Synonym
Ecraprost; AS-013; AS 013; AS013; Circulase; Lipo-pro-prostaglandin E1;
IUPAC/Chemical Name
butyl 7-((4R,5R)-2-(butyryloxy)-4-hydroxy-5-((S,E)-3-hydroxyoct-1-en-1-yl)cyclopent-1-en-1-yl)heptanoate
InChi Key
HITYEEHTEOQBAC-OSIGYOHNSA-N
InChi Code
InChI=1S/C28H48O6/c1-4-7-11-15-22(29)18-19-23-24(26(21-25(23)30)34-28(32)14-6-3)16-12-9-10-13-17-27(31)33-20-8-5-2/h18-19,22-23,25,29-30H,4-17,20-21H2,1-3H3/b19-18+/t22-,23+,25+/m0/s1
SMILES Code
CCCCC[C@H](O)/C=C/[C@@H]1C(CCCCCCC(OCCCC)=O)=C(OC(CCC)=O)C[C@H]1O
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>3 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.03.00
Preparing Stock Solutions
The following data is based on the
product
molecular weight
480.68
Batch specific molecular weights may vary
from batch to batch
due to the degree of hydration, which will
affect the solvent
volumes required to prepare stock solutions.
| Concentration / Solvent Volume / Mass |
1 mg |
5 mg |
10 mg |
| 1 mM |
1.15 mL |
5.76 mL |
11.51 mL |
| 5 mM |
0.23 mL |
1.15 mL |
2.3 mL |
| 10 mM |
0.12 mL |
0.58 mL |
1.15 mL |
| 50 mM |
0.02 mL |
0.12 mL |
0.23 mL |
1: Nehler MR, Brass EP, Anthony R, Dormandy J, Jiao J, McNamara TO, Hiatt WR; Circulase investigators. 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. J Vasc Surg. 2007 May;45(5):953-60; discussion 960-1. Epub 2007 Mar 9. PubMed PMID: 17350216.
2: Ecraprost: AS 013, Circulase. Drugs R D. 2004;5(1):31-4. Review. PubMed PMID: 14725489.
3: Brass EP, Anthony R, Dormandy J, Hiatt WR, Jiao J, Nakanishi A, McNamara T, Nehler M; Circulase investigators. 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. J Vasc Surg. 2006 Apr;43(4):752-9. PubMed PMID: 16616232.
4: Robertson L, Ghouri MA, Kovacs F. Antiplatelet and anticoagulant drugs for prevention of restenosis/reocclusion following peripheral endovascular treatment. Cochrane Database Syst Rev. 2012 Aug 15;(8):CD002071. doi: 10.1002/14651858.CD002071.pub3. Review. PubMed PMID: 22895926.
5: Amendt K. PGE1 and other prostaglandins in the treatment of intermittent claudication: a meta-analysis. Angiology. 2005 Jul-Aug;56(4):409-15. PubMed PMID: 16079924.
6: Igarashi R, Takenaga M, Takeuchi J, Kitagawa A, Matsumoto K, Mizushima Y. Marked hypotensive and blood flow-increasing effects of a new lipo-PGE(1) (lipo-AS013) due to vascular wall targeting. J Control Release. 2001 Apr 2;71(2):157-64. PubMed PMID: 11274747.
7: Tsutsumiuchi R, Saito H, Imagawa T, Kitamori T, Odake T, Sawada T. In vivo determination of ultratrace amounts of prostaglandin in plasma by high-performance liquid chromatography/laser-induced fluorometry/ultrasensitive laser spectrometry under severe conditions. Anal Chem. 1997 Dec 15;69(24):5006-10. PubMed PMID: 9414614.
8: Hokamura K, Umemura K, Nakamura N, Watanabe M, Takashima T, Nakashima M. Effect of lipo-pro-prostaglandin E1, AS-013 on rat inner ear microcirculatory thrombosis. Prostaglandins Leukot Essent Fatty Acids. 1998 Sep;59(3):203-7. PubMed PMID: 9844994.
