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SML1842

Sigma-Aldrich

Ibuprofen Arginate

≥98% (HPLC)

Synonym(s):

α-Methyl-4-(2-methylpropyl)benzeneacetate, L-arginine (1:1), (S)-1-(4-Amino-4-carboxybutyl)guanidinium 2-(4-isobutylphenyl)propanoate, Ibu-L-Arg, Ibuprofen L-arginine, Ibuprofen arginine

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About This Item

Empirical Formula (Hill Notation):
C19H32N4O4
CAS Number:
Molecular Weight:
380.48
UNSPSC Code:
51111800
NACRES:
NA.77

Quality Level

assay

≥98% (HPLC)

form

powder

color

white to beige

solubility

H2O: 20 mg/mL, clear

storage temp.

−20°C

SMILES string

CC(CC1=CC=C(C(C([O-])=O)C)C=C1)C.O=C(O)[C@@H](N)CCCNC([NH3+])=N

InChI

1S/C13H18O2.C6H14N4O2/c1-9(2)8-11-4-6-12(7-5-11)10(3)13(14)15;7-4(5(11)12)2-1-3-10-6(8)9/h4-7,9-10H,8H2,1-3H3,(H,14,15);4H,1-3,7H2,(H,11,12)(H4,8,9,10)/t;4-/m.0/s1

InChI key

GCCOJNYCFNSJII-VWMHFEHESA-N

Biochem/physiol Actions

Ibuprofen arginate is the more soluble arginate salt form of the nonsteroidal anti-inflammatory drug (NSAID) ibuprofen. Ibuprofen arginate retains the inhibitory potency against COX-2 as ibuprofen and its sodium salt, however only ibuprofen arginate is able to augment cellular NO pathway through codelivery of the NOS substrate arginine. Ibuprofen arginate, but not the sodium salt form, is shown to reverse the inhibitory effects of the cardiotoxic hormone asymmetric dimethylarginine (ADMA) and NG-nitro-L-argininemethyl ester (L-NAME) against nitric oxide synthase (eNOS & iNOS) in cultures in vitro (Murine RAW264.7 macrophages and isolated mouse & rat aorta) and effectively prevent L-NAME-induced arterial blood pressure increase in anesthetized rats in vivo (0.5 mg/kg L-NAME; 114.8 μmol/kg ibuprofen arginate, equivalent to 20 mg/kg L-Arg via femoral artery cannulation).

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable


Certificates of Analysis (COA)

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Lobna A Saleh et al.
Pharmacology, biochemistry, and behavior, 125, 29-39 (2014-08-08)
Prostaglandins (PGs) and nitric oxide (NO) may be involved in the pathophysiology of depression. Since NSAIDs decrease PGs and NO production, they may have an antidepressant effect. The aim of the present work was to explore a possible antidepressant action
Pharmacological assessment of ibuprofen arginate on platelet aggregation and colon cancer cell killing.
Ahmetaj-Shala, B., et al.
Biochemical and Biophysical Research Communications, 18484(4), 762-766 (2017)
Ghada M El-Lithy et al.
Translational research : the journal of laboratory and clinical medicine, 177, 85-97 (2016-07-10)
Diabetic neuropathy (DN) is a common complication of diabetes mellitus that is hardly reversible at the late stages. Since treatment of neuropathic pain is predominantly symptomatic, a prophylactic measure would be useful. Both ibuprofen and L-arginine exert antiallodynic effects on
Nicholas S Kirkby et al.
FASEB journal : official publication of the Federation of American Societies for Experimental Biology, 30(12), 4172-4179 (2016-09-08)
Nonsteroidal antiinflammatory drugs, including ibuprofen, are among the most commonly used medications and produce their antiinflammatory effects by blocking cyclooxygenase (COX)-2. Their use is associated with increased risk of heart attacks caused by blocking COX-2 in the vasculature and/or kidney

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