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MedKoo Cat#: 584739 | Name: Beraprost

Description:

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

Beraprost is a stable prostacyclin analog.

Chemical Structure

Beraprost
CAS#88430-50-6 (free acid)

Theoretical Analysis

MedKoo Cat#: 584739

Name: Beraprost

CAS#: 88430-50-6 (free acid)

Chemical Formula: C24H30O5

Exact Mass: 398.2093

Molecular Weight: 398.50

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

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 #
88430-50-6 (free acid) 88475-69-8 (sodium)
Synonym
Beraprost; MDL 201229; MDL-201229; ML 1229; ML-1229
IUPAC/Chemical Name
(E)-4-(2-hydroxy-1-(3-hydroxy-4-methyloct-1-en-6-yn-1-yl)-2,3,3a,8b-tetrahydro-1H-cyclopenta[b]benzofuran-5-yl)butanoic acid
InChi Key
CTPOHARTNNSRSR-OUKQBFOZSA-N
InChi Code
InChI=1S/C24H30O5/c1-3-4-7-15(2)19(25)13-12-17-20(26)14-21-23(17)18-10-5-8-16(24(18)29-21)9-6-11-22(27)28/h5,8,10,12-13,15,17,19-21,23,25-26H,6-7,9,11,14H2,1-2H3,(H,27,28)/b13-12+
SMILES Code
O=C(O)CCCC1=C(OC2C3C(/C=C/C(O)C(C)CC#CC)C(O)C2)C3=CC=C1
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 398.50 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: Zhang P, Xu L, Guan H, Liu L, Liu J, Huang Z, Cao X, Liao Z, Xiao H, Li Y. Beraprost sodium, a prostacyclin analogue, reduces fructose-induced hepatocellular steatosis in mice and in vitro via the microRNA-200a and SIRT1 signaling pathway. Metabolism. 2017 Aug;73:9-21. doi: 10.1016/j.metabol.2017.05.003. Epub 2017 May 11. PubMed PMID: 28732575. 2: Zhang H, Li X, Huang J, Li H, Su Z, Wang J. Comparative Efficacy and Safety of Prostacyclin Analogs for Pulmonary Arterial Hypertension: A Network Meta-Analysis. Medicine (Baltimore). 2016 Jan;95(4):e2575. doi: 10.1097/MD.0000000000002575. Review. PubMed PMID: 26825901; PubMed Central PMCID: PMC5291571. 3: Del Pozo R, Hernandez Gonzalez I, Escribano-Subias P. The prostacyclin pathway in pulmonary arterial hypertension: a clinical review. Expert Rev Respir Med. 2017 Jun;11(6):491-503. doi: 10.1080/17476348.2017.1317599. Epub 2017 Apr 24. Review. PubMed PMID: 28399721. 4: Kim M, Kim JU, Kim SM, Kim H. Effectiveness of beraprost sodium in maintaining vascular access patency in patients on hemodialysis. Int Urol Nephrol. 2017 Jul;49(7):1287-1295. doi: 10.1007/s11255-017-1586-y. Epub 2017 Apr 13. PubMed PMID: 28409403. 5: Shimamura M, Miyakawa J, Doi M, Okada K, Kurumatani H, Mori Y, Oshida K, Nakajo I, Oikawa K, Ushigome F, Miyashita A, Isono M, Miyamoto Y. The Pharmacokinetics of Beraprost Sodium Following Single Oral Administration to Subjects With Impaired Kidney Function. J Clin Pharmacol. 2017 Apr;57(4):524-535. doi: 10.1002/jcph.835. Epub 2016 Nov 15. PubMed PMID: 27681484. 6: El Yafawi R, Wirth JA. What Is the Role of Oral Prostacyclin Pathway Medications in Pulmonary Arterial Hypertension Management? Curr Hypertens Rep. 2017 Oct 25;19(12):97. doi: 10.1007/s11906-017-0796-0. Review. PubMed PMID: 29071454. 7: Yamaguchi S, Inada C, Tamura M, Sato N, Yamada M, Itaba S, Okazaki S, Matsuura H, Fujii S, Matsuda F, Goto Y, Mochizuki H, Kurumatani H, Miyamoto M. Beraprost sodium improves survival rates in anti-glomerular basement membrane glomerulonephritis and 5/6 nephrectomized chronic kidney disease rats. Eur J Pharmacol. 2013 Aug 15;714(1-3):325-31. doi: 10.1016/j.ejphar.2013.07.032. Epub 2013 Jul 30. PubMed PMID: 23911885. 8: Perez Diaz N, Zloh M, Patel P, Mackenzie LS. In silico modelling of prostacyclin and other lipid mediators to nuclear receptors reveal novel thyroid hormone receptor antagonist properties. Prostaglandins Other Lipid Mediat. 2016 Jan;122:18-27. doi: 10.1016/j.prostaglandins.2015.12.002. Epub 2015 Dec 11. PubMed PMID: 26686607. 9: Oshida K, Shimamura M, Seya K, Ando A, Miyamoto Y. Identification of Transporters Involved in Beraprost Sodium Transport In Vitro. Eur J Drug Metab Pharmacokinet. 2017 Feb;42(1):117-128. doi: 10.1007/s13318-016-0327-4. PubMed PMID: 26961540. 10: Velayati A, Valerio MG, Shen M, Tariq S, Lanier GM, Aronow WS. Update on pulmonary arterial hypertension pharmacotherapy. Postgrad Med. 2016 Jun;128(5):460-73. doi: 10.1080/00325481.2016.1188664. Review. PubMed PMID: 27232660. 11: Chen Y, Yang S, Yao W, Zhu H, Xu X, Meng G, Zhang W. Prostacyclin analogue beraprost inhibits cardiac fibroblast proliferation depending on prostacyclin receptor activation through a TGF β-Smad signal pathway. PLoS One. 2014 May 22;9(5):e98483. doi: 10.1371/journal.pone.0098483. eCollection 2014. PubMed PMID: 24852754; PubMed Central PMCID: PMC4031177. 12: Arai T. Long-term effects of beraprost sodium on arteriosclerosis obliterans: a single-center retrospective study of Japanese patients. Adv Ther. 2013 May;30(5):528-40. doi: 10.1007/s12325-013-0030-7. Epub 2013 Jun 8. PubMed PMID: 23749750. 13: Lee E, Kim J, Kim YM, Ha KS, Jeoung DI, Sin JI, Choe J. Beraprost enhances production of antigen-specific IgG isotypes without modulating germinal center B cell generation and the affinity maturation. Int Immunopharmacol. 2013 Apr;15(4):735-42. doi: 10.1016/j.intimp.2013.03.004. Epub 2013 Mar 15. PubMed PMID: 23499642. 14: Umemiya S, Sakamoto D, Kawauchi G, Hayashi Y. Enantioselective Total Synthesis of Beraprost Using Organocatalyst. Org Lett. 2017 Mar 3;19(5):1112-1115. doi: 10.1021/acs.orglett.7b00134. Epub 2017 Feb 23. PubMed PMID: 28231006. 15: Misawa H, Ohashi W, Tomita K, Hattori K, Shimada Y, Hattori Y. Prostacyclin mimetics afford protection against lipopolysaccharide/d-galactosamine-induced acute liver injury in mice. Toxicol Appl Pharmacol. 2017 Nov 1;334:55-65. doi: 10.1016/j.taap.2017.09.003. Epub 2017 Sep 5. PubMed PMID: 28887131. 16: Sakao S, Tanabe N, Kasahara Y, Tatsumi K. Long-term survival of Japanese patients with pulmonary arterial hypertension treated with beraprost sodium, an oral prostacyclin analogue. Intern Med. 2014;53(17):1913-20. Epub 2014 Sep 1. PubMed PMID: 25175122. 17: Ono S, Nagaoka T, Omae T, Tanano I, Kamiya T, Otani S, Ishibazawa A, Yoshida A. Beraprost sodium, a stable prostacyclin analogue, elicits dilation of isolated porcine retinal arterioles: roles of eNOS and potassium channels. Invest Ophthalmol Vis Sci. 2014 Jul 31;55(9):5752-9. doi: 10.1167/iovs.14-14902. PubMed PMID: 25082887. 18: Takenaka M, Iio A, Sato R, Sakamoto T, Kurumatani H; KT-140 Clinical Study Group. A Double-blind, Placebo-controlled, Multicenter, Prospective, Randomized Study of Beraprost Sodium Treatment for Cats with Chronic Kidney Disease. J Vet Intern Med. 2018 Jan;32(1):236-248. doi: 10.1111/jvim.14839. Epub 2017 Nov 13. PubMed PMID: 29131397; PubMed Central PMCID: PMC5787173. 19: Choe J, Yoon Y, Kim J, Jung YJ. Positive feedback effect of PGE(2) on cyclooxygenase-2 expression is mediated by inhibition of Akt phosphorylation in human follicular dendritic cell-like cells. Mol Immunol. 2017 Jul;87:60-66. doi: 10.1016/j.molimm.2017.04.004. Epub 2017 Apr 11. PubMed PMID: 28407559. 20: Yoon HS, Choi WJ, Sung IH, Lee HS, Chung HJ, Lee JW. Effects of Beraprost sodium on subjective symptoms in diabetic patients with peripheral arterial disease. Clin Orthop Surg. 2013 Jun;5(2):145-51. doi: 10.4055/cios.2013.5.2.145. Epub 2013 May 15. PubMed PMID: 23730480; PubMed Central PMCID: PMC3664675.

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