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

MedKoo CAT#: 412292

CAS#: 69552-46-1

Description: Carboprostacyclin is a potent stable prostacyclin analog which inhibits platelet aggretation.

Chemical Structure

CAS# 69552-46-1

Theoretical Analysis

MedKoo Cat#: 412292
Name: Carboprostacyclin
CAS#: 69552-46-1
Chemical Formula: C21H34O4
Exact Mass: 350.2457
Molecular Weight: 350.49
Elemental Analysis: C, 71.96; H, 9.78; O, 18.26

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 or click below button.
Note: Price will be listed if it is available in the future.

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Synonym: Carboprostacyclin; Carbacyclin

IUPAC/Chemical Name: Pentanoic acid, 5-((3aS,4R,5R,6aS)-hexahydro-5-hydroxy-4-((1E,3S)-3-hydroxy-1-octenyl)-2(1H)-pentalenylidene)-, (5E)-


InChi Code: InChI=1S/C21H34O4/c1-2-3-4-8-17(22)10-11-18-19-13-15(7-5-6-9-21(24)25)12-16(19)14-20(18)23/h7,10-11,16-20,22-23H,2-6,8-9,12-14H2,1H3,(H,24,25)/b11-10+,15-7+/t16-,17-,18+,19-,20+/m0/s1

SMILES Code: O=C(O)CCC/C=C1C[C@@]2([H])C[C@@H](O)[C@H](/C=C/[C@@H](O)CCCCC)[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: >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

Preparing Stock Solutions

The following data is based on the product molecular weight 350.49 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

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1: Fang C, Schmaier AH. Novel anti-thrombotic mechanisms mediated by Mas receptor as result of balanced activities between the kallikrein/kinin and the renin-angiotensin systems. Pharmacol Res. 2020 Jul 24;160:105096. doi: 10.1016/j.phrs.2020.105096. Epub ahead of print. PMID: 32712319; PMCID: PMC7378497.

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3: Magadum A, Ding Y, He L, Kim T, Vasudevarao MD, Long Q, Yang K, Wickramasinghe N, Renikunta HV, Dubois N, Weidinger G, Yang Q, Engel FB. Live cell screening platform identifies PPARδ as a regulator of cardiomyocyte proliferation and cardiac repair. Cell Res. 2017 Aug;27(8):1002-1019. doi: 10.1038/cr.2017.84. Epub 2017 Jun 16. PMID: 28621328; PMCID: PMC5539351.

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5: Ghandour RA, Giroud M, Vegiopoulos A, Herzig S, Ailhaud G, Amri EZ, Pisani DF. IP-receptor and PPARs trigger the conversion of human white to brite adipocyte induced by carbaprostacyclin. Biochim Biophys Acta. 2016 Apr;1861(4):285-93. doi: 10.1016/j.bbalip.2016.01.007. Epub 2016 Jan 14. PMID: 26775637.

6: Priestley JR, Buelow MW, McEwen ST, Weinberg BD, Delaney M, Balus SF, Hoeppner C, Dondlinger L, Lombard JH. Reduced angiotensin II levels cause generalized vascular dysfunction via oxidant stress in hamster cheek pouch arterioles. Microvasc Res. 2013 Sep;89:134-45. doi: 10.1016/j.mvr.2013.04.004. Epub 2013 Apr 27. PMID: 23628292; PMCID: PMC3758804.

7: Liu X, Terry T, Pan S, Yang Z, Willerson JT, Dixon RA, Liu Q. Targeted delivery of carbaprostacyclin to ischemic hindlimbs enhances adaptive remodeling of the microvascular network. Hypertension. 2013 May;61(5):1036-43. doi: 10.1161/HYPERTENSIONAHA.111.00458. Epub 2013 Mar 25. PMID: 23529172.

8: Barbieri SS, Amadio P, Gianellini S, Zacchi E, Weksler BB, Tremoli E. Tobacco smoke regulates the expression and activity of microsomal prostaglandin E synthase-1: role of prostacyclin and NADPH-oxidase. FASEB J. 2011 Oct;25(10):3731-40. doi: 10.1096/fj.11-181776. Epub 2011 Jul 7. PMID: 21737615.

9: Kang HJ, Hwang SJ, Yoon JA, Jun JH, Lim HJ, Yoon TK, Song H. Activation of peroxisome proliferators-activated receptor δ (PPARδ) promotes blastocyst hatching in mice. Mol Hum Reprod. 2011 Oct;17(10):653-60. doi: 10.1093/molehr/gar030. Epub 2011 Apr 20. PMID: 21511721.

10: Kurtz M, Capobianco E, Martínez N, Fernández J, Higa R, White V, Jawerbaum A. Carbaprostacyclin, a PPARdelta agonist, ameliorates excess lipid accumulation in diabetic rat placentas. Life Sci. 2010 May 22;86(21-22):781-90. doi: 10.1016/j.lfs.2010.03.008. Epub 2010 Mar 22. PMID: 20338185.

11: Di Francesco L, Totani L, Dovizio M, Piccoli A, Di Francesco A, Salvatore T, Pandolfi A, Evangelista V, Dercho RA, Seta F, Patrignani P. Induction of prostacyclin by steady laminar shear stress suppresses tumor necrosis factor- alpha biosynthesis via heme oxygenase-1 in human endothelial cells. Circ Res. 2009 Feb 27;104(4):506-13. doi: 10.1161/CIRCRESAHA.108.191114. Epub 2009 Jan 2. PMID: 19122175.

12: Lymboussaki A, Gemelli C, Testa A, Facchini G, Ferrari F, Mavilio F, Grande A. PPARdelta is a ligand-dependent negative regulator of vitamin D3-induced monocyte differentiation. Carcinogenesis. 2009 Feb;30(2):230-7. doi: 10.1093/carcin/bgn272. Epub 2008 Dec 4. PMID: 19056929.

13: Kamio K, Sato T, Liu X, Sugiura H, Togo S, Kobayashi T, Kawasaki S, Wang X, Mao L, Ahn Y, Holz O, Magnussen H, Rennard SI. Prostacyclin analogs stimulate VEGF production from human lung fibroblasts in culture. Am J Physiol Lung Cell Mol Physiol. 2008 Jun;294(6):L1226-32. doi: 10.1152/ajplung.00129.2007. Epub 2008 Apr 18. PMID: 18424619.

14: El-Haroun H, Clarke DL, Deacon K, Bradbury D, Clayton A, Sutcliffe A, Knox AJ. IL-1beta, BK, and TGF-beta1 attenuate PGI2-mediated cAMP formation in human pulmonary artery smooth muscle cells by multiple mechanisms involving p38 MAP kinase and PKA. Am J Physiol Lung Cell Mol Physiol. 2008 Mar;294(3):L553-62. doi: 10.1152/ajplung.00044.2006. Epub 2007 Dec 21. PMID: 18156442.

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16: Kuroda T, Hirota H, Fujio Y, Sugiyama S, Masaki M, Hiramoto Y, Shioyama W, Okamoto K, Hori M, Yamauchi-Takihara K. Carbacyclin induces carnitine palmitoyltransferase-1 in cardiomyocytes via peroxisome proliferator-activated receptor (PPAR) delta independent of the IP receptor signaling pathway. J Mol Cell Cardiol. 2007 Jul;43(1):54-62. doi: 10.1016/j.yjmcc.2007.04.003. Epub 2007 Apr 12. PMID: 17540403.

17: Snitsarev V, Whiteis CA, Chapleau MW, Abboud FM. Mechano- and chemosensitivity of rat nodose neurones--selective excitatory effects of prostacyclin. J Physiol. 2007 Jul 1;582(Pt 1):177-94. doi: 10.1113/jphysiol.2007.133330. Epub 2007 May 3. PMID: 17478531; PMCID: PMC2075280.

18: Liou JY, Matijevic-Aleksic N, Lee S, Wu KK. Prostacyclin inhibits endothelial cell XIAP ubiquitination and degradation. J Cell Physiol. 2007 Sep;212(3):840-8. doi: 10.1002/jcp.21082. PMID: 17450518.

19: Zhou W, Lu T, Spector AA, Lee HC. Inhibition of PGI2 signaling by miconazole in vascular smooth muscle cells. Prostaglandins Other Lipid Mediat. 2006 Jul;80(1-2):28-34. doi: 10.1016/j.prostaglandins.2006.03.005. Epub 2006 May 11. PMID: 16846784.

20: Sheddan NA, Mulzer J. Cross metathesis as a general strategy for the synthesis of prostacyclin and prostaglandin analogues. Org Lett. 2006 Jul 6;8(14):3101-4. doi: 10.1021/ol061141u. PMID: 16805562.