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MedKoo Cat#: 510295 | Name: U-73122
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Description:

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

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.

Chemical Structure

U-73122
U-73122
CAS#12648-68-7

Theoretical Analysis

MedKoo Cat#: 510295

Name: U-73122

CAS#: 12648-68-7

Chemical Formula: C29H40N2O3

Exact Mass: 464.3039

Molecular Weight: 464.64

Elemental Analysis: C, 74.96; H, 8.68; N, 6.03; O, 10.33

Price and Availability

Size Price Availability Quantity
100mg USD 1,650.00
200mg USD 2,150.00
500mg USD 2,950.00
1g USD 4,750.00
2g USD 5,950.00
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Related CAS #
No Data
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
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).
HS Tariff Code
2934.99.9001
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 464.64 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: 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.