Uridine triphosphate

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MedKoo CAT#: 206733

CAS#: 63-39-8 (free base)

Description: Uridine triphosphate, also known as INS-316; KRN-316; UTP, is a purinoceptor P2U agonist potentially for the treatment of lung cancer. Uridine triphosphate increases proliferation of human cancerous pancreatic duct epithelial cells by activating P2Y2 receptor. Uridine triphosphate (UTP) induces profibrotic responses in cardiac fibroblasts by activation of P2Y2 receptors. Uridine triphosphate prolongs action potential duration of guinea pig papillary muscles via P2Y2 purinoceptors.

Chemical Structure

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Uridine triphosphate
CAS# 63-39-8 (free base)
Instruction

Theoretical Analysis

MedKoo Cat#: 206733
Name: Uridine triphosphate
CAS#: 63-39-8 (free base)
Chemical Formula: C9H15N2O15P3
Exact Mass: 483.97
Molecular Weight: 484.139
Elemental Analysis: C, 22.33; H, 3.12; N, 5.79; O, 49.57; P, 19.19

Price and Availability

This product is not in stock, which may be available by custom synthesis. For cost-effective reason, minimum order is 1g (price is usually high, lead time is 2~3 months, depending on the technical challenge). Quote less than 1g will not be provided. To request quote, please email to sales @medkoo.com or click below button.
Note: Price will be listed if it is available in the future.

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Related CAS #: 14264-46-1 (4Na)   63-39-8 (free base)  

Synonym: Uridine triphosphate; INS-316; INS 316; INS316; KRN-316; KRN 316; KRN316;UTP.

IUPAC/Chemical Name: (((2R,3S,4R,5R)-5-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-3,4-dihydroxytetrahydrofuran-2-yl)methyl)triphosphoric acid

InChi Key: PGAVKCOVUIYSFO-XVFCMESISA-N

InChi Code: InChI=1S/C9H15N2O15P3/c12-5-1-2-11(9(15)10-5)8-7(14)6(13)4(24-8)3-23-28(19,20)26-29(21,22)25-27(16,17)18/h1-2,4,6-8,13-14H,3H2,(H,19,20)(H,21,22)(H,10,12,15)(H2,16,17,18)/t4-,6-,7-,8-/m1/s1

SMILES Code: O[C@@H]([C@H]([C@H](N1C(NC(C=C1)=O)=O)O2)O)[C@H]2COP(O)(OP(OP(O)(O)=O)(O)=O)=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:
In vitro activity:
In vivo activity:

Preparing Stock Solutions

The following data is based on the product molecular weight 484.14 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:
In vitro protocol:
In vivo protocol:

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1: Kam WR, Liu Y, Ding J, Sullivan DA. Do Cyclosporine A, an IL-1 Receptor Antagonist, Uridine Triphosphate, Rebamipide, and/or Bimatoprost Regulate Human Meibomian Gland Epithelial Cells? Invest Ophthalmol Vis Sci. 2016 Aug 1;57(10):4287-94. doi: 10.1167/iovs.16-19937. PubMed PMID: 27552406; PubMed Central PMCID: PMC5015965.

2: Jonckers TH, Tahri A, Vijgen L, Berke JM, Lachau-Durand S, Stoops B, Snoeys J, Leclercq L, Tambuyzer L, Lin TI, Simmen K, Raboisson P. Discovery of 1-((2R,4aR,6R,7R,7aR)-2-Isopropoxy-2-oxidodihydro-4H,6H-spiro[furo[3,2-d][1,3,2]d ioxaphosphinine-7,2'-oxetan]-6-yl)pyrimidine-2,4(1H,3H)-dione (JNJ-54257099), a 3'-5'-Cyclic Phosphate Ester Prodrug of 2'-Deoxy-2'-Spirooxetane Uridine Triphosphate Useful for HCV Inhibition. J Med Chem. 2016 Jun 23;59(12):5790-8. doi: 10.1021/acs.jmedchem.6b00382. Epub 2016 Jun 3. PubMed PMID: 27181575.

3: Li W, Wei S, Liu C, Song M, Wu H, Yang Y. Regulation of the osteogenic and adipogenic differentiation of bone marrow-derived stromal cells by extracellular uridine triphosphate: The role of P2Y2 receptor and ERK1/2 signaling. Int J Mol Med. 2016 Jan;37(1):63-73. doi: 10.3892/ijmm.2015.2400. Epub 2015 Nov 3. PubMed PMID: 26531757; PubMed Central PMCID: PMC4687443.

4: Vieira CL, Vasconcelos BC, Leão JC, Laureano Filho JR. Effect of the use of combination uridine triphosphate, cytidine monophosphate, and hydroxycobalamin on the recovery of neurosensory disturbance after bilateral sagittal split osteotomy: a randomized, double-blind trial. Int J Oral Maxillofac Surg. 2016 Feb;45(2):186-93. doi: 10.1016/j.ijom.2015.09.007. Epub 2015 Oct 14. PubMed PMID: 26458536.

5: Gidlöf O, Sathanoori R, Magistri M, Faghihi MA, Wahlestedt C, Olde B, Erlinge D. Extracellular Uridine Triphosphate and Adenosine Triphosphate Attenuate Endothelial Inflammation through miR-22-Mediated ICAM-1 Inhibition. J Vasc Res. 2015;52(2):71-80. doi: 10.1159/000431367. Epub 2015 Jun 13. PubMed PMID: 26088024.

6: Sivertsen J, Jensen J, Galatius S, Raunsø J, Rosenmeier J. Comparison of the novel vasodilator uridine triphosphate and adenosine for the measurement of fractional flow reserve. J Invasive Cardiol. 2014 Oct;26(10):512-8. PubMed PMID: 25274861.

7: Choi JH, Ji YG, Lee DH. Uridine triphosphate increases proliferation of human cancerous pancreatic duct epithelial cells by activating P2Y2 receptor. Pancreas. 2013 May;42(4):680-6. doi: 10.1097/MPA.0b013e318271bb4b. PubMed PMID: 23462325.

8: Braun OO, Lu D, Aroonsakool N, Insel PA. Uridine triphosphate (UTP) induces profibrotic responses in cardiac fibroblasts by activation of P2Y2 receptors. J Mol Cell Cardiol. 2010 Sep;49(3):362-9. doi: 10.1016/j.yjmcc.2010.05.001. Epub 2010 May 13. PubMed PMID: 20471392; PubMed Central PMCID: PMC2917486.

9: Mibielli MA, Nunes CP, Cohen JC, Scussel AB Jr, Higashi R, Bendavit GG, Oliveira L, Geller M. Treatment of acute, non-traumatic pain using a combination of diclofenac-cholestyramine, uridine triphosphate, cytidine monophosphate, and hydroxycobalamin. Proc West Pharmacol Soc. 2010;53:5-12. PubMed PMID: 22128442.

10: Wihlborg AK, Balogh J, Wang L, Borna C, Dou Y, Joshi BV, Lazarowski E, Jacobson KA, Arner A, Erlinge D. Positive inotropic effects by uridine triphosphate (UTP) and uridine diphosphate (UDP) via P2Y2 and P2Y6 receptors on cardiomyocytes and release of UTP in man during myocardial infarction. Circ Res. 2006 Apr 14;98(7):970-6. Epub 2006 Mar 16. PubMed PMID: 16543499; PubMed Central PMCID: PMC3492942.

11: Erlinge D, Harnek J, van Heusden C, Olivecrona G, Jern S, Lazarowski E. Uridine triphosphate (UTP) is released during cardiac ischemia. Int J Cardiol. 2005 Apr 28;100(3):427-33. PubMed PMID: 15837087.

12: Liu GJ, Werry EL, Bennett MR. Secretion of ATP from Schwann cells in response to uridine triphosphate. Eur J Neurosci. 2005 Jan;21(1):151-60. PubMed PMID: 15654852.

13: Abdipranoto A, Liu GJ, Werry EL, Bennett MR. Mechanisms of secretion of ATP from cortical astrocytes triggered by uridine triphosphate. Neuroreport. 2003 Dec 2;14(17):2177-81. PubMed PMID: 14625443.

14: Seow CY, White HD, Ford LE. Effects of substituting uridine triphosphate for ATP on the crossbridge cycle of rabbit muscle. J Physiol. 2001 Dec 15;537(Pt 3):907-21. PubMed PMID: 11744764; PubMed Central PMCID: PMC2279008.

15: Shah MK, Kadowitz PJ. Cyclic adenosine monophosphate-dependent vascular responses to purinergic agonists adenosine triphosphate and uridine triphosphate in the anesthetized mouse. J Cardiovasc Pharmacol. 2002 Jan;39(1):142-9. PubMed PMID: 11743236.

16: Qin K, Ren LM, Zhao D. Uridine triphosphate prolongs action potential duration of guinea pig papillary muscles via P2Y2 purinoceptors. Acta Pharmacol Sin. 2001 Jan;22(1):21-5. PubMed PMID: 11730556.

17: Kanoh S, Kondo M, Tamaoki J, Kobayashi H, Motoyoshi K, Nagai A. Differential regulations between adenosine triphosphate (ATP)- and uridine triphosphate-induced Cl(-) secretion in bovine tracheal epithelium. Direct stimulation of P1-like receptor by ATP. Am J Respir Cell Mol Biol. 2001 Sep;25(3):370-6. PubMed PMID: 11588016.

18: Welsh DG, Brayden JE. Mechanisms of coronary artery depolarization by uridine triphosphate. Am J Physiol Heart Circ Physiol. 2001 Jun;280(6):H2545-53. PubMed PMID: 11356609.

19: Smitham JE, Barrett KE. Differential effects of apical and basolateral uridine triphosphate on intestinal epithelial chloride secretion. Am J Physiol Cell Physiol. 2001 Jun;280(6):C1431-9. PubMed PMID: 11350738.

20: Ghosal S, Taylor CJ, Colledge WH, Ratcliff R, Evans MJ. Sodium channel blockers and uridine triphosphate: effects on nasal potential difference in cystic fibrosis mice. Eur Respir J. 2000 Jan;15(1):146-50. PubMed PMID: 10678637.