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MedKoo Cat#: 561253 | Name: Butaprost

Description:

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

Butaprost is a prostanoid EP2 receptor agonist. Butaprost has been used to pharmacologically define the EP receptor expression profile of various human and animal tissues and cells.

Chemical Structure

Butaprost
Butaprost
CAS#69648-38-0

Theoretical Analysis

MedKoo Cat#: 561253

Name: Butaprost

CAS#: 69648-38-0

Chemical Formula: C24H40O5

Exact Mass: 408.2876

Molecular Weight: 408.58

Elemental Analysis: C, 70.55; H, 9.87; O, 19.58

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 #
No Data
Synonym
Butaprost; (R)-Butaprost; TR-4979; Butaprostum
IUPAC/Chemical Name
methyl 7-((1R,2R,3R)-3-hydroxy-2-((S,E)-4-hydroxy-4-(1-propylcyclobutyl)but-1-en-1-yl)-5-oxocyclopentyl)heptanoate
InChi Key
XRISENIKJUKIHD-IOOSKWMSSA-N
InChi Code
InChI=1S/C24H40O5/c1-3-14-24(15-9-16-24)22(27)12-8-11-19-18(20(25)17-21(19)26)10-6-4-5-7-13-23(28)29-2/h8,11,18-19,21-22,26-27H,3-7,9-10,12-17H2,1-2H3/b11-8+/t18-,19-,21-,22+/m1/s1
SMILES Code
O=C(OC)CCCCCC[C@@H]1[C@@H](/C=C/C[C@H](O)C2(CCC)CCC2)[C@H](O)CC1=O
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

Preparing Stock Solutions

The following data is based on the product molecular weight 408.58 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: Nilsson SF, Drecoll E, Lütjen-Drecoll E, Toris CB, Krauss AH, Kharlamb A, Nieves A, Guerra T, Woodward DF. The prostanoid EP2 receptor agonist butaprost increases uveoscleral outflow in the cynomolgus monkey. Invest Ophthalmol Vis Sci. 2006 Sep;47(9):4042-9. PubMed PMID: 16936121. 2: Duckworth N, Marshall K, Clayton JK. An investigation of the effect of the prostaglandin EP2 receptor agonist, butaprost, on the human isolated myometrium from pregnant and non-pregnant women. J Endocrinol. 2002 Feb;172(2):263-9. PubMed PMID: 11834444. 3: Liang Y, Li C, Guzman VM, Chang WW, Evinger AJ, Pablo JV, Woodward DF. Upregulation of orphan nuclear receptor Nur77 following PGF(2alpha), Bimatoprost, and Butaprost treatments. Essential role of a protein kinase C pathway involved in EP(2) receptor activated Nur77 gene transcription. Br J Pharmacol. 2004 Jun;142(4):737-48. Epub 2004 May 24. PubMed PMID: 15159280; PubMed Central PMCID: PMC1575044. 4: Osborne NN, Li GY, Ji D, Andrade da Costa BL, Fawcett RJ, Kang KD, Rittenhouse KD. Expression of prostaglandin PGE2 receptors under conditions of aging and stress and the protective effect of the EP2 agonist butaprost on retinal ischemia. Invest Ophthalmol Vis Sci. 2009 Jul;50(7):3238-48. doi: 10.1167/iovs.08-3185. Epub 2009 Mar 5. PubMed PMID: 19264896. 5: Andrade da Costa BL, Kang KD, Rittenhouse KD, Osborne NN. The localization of PGE2 receptor subtypes in rat retinal cultures and the neuroprotective effect of the EP2 agonist butaprost. Neurochem Int. 2009 Sep;55(4):199-207. doi: 10.1016/j.neuint.2009.02.015. Epub 2009 Mar 5. PubMed PMID: 19524109. 6: Shin JH, Seo JH, Jung JH, Kim TW. Anti-scarring effects of butaprost on human subconjunctival Tenon's fibroblasts. Int J Ophthalmol. 2017 Jul 18;10(7):1028-1033. doi: 10.18240/ijo.2017.07.02. eCollection 2017. PubMed PMID: 28730102; PubMed Central PMCID: PMC5514261. 7: Liang Y, Li C, Guzman VM, Evinger AJ 3rd, Protzman CE, Krauss AH, Woodward DF. Comparison of prostaglandin F2alpha, bimatoprost (prostamide), and butaprost (EP2 agonist) on Cyr61 and connective tissue growth factor gene expression. J Biol Chem. 2003 Jul 18;278(29):27267-77. Epub 2003 Apr 30. PubMed PMID: 12724323. 8: Mo C, Zhao R, Vallejo J, Igwe O, Bonewald L, Wetmore L, Brotto M. Prostaglandin E2 promotes proliferation of skeletal muscle myoblasts via EP4 receptor activation. Cell Cycle. 2015;14(10):1507-16. doi: 10.1080/15384101.2015.1026520. PubMed PMID: 25785867; PubMed Central PMCID: PMC4615122. 9: Kalouche G, Beguier F, Bakria M, Melik-Parsadaniantz S, Leriche C, Debeir T, Rostène W, Baudouin C, Vigé X. Activation of Prostaglandin FP and EP2 Receptors Differently Modulates Myofibroblast Transition in a Model of Adult Primary Human Trabecular Meshwork Cells. Invest Ophthalmol Vis Sci. 2016 Apr;57(4):1816-25. doi: 10.1167/iovs.15-17693. PubMed PMID: 27082296. 10: Hu S, Sun W, Wei W, Wang D, Jin J, Wu J, Chen J, Wu H, Wang Q. Involvement of the prostaglandin E receptor EP2 in paeoniflorin-induced human hepatoma cell apoptosis. Anticancer Drugs. 2013 Feb;24(2):140-9. doi: 10.1097/CAD.0b013e32835a4dac. PubMed PMID: 23069790. 11: Martinez-Cutillas M, Mañé N, Gallego D, Jimenez M, Martin MT. EP2 and EP4 receptors mediate PGE2 induced relaxation in murine colonic circular muscle: pharmacological characterization. Pharmacol Res. 2014 Dec;90:76-86. doi: 10.1016/j.phrs.2014.10.001. Epub 2014 Oct 20. PubMed PMID: 25461458. 12: Olesen ET, Moeller HB, Assentoft M, MacAulay N, Fenton RA. The vasopressin type 2 receptor and prostaglandin receptors EP2 and EP4 can increase aquaporin-2 plasma membrane targeting through a cAMP-independent pathway. Am J Physiol Renal Physiol. 2016 Nov 1;311(5):F935-F944. doi: 10.1152/ajprenal.00559.2015. Epub 2016 Aug 24. PubMed PMID: 27558562. 13: Fu Y, Yang MS, Jiang J, Ganesh T, Joe E, Dingledine R. EP2 Receptor Signaling Regulates Microglia Death. Mol Pharmacol. 2015 Jul;88(1):161-70. doi: 10.1124/mol.115.098202. Epub 2015 Feb 25. PubMed PMID: 25715797; PubMed Central PMCID: PMC4468645. 14: Mikawa S, Ohta Y, Kaji N, Islam MS, Murata T, Ozaki H, Hori M. Time-dependent changes in inhibitory action of lipopolysaccharide on intestinal motility in rat. J Vet Med Sci. 2015 Nov;77(11):1443-9. doi: 10.1292/jvms.15-0198. Epub 2015 Jun 8. PubMed PMID: 26051129; PubMed Central PMCID: PMC4667662. 15: Woo SM, Min KJ, Chae IG, Chun KS, Kwon TK. Silymarin suppresses the PGE2 -induced cell migration through inhibition of EP2 activation; G protein-dependent PKA-CREB and G protein-independent Src-STAT3 signal pathways. Mol Carcinog. 2015 Mar;54(3):216-28. doi: 10.1002/mc.22092. Epub 2013 Oct 11. PubMed PMID: 24127286. 16: Olesen ET, Rützler MR, Moeller HB, Praetorius HA, Fenton RA. Vasopressin-independent targeting of aquaporin-2 by selective E-prostanoid receptor agonists alleviates nephrogenic diabetes insipidus. Proc Natl Acad Sci U S A. 2011 Aug 2;108(31):12949-54. doi: 10.1073/pnas.1104691108. Epub 2011 Jul 18. PubMed PMID: 21768374; PubMed Central PMCID: PMC3150913. 17: Machado-Carvalho L, Torres R, Perez-Gonzalez M, Alobid I, Mullol J, Pujols L, Roca-Ferrer J, Picado C. Altered expression and signalling of EP2 receptor in nasal polyps of AERD patients: role in inflammation and remodelling. Rhinology. 2016 Sep;54(3):254-65. doi: 10.4193/Rhin15.207. PubMed PMID: 26747755. 18: Mohan S, Narumiya S, Doré S. Neuroprotective role of prostaglandin PGE2 EP2 receptor in hemin-mediated toxicity. Neurotoxicology. 2015 Jan;46:53-9. doi: 10.1016/j.neuro.2014.10.012. Epub 2014 Nov 13. PubMed PMID: 25451967; PubMed Central PMCID: PMC4681391. 19: Perusquía M, Flores-Soto E, Sommer B, Campuzano-González E, Martínez-Villa I, Martínez-Banderas AI, Montaño LM. Testosterone-induced relaxation involves L-type and store-operated Ca2+ channels blockade, and PGE 2 in guinea pig airway smooth muscle. Pflugers Arch. 2015 Apr;467(4):767-77. doi: 10.1007/s00424-014-1534-y. Epub 2014 May 29. PubMed PMID: 24872164. 20: Kalouche G, Boucher C, Coste A, Debussche L, Orsini C, Baudouin C, Debeir T, Vigé X, Rostène W. Prostaglandin EP2 receptor signaling protects human trabecular meshwork cells from apoptosis induced by ER stress through down-regulation of p53. Biochim Biophys Acta. 2016 Sep;1863(9):2322-32. doi: 10.1016/j.bbamcr.2016.06.008. Epub 2016 Jun 17. PubMed PMID: 27321910.

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