Dexibuprofen

Base Information

• Chemical Name: Dexibuprofen
• CAS No.: 51146-56-6
• Molecular Formula: C13H18O2
• Molecular Weight: 206.285
• Hs Code.: 29163990
• NSC Number: 759814
• UNII: 671DKG7P5S
• DSSTox Substance ID: DTXSID9048724
• Nikkaji Number: J384.813B
• Wikipedia: Dexibuprofen
• Wikidata: Q420051
• NCI Thesaurus Code: C166907
• Pharos Ligand ID: JSNTLJLJ4C6J
• Metabolomics Workbench ID: 52339
• ChEMBL ID: CHEMBL175
• Mol file: 51146-56-6.mol

Synonyms:dexibuprofen

Chemical Property of Dexibuprofen

Chemical Property:

• Appearance/Colour: colourless, crystalline solid
• Vapor Pressure: 0.000139mmHg at 25°C
• Melting Point: 49-53 °C(lit.)
• Refractive Index: 59 ° (C=2, EtOH)
• Boiling Point: 319.6 °C at 760 mmHg
• PKA: 4.41±0.10(Predicted)
• Flash Point: 216.7 °C
• PSA: 37.30000
• Density: 1.029 g/cm³
• LogP: 3.07320
• Storage Temp.: Store at RT
• Solubility.: 45% (w/v) aq 2-hydroxypropyl-β-cyclodextrin: 1.5 mg/mL
• Water Solubility.: insoluble
• XLogP3: 3.5
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 4
• Exact Mass: 206.130679813
• Heavy Atom Count: 15
• Complexity: 203

Purity/Quality:

99% ^*data from raw suppliers

(S)-(+)-Ibuprofen ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 63-22
• Safety Statements: 45-36/37

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• 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
• Recent ClinicalTrials: Phase I Study to Evaluate the Safety of Dexibuprofen 200mg Under Fasting and Fed Conditions
• Recent EU Clinical Trials: Efficacy of Non-Steroidal Anti-Inflammatory (Ibuprofen) Chronotherapy in Healing After Mandibular Third Molar Surgical Extraction – A Randomized Clinical Trial
• Description: Dexibuprofen, the S-(+)-isomer of the widely used NSAID agent ibuprofen, was launched in Austria for the treatment of rheumatoid arthritis. While the racemic compound is commonly used clinically, the antiinflammatory activity is mediated via the S-isomer by inhibition of prostaglandin synthesis. It has also been demonstrated that the R-isomer is converted to the Santipode in vivo via a CoA thioester intermediate. Since CoA plays a pivotal role in intermediary metabolism and maintenance of the [acyl-CoA], generation of R-ibuprofen-CoA competitively inhibits many CoA-dependent reactions, which consequently produces perturbations of hepatocyte Intermediary metabolism and mitocondrial function. Pure S-ibuprofen usage, therefore, is preferred allowing a reduction in dosage level and an improved side effect profile. Ibuprofen is a non-steroidal anti-inflammatory drug with diverse biochemical actions, most notably inhibiting COX-1 and COX-2 (IC50s = 2.6 and 1.53, μM, respectively). It is commonly synthesized as a racemic mixture of (S)- and (R)-isomers. (S)-Ibuprofen is an enantiomer that more potently inhibits COX activity, thromboxane formation, and platelet aggregation than the (R)-form. (S)-Ibuprofen also inhibits activation of NF-κB more effectively than (R)-ibuprofen (IC50s = 62 and 122 μM, respectively). However, the enantiomers are equipotent in blocking superoxide formation, β-glucuronidase release, and LTB4 generation by stimulated neutrophils (IC50 values range from 0.14 to 0.58 μM). A majority of (R)-ibuprofen can be inverted to (S)-ibuprofen in humans after oral administration.
• Uses: A nonsteroidal anti-inflammatory drug (NSAID); activity resides primarily in the (S)-isomer Ibuprofen is a non-steroidal anti-inflammatory drug with diverse biochemical actions, most notably inhibiting COX-1 and COX-2 (IC50s = 2.6 and 1.53, μM, respectively). It is commonly synthesized as a racemic mixture of (S)- and (R)-isomers. (S)-Ibuprofen is an enantiomer that more potently inhibits COX activity, thromboxane formation, and platelet aggregation than the (R)-form. (S)-Ibuprofen also inhibits activation of NF-κB more effectively than (R)-ibuprofen (IC50s = 62 and 122 μM, respectively). However, the enantiomers are equipotent in blocking superoxide formation, β-glucuronidase release, and LTB4 generation by stimulated neutrophils (IC50 values range from 0.14 to 0.58 μM). A majority of (R)-ibuprofen can be inverted to (S)-ibuprofen in humans after oral administration.
• Clinical Use: NSAID and analgesic
• Drug interactions: Potentially hazardous interactions with other drugsACE inhibitors and angiotensin-II antagonists: antagonism of hypotensive effect, increased risk of nephrotoxicity and hyperkalaemia.Analgesics: avoid concomitant use of 2 or more NSAIDs, including aspirin (increased side effects); avoid with ketorolac (increased risk of side effects and haemorrhage).Antibacterials: possibly increased risk of convulsions with quinolones.Anticoagulants: effects of coumarins and phenindione enhanced; possibly increased risk of bleeding with heparins, dabigatran and edoxaban - avoid long term use with edoxaban.Antidepressants: increased risk of bleeding with SSRIs and venlaflaxine.Antidiabetic agents: effects of sulphonylureas enhanced.Antiepileptics: possibly increased phenytoin concentration.Antivirals: increased risk of haematological toxicity with zidovudine; concentration possibly increased by ritonavirCiclosporin: may potentiate nephrotoxicityCytotoxics: reduced excretion of methotrexate; increased risk of bleeding with erlotinibDiuretics: increased risk of nephrotoxicity; antagonism of diuretic effect; hyperkalaemia with potassium-sparing diuretics.Lithium: excretion decreased.Pentoxifylline: increased risk of bleeding.Tacrolimus: increased risk of nephrotoxicity

Technology Process of Dexibuprofen

There total 198 articles about Dexibuprofen which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 99.0%

(2S)-2-<4-(2-Methylpropyl)phenyl>propan-1-ol (114937-30-3) → (S)-ibuprofen (51146-56-6,58560-75-1)

Guidance literature:

With 2,2,6,6-tetramethyl-piperidine-N-oxyl; sodium hypochlorite; sodium chlorite; In water; acetonitrile; at 35 ℃; for 4h; aq. phosphate buffer;

DOI:10.1055/s-0030-1258580

Reference yield: 99.0%

S-ibuprofen, S-1-phenylethylamine salt → (S)-ibuprofen (51146-56-6,58560-75-1)

Guidance literature:

With hydrogenchloride; In water; ethyl acetate; at 22 ℃; for 0.5h;

DOI:10.1039/d1cc04556c

Reference yield: 98.0%

2-(4-isobutylphenyl)acrylic acid (6448-14-2) → (S)-ibuprofen (51146-56-6,58560-75-1)

Guidance literature:

With C₄₈H₅₀Cl₄N₂O₂P₂Ru₃; hydrogen; sodium hydrogencarbonate; In methanol; at 20 ℃; for 24h; under 3750.38 Torr; enantioselective reaction; Autoclave;

DOI:10.1021/acs.orglett.6b00748

upstream raw materials:

Vinyl bromide

1-(4-isobutylphenyl)ethylzinc bromide

carbon monoxide

p-isobutylstyrene

Downstream raw materials:

ibuprofen

(S)-(+)-methyl 2-(4-isobutylphenyl)propionate

Refernces

• 1、 Contesini, Fabiano Jares,de Oliveira Carvalho, Patricia. "Esterification of (RS)-Ibuprofen by native and commercial lipases in a two-phase system containing ionic liquids". . p. 2069 - 2073. Retrieved 2006.
• 2、 Fan, Qing-Hua,Chen, Yong-Ming,Chen, Xiao-Min,Jiang, Da-Zhi,Xi, Fu,Chan, Albert S. C.. "Highly effective and recyclable dendritic BINAP ligands for asymmetric hydrogenation". . p. 789 - 790. Retrieved 2000.
• 3、 Gill, Iqbal,Ballesteros, Antonio. "Encapsulation of biologicals within silicate, siloxane, and hybrid sol- gel polymers: An efficient and generic approach". . p. 8587 - 8598. Retrieved 1998.
• 4、 Tang, Kewen,Song, Litao,Pan, Yang,Jiang, Xinyu,Miao, Jiabing. "Enantioselective partitioning of racemic ibuprofen in a biphasic recognition chiral extraction system". . p. 119 - 124. Retrieved 2010.
• 5、 Fan, Qing-Hua,Liu, Guo-Hua,Deng, Guo-Jun,Chen, Xiao-Min,Chan, Albert S.C.. "New soluble bifunctional polymeric chiral ligands for enantioselectively catalytic reactions". . p. 9047 - 9050. Retrieved 2001.
• 6、 Fu, Kaiyue,Ma, Yu,Sun, Yaxin,Tang, Bo,Yang, Guang,Yang, Peng,Yue, Jieyu,Zhang, Li,Zhou, Jianrong Steve. "Enantioselective Synthesis of Chiral Carboxylic Acids from Alkynes and Formic Acid by Nickel-Catalyzed Cascade Reactions: Facile Synthesis of Profens". supporting information. . Retrieved 2021/11/22.
• 7、 Guan, Zheng-Hui,Ren, Zhi-Hui,Wang, Yuan,Yang, Hui-Yi,Yao, Ya-Hong,Zou, Xian-Jin. "Palladium-Catalyzed Asymmetric Markovnikov Hydroxycarbonylation and Hydroalkoxycarbonylation of Vinyl Arenes: Synthesis of 2-Arylpropanoic Acids". supporting information. p. 23117 - 23122. Retrieved 2021/09/18.