

[Na+].CCCCC[C@H](O)\C=C\[C@H]1[C@H](O)CC(=O)[C@@H]1CCCCCCC([O-])=O

InChI

InChIKey=BMHCMWOSEOFUFU-HZTJSMSYSA-M
InChI=1S/C20H34O5.Na/c1-2-3-6-9-15(21)12-13-17-16(18(22)14-19(17)23)10-7-4-5-8-11-20(24)25;/h12-13,15-17,19,21,23H,2-11,14H2,1H3,(H,24,25);/q;+1/p-1/b13-12+;/t15-,16+,17+,19+;/m0./s1

HIDE SMILES / InChI

Molecular Formula Na
Molecular Weight 22.9898
Charge 1
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula C20H33O5
Molecular Weight 353.473
Charge -1
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 4 / 4
E/Z Centers 1
Optical Activity UNSPECIFIED

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.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
Palliative
PROSTIN VR PEDIATRIC

Approved Use

PROSTIN VR PEDIATRIC Sterile Solution is indicated for palliative, not definitive, therapy to temporarily maintain the patency of the ductus arteriosus until corrective or palliative surgery can be performed in neonates who have congenital heart defects and who depend upon the patent ductus for survival. Such congenital heart defects include pulmonary atresia, pulmonary stenosis, tricuspid atresia, tetralogy of Fallot, interruption of the aortic arch, coarctation of the aorta, or transposition of the great vessels with or without other defects.

Launch Date

1981
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
7.09 pg/mL
20 μg single, intravenous
dose: 20 μg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
ALPROSTADIL plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
174 pg × min/mL
20 μg single, intravenous
dose: 20 μg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
ALPROSTADIL plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
9.5 min
20 μg single, intravenous
dose: 20 μg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
ALPROSTADIL plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
Funbound

Funbound

ValueDoseCo-administeredAnalytePopulation
7%
20 μg single, intravenous
dose: 20 μg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
ALPROSTADIL plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Other InhibitorOther SubstrateOther Inducer





Drug as victim
Sourcing

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

TitleDatePubMed
Effect of lipo-pro-prostaglandin E1, AS-013 on rat inner ear microcirculatory thrombosis.
1998 Sep
Marked hypotensive and blood flow-increasing effects of a new lipo-PGE(1) (lipo-AS013) due to vascular wall targeting.
2001 Apr 2
Ecraprost: AS 013, Circulase.
2004
Parenteral therapy with lipo-ecraprost, a lipid-based formulation of a PGE1 analog, does not alter six-month outcomes in patients with critical leg ischemia.
2006 Apr
Adjunctive parenteral therapy with lipo-ecraprost, a prostaglandin E1 analog, in patients with critical limb ischemia undergoing distal revascularization does not improve 6-month outcomes.
2007 May
Antiplatelet and anticoagulant drugs for prevention of restenosis/reocclusion following peripheral endovascular treatment.
2012 Aug 15
Patents

Patents

Sample Use Guides

Patients meeting clinical and hemodynamic criteria for critical limb ischemia who were undergoing either bypass or endovascular revascularization of the below knee popliteal or more distal arteries were randomized to receive placebo or a 60-microg dose of lipo-ecraprost administered intravenously starting Route of Administration: Intravenous
In Vitro Use Guide
Unknown
Substance Class Chemical
Created
by admin
on Fri Dec 15 15:17:33 GMT 2023
Edited
by admin
on Fri Dec 15 15:17:33 GMT 2023
Record UNII
1L2580N9LI
Record Status Validated (UNII)
Record Version
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Name Type Language
ALPROSTADIL SODIUM
Common Name English
PROSTAGLANDIN E1 SODIUM
Common Name English
PROST-13-EN-1-OIC ACID, 11,15-DIHYDROXY-9-OXO-, SODIUM SALT (1:1), (11.ALPHA.,13E,15S)-
Systematic Name English
PGE1 SODIUM SALT
Common Name English
CYCLOPENTANEHEPTANOIC ACID, 3-HYDROXY-2-(3-HYDROXY-1-OCTENYL)-5-OXO-, MONOSODIUM SALT, STEREOISOMER
Systematic Name English
PROST-13-EN-1-OIC ACID, 11,15-DIHYDROXY-9-OXO-, MONOSODIUM SALT, (11.ALPHA.,13E,15S)-
Systematic Name English
Code System Code Type Description
FDA UNII
1L2580N9LI
Created by admin on Fri Dec 15 15:17:33 GMT 2023 , Edited by admin on Fri Dec 15 15:17:33 GMT 2023
PRIMARY
EPA CompTox
DTXSID201018715
Created by admin on Fri Dec 15 15:17:33 GMT 2023 , Edited by admin on Fri Dec 15 15:17:33 GMT 2023
PRIMARY
PUBCHEM
91618034
Created by admin on Fri Dec 15 15:17:33 GMT 2023 , Edited by admin on Fri Dec 15 15:17:33 GMT 2023
PRIMARY
CAS
27930-45-6
Created by admin on Fri Dec 15 15:17:33 GMT 2023 , Edited by admin on Fri Dec 15 15:17:33 GMT 2023
PRIMARY
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PARENT -> SALT/SOLVATE
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ACTIVE MOIETY