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MedKoo Cat#: 574421 | Name: Taprostene
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Description:

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

Taprostene is a stable prostacyclin (PGI2) analog and agonist of the prostacyclin receptor, IP. It does not activate the PGE2 receptor EP4 which, like IP, promotes vascular smooth muscle relaxation when stimulated. Taprostene has been used extensively to study the role of the IP receptor in tissue preparations and in vivo. It has also been used in the screening and evaluation of potential IP antagonists.

Chemical Structure

Taprostene
Taprostene
CAS#108945-35-3 (free base)

Theoretical Analysis

MedKoo Cat#: 574421

Name: Taprostene

CAS#: 108945-35-3 (free base)

Chemical Formula: C24H30O5

Exact Mass: 398.2093

Molecular Weight: 398.49

Elemental Analysis: C, 72.34; H, 7.59; O, 20.07

Price and Availability

Size Price Availability Quantity
1mg USD 450.00 2 Weeks
5mg USD 1,150.00 2 Weeks
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Related CAS #
87440-45-7 (Na) 108945-35-3 (free base)
Synonym
CG 4203, Rheocyclan, Taprostene
IUPAC/Chemical Name
3-[(Z)-[(3aR,4R,5R,6aS)-4-[(1E,3S)-3-cyclohexyl-3-hydroxy-1-propenyl]hexahydro-5-hydroxy-2H-cyclopenta[b]furan-2-ylidene]methyl]-benzoic acid
InChi Key
ZLJOKYGJNOQXDP-UHKCRUDESA-N
InChi Code
InChI=1S/C24H30O5/c25-21(16-6-2-1-3-7-16)10-9-19-20-13-18(29-23(20)14-22(19)26)12-15-5-4-8-17(11-15)24(27)28/h4-5,8-12,16,19-23,25-26H,1-3,6-7,13-14H2,(H,27,28)/b10-9+,18-12-/t19-,20-,21+,22-,23+/m1/s1
SMILES Code
O[C@@H]([C@@H]1/C=C/[C@H](O)C2CCCCC2)C[C@]([C@]1([H])C/3)([H])OC3=C/C4=CC=CC(C(O)=O)=C4
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

Preparing Stock Solutions

The following data is based on the product molecular weight 398.49 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
1: Joshi R, Paracha TU, Mostafa MM, Thorne AJ, Jayasinghe V, Yan D, Hamed O, Newton R, Giembycz MA. Comparison of the Genomic Activity of an EP4-Receptor and β2-Adrenoceptor Agonist in BEAS-2B Human Bronchial Epithelial Cells: In Search of Compartmentalized, cAMP-Dependent Gene Expression. J Pharmacol Exp Ther. 2024 Sep 18;391(1):64-81. doi: 10.1124/jpet.124.002226. PMID: 39060164. 2: Combe SH, Hosseini A, Parra A, Schreiner PR. Mild Aliphatic and Benzylic Hydrocarbon C-H Bond Chlorination Using Trichloroisocyanuric Acid. J Org Chem. 2017 Mar 3;82(5):2407-2413. doi: 10.1021/acs.joc.6b02829. Epub 2017 Feb 10. PMID: 28106993. 3: Vitale V, Monami M, Mannucci E. Prostanoids in patients with peripheral arterial disease: A meta-analysis of placebo-controlled randomized clinical trials. J Diabetes Complications. 2016 Jan-Feb;30(1):161-6. doi: 10.1016/j.jdiacomp.2015.09.006. Epub 2015 Sep 12. PMID: 26516035. 4: Hoang KG, Allison S, Murray M, Petrovic N. Prostanoids regulate angiogenesis acting primarily on IP and EP4 receptors. Microvasc Res. 2015 Sep;101:127-34. doi: 10.1016/j.mvr.2015.07.004. Epub 2015 Jul 17. PMID: 26188701. 5: Robertson L, Andras A. Prostanoids for intermittent claudication. Cochrane Database Syst Rev. 2013 Apr 30;(4):CD000986. doi: 10.1002/14651858.CD000986.pub3. PMID: 23633305. 6: Belch JJ, Ray S, Rajput-Ray M, Engeset J, Fagrell B, Lepäntalo M, McKay A, Mackay IR, Ostergren J, Ruckley CV, Salenius J. The Scottish-Finnish-Swedish PARTNER study of taprostene versus placebo treatment in patients with critical limb ischemia. Int Angiol. 2011 Apr;30(2):150-5. PMID: 21427652. 7: Wilson SM, Sheddan NA, Newton R, Giembycz MA. Evidence for a second receptor for prostacyclin on human airway epithelial cells that mediates inhibition of CXCL9 and CXCL10 release. Mol Pharmacol. 2011 Mar;79(3):586-95. doi: 10.1124/mol.110.069674. Epub 2010 Dec 20. PMID: 21173040. 8: Labus J, Breil J, Stützer H, Michel O. Meta-analysis for the effect of medical therapy vs. placebo on recovery of idiopathic sudden hearing loss. Laryngoscope. 2010 Sep;120(9):1863-71. doi: 10.1002/lary.21011. PMID: 20803741. 9: Wilson SM, Shen P, Rider CF, Traves SL, Proud D, Newton R, Giembycz MA. Selective prostacyclin receptor agonism augments glucocorticoid-induced gene expression in human bronchial epithelial cells. J Immunol. 2009 Nov 15;183(10):6788-99. doi: 10.4049/jimmunol.0902738. Epub 2009 Oct 30. PMID: 19880449. 10: Ayer LM, Wilson SM, Traves SL, Proud D, Giembycz MA. 4,5-Dihydro-1H-imidazol-2-yl)-[4-(4-isopropoxy-benzyl)-phenyl]-amine (RO1138452) is a selective, pseudo-irreversible orthosteric antagonist at the prostacyclin (IP)-receptor expressed by human airway epithelial cells: IP-receptor-mediated inhibition of CXCL9 and CXCL10 release. J Pharmacol Exp Ther. 2008 Feb;324(2):815-26. doi: 10.1124/jpet.107.129312. Epub 2007 Oct 25. PMID: 17962517. 11: Jones RL, Chan KM. Investigation of the agonist activity of prostacyclin analogues on prostanoid EP4 receptors using GW 627368 and taprostene: evidence for species differences. Prostaglandins Leukot Essent Fatty Acids. 2005 Apr;72(4):289-99. doi: 10.1016/j.plefa.2004.12.002. PMID: 15763441. 12: Chan KM, Jones RL. Partial agonism of taprostene at prostanoid IP receptors in vascular preparations from guinea-pig, rat, and mouse. J Cardiovasc Pharmacol. 2004 Jun;43(6):795-807. doi: 10.1097/00005344-200406000-00009. PMID: 15167273. 13: Chow KB, Jones RL, Wise H. Agonists can discriminate between cloned human and mouse prostacyclin receptors. Prostaglandins Leukot Essent Fatty Acids. 2004 May;70(5):423-9. doi: 10.1016/j.plefa.2003.08.022. PMID: 15062844. 14: 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. 15: Jones RL, Chan K. Distinction between relaxations induced via prostanoid EP(4) and IP(1) receptors in pig and rabbit blood vessels. Br J Pharmacol. 2001 Sep;134(2):313-24. doi: 10.1038/sj.bjp.0704252. PMID: 11564649; PMCID: PMC1572952. 16: Rudd JA, Qian Ym, Tsui KK, Jones RL. Non-prostanoid prostacyclin mimetics as neuronal stimulants in the rat: comparison of vagus nerve and NANC innervation of the colon. Br J Pharmacol. 2000 Feb;129(4):782-90. doi: 10.1038/sj.bjp.0703090. PMID: 10683203; PMCID: PMC1571884. 17: Sobal G, Sinzinger H. Effects of PGI2 and analogues (taprostene, iloprost) on oxidation of native and glycated LDL. Life Sci. 1999;65(12):1237-46. doi: 10.1016/s0024-3205(99)00359-8. PMID: 10503939. 18: Belch JJ, Söhngen M, Robb R, Voleske P, Söhngen W. Neutrophil count and amputation in critical limb ischaemia. Int Angiol. 1999 Jun;18(2):140-4. PMID: 10424370. 19: Murohara T, Horowitz JR, Silver M, Tsurumi Y, Chen D, Sullivan A, Isner JM. Vascular endothelial growth factor/vascular permeability factor enhances vascular permeability via nitric oxide and prostacyclin. Circulation. 1998 Jan 6-13;97(1):99-107. doi: 10.1161/01.cir.97.1.99. PMID: 9443437. 20: Tam FS, Chan K, Borreau JP, Jones RL. The mechanisms of enhancement and inhibition of field stimulation responses of guinea-pig vas deferens by prostacyclin analogues. Br J Pharmacol. 1997 Aug;121(7):1413-21. doi: 10.1038/sj.bjp.0701275. PMID: 9257922; PMCID: PMC1564834.

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