MedKoo Cat#: 412867 | Name: Cicaprost

Description:

WARNING: This product is for research use only, not for human or veterinary use.

Cicaprost is a prostacyclin receptor (IP) agonist and orally active prostacyclin analog with potent systemic and pulmonary vasodilatation and anti-inflammatory activity. In preclinical models, Cicaprost treatment largely prevented the hypercholesterolemia-related impairment of coronary vasodilation and nitric oxide release in Isolated Langendorff-hearts. Cicaprost inhibits proinflammatory chemokines production not only from lipopolysaccharides (LPS) or (tumor necrosis factor-alpha) induced primary human monocyte-derived macrophages but also from LPS-stimulated monocyte-derived dendritic cells. Besides that Cicapost strongly inhibits lymph node and organ metastases of spontaneously metastasizing mammary tumors with a mode of action different from cytostatic or antihormonal drugs. In animal models, Cicaprost prevents metastasis if given continuously from the day of tumor implantation, and is effective in reducing metastasis if treatment is begun following surgical removal of the primary tumor when micrometastases are already present. Clinical trials of Cicaprost in healthy male volunteers demonstrate significant anti-platelet and vasodilatory effects.

Chemical Structure

Cicaprost
Cicaprost
CAS#95722-07-9

Theoretical Analysis

MedKoo Cat#: 412867

Name: Cicaprost

CAS#: 95722-07-9

Chemical Formula: C22H30O5

Exact Mass: 374.2093

Molecular Weight: 374.48

Elemental Analysis: C, 70.56; H, 8.08; O, 21.36

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.
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Related CAS #
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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
Appearance
Solid powder
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
More Info

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.

Recalculate based on batch purity %
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.