U-78517F | CAS#133681-84-2

MedKoo Cat#: 462838 | Name: U-78517F

Description:

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

U-78517F is a potent inhibitor of lipid peroxidation.

Chemical Structure

U-78517F

CAS#133681-84-2

Theoretical Analysis

MedKoo Cat#: 462838

Name: U-78517F

CAS#: 133681-84-2

Chemical Formula: C30H46Cl2N6O2

Exact Mass: 592.3059

Molecular Weight: 593.64

Elemental Analysis: C, 60.70; H, 7.81; Cl, 11.94; N, 14.16; O, 5.39

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Synonym

U 78517F; U78517F; U-78517F;

IUPAC/Chemical Name

2-((4-(2,6-di(pyrrolidin-1-yl)pyrimidin-4-yl)piperazin-1-yl)methyl)-2,5,7,8-tetramethylchroman-6-ol dihydrochloride

InChi Key

KJGXSMZHYBXPIS-UHFFFAOYSA-N

InChi Code

InChI=1S/C30H44N6O2.2ClH/c1-21-22(2)28-24(23(3)27(21)37)9-10-30(4,38-28)20-33-15-17-35(18-16-33)26-19-25(34-11-5-6-12-34)31-29(32-26)36-13-7-8-14-36;;/h19,37H,5-18,20H2,1-4H3;2*1H

SMILES Code

Cc1c(O)c(C)c2c(OC(CN3CCN(c4nc(N5CCCC5)nc(N6CCCC6)c4)CC3)(CC2)C)c1C.Cl.Cl

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

>3 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

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 593.64 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.

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: Hall ED, Braughler JM, Yonkers PA, Smith SL, Linseman KL, Means ED, Scherch HM, Von Voigtlander PF, Lahti RA, Jacobsen EJ. U-78517F: a potent inhibitor of lipid peroxidation with activity in experimental brain injury and ischemia. J Pharmacol Exp Ther. 1991 Aug;258(2):688-94. PMID: 1865365. 2: Zhao W, Richardson JS, Mombourquette MJ, Weil JA. An in vitro EPR study of the free-radical scavenging actions of the lazaroid antioxidants U-74500A and U-78517F. Free Radic Biol Med. 1995 Jul;19(1):21-30. doi: 10.1016/0891-5849(95)00007-k. PMID: 7635355. 3: King WA, Black KL, Ikezaki K, Conklin S, Becker DP. Tumor-associated neurological dysfunction prevented by lazaroids in rats. J Neurosurg. 1991 Jan;74(1):112-5. doi: 10.3171/jns.1991.74.1.0112. PMID: 1984489. 4: Uhler TA, Frim DM, Pakzaban P, Isacson O. The effects of megadose methylprednisolone and U-78517F on toxicity mediated by glutamate receptors in the rat neostriatum. Neurosurgery. 1994 Jan;34(1):122-7; discussion 127-8. PMID: 7907169. 5: Zhao W, Richardson JS, Mombourquette MJ, Weil JA, Ijaz S, Shuaib A. Neuroprotective effects of hypothermia and U-78517F in cerebral ischemia are due to reducing oxygen-based free radicals: an electron paramagnetic resonance study with gerbils. J Neurosci Res. 1996 Aug 1;45(3):282-8. doi: 10.1002/(SICI)1097-4547(19960801)45:3<282::AID-JNR10>3.0.CO;2-6. PMID: 8841989. 6: Johnson HG, McNee ML, Nugent RA. Canine in vivo tracheal chemotaxis of eosinophils to antigen in sensitized dogs: inhibition by a steroid, a systemic lazaroid U-78517F, and several topical H1 antihistamines. Am Rev Respir Dis. 1992 Sep;146(3):621-5. doi: 10.1164/ajrccm/146.3.621. PMID: 1355641. 7: Linseman DA, Wall TM, Hartman JC. The trolox analog, U-78517F, attenuates hypoxic injury in isolated cardiac myocytes. J Mol Cell Cardiol. 1994 Sep;26(9):1249-57. doi: 10.1006/jmcc.1994.1143. PMID: 7815467. 8: Kumar U, Dunlop DM, Richardson JS. The acute neurotoxic effect of beta- amyloid on mature cultures of rat hippocampal neurons is attenuated by the anti- oxidant U-78517F. Int J Neurosci. 1994 Dec;79(3-4):185-90. doi: 10.3109/00207459408986079. PMID: 7744560. 9: Linseman KL, Larson P, Braughler JM, McCall JM. Iron-initiated tissue oxidation: lipid peroxidation, vitamin E destruction and protein thiol oxidation. Inhibition by a novel antioxidant, U-78517F. Biochem Pharmacol. 1993 Apr 6;45(7):1477-82. doi: 10.1016/0006-2952(93)90048-2. PMID: 8471069. 10: Domenici MR, Longo R, de Carolis AS, Frank C, Sagratella S. Protective actions of 21-aminosteroids and MK-801 on hypoxia-induced electrophysiological changes in rat hippocampal slices. Eur J Pharmacol. 1993 Mar 23;233(2-3):291-3. doi: 10.1016/0014-2999(93)90064-o. PMID: 8467875. 11: King WA, Black KL, Ikezaki K, Conklin S, Becker DP. Novel 21-aminosteroids prevent tumour associated neurological dysfunction. Acta Neurochir Suppl (Wien). 1990;51:160-2. doi: 10.1007/978-3-7091-9115-6_54. PMID: 2089884. 12: Durmaz R, Deliorman S, Isiksoy S, Uyar R, Erol K, Tel E. Antiproliferative properties of the lazaroids U-83836E and U-74389G on glioma cells in vitro. Pathol Oncol Res. 1999;5(3):223-8. doi: 10.1053/paor.1999.0202. PMID: 10491022. 13: Pakala R, Pakala R, Benedict CR. Novel 21-aminosteroidlike compounds prevent iron-induced free radical-mediated injury to vascular endothelial cells. J Cardiovasc Pharmacol. 1995 Jun;25(6):871-9. doi: 10.1097/00005344-199506000-00004. PMID: 7564331. 14: Wu RM, Murphy DL, Chiueh CC. Suppression of hydroxyl radical formation and protection of nigral neurons by l-deprenyl (selegiline). Ann N Y Acad Sci. 1996 Jun 15;786:379-90. doi: 10.1111/j.1749-6632.1996.tb39078.x. PMID: 8687036. 15: Ugazio G, Bosia S, Burdino E, Grignolo F. Amelioration of diabetes and cataract by Na3VO4 plus U-83836E in streptozotocin treated rats. Res Commun Mol Pathol Pharmacol. 1994 Sep;85(3):313-28. PMID: 7827806. 16: Chiueh CC. Iron overload, oxidative stress, and axonal dystrophy in brain disorders. Pediatr Neurol. 2001 Aug;25(2):138-47. doi: 10.1016/s0887-8994(01)00266-1. PMID: 11551744. 17: Karlsson J, Love RM, Clarke DJ, Brundin P. Effects of anaesthetics and lazaroid U-83836E on survival of transplanted rat dopaminergic neurones. Brain Res. 1999 Mar 13;821(2):546-50. doi: 10.1016/s0006-8993(99)01176-2. PMID: 10064845. 18: Hall ED. Novel inhibitors of iron-dependent lipid peroxidation for neurodegenerative disorders. Ann Neurol. 1992;32 Suppl:S137-42. doi: 10.1002/ana.410320724. PMID: 1510373. 19: Durmaz R, Kanbak G, Akyüz F, Isiksoy S, Yücel F, Inal M, Tel E. Lazaroid attenuates edema by stabilizing ATPase in the traumatized rat brain. Can J Neurol Sci. 2003 May;30(2):143-9. doi: 10.1017/s0317167100053415. PMID: 12774954. 20: Chiueh CC, Wu RM, Mohanakumar KP, Sternberger LM, Krishna G, Obata T, Murphy DL. In vivo generation of hydroxyl radicals and MPTP-induced dopaminergic toxicity in the basal ganglia. Ann N Y Acad Sci. 1994 Nov 17;738:25-36. doi: 10.1111/j.1749-6632.1994.tb21786.x. PMID: 7832434.