Synonym
Cicaprost; ZK96480; ZK-96480; ZK 96480
IUPAC/Chemical Name
(2-((2E,3aS,4S,5R,6aS)-Hexahydro-5-hydroxy-4-((3S,4S)-3-hydroxy-4-methyl-1,6-nonadiynyl)-2(1H)-pentalenylidene)ethoxy)acetic acid
InChi Key
ARUGKOZUKWAXDS-SEWALLKFSA-N
InChi Code
InChI=1S/C22H30O5/c1-3-4-5-6-15(2)20(23)8-7-18-19-12-16(9-10-27-14-22(25)26)11-17(19)13-21(18)24/h9,15,17-21,23-24H,3,6,10-14H2,1-2H3,(H,25,26)/b16-9+/t15-,17-,18+,19-,20+,21+/m0/s1
SMILES Code
O=C(O)COC/C=C1C[C@@]2([H])C[C@@H](O)[C@H](C#C[C@@H](O)[C@@H](C)CC#CCC)[C@@]2([H])C\1
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
>2 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
2934.99.9001
Preparing Stock Solutions
The following data is based on the
product
molecular weight
374.48
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: Zhou W, Zhang J, Toki S, Goleniewska K, Johnson MO, Bloodworth MH, Newcomb DC, Peebles RS Jr. The PGI2 Analog Cicaprost Inhibits IL-33-Induced Th2 Responses, IL-2 Production, and CD25 Expression in Mouse CD4+ T Cells. J Immunol. 2018 Oct 1;201(7):1936-1945. doi: 10.4049/jimmunol.1700605. Epub 2018 Aug 20. PMID: 30127087; PMCID: PMC6162094.
2: Schneider MR, Schirner M, Lichtner RB, Graf H. Antimetastatic action of the prostacyclin analogue cicaprost in experimental mammary tumors. Breast Cancer Res Treat. 1996;38(1):133-41. doi: 10.1007/BF01803791. PMID: 8825130.
3: Wang JW, Vu C, Poloso NJ. A Prostacyclin Analog, Cicaprost, Exhibits Potent Anti-Inflammatory Activity in Human Primary Immune Cells and a Uveitis Model. J Ocul Pharmacol Ther. 2017 Apr;33(3):186-192. doi: 10.1089/jop.2016.0167. Epub 2017 Jan 10. PMID: 28072560.
4: Hildebrand M. Pharmacokinetics of iloprost and cicaprost in mice. Prostaglandins. 1992 Nov;44(5):431-42. doi: 10.1016/0090-6980(92)90138-j. PMID: 1281921.
5: Schirner M, Schneider MR. Cicaprost inhibits metastases of animal tumors. Prostaglandins. 1991 Nov;42(5):451-61. doi: 10.1016/0090-6980(91)90036-f. PMID: 1763201.
6: Lau CS, Belch JJ, Madhok R, Cappell H, Herrick A, Jayson M, Thompson JM. A randomised, double-blind study of cicaprost, an oral prostacyclin analogue, in the treatment of Raynaud's phenomenon secondary to systemic sclerosis. Clin Exp Rheumatol. 1993 Jan-Feb;11(1):35-40. PMID: 8453795.
7: Orie NN, Fry CH, Clapp LH. Evidence that inward rectifier K+ channels mediate relaxation by the PGI2 receptor agonist cicaprost via a cyclic AMP-independent mechanism. Cardiovasc Res. 2006 Jan;69(1):107-15. doi: 10.1016/j.cardiores.2005.08.004. Epub 2005 Sep 23. PMID: 16183044.
8: Sobolewski A, Jourdan KB, Upton PD, Long L, Morrell NW. Mechanism of cicaprost-induced desensitization in rat pulmonary artery smooth muscle cells involves a PKA-mediated inhibition of adenylyl cyclase. Am J Physiol Lung Cell Mol Physiol. 2004 Aug;287(2):L352-9. doi: 10.1152/ajplung.00270.2003. Epub 2004 Apr 23. PMID: 15107293.
9: Hildebrand M, Nieuweboer B, Schütt A. Development and validation of a sensitive and specific radioimmunoassay for the determination of cicaprost in biological samples. J Immunoassay. 1994 May;15(2):171-90. doi: 10.1080/15321819408013946. PMID: 8040351.
10: Braun M, Hohlfeld T, Kienbaum P, Weber AA, Sarbia M, Schrör K. Antiatherosclerotic effects of oral cicaprost in experimental hypercholesterolemia in rabbits. Atherosclerosis. 1993 Oct;103(1):93-105. doi: 10.1016/0021-9150(93)90043-t. PMID: 8280189.