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(S)-(+)-Ibuprofen

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CAS:51146-56-6
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(S)-(+)-Ibuprofen manufacturers

  • (S)-(+)-Ibuprofen
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  • (S)-(+)-Ibuprofen
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  • CAS:51146-56-6
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(S)-(+)-Ibuprofen Basic information
Product Name:(S)-(+)-Ibuprofen
Synonyms:(S)-(+)-2-(4-ISOBUTYLPHENYL)PROPIONIC ACID;(S)-(+)-4-ISOBUTYL-ALPHA-METHYLPHENYLACETIC ACID;(S)-(+)-IBUPROFEN;(2s)-2-[4-(2-methylpropyl)phenyl]propionic acid;(S)-(+)-Ibuprofen ReagentPlus(R), 99%;(S)-2-(4-Isobutylphenyl)propanoic acid, 95+%;(S)-((addition))-Ibuprofen;(S)-(+)-4-Isobutyl-a-methylphenylacetic acid
CAS:51146-56-6
MF:C13H18O2
MW:206.28
EINECS:610-620-9
Product Categories:AMIDATE;Inhibitors;Chiral Reagents;Chiral Compound;Intermediates & Fine Chemicals;Pharmaceuticals
Mol File:51146-56-6.mol
(S)-(+)-Ibuprofen Structure
(S)-(+)-Ibuprofen Chemical Properties
Melting point 49-53 °C(lit.)
alpha 57 º (c=2, EtOH)
Boiling point 285.14°C (rough estimate)
density 1.0364 (rough estimate)
refractive index 59 ° (C=2, EtOH)
Fp >230 °F
storage temp. Sealed in dry,Room Temperature
solubility 45% (w/v) aq 2-hydroxypropyl-β-cyclodextrin: 1.5 mg/mL
form solid
pka4.41±0.10(Predicted)
color white
Optical Rotation[α]20/D +59°, c = 2 in ethanol
Water Solubility insoluble
BRN 3590022
Stability:Stable. Incompatible with strong oxidizing agents.
InChIKeyHEFNNWSXXWATRW-JTQLQIEISA-N
CAS DataBase Reference51146-56-6(CAS DataBase Reference)
Safety Information
Hazard Codes Xn
Risk Statements 63-22
Safety Statements 45-36/37
WGK Germany 3
HS Code 29163990
MSDS Information
ProviderLanguage
ACROS English
SigmaAldrich English
(S)-(+)-Ibuprofen Usage And Synthesis
DescriptionDexibuprofen, 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.
DescriptionIbuprofen 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.
Chemical PropertiesColourless, Crystalline Solid
OriginatorGebro Broschek (Austria)
UsesIbuprofen 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.
Usessedative
UsesA nonsteroidal anti-inflammatory drug (NSAID); activity resides primarily in the (S)-isomer
DefinitionChEBI: Dexibuprofen is an ibuprofen. It has a role as a non-narcotic analgesic and a non-steroidal anti-inflammatory drug. It is an enantiomer of a levibuprofen.
Brand nameSeractil
General Description(S)-(+)-Ibuprofen is the enantiomer associated with the anti-inflammatory action of ibuprofen, which is widely used as a nonsteroidal anti-inflammatory drug in racemic form.
Biological ActivityNon-steroidal anti-inflammatory drug (NSAID) that inhibits cyclooxygenase 1 and cyclooxygenase 2 (IC 50 values are 12 and 80 μ M respectively). Active isomer of ibuprofen.
Clinical UseNSAID and analgesic
Drug interactionsPotentially hazardous interactions with other drugs
ACE 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 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 bleeding.
Tacrolimus: increased risk of nephrotoxicity
MetabolismDexibuprofen is the S(+)-enantiomer of ibuprofen. After metabolic transformation in the liver (hydroxylation and carboxylation), the pharmacologically inactive metabolites are completely excreted, mainly by the kidneys (90%), but also in the bile.
Purification MethodsCrystallise the (+) and (-) acids from EtOH or aqueous EtOH. The racemate which crystallises from pet ether with m 75-77o is sparingly soluble in H2O and has IR (film) 1705 (C=O), 2300—3700 (OH broad)cm-1. It is used as a non-steroidal anti-inflammatory. [Shiori et al. J Org Chem 43 2936 1978, Kaiser et al. J Pharm Sci 65 269 1976, J Pharm Sci 81 221 1992, Freer Acta Cryst (C) 49 1378 1993 for the (S+)-enantiomer.]
(S)-(+)-Ibuprofen Preparation Products And Raw materials
Raw materials1-DEOXY-1-(OCTYLAMINO)-D-GLUCITOL-->(R)-(+)-4-Isopropyl-2-oxazolidinone
Tag:(S)-(+)-Ibuprofen(51146-56-6) Related Product Information
Imidocarb dipropionate Isobutyl nitrite IBUPROFEN,α-Methyl-4-(isobutyl)phenylacetic acid, Ibuprofen,Ibuprofen (FDA),rac Ibuprofen,R,S-Ibuprofen,(+/-)-IBUPROFEN 1-Bromo-2-methylpropane α-Lipoic Acid Propionic acid Nandrolone phenylpropionate 3-(4-Hydroxyphenyl)propionic acid Ethyl 2-(Chlorosulfonyl)acetate PHENYL VALERATE 3-Phenylpropionic acid Isobutylbenzene Propionic anhydride Phenylacetic acid isobutyl ester Ascoric Acid IBUPROFEN IMPURITY E,IBUPROFEN IMP E IBUPROFEN IMP D,IBUPROFEN IMPURITY D IBUPROFEN IMPURITY J

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