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AB141015

(S)-(+)-Ibuprofen, Non-selective COX inhibitor

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MW 206.28 Da, Purity >99%. Non-selective COX inhibitor (IC50 values are 2.9 and 1.1 μM for COX1 and COX2, respectively). Non-steroidal anti-inflammatory drug (NSAID). Rapidly crosses the blood-brain barrier.

View Alternative Names

17-beta-HSD 5, 17-beta-hydroxysteroid dehydrogenase type 5, 2-dihydrobenzene-1, 2-diol dehydrogenase, 20-alpha-hydroxysteroid dehydrogenase, 3 alpha hydroxysteroid dehydrogenase type II, 3 alpha hydroxysteroid dehydrogenase type III, 3-alpha-HSD type 2, 3-alpha-HSD type II, 3-alpha-HSD type II, brain, 3-alpha-HSD3, 3-alpha-hydroxysteroid dehydrogenase type 2, AK1C2_HUMAN, AK1C3_HUMAN, AKR1C pseudo, AKR1C2, ALS10, Akr1c18, Aldo-keto reductase family 1 member C2, Aldo-keto reductase family 1 member C3, BABP, Bile acid binding protein, C C, C-C CKR-1, C-X-C chemokine receptor type 1, C-X-C chemokine receptor type 2, CD 181, CD 182, CD128, CD181 antigen, CD182 antigen, CDw128a, CDw128b, CKR 1, CMKAR1, CMKAR2, CXCR1_HUMAN, CXCR2_HUMAN, Chemokine (C X C motif) receptor 1, Chemokine (C X C) receptor 1, Chemokine (CXC) receptor 2, Chemokine receptor 1, Chlordecone reductase, Chlordecone reductase homolog, Chlordecone reductase homolog HAKRD, Chlordecone reductase homolog HAKRb, Cyclooxygenase, Cyclooxygenase 2b, Cyclooxygenase 3, included, Cyclooxygenase-1, Cyclooxygenase-2, DD, DD-2, DD-3, DD/BABP, DDH 2, DDH1, DDX, Dihydrodiol dehydrogenase 2, Dihydrodiol dehydrogenase 3, Dihydrodiol dehydrogenase X, Dihydrodiol dehydrogenase type I, Dihydrodiol dehydrogenase/bile acid-binding protein, EC 1.14.99.1, FLJ53800, GRIPGHS, GRO/MGSA receptor, Glucocorticoid-regulated inflammatory Prostaglandin G/H synthase, Glucocorticoid-regulated inflammatory cyclooxygenase, HA1753, HAKRB, HAKRD, HAKRe, HBAB, HSD17B5, High affinity interleukin-8 receptor A, High affinity interleukin-8 receptor B, IL-8 receptor type 1, IL-8 receptor type 2, IL-8R A, IL-8R B, IL8 receptor, IL8R1, IL8R2, IL8RBA, Indanol dehydrogenase, Interleukin 8 Receptor B, Interleukin 8 receptor alpha, Interleukin 8 receptor type 1, Interleukin 8 receptor type A, Interleukin 8 receptor, beta, Interleukin 8 receptor, type 2, KIAA0119, MCDR 2, Macrophage activation-associated marker protein P71/73, OTTHUMP00000002171, OTTHUMP00000002172, OTTHUMP00000002173, OTTHUMP00000033524, OTTHUMP00000044759, PCOX1, PES-2, PGFS, PGG/HS, PGH synthase 1, PGH synthase 2, PGH1_HUMAN, PGH2_HUMAN, PGHS-1, PGHS-2, PHS 1, PHS 2, PHS II, PTGHS, PTGS1, PTGS2, Partial COX1 proteins, included, Prostaglandin F synthase, Prostaglandin G/H synthase, Prostaglandin G/H synthase 1, Prostaglandin G/H synthase 2, Prostaglandin G/H synthase 2 precursor, Prostaglandin G/H synthase and cyclooxygenase, Prostaglandin H2 synthase 1, Prostaglandin H2 synthase 2, Prostaglandin-endoperoxide synthase 1, Prostaglandin-endoperoxide synthase 1 (prostaglandin G/H synthase and cyclooxygenase), Prostaglandin-endoperoxide synthase 2, Pseudo chlordecone reductase, SRXY8, TADBP_HUMAN, TAR DNA binding protein, TAR DNA-binding protein 43, TARDBP, TDP-43, TIS10, TIS10 protein, Testosterone 17-beta-dehydrogenase 5, Trans-1, Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase, Type II dihydrodiol dehydrogenase, Type III 3-alpha-hydroxysteroid dehydrogenase, Type IIb 3 alpha hydroxysteroid dehydrogenase, fj02a10, hCox 2, hluPGFS, prostaglandin-endoperoxide synthase 2 (prostaglandin G/H synthase and cyclooxygenase), ptgs2a, unp1239, wu:fj02a10

2 Images
Immunocytochemistry/ Immunofluorescence - (S)-(+)-Ibuprofen, Non-selective COX inhibitor (AB141015)
  • ICC/IF

Unknown

Immunocytochemistry/ Immunofluorescence - (S)-(+)-Ibuprofen, Non-selective COX inhibitor (AB141015)

ab125307 staining HSC70 in HeLa cells treated with (S)-(+)-ibuprofen (ab141015), by ICC/IF. Increase of HSC70 nuclear expression correlates with increased concentration of (S)-(+)-ibuprofen, as described in literature.
The cells were incubated at 37°C for 1 hour in media containing different concentrations of ab141015 ((S)-(+)-ibuprofen) in DMSO, fixed with 4% formaldehyde for 10 minutes at room temperature and blocked with PBS containing 10% goat serum, 0.3 M glycine, 1% BSA and 0.1% tween for 2h at room temperature. Staining of the treated cells with ab125307 (5 µg/ml) was performed overnight at 4°C in PBS containing 1% BSA and 0.1% tween. A DyLight 488 anti-rabbit polyclonal antibody (ab96899) at 1/250 dilution was used as the secondary antibody. Nuclei were counterstained with DAPI and are shown in blue.

Chemical Structure - (S)-(+)-Ibuprofen, Non-selective COX inhibitor (AB141015)
  • Chemical Structure

Lab

Chemical Structure - (S)-(+)-Ibuprofen, Non-selective COX inhibitor (AB141015)

2D chemical structure image of ab141015, (S)-(+)-Ibuprofen, Non-selective COX inhibitor

Key facts

CAS number

51146-56-6

Purity

>99%

Form

Solid

form

Molecular weight

206.28 Da

Molecular formula

C<sub>1</sub><sub>3</sub>H<sub>1</sub><sub>8</sub>O<sub>2</sub>

PubChem

39912

Nature

Synthetic

Solubility

Soluble in DMSO to 100 mM

Soluble in ethanol to 100 mM

Biochemical name

Dexibuprofen

Biological description

Non-selective COX inhibitor (IC50 values are 2.9 and 1.1 μM for COX1 and COX2, respectively). Non-steroidal anti-inflammatory drug (NSAID). Rapidly crosses the blood-brain barrier.

Canonical smiles

CC(C)CC1=CC=C(C=C1)C(C)C(=O)O

Isomeric smiles

C[C@@H](C1=CC=C(C=C1)CC(C)C)C(=O)O

InChi

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)/t10-/m0/s1

InChiKey

HEFNNWSXXWATRW-JTQLQIEISA-N

IUPAC Name

(2S)-2-[4-(2-methylpropyl)phenyl]propanoic acid

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Properties and storage information

Shipped at conditions
Ambient - Can Ship with Ice
Appropriate short-term storage conditions
Ambient
Appropriate long-term storage conditions
Ambient
Storage information
The product can be stored for up to 12 months
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Supplementary information

This supplementary information is collated from multiple sources and compiled automatically.

Cyclooxygenase (COX) enzymes including COX-1 and COX-2 also known as prostaglandin-endoperoxide synthase 1 and 2 are involved in the conversion of arachidonic acid to prostaglandins. COX-1 typically weighs about 70 kDa while COX-2 is around 72 kDa. COX-1 is constitutively expressed in most tissues providing homeostatic functions whereas COX-2 expression is inducible and often upregulated in specific tissues during inflammation or other pathophysiological conditions. COX enzymes are important targets for non-steroidal anti-inflammatory drugs (NSAIDs) including ibuprofen which acts as a COX inhibitor; these drugs help to reduce inflammation and pain.
Biological function summary

The cyclooxygenase enzymes play essential roles in mediating the inflammatory response regulating vascular homeostasis and protecting the gastric mucosa. COX-2 in particular is usually expressed during inflammatory processes and is part of the cellular response to cytokines and growth factors. It is involved in the synthesis of pro-inflammatory prostaglandins and when upregulated can significantly increase inflammation at the injury or infection site. COX inhibitors including ibuprofen and others target these enzymes to modulate these biological functions effectively.

Pathways

The COX enzymes are key components of the prostaglandin synthesis pathway. They catalyze the rate-limiting step of this pathway helping convert arachidonic acid to prostaglandin H2 a precursor of various prostaglandins and thromboxanes. COX-2's activity in the inflammation pathway is linked with the nuclear factor kappa B (NF-κB) pathway which regulates the immune response. AKR1C3 another enzyme related to the production of prostaglandins interacts in similar pathways highlighting the interconnected nature of these biological processes.

COX-2 is strongly associated with inflammation-related conditions such as arthritis and cancer. For instance overexpression of COX-2 is found in several cancers and contributes to tumor growth and metastasis. COX-1 while less associated with inflammation plays a role in maintaining gastrointestinal integrity. NSAIDs like ibuprofen which target COX enzymes help manage pain and inflammation in conditions like arthritis but can have side effects such as gastrointestinal irritation due to COX-1 inhibition. CXCR2 and TDP-43 are other proteins that may interact with the inflammatory pathways COX-2 is involved in potentially influencing both disease progression and therapy outcomes.
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Product protocols

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