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U5882

Sigma-Aldrich

U-74389G

Synonym(s):

21-[4-(2,6-Di-1-pyrrolidinyl-4-pyrimidinyl)-1-piperazinyl]pregna-1,4,9[11]-triene-3,20-dione maleate salt

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About This Item

Empirical Formula (Hill Notation):
C37H50N6O2 · C4H4O4
CAS Number:
153190-29-5
Molecular Weight:
726.90
MDL number:
MFCD01074991
UNSPSC Code:
12352200
PubChem Substance ID:
24278768
NACRES:
NA.77

solubility

ethanol: soluble 20 mg/mL, clear, light yellow

storage temp.

−20°C

SMILES string

OC(=O)\C=C/C(O)=O.[H][C@@]12CCC3=CC(=O)C=C[C@]3(C)C1=CC[C@]4(C)[C@H](CC[C@@]24[H])C(=O)CN5CCN(CC5)c6cc(nc(n6)N7CCCC7)N8CCCC8

InChI

1S/C37H50N6O2.C4H4O4/c1-36-13-11-27(44)23-26(36)7-8-28-29-9-10-31(37(29,2)14-12-30(28)36)32(45)25-40-19-21-42(22-20-40)34-24-33(41-15-3-4-16-41)38-35(39-34)43-17-5-6-18-43;5-3(6)1-2-4(7)8/h11-13,23-24,28-29,31H,3-10,14-22,25H2,1-2H3;1-2H,(H,5,6)(H,7,8)/b;2-1-/t28-,29-,31+,36-,37-;/m0./s1

InChI key

ABCSSKWSUJMJCP-WQDFMEOSSA-N

Application

U-74389G has been shown to significantly decrease the level of ethanol-induced gastric mucosal necrosis in portal hypertensive (PHT) rats. Furthermore, U-74389G has been widely used in animal models of ischemic injury and hypertension.

Biochem/physiol Actions

Free radical lipid peroxidation inhibitor in cultured brain cells, monocytic THP1 cells, and LLC-PK1 cell layers.

Preparation Note

U-74389G is soluble in ethanol at 20 mg/ml and yields a clear, light yellow solution.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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D J Crutchley et al.
Circulation, 92(2), 238-243 (1995-07-15)
Transition metals such as copper are known to initiate free radical formation and lipid peroxidation. Recent reports suggest that intracellular reactive oxygen intermediates can induce the transcription of a number of important genes. The present study examines the effects of
Alexios Bimpis et al.
Metabolic brain disease, 28(3), 439-446 (2013-01-25)
Spontaneous intracerebral hemorrhage (ICH) represents a partially-understood cerebrovascular disease of high incidence, morbidity and mortality. We, herein, report the findings of our study concerning the role of two important adenosinetriphosphatases (ATPases) in a porcine model of spontaneous ICH that we
Dimosthenis T Chrysikos et al.
The Journal of surgical research, 187(2), 450-457 (2013-12-18)
Oxidative stress is a crucial factor in the pathophysiology of acute pancreatitis and its systemic complications. Lazaroids are a novel class of antioxidants that potently protect pancreatic acinar cells against oxidant attack. The aim of our study was to evaluate
Rachel L Hill et al.
Neuropharmacology, 170, 108023-108023 (2020-03-07)
The 21-aminosteroid ("lazaroid") U-74389G (U74), an inhibitor of lipid peroxidation (LP), was used to protect mitochondrial function following TBI in young adult male rats. The animals received a severe (2.2 mm) controlled cortical impact-TBI. U74 was administered intravenous at 15 min and
F Shi et al.
Free radical biology & medicine, 19(3), 349-357 (1995-09-01)
Selected 21-aminosteroids (U74500A, U74006F, and U74389G) and a 2-(aminomethyl)chromans (U78517F) were tested for their efficacy in preventing arachidonate-induced lipid peroxidation and permeability alterations in brain microvessel endothelial cells (BMECs). The 21-aminosteroids and 2-(aminomethyl)chromans were effective in varying degrees in inhibiting
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