(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)

Flash point:

>230 °F

storage temp. 

Sealed in dry,Room Temperature

solubility 

45% (w/v) aq 2-hydroxypropyl-β-cyclodextrin: 1.5 mg/mL

form 

solid

pka

4.41±0.10(Predicted)

color 

white

optical activity

[α]20/D +59°, c = 2 in ethanol

Water Solubility 

insoluble

BRN 

3590022

Stability:

Stable. Incompatible with strong oxidizing agents.

InChIKey

HEFNNWSXXWATRW-JTQLQIEISA-N

CAS DataBase Reference

51146-56-6(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xn

Risk Statements 

63-22

Safety Statements 

45-36/37

WGK Germany 

3

HS Code 

29163990

MSDS

• Language:English Provider:ACROS
• Language:English Provider:SigmaAldrich

(S)-(+)-Ibuprofen Usage And Synthesis

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.

Description

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.

Chemical Properties

Colourless, Crystalline Solid

Originator

Gebro Broschek (Austria)

Uses

A nonsteroidal anti-inflammatory drug (NSAID); activity resides primarily in the (S)-isomer

Uses

sedative

Uses

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.

Definition

ChEBI: 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 name

Seractil

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 Activity

Non-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 Use

NSAID and analgesic

Drug interactions

Potentially 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

Metabolism

Dexibuprofen 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 Methods

Crystallise 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 (51146-56-6)Related Product Information

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• IBUPROFEN IMPURITY E,IBUPROFEN IMP E
• IBUPROFEN IMP D,IBUPROFEN IMPURITY D
• IBUPROFEN IMPURITY J