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I4883

Sigma-Aldrich

Ibuprofen

≥98% (GC), powder, COX inhibitor

Synonym(s):

2-(4-Isobutylphenyl)propanoic acid, Brufen, Motrin, Rebugen, α-Methyl-4-(isobutyl)phenylacetic acid, (±)-2-(4-Isobutylphenyl)propanoic acid

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About This Item

Empirical Formula (Hill Notation):
C13H18O2
CAS Number:
15687-27-1
Molecular Weight:
206.28
EC Number:
239-784-6
MDL number:
MFCD00010393
UNSPSC Code:
12352200
PubChem Substance ID:
24277715
NACRES:
NA.77

product name

Ibuprofen, ≥98% (GC)

biological source

synthetic (organic)

Assay

≥98% (GC)

form

powder

mp

77-78  °C

solubility

ethanol: 50 mg/mL, clear, colorless to faintly yellow

SMILES string

CC(C)Cc1ccc(cc1)C(C)C(O)=O

InChI

1S/C13H18O2/c1-9(2)8-11-4-6-12(7-5-11)10(3)13(14)15/h4-7,9-10H,8H2,1-3H3,(H,14,15)

InChI key

HEFNNWSXXWATRW-UHFFFAOYSA-N

Gene Information

human ... ALB(213) , ALOX5(240) , CYP1A2(1544) , CYP2C9(1559) , IL8RA(3577) , PTGS1(5742) , PTGS2(5743)
mouse ... Alox5(11689)
rat ... Alox5(25290) , Ptgs1(24693)

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General description

Ibuprofen is a commonly used nonsteroidal anti-inflammatory drug (NSAID) known for its pain-relieving, anti-inflammatory, and fever-reducing properties. It can hinder the effectiveness of various antihypertensive medications, including β-adrenergic blockers, angiotensin-converting enzyme inhibitors, angiotensin receptor blockers, and diuretics. Ibuprofen exists in an unbound state in cerebrospinal fluid and is accumulated in the synovial fluid of inflamed joints in arthritis patients.

Application

Ibuprofen has been used:
  • to study its vascular and pulmonary effects on neonatal lung development
  • to study its effects on cell apoptosis, cell proliferation, and histology changes in human cholangiocarcinoma cell lines
  • in the preparation of a terpene-based therapeutic deep eutectic system (THEDES) to investigate its physicochemical, antimicrobial, and anticancer properties

Biochem/physiol Actions

Cyclooxygenase (COX) inhibitor that has greater activity against COX-1 than against COX-2.

Other Notes

2024 CiteAb Award Winner for Supplier Succeeding in Parkinson′s Research

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H302,H319,H335

Hazard Classifications

Acute Tox. 4 Oral - Eye Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 1

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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Jennifer S Chen et al.
bioRxiv : the preprint server for biology (2020-10-01)
Identifying drugs that regulate severe acute respiratory syndrome coronavirus 2 (SARS-CoV-2) infection and its symptoms has been a pressing area of investigation during the coronavirus disease 2019 (COVID-19) pandemic. Nonsteroidal anti-inflammatory drugs (NSAIDs), which are frequently used for the relief
Mateusz P Czub et al.
Journal of medicinal chemistry, 63(13), 6847-6862 (2020-05-30)
Every day, hundreds of millions of people worldwide take nonsteroidal anti-inflammatory drugs (NSAIDs), often in conjunction with multiple other medications. In the bloodstream, NSAIDs are mostly bound to serum albumin (SA). We report the crystal structures of equine serum albumin
Ratana Leksomboon et al.
Asian Pacific journal of cancer prevention : APJCP, 23(4), 1351-1358 (2022-04-30)
To examine the effects of ibuprofen, naproxen and diclofenac, non-steroidal anti-inflammatory drugs (NSAIDs) on cell proliferation activity of the human CCA cell lines. KKU-M139 and KKU-213B cell lines were used in this study. The cell viability was assessed by the
Tzu-Feng Wang et al.
Cells, 11(3) (2022-02-16)
Parkinson's disease (PD) is an age-related neurodegenerative disease caused by a selective loss of dopaminergic (DA) neurons in the substantia nigra (SN). Microglial activation is implicated in the pathogenesis of PD. This study aimed to characterize the role of microglial
Morshed A Chowdhury et al.
Journal of medicinal chemistry, 52(6), 1525-1529 (2009-03-20)
A novel class of 1-(4-methanesulfonylphenyl and 4-aminosulfonylphenyl)-5-[4-(1-difluoromethyl-1,2-dihydropyrid-2-one)]-3-trifluoromethyl-1H-pyrazole hybrid cyclooxygenase-2 (COX-2)/5-lipoxygenase (5-LOX) inhibitory anti-inflammatory agents was designed. Replacement of the tolyl ring present in celecoxib by the N-difluoromethyl-1,2-dihydropyrid-2-one moiety provided compounds showing dual selective COX-2/5-LOX inhibitory activities. 1-(4-Aminosulfonylphenyl)-5-[4-(1-difluoromethyl-1,2-dihydropyrid-2-one)]-3-trifluoromethyl-1H-pyrazole exhibited good anti-inflammatory
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Chromatograms

suitable for GC

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