BPTU | CAS#870544-59-5 | P2Y1 antagonist

MedKoo Cat#: 561831 | Name: BPTU

Description:

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

BPTU is a P2Y1 antagonist. It has been shown to provide antithrombotic efficacy and reduce bleeding liability.

Chemical Structure

BPTU

CAS#870544-59-5

Theoretical Analysis

MedKoo Cat#: 561831

Name: BPTU

CAS#: 870544-59-5

Chemical Formula: C23H22F3N3O3

Exact Mass: 445.1613

Molecular Weight: 445.44

Elemental Analysis: C, 62.02; H, 4.98; F, 12.80; N, 9.43; O, 10.78

Price and Availability

Size	Price	Availability
25mg	USD 250.00	2 Weeks
50mg	USD 450.00	2 Weeks
100mg	USD 750.00	2 Weeks
250mg	USD 1,350.00	2 Weeks
500mg	USD 2,250.00	2 Weeks
1g	USD 3,250.00	2 Weeks

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Synonym

BPTU; BMS-646786; BMS 646786; BMS646786;

IUPAC/Chemical Name

1-[2-(2-tert-Butylphenoxy)pyridin-3-yl]-3-[4-(trifluoromethoxy)phenyl]urea

InChi Key

AHFLGPTXSIRAQK-UHFFFAOYSA-N

InChi Code

InChI=1S/C23H22F3N3O3/c1-22(2,3)17-7-4-5-9-19(17)31-20-18(8-6-14-27-20)29-21(30)28-15-10-12-16(13-11-15)32-23(24,25)26/h4-14H,1-3H3,(H2,28,29,30)

SMILES Code

O=C(NC1=CC=C(OC(F)(F)F)C=C1)NC2=CC=CN=C2OC3=CC=CC=C3C(C)(C)C

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

Product Data

Product Data

Instruction

View handling instruction

Biological target:

BPTU (BMS-646786) is a non-nucleotide P2Y1 receptor allosteric antagonist with antithrombotic activity.

In vitro activity:

BPTU concentration dependently (0.1 and 1 µmol L-1 ) inhibited the rise in intracellular Ca2+ evoked by ADP in tSA201 cells. In the pig small intestine, 30 µmol L-1 BPTU reduced the fast inhibitory junction potential by 80%. Reference: Neurogastroenterol Motil. 2021 Jul;33(7):e14101. https://pubmed.ncbi.nlm.nih.gov/33619847/

In vivo activity:

BPTU concentration dependently inhibited purinergic inhibitory junction potentials and inhibition of spontaneous motility induced by electrical field stimulation in the colon of rats (EC50 = 0.3 μM) and mice (EC50 = 0.06 μM). Mechanical inhibitory responses were also concentration-dependently blocked in the stomach of both species. Compared to MRS2500, BPTU displays a lower potency. In the rat colon nicotine induced relaxation was also blocked by BPTU. BPTU also blocked the cessation of spontaneous contractility elicited by ADPβS and the P2Y1 agonist MRS2365. BPTU is a novel antagonist with different structural and functional properties than nucleotidic antagonists that is able to block the P2Y1 receptor located at the neuromuscular junction of the GI tract. Reference: Neuropharmacology. 2016 Nov;110(Pt A):376-385. https://pubmed.ncbi.nlm.nih.gov/27496690/

	Solvent	mg/mL	mM
Solubility
	DMSO	34.3	76.98
	DMSO:PBS (pH 7.2) (1:2)	0.3	0.67
	DMF	15.0	33.67
	Ethanol	29.8	66.83

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 445.44 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.

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. Traserra S, Barber C, Maclnnes J, Relea L, MacPherson LC, Cunningham MR, Vergara P, Accarino A, Kennedy C, Jimenez M. Different responses of the blockade of the P2Y1 receptor with BPTU in human and porcine intestinal tissues and in cell cultures. Neurogastroenterol Motil. 2021 Jul;33(7):e14101. doi: 10.1111/nmo.14101. Epub 2021 Feb 22. PMID: 33619847. 2. Mañé N, Jiménez-Sábado V, Jiménez M. BPTU, an allosteric antagonist of P2Y1 receptor, blocks nerve mediated inhibitory neuromuscular responses in the gastrointestinal tract of rodents. Neuropharmacology. 2016 Nov;110(Pt A):376-385. doi: 10.1016/j.neuropharm.2016.07.033. Epub 2016 Aug 3. PMID: 27496690. 3. Verrijk R, Smolders IJ, Huiskamp R, Gavin PR, Philipp KH, Begg AC. Pharmacokinetics in melanoma-bearing mice of 5-dihydroxyboryl-6-propyl-2-thiouracil (BPTU), a candidate compound for boron neutron capture therapy. Br J Cancer. 1994 Apr;69(4):641-7. doi: 10.1038/bjc.1994.125. PMID: 8142252; PMCID: PMC1968811.

In vitro protocol:

In vivo protocol:

1. Mañé N, Jiménez-Sábado V, Jiménez M. BPTU, an allosteric antagonist of P2Y1 receptor, blocks nerve mediated inhibitory neuromuscular responses in the gastrointestinal tract of rodents. Neuropharmacology. 2016 Nov;110(Pt A):376-385. doi: 10.1016/j.neuropharm.2016.07.033. Epub 2016 Aug 3. PMID: 27496690. 2. Verrijk R, Smolders IJ, Huiskamp R, Gavin PR, Philipp KH, Begg AC. Pharmacokinetics in melanoma-bearing mice of 5-dihydroxyboryl-6-propyl-2-thiouracil (BPTU), a candidate compound for boron neutron capture therapy. Br J Cancer. 1994 Apr;69(4):641-7. doi: 10.1038/bjc.1994.125. PMID: 8142252; PMCID: PMC1968811.

1: Ciancetta A, O'Connor RD, Paoletta S, Jacobson KA. Demystifying P2Y(1) Receptor Ligand Recognition through Docking and Molecular Dynamics Analyses. J Chem Inf Model. 2017 Dec 26;57(12):3104-3123. doi: 10.1021/acs.jcim.7b00528. Epub 2017 Nov 28. PubMed PMID: 29182323. 2: Gao ZG, Jacobson KA. Distinct Signaling Patterns of Allosteric Antagonism at the P2Y(1) Receptor. Mol Pharmacol. 2017 Nov;92(5):613-626. doi: 10.1124/mol.117.109660. Epub 2017 Sep 1. PubMed PMID: 28864555; PubMed Central PMCID: PMC5635520. 3: Mañé N, Jiménez-Sábado V, Jiménez M. BPTU, an allosteric antagonist of P2Y1 receptor, blocks nerve mediated inhibitory neuromuscular responses in the gastrointestinal tract of rodents. Neuropharmacology. 2016 Nov;110(Pt A):376-385. doi: 10.1016/j.neuropharm.2016.07.033. Epub 2016 Aug 3. PubMed PMID: 27496690. 4: Yuan S, Chan HC, Vogel H, Filipek S, Stevens RC, Palczewski K. The Molecular Mechanism of P2Y1 Receptor Activation. Angew Chem Int Ed Engl. 2016 Aug 22;55(35):10331-5. doi: 10.1002/anie.201605147. Epub 2016 Jul 27. PubMed PMID: 27460867; PubMed Central PMCID: PMC4996126. 5: Zhang D, Gao ZG, Zhang K, Kiselev E, Crane S, Wang J, Paoletta S, Yi C, Ma L, Zhang W, Han GW, Liu H, Cherezov V, Katritch V, Jiang H, Stevens RC, Jacobson KA, Zhao Q, Wu B. Two disparate ligand-binding sites in the human P2Y1 receptor. Nature. 2015 Apr 16;520(7547):317-21. doi: 10.1038/nature14287. Epub 2015 Mar 30. PubMed PMID: 25822790; PubMed Central PMCID: PMC4408927. 6: Buckheit RW Jr, Fliakas-Boltz V, Yeagy-Bargo S, Weislow O, Mayers DL, Boyer PL, Hughes SH, Pan BC, Chu SH, Bader JP. Resistance to 1-[(2-hydroxyethoxy)methyl]-6-(phenylthio)thymine derivatives is generated by mutations at multiple sites in the HIV-1 reverse transcriptase. Virology. 1995 Jun 20;210(1):186-93. PubMed PMID: 7540784. 7: Verrijk R, Smolders IJ, Huiskamp R, Gavin PR, Philipp KH, Begg AC. Pharmacokinetics in melanoma-bearing mice of 5-dihydroxyboryl-6-propyl-2-thiouracil (BPTU), a candidate compound for boron neutron capture therapy. Br J Cancer. 1994 Apr;69(4):641-7. PubMed PMID: 8142252; PubMed Central PMCID: PMC1968811.