U-73122
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    WARNING: This product is for research use only, not for human or veterinary use.

MedKoo CAT#: 510295

CAS#: 12648-68-7

Description: U-73122 is a potent phospholipase C inhibitor or PI-PLC inhibitor. U-73122 is widely used as a tool to investigate the involvement of the phosphoinositide-specific phospholipase C (PLC) in signal transduction, particularly in studies attempting to characterize pathways leading to intracellular Ca2+ mobilization upon agonist challenge. U-73122 directly blocks PLC isoenzymes in vivo and in vitro.


Price and Availability

Size
Price

100mg
USD 1650
1g
USD 4750
Size
Price

200mg
USD 2150
2g
USD 5950
Size
Price

500mg
USD 2950
5g
Ask price

U73122, purity > 98%, is in stock. Current shipping out time is about 2 weeks after order is received. CoA, QC data and MSDS documents are available in one week after order is received. Delivery time: overnight (USA/Canada); 3-5 days (worldwide).


Chemical Structure

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Theoretical Analysis

MedKoo Cat#: 510295
Name: U-73122
CAS#: 12648-68-7
Chemical Formula: C29H40N2O3
Exact Mass: 464.30389
Molecular Weight: 464.64
Elemental Analysis: C, 74.96; H, 8.68; N, 6.03; O, 10.33


Synonym: U73122, U 73122, U73122.

IUPAC/Chemical Name: 1-(6-(((8R,9S,13S,14S,17S)-3-methoxy-13-methyl-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthren-17-yl)amino)hexyl)-1H-pyrrole-2,5-dione

InChi Key: LUFAORPFSVMJIW-ZRJUGLEFSA-N

InChi Code: InChI=1S/C29H40N2O3/c1-29-16-15-23-22-10-8-21(34-2)19-20(22)7-9-24(23)25(29)11-12-26(29)30-17-5-3-4-6-18-31-27(32)13-14-28(31)33/h8,10,13-14,19,23-26,30H,3-7,9,11-12,15-18H2,1-2H3/t23-,24-,25+,26+,29+/m1/s1

SMILES Code: O=C(C=C1)N(CCCCCCN[C@H]2CC[C@@]3([H])[C@]4([H])CCC5=CC(OC)=CC=C5[C@@]4([H])CC[C@]23C)C1=O


Technical Data

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, not in water

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).

Harmonized System Code:
293490


References

1: Lo Vasco VR, Leopizzi M, Di Maio V, Della Rocca C. U-73122 reduces the cell growth in cultured MG-63 ostesarcoma cell line involving Phosphoinositide-specific Phospholipases C. Springerplus. 2016 Feb 24;5:156. doi: 10.1186/s40064-016-1768-6. eCollection 2016. PubMed PMID: 27026853; PubMed Central PMCID: PMC4766154.

2: Hughes SA, Gibson WJ, Young JM. The interaction of U-73122 with the histamine H1 receptor: implications for the use of U-73122 in defining H1 receptor-coupled signalling pathways. Naunyn Schmiedebergs Arch Pharmacol. 2000 Dec;362(6):555-8. PubMed PMID: 11138848.

3: Hollywood MA, Sergeant GP, Thornbury KD, McHale NG. The PI-PLC inhibitor U-73122 is a potent inhibitor of the SERCA pump in smooth muscle. Br J Pharmacol. 2010 Jul;160(6):1293-4. doi: 10.1111/j.1476-5381.2010.00795.x. PubMed PMID: 20590620; PubMed Central PMCID: PMC2938801.

4: Chen YJ, Sheng WY, Huang PR, Wang TC. Potent inhibition of human telomerase by U-73122. J Biomed Sci. 2006 Sep;13(5):667-74. Epub 2006 Jul 19. PubMed PMID: 16850179.

5: Chen TH, Hsu WH. U-73122 inhibits carbachol-induced increases in [Ca2+]i, IP3, and insulin release in beta-TC3 cells. Life Sci. 1995;56(5):PL103-8. PubMed PMID: 7837924.

6: Wiciński M, Grześk G, Malinowski B, Grześk E, Sinjab AT, Krzyzanowski M, Michalska A, Bylina D, Dziecioł J, Szadujkis-Szadurska K, Czeczuk A. Imidazole-induced contractility of vascular smooth muscle cells in the presence of U-73122, ODQ, indomethacin and 7-nitroindazole. Pol J Vet Sci. 2013;16(2):293-7. PubMed PMID: 23971197.

7: Feisst C, Albert D, Steinhilber D, Werz O. The aminosteroid phospholipase C antagonist U-73122 (1-[6-[[17-beta-3-methoxyestra-1,3,5(10)-trien-17-yl]amino]hexyl]-1H-pyrrole-2,5- dione) potently inhibits human 5-lipoxygenase in vivo and in vitro. Mol Pharmacol. 2005 May;67(5):1751-7. Epub 2005 Jan 31. PubMed PMID: 15684042.

8: Smith RJ, Justen JM, McNab AR, Rosenbloom CL, Steele AN, Detmers PA, Anderson DC, Manning AM. U-73122: a potent inhibitor of human polymorphonuclear neutrophil adhesion on biological surfaces and adhesion-related effector functions. J Pharmacol Exp Ther. 1996 Jul;278(1):320-9. PubMed PMID: 8764366.

9: Thompson AK, Mostafapour SP, Denlinger LC, Bleasdale JE, Fisher SK. The aminosteroid U-73122 inhibits muscarinic receptor sequestration and phosphoinositide hydrolysis in SK-N-SH neuroblastoma cells. A role for Gp in receptor compartmentation. J Biol Chem. 1991 Dec 15;266(35):23856-62. PubMed PMID: 1660886.

10: Alter CA, Amagasu M, Shah K, Jolly YC, Major C, Wolf BA. U-73122 does not specifically inhibit phospholipase C in rat pancreatic islets and insulin-secreting beta-cell lines. Life Sci. 1994;54(8):PL107-12. PubMed PMID: 8107526.

11: Grierson JP, Meldolesi J. Calcium homeostasis in mouse fibroblast cells: affected by U-73122, a putative phospholipase C beta blocker, via multiple mechanisms. Br J Pharmacol. 1995 May;115(1):11-4. PubMed PMID: 7647965; PubMed Central PMCID: PMC1908738.

12: Lo Vasco VR, Fabrizi C, Panetta B, Fumagalli L, Cocco L. Expression pattern and sub-cellular distribution of phosphoinositide specific phospholipase C enzymes after treatment with U-73122 in rat astrocytoma cells. J Cell Biochem. 2010 Jul 1;110(4):1005-12. doi: 10.1002/jcb.22614. PubMed PMID: 20564200.

13: Li SB, Chen TH, Zhu-Ge RH, Hsu WH. Effect of U-73122 on calcium channel activity in porcine myometrial cells and pancreatic beta-cell line RINm5F. Zhongguo Yao Li Xue Bao. 1997 Sep;18(5):385-90. PubMed PMID: 10322922.

14: Macmillan D, McCarron JG. The phospholipase C inhibitor U-73122 inhibits Ca(2+) release from the intracellular sarcoplasmic reticulum Ca(2+) store by inhibiting Ca(2+) pumps in smooth muscle. Br J Pharmacol. 2010 Jul;160(6):1295-301. doi: 10.1111/j.1476-5381.2010.00771.x. PubMed PMID: 20590621; PubMed Central PMCID: PMC2938802.

15: Wang JP. U-73122, an aminosteroid phospholipase C inhibitor, may also block Ca2+ influx through phospholipase C-independent mechanism in neutrophil activation. Naunyn Schmiedebergs Arch Pharmacol. 1996 May;353(6):599-605. PubMed PMID: 8738291.

16: Wang XD, Kiang JG, Smallridge RC. A phospholipase C inhibitor, U-73122, blocks TSH-induced inositol trisphosphate production, Ca2+ increase and arachidonic acid release in FRTL-5 thyroid cells. Biochim Biophys Acta. 1994 Aug 11;1223(1):101-6. PubMed PMID: 8061042.

17: Smallridge RC, Kiang JG, Gist ID, Fein HG, Galloway RJ. U-73122, an aminosteroid phospholipase C antagonist, noncompetitively inhibits thyrotropin-releasing hormone effects in GH3 rat pituitary cells. Endocrinology. 1992 Oct;131(4):1883-8. PubMed PMID: 1396332.

18: Badawi JK, Seja T, Bross S. In vitro effects of the cyclooxygenase inhibitor indomethacin and of the phospholipase-C inhibitor U-73122 on carbachol-induced contractions of porcine detrusor muscle. Fundam Clin Pharmacol. 2008 Dec;22(6):667-72. doi: 10.1111/j.1472-8206.2008.00625.x. PubMed PMID: 19049671.

19: Nagy K, Contzen K. Inhibition of phospholipase C by U-73122 blocks one component of the receptor current in Limulus photoreceptor. Vis Neurosci. 1997 Sep-Oct;14(5):995-8. PubMed PMID: 9364735.

20: Salari H, Bramley A, Langlands J, Howard S, Chan-Yeung M, Chan H, Schellenberg R. Effect of phospholipase C inhibitor U-73122 on antigen-induced airway smooth muscle contraction in guinea pigs. Am J Respir Cell Mol Biol. 1993 Oct;9(4):405-10. PubMed PMID: 8398179.