Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C13H18O2 |
Molecular Weight | 206.2808 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 1 / 1 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
CC(C)CC1=CC=C(C=C1)[C@@H](C)C(O)=O
InChI
InChIKey=HEFNNWSXXWATRW-SNVBAGLBSA-N
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-/m1/s1
(R)-Ibuprofen, a nonsteroidal anti-inflammatory, is the less active enantiomer of ibuprofen. (S)-enantiomer of ibuprofen has the desired therapeutic effect (160 times more active than its (R)-enantiomer) in the in vitro inhibition of prostaglandin synthesis, while the (R)- ibuprofen is inactive. The accumulation of (R)- ibuprofen can cause serious side effects to the human body such as gastrointestinal pain and production of “hybrid” triglycerides between (R)- ibuprofen and Coenzyme A, which disrupt normal lipid metabolism and membrane function. The R(-)-isomer is almost inactive in inhibiting COX-2.
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: Prostaglandin synthetase system Sources: https://www.ncbi.nlm.nih.gov/pubmed/6706 |
8.6 mM [IC50] | ||
Target ID: CHEMBL4321 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
PubMed
Title | Date | PubMed |
---|---|---|
Pharmacological differences between the optical isomers of ibuprofen: evidence for metabolic inversion of the (-)-isomer. | 1976 Mar |
|
Commercially viable resolution of ibuprofen. | 2009 Aug |
|
Lack of enantiomeric influence on the brain cytoprotective effect of ibuprofen and flurbiprofen. | 2011 Aug |
Patents
Sample Use Guides
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/7849231
Single dose is 300 mg
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/21713382
The concentrations of (R)-Ibuprofen that inhibited lactate dehydrogenase efflux by 50% with respect to control samples
(IC50) is 38.02 uM.
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47835
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51146-57-7
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SUBSTANCE RECORD