Ciprostene calcium | CAS#81703-55-1 (Ca) | ADP-induced platelet aggregation inhibitor

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

MedKoo CAT#: 462831

CAS#: 81703-55-1 (Ca)

Description: Ciprostene is the 9β-methyl analog of carbaprostacyclin and a stable analog of PGI2. Ciprostene exhibits biological activity similar to PGI2, but is 30-fold less potent. In patas monkeys, ciprostene induces hypotension and causes tachycardia when administered at a dose of 0.16 µg/kg/min. In addition, ciprostene inhibits ADP-induced platelet aggregation ex vivo and in vitro with ID50 values of 9.1 µg/kg/min and 60 ng/ml, respectively.

Chemical Structure

Ciprostene calcium

CAS# 81703-55-1 (Ca)

Instruction

Theoretical Analysis

MedKoo Cat#: 462831
Name: Ciprostene calcium
CAS#: 81703-55-1 (Ca)
Chemical Formula: C44H70CaO8
Exact Mass: 766.47
Molecular Weight: 767.114
Elemental Analysis: C, 68.89; H, 9.20; Ca, 5.22; O, 16.68

Price and Availability

Size	Price	Availability
1mg	USD 350	2 Weeks
5mg	USD 1085	2 Weeks
Bulk inquiry Welcome, Customer: Please do not inquire quote if your intended use is for a patient since our products are for research use and for chemical synthesis use, not for human use . For in-stock products, we listed price in the web page. You may inquire prices for which sizes were not listed. If no price is listed, this means the product is not in stock at the moment, which may be available via custom synthesis. For cost-effective reason, minimum order of 1g is requested (typically very expensive). The lead time is usually 2-4 months. Quote of less than 1g will not be provided. MedKoo may not offer quote for below reasons: (1) current available synthetic method appears to be extremely expensive which is obviously not affordable to most customers; (2) Key raw material to make the product is temporally not available; (3) DEA controlled substances; (4) the product is under patent protection in customer’s country.

Related CAS #: 81845-44-5 (free base) 81703-55-1 (Ca)

Synonym: Ciprostene calcium;

IUPAC/Chemical Name: calcium 5-((3aS,5R,6R,6aR,E)-5-hydroxy-6-((S,Z)-3-hydroxyoct-1-en-1-yl)-3a-methylhexahydropentalen-2(1H)-ylidene)pentanoate 5-((3aS,5R,6R,6aR,Z)-5-hydroxy-6-((S,E)-3-hydroxyoct-1-en-1-yl)-3a-methylhexahydropentalen-2(1H)-ylidene)pentanoate

InChi Key: NJTMVDAFPIEZAJ-XEDIHLBKSA-L

InChi Code: InChI=1S/2C22H36O4.Ca/c2*1-3-4-5-9-17(23)11-12-18-19-13-16(8-6-7-10-21(25)26)14-22(19,2)15-20(18)24;/h2*8,11-12,17-20,23-24H,3-7,9-10,13-15H2,1-2H3,(H,25,26);/q;;+2/p-2/b12-11+,16-8-;12-11-,16-8+;/t2*17-,18+,19+,20+,22-;/m00./s1

SMILES Code: CCCCC[C@@H](/C=C/[C@H]1[C@@H](C[C@]2([C@@H]1C/C(C2)=C/CCCC([O-])=O)C)O)O.CCCCC[C@@H](/C=C\[C@H]3[C@@H](C[C@]4([C@@H]3C/C(C4)=C\CCCC([O-])=O)C)O)O.[Ca+2]

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: >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: 2934.99.9001

More Info:

Instruction:

View handling instruction

Biological target:
In vitro activity:
In vivo activity:

Preparing Stock Solutions

The following data is based on the product molecular weight 767.11 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

Formulation protocol:
In vitro protocol:
In vivo protocol:

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1: Linet OI, Nishizawa EE, Schaub RG, VanderLugt JT, Greenwald CA. Tolerance and pharmacology of ciprostene, a stable epoprostenol (prostacyclin) analogue in humans. J Clin Pharmacol. 1986 Feb;26(2):131-40. doi: 10.1002/j.1552-4604.1986.tb02921.x. PMID: 3005377.

2: Linet OI, Luderer JR, Froeschke M, Welch S, Metzler CM, Eckert SM. Ciprostene in patients with peripheral vascular disease (PVD). An open-label, tolerance trial. Prostaglandins Leukot Essent Fatty Acids. 1988 Oct;34(1):9-14. doi: 10.1016/0952-3278(88)90018-x. PMID: 3068680.

3: The effect of ciprostene in patients with peripheral vascular disease (PVD) characterized by ischemic ulcers. The Ciprostene Study Group. J Clin Pharmacol. 1991 Jan;31(1):81-7. doi: 10.1002/j.1552-4604.1991.tb01891.x. PMID: 2045533.

4: Salerno GM, McBride DM, Bleicher JN, Watson P, Stromberg BV. Ciprostene and indomethacin partially reverse the mechanisms of distal end necrosis in the rat random skin flap. Ann Plast Surg. 1992 Jun;28(6):526-33; discussion 534. PMID: 1622033.

5: Darius H, Nixdorff U, Zander J, Rupprecht HJ, Erbel R, Meyer J. Effects of ciprostene on restenosis rate during therapeutic transluminal coronary angioplasty. Agents Actions Suppl. 1992;37:305-11. doi: 10.1007/978-3-0348-7262-1_42. PMID: 1632305.

6: Allan G, Follenfant MJ, Lidbury P, Oliver PL, Whittle BJ. The cardiovascular and platelet actions of 9 beta-methyl carbacyclin (ciprostene), a chemically stable analogue of prostacyclin, in the dog and monkey. Br J Pharmacol. 1985 Jun;85(2):547-55. doi: 10.1111/j.1476-5381.1985.tb08892.x. PMID: 3896365; PMCID: PMC1916618.

7: Schaub RG. Ciprostene, a stable prostacyclin analog, produces peripheral vasodilation, platelet inhibition and increased clot dissolution in the cat. Prostaglandins. 1988 Mar;35(3):467-74. doi: 10.1016/0090-6980(88)90137-2. PMID: 3287459.

8: Wolf DL, Metzler CM, Froeschke MO, Luderer JR. Continuous intravenous dosing with ciprostene using a portable pump in ambulatory patients. J Clin Pharmacol. 1993 Feb;33(2):150-3. doi: 10.1002/j.1552-4604.1993.tb03936.x. PMID: 8440764.

9: Komatsu S, Murata S, Aoyama H, Zenki T, Ozawa N, Tateishi M, Vrbanac JJ. Micro-quantitative determination of ciprostene in plasma by gas chromatography- mass spectrometry coupled with an antibody extraction. J Chromatogr. 1991 Aug 23;568(2):460-6. doi: 10.1016/0378-4347(91)80184-e. PMID: 1783651.

10: Jones DA, Benjamin CW, Linseman DA. Activation of thromboxane and prostacyclin receptors elicits opposing effects on vascular smooth muscle cell growth and mitogen-activated protein kinase signaling cascades. Mol Pharmacol. 1995 Nov;48(5):890-6. PMID: 7476920.

11: Fink AN, Frishman WH, Azizad M, Agarwal Y. Use of prostacyclin and its analogues in the treatment of cardiovascular disease. Heart Dis. 1999 Mar- Apr;1(1):29-40. PMID: 11720602.

12: Theis DL, Rusk ML, Plaisted SM, Snider BG. High-performance liquid chromatography method for the separation of isomers of 9 beta-methylcarbacyclin (ciprostene) and the analysis of pharmaceutical samples. J Chromatogr. 1985 Mar 8;321(1):209-15. doi: 10.1016/s0021-9673(01)90437-6. PMID: 3886680.

13: Yamada Y, Ohinata K, Lipkowski AW, Yoshikawa M. Rapakinin, Arg-Ile-Tyr, derived from rapeseed napin, shows anti-opioid activity via the prostaglandin IP receptor followed by the cholecystokinin CCK(2) receptor in mice. Peptides. 2011 Feb;32(2):281-5. doi: 10.1016/j.peptides.2010.11.015. Epub 2010 Dec 1. PMID: 21129424.

14: Kohyama T, Liu X, Kim HJ, Kobayashi T, Ertl RF, Wen FQ, Takizawa H, Rennard SI. Prostacyclin analogs inhibit fibroblast migration. Am J Physiol Lung Cell Mol Physiol. 2002 Aug;283(2):L428-32. doi: 10.1152/ajplung.00432.2001. PMID: 12114205.

15: Crutchley DJ, Solomon DE, Conanan LB. Prostacyclin analogues inhibit tissue factor expression in the human monocytic cell line THP-1 via a cyclic AMP- dependent mechanism. Arterioscler Thromb. 1992 Jun;12(6):664-70. doi: 10.1161/01.atv.12.6.664. PMID: 1375507.

16: Hall ED, Wolf DL. A pharmacological analysis of the pathophysiological mechanisms of posttraumatic spinal cord ischemia. J Neurosurg. 1986 Jun;64(6):951-61. doi: 10.3171/jns.1986.64.6.0951. PMID: 3084721.

17: Hall ED. Beneficial effects of acute intravenous ibuprofen on neurologic recovery of head-injured mice: comparison of cyclooxygenase inhibition with inhibition of thromboxane A2 synthetase or 5-lipoxygenase. Cent Nerv Syst Trauma. 1985 Summer;2(2):75-83. doi: 10.1089/cns.1985.2.75. PMID: 3938345.

18: Shirotani M, Yui Y, Hattori R, Kawai C. U-61,431F, a stable prostacyclin analogue, inhibits the proliferation of bovine vascular smooth muscle cells with little antiproliferative effect on endothelial cells. Prostaglandins. 1991 Feb;41(2):97-110. doi: 10.1016/0090-6980(91)90023-9. PMID: 1708156.

19: Crutchley DJ, Conanan LB, Toledo AW, Solomon DE, Que BG. Effects of prostacyclin analogues on human endothelial cell tissue factor expression. Arterioscler Thromb. 1993 Jul;13(7):1082-9. doi: 10.1161/01.atv.13.7.1082. PMID: 7686394.

20: Gove CD, Hughes RD, Kmiec Z, Noda Y, Williams R. In vivo and in vitro studies on the protective effects of 9 beta-methylcarbacyclin, a stable prostacyclin analogue, in galactosamine-induced hepatocellular damage. Prostaglandins Leukot Essent Fatty Acids. 1990 May;40(1):73-7. doi: 10.1016/0952-3278(90)90120-a. PMID: 2119044.

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Ciprostene calcium featured