Dexketoprofen

Base Information

• Chemical Name: Dexketoprofen
• CAS No.: 22161-81-5
• Molecular Formula: C16H14O3
• Molecular Weight: 254.285
• Hs Code.: 2942000000
• European Community (EC) Number: 606-944-5
• UNII: 6KD9E78X68
• DSSTox Substance ID: DTXSID40905141
• Wikipedia: Dexketoprofen
• Wikidata: Q425440
• NCI Thesaurus Code: C87321
• Pharos Ligand ID: S32X7K97TM3T
• Metabolomics Workbench ID: 49592
• ChEMBL ID: CHEMBL75435
• Mol file: 22161-81-5.mol

Synonyms:Adolquir;Badyket;dexketoprofen;dexketoprofen trometamol;Enangel;Enantyum;Keral;Ketesse;Quiralam;Quirgel;Sympal

Chemical Property of Dexketoprofen

Chemical Property:

• Appearance/Colour: white or almost white, crystalline powder.
• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 75-78 °C(lit.)
• Refractive Index: 1.592
• Boiling Point: 431.3 °C at 760 mmHg
• PKA: 4.23±0.10(Predicted)
• Flash Point: 228.8 °C
• PSA: 54.37000
• Density: 1.198 g/cm³
• LogP: 3.10570
• Storage Temp.: -20°C Freezer
• Solubility.: insoluble in H2O; ≥10.6 mg/mL in DMSO; ≥20.55 mg/mL in EtOH
• XLogP3: 3.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 4
• Exact Mass: 254.094294304
• Heavy Atom Count: 19
• Complexity: 331

Purity/Quality:

99% ^*data from raw suppliers

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

Safty Information:

• Pictogram(s): Xn, T
• Hazard Codes: Xn,T
• Statements: 22-36/37/38-50/53-25
• Safety Statements: 26-60-61-45

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C1=CC(=CC=C1)C(=O)C2=CC=CC=C2)C(=O)O
• Isomeric SMILES: C[C@@H](C1=CC(=CC=C1)C(=O)C2=CC=CC=C2)C(=O)O
• Recent ClinicalTrials: Dexketoprofen Dosage According to Chronotherapy
• Recent EU Clinical Trials: Comparative study between continuous perfusion and split doses in the treatment of postoperative pain
• Uses: COX inhibitor
• Clinical Use: #N/A
• Drug interactions: Potentially hazardous interactions with other drugsACE inhibitors and angiotensin-II antagonists: antagonism of hypotensive effect; increased risk of nephrotoxicity and hyperkalaemiaAnalgesics: 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 quinolonesAnticoagulants: effects of coumarins and phenindione enhanced; possibly increased risk of bleeding with heparins, dabigatran and edoxaban - avoid long term use with edoxabanAntidepressants: 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 ritonavir.Ciclosporin: may potentiate nephrotoxicity.Cytotoxics: reduced excretion of methotrexate; increased risk of bleeding with erlotinib.Diuretics: increased risk of nephrotoxicity; antagonism of diuretic effect, hyperkalaemia with potassium-sparing diuretics.Lithium: excretion decreased.Pentoxifylline: increased risk of bleedingProbenecid: excretion reduced by probenecid.Tacrolimus: increased risk of nephrotoxicity

Technology Process of Dexketoprofen

There total 63 articles about Dexketoprofen 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: 98.3%

(S)-3-methyl-2-phenylbutylammonium (S)-2-(3-benzoylphenyl)propionate → S-ketoprofen (22161-81-5,22161-86-0)

Guidance literature:

With hydrogenchloride; In water; at 50 ℃;

DOI:10.1021/op010081z

Reference yield: 95.0%

(2S)-[3-(2-hydroxy-1-methyl-ethyl)-phenyl]-phenyl-methanone (1173289-23-0) → S-ketoprofen (22161-81-5,22161-86-0)

Guidance literature:

With Jones reagent; In acetone; for 12h; Inert atmosphere;

DOI:10.1021/ja910778p

Reference yield: 85.6%

3-(3-benzoyl-phenyl)-2S,3R-dimethyl-oxirane-2-carboxy-5-methyl-2-(1-methyl-1-phenyl-ethyl)-cyclohexane ester → S-ketoprofen (22161-81-5,22161-86-0)

Guidance literature:

3-(3-benzoyl-phenyl)-2S,3R-dimethyl-oxirane-2-carboxy-5-methyl-2-(1-methyl-1-phenyl-ethyl)-cyclohexane ester; With sodium carbonate; In dichloromethane; water; for 1h;

With dihydrogen peroxide; acetic acid; at 85 ℃; for 9h;

upstream raw materials:

ketoprofen methyl ester

ketoprofen

ethyl 2-<3-benzoylphenyl>propionate

2-chloroethyl ester of 2-(3-benzoylphenyl)propionic acid

Downstream raw materials:

(S)-2-(3-Benzoyl-phenyl)-propionic acid (R)-1,2-dimethyl-cyclohexa-2,5-dienylmethyl ester

(S)-2-(3-Benzoyl-phenyl)-propionic acid (S)-1,2-dimethyl-cyclohexa-2,5-dienylmethyl ester

C₂₆H₂₆N₂O₇

C₂₆H₂₆N₂O₇

Refernces

• 1、 Gérard, Doriane,Guéroult, Marc,Casas-Godoy, Leticia,Condoret, Jean-Stéphane,André, Isabelle,Marty, Alain,Duquesne, Sophie. "Efficient resolution of profen ethyl ester racemates by engineered Yarrowia lipolytica Lip2p lipase". . p. 433 - 441. Retrieved 2017.
• 2、 Wu,Xu,Liu. "A practical enzymatic method for preparation of (S)-ketoprofen with a crude Candida rugosa lipase". . p. 3491 - 3496. Retrieved 2001.
• 3、 Gherdaoui, Dehbiya,Bekdouche, Hafsa,Zerkout, Said,Fegas, Rachid,Righezza, Michel. "Chiral separation of ketoprofen on an achiral NH2 column by HPLC using vancomycin as chiral mobile phase additive". . p. 2319 - 2323. Retrieved 2016.
• 4、 Hernaiz, Maria J.,Sanchez-Montero, Jose M.,Sinisterra, Jose V.. "Comparison of the enzymatic activity of commercial and semipurified lipase of Candida cylindracea in the hydrolysis of the esters of (R,S) 2-aryl propionic acids". . p. 10749 - 10760. Retrieved 1994.
• 5、 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.
• 6、 -. "Method for synthesizing dexketoprofen intermediate". Paragraph 0030-0032. . Retrieved 2019/01/16.