BW245C
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    WARNING: This product is for research use only, not for human or veterinary use.

Hodoodo CAT#: H584316

CAS#: 72814-32-5

Description: BW245C has potent platelet anti-aggregating actions following parenteral or oral administration which makes this hydantoin a potentially-useful anti-thrombotic prostaglandin analogue.


Chemical Structure

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BW245C
CAS# 72814-32-5

Theoretical Analysis

Hodoodo Cat#: H584316
Name: BW245C
CAS#: 72814-32-5
Chemical Formula: C19H32N2O5
Exact Mass: 368.23
Molecular Weight: 368.474
Elemental Analysis: C, 61.93; H, 8.75; N, 7.60; O, 21.71

Price and Availability

Size Price Availability Quantity
1mg USD 210
5mg USD 500
10mg USD 895
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Synonym: BW245C; BW 245C; BW-245C

IUPAC/Chemical Name: 4-Imidazolidineheptanoic acid, 3-((3R)-3-cyclohexyl-3-hydroxypropyl)-2,5-dioxo-, (4S)-rel-

InChi Key: ZIDQIOZJEJFMOH-JKSUJKDBSA-N

InChi Code: InChI=1S/C19H32N2O5/c22-16(14-8-4-3-5-9-14)12-13-21-15(18(25)20-19(21)26)10-6-1-2-7-11-17(23)24/h14-16,22H,1-13H2,(H,23,24)(H,20,25,26)/t15-,16+/m0/s1

SMILES Code: O=C(O)CCCCCC[C@@H](C(N1)=O)N(CC[C@H](C2CCCCC2)O)C1=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:

Biological target: A selective DP1 receptor agonist.
In vitro activity: The specific DP1 agonist BW245c significantly enhanced the percentage of viable cells (Annexin V−/PI−) from 25 to 50% of all eosinophils; by comparison, IL‐5 maintained 59% of the cells viable (Fig. 1A). BW245c concentration‐dependently inhibits apoptosis of eosinophils, with a half maximal efficacy (EC50) of 0.826 μM (Supplementary Fig. 1). PGD2 itself moderately increased the percentage of viable cells to 39%. Reference: J Leukoc Biol. 2018 Jul; 104(1): 159–171. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6032830/
In vivo activity: Despite being on high fat diet, mice receiving DP1 receptor agonist (BW245C) sustained a significant inhibition of weight gain throughout the study gaining only 11.4% body weight compared to the controls gaining 61% body weight. Reference: Obes Res Clin Pract. 2018 Mar-Apr;12(2):229-241. https://pubmed.ncbi.nlm.nih.gov/28602634/

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
PBS (pH 7.2) 2.4 6.43

Preparing Stock Solutions

The following data is based on the product molecular weight 368.47 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
Formulation protocol: 1. Peinhaupt M, Roula D, Theiler A, Sedej M, Schicho R, Marsche G, Sturm EM, Sabroe I, Rothenberg ME, Heinemann A. DP1 receptor signaling prevents the onset of intrinsic apoptosis in eosinophils and functions as a transcriptional modulator. J Leukoc Biol. 2018 Jul;104(1):159-171. doi: 10.1002/JLB.3MA1017-404R. Epub 2018 Apr 1. PMID: 29607536; PMCID: PMC6032830. 2. Kumar S, Palaia T, Hall C, Ragolia L. DP1 receptor agonist, BW245C inhibits diet-induced obesity in ApoE-/- mice. Obes Res Clin Pract. 2018 Mar-Apr;12(2):229-241. doi: 10.1016/j.orcp.2017.05.003. Epub 2017 Jun 8. PMID: 28602634. 3. van den Brule S, Wallemme L, Uwambayinema F, Huaux F, Lison D. The D prostanoid receptor agonist BW245C [(4S)-(3-[(3R,S)-3-cyclohexyl-3-hydroxypropyl]-2,5-dioxo)-4-imidazolidineheptanoic acid] inhibits fibroblast proliferation and bleomycin-induced lung fibrosis in mice. J Pharmacol Exp Ther. 2010 Nov;335(2):472-9. doi: 10.1124/jpet.110.169250. Epub 2010 Aug 18. PMID: 20719937.
In vitro protocol: 1. Peinhaupt M, Roula D, Theiler A, Sedej M, Schicho R, Marsche G, Sturm EM, Sabroe I, Rothenberg ME, Heinemann A. DP1 receptor signaling prevents the onset of intrinsic apoptosis in eosinophils and functions as a transcriptional modulator. J Leukoc Biol. 2018 Jul;104(1):159-171. doi: 10.1002/JLB.3MA1017-404R. Epub 2018 Apr 1. PMID: 29607536; PMCID: PMC6032830.
In vivo protocol: 1. Kumar S, Palaia T, Hall C, Ragolia L. DP1 receptor agonist, BW245C inhibits diet-induced obesity in ApoE-/- mice. Obes Res Clin Pract. 2018 Mar-Apr;12(2):229-241. doi: 10.1016/j.orcp.2017.05.003. Epub 2017 Jun 8. PMID: 28602634. 2. van den Brule S, Wallemme L, Uwambayinema F, Huaux F, Lison D. The D prostanoid receptor agonist BW245C [(4S)-(3-[(3R,S)-3-cyclohexyl-3-hydroxypropyl]-2,5-dioxo)-4-imidazolidineheptanoic acid] inhibits fibroblast proliferation and bleomycin-induced lung fibrosis in mice. J Pharmacol Exp Ther. 2010 Nov;335(2):472-9. doi: 10.1124/jpet.110.169250. Epub 2010 Aug 18. PMID: 20719937.

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1: Ahmad AS. PGD2 DP1 receptor stimulation following stroke ameliorates cerebral blood flow and outcomes. Neuroscience. 2014 Oct 24;279:260-8. doi: 10.1016/j.neuroscience.2014.08.050. Epub 2014 Sep 10. PubMed PMID: 25218962.

2: van den Brule S, Wallemme L, Uwambayinema F, Huaux F, Lison D. The D prostanoid receptor agonist BW245C [(4S)-(3-[(3R,S)-3-cyclohexyl-3-hydroxypropyl]-2,5-dioxo)-4-imidazolidineheptanoi c acid] inhibits fibroblast proliferation and bleomycin-induced lung fibrosis in mice. J Pharmacol Exp Ther. 2010 Nov;335(2):472-9. doi: 10.1124/jpet.110.169250. Epub 2010 Aug 18. PubMed PMID: 20719937.

3: Koch KA, Wessale JL, Moreland R, Reinhart GA, Cox BF. Effects of BW245C, a prostaglandin dp receptor agonist, on systemic and regional haemodynamics in the anaesthetized rat. Clin Exp Pharmacol Physiol. 2005 Nov;32(11):931-5. PubMed PMID: 16405449.

4: Al-Sinawi LA, Mekki QA, Hassan S, Hedges A, Burke C, Moody SG, O'Grady J. Effect of a hydantoin prostaglandin analogue, BW245C, during oral dosing in man. Prostaglandins. 1985 Jan;29(1):99-111. PubMed PMID: 3975430.

5: Whittle BJ, Moncada S, Mullane K, Vane JR. Platelet and cardiovascular activity of the hydantoin BW245C, a potent prostaglandin analogue. Prostaglandins. 1983 Feb;25(2):205-23. PubMed PMID: 6344147.

6: Nakajima M, Goh Y, Azuma I, Hayaishi O. Effects of prostaglandin D2 and its analogue, BW245C, on intraocular pressure in humans. Graefes Arch Clin Exp Ophthalmol. 1991;229(5):411-3. PubMed PMID: 1937072.

7: Hamid S, Whittle BJ. Interaction of prostaglandin D2 with prostacyclin, carbacyclin and the hydantoin prostaglandin, BW245C, in guinea-pig platelets. Br J Pharmacol. 1985 May;85(1):285-90. PubMed PMID: 2992652; PubMed Central PMCID: PMC1916783.

8: Trist DG, Collins BA, Wood J, Kelly MG, Robertson AD. The antagonism by BW A868C of PGD2 and BW245C activation of human platelet adenylate cyclase. Br J Pharmacol. 1989 Feb;96(2):301-6. PubMed PMID: 2466517; PubMed Central PMCID: PMC1854363.

9: Barraclough P, Brockwell M, Caldwell AG, Demaine DA, Harris CJ, King WR, Stepney RJ, Wharton CJ, Whittle BJ. Synthesis and inhibitory activity on platelet aggregation of 13'-aza and other omega-chain modified BW245C analogues. Arch Pharm (Weinheim). 1994 May;327(5):307-17. PubMed PMID: 8010883.

10: Maruyama T, Ayabe S, Murata T, Hori M, Ozaki H. Relaxant effect of prostaglandin D(2)--receptor DP agonist on liver myofibroblast contraction. J Pharmacol Sci. 2011;116(2):197-203. Epub 2011 May 25. PubMed PMID: 21613754.

11: Kobayashi K, Tsubosaka Y, Hori M, Narumiya S, Ozaki H, Murata T. Prostaglandin D2-DP signaling promotes endothelial barrier function via the cAMP/PKA/Tiam1/Rac1 pathway. Arterioscler Thromb Vasc Biol. 2013 Mar;33(3):565-71. doi: 10.1161/ATVBAHA.112.300993. Epub 2013 Jan 10. PubMed PMID: 23307871.

12: Fujita T, Soontrapa K, Ito Y, Iwaisako K, Moniaga CS, Asagiri M, Majima M, Narumiya S. Hepatic stellate cells relay inflammation signaling from sinusoids to parenchyma in mouse models of immune-mediated hepatitis. Hepatology. 2016 Apr;63(4):1325-39. doi: 10.1002/hep.28112. Epub 2015 Sep 30. PubMed PMID: 26248612.

13: Lydford SJ, McKechnie KC, Leff P. Interaction of BW A868C, a prostanoid DP-receptor antagonist, with two receptor subtypes in the rabbit isolated saphenous vein. Prostaglandins. 1996 Aug;52(2):125-39. Erratum in: Prostaglandins 1997 Jan;53(1):59-62. PubMed PMID: 8880898.

14: Ayabe S, Kida T, Hori M, Ozaki H, Murata T. Prostaglandin D2 inhibits collagen secretion from lung fibroblasts by activating the DP receptor. J Pharmacol Sci. 2013;121(4):312-7. Epub 2013 Mar 29. PubMed PMID: 23538675.

15: Ma J, Yang Q, Wei Y, Yang Y, Ji C, Hu X, Mai S, Kuang S, Tian X, Luo Y, Liang G, Yang J. Effect of the PGD2-DP signaling pathway on primary cultured rat hippocampal neuron injury caused by aluminum overload. Sci Rep. 2016 Apr 19;6:24646. doi: 10.1038/srep24646. PubMed PMID: 27089935; PubMed Central PMCID: PMC4835855.

16: Kobzar G, Mardla V, Samel N. Lactate is a possible mediator of the glucose effect on platelet inhibition. Platelets. 2014;25(4):239-45. doi: 10.3109/09537104.2013.816670. Epub 2013 Aug 2. PubMed PMID: 23909711.

17: Sharif NA, Crider JY. Intracellular signaling in human iridial fibroblasts and iridial melanocytes in response to prostaglandins, endothelin, isoproterenol, and other pharmacological agents. Curr Eye Res. 2011 Apr;36(4):310-20. doi: 10.3109/02713683.2010.542869. PubMed PMID: 21405953.

18: Hubertus K, Mischnik M, Timmer J, Herterich S, Mark R, Moulard M, Walter U, Geiger J. Reciprocal regulation of human platelet function by endogenous prostanoids and through multiple prostanoid receptors. Eur J Pharmacol. 2014 Oct 5;740:15-27. doi: 10.1016/j.ejphar.2014.06.030. Epub 2014 Jul 6. PubMed PMID: 25003953.

19: Liu YJ, Jackson DM, Blackham A. Effects of BW A868C, a selective prostaglandin DP receptor antagonist, in dog isolated vascular preparations. Eur J Pharmacol. 1996 May 15;303(3):187-92. PubMed PMID: 8813566.

20: Narumiya S, Toda N. Different responsiveness of prostaglandin D2-sensitive systems to prostaglandin D2 and its analogues. Br J Pharmacol. 1985 Jun;85(2):367-75. PubMed PMID: 2992661; PubMed Central PMCID: PMC1916609.