Cicaprost

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

MedKoo CAT#: 412867

CAS#: 95722-07-9

Description: 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

img
Cicaprost
CAS# 95722-07-9
Instruction

Theoretical Analysis

MedKoo Cat#: 412867
Name: Cicaprost
CAS#: 95722-07-9
Chemical Formula: C22H30O5
Exact Mass: 374.21
Molecular Weight: 374.480
Elemental Analysis: C, 70.56; H, 8.08; O, 21.36

Price and Availability

This product is not in stock, which may be available by custom synthesis. For cost-effective reason, minimum order is 1g (price is usually high, lead time is 2~3 months, depending on the technical challenge). Quote less than 1g will not be provided. To request quote, please email to sales @medkoo.com or click below button.
Note: Price will be listed if it is available in the future.

Request quote for custom synthesis

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:

Biological target:
In vitro activity:
In vivo activity:

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
Formulation protocol:
In vitro protocol:
In vivo protocol:

Molarity Calculator

Calculate the mass, volume, or concentration required for a solution.
=
x
x
g/mol

*When preparing stock solutions always use the batch-specific molecular weight of the product found on the vial label and SDS / CoA (available online).

Reconstitution Calculator

The reconstitution calculator allows you to quickly calculate the volume of a reagent to reconstitute your vial. Simply enter the mass of reagent and the target concentration and the calculator will determine the rest.

=
÷

Dilution Calculator

Calculate the dilution required to prepare a stock solution.
x
=
x

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.