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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
Structure of IBUPROFEN, (-)-

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

HIDE SMILES / InChI

Molecular Formula C13H18O2
Molecular Weight 206.2808
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 1 / 1
E/Z Centers 0
Optical Activity UNSPECIFIED

Description

(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 TargetPharmacologyConditionPotency
8.6 mM [IC50]

Conditions

ConditionModalityTargetsHighest PhaseProduct

PubMed

Sample Use Guides

In Vivo Use Guide
Single dose is 300 mg
Route of Administration: Oral
In Vitro Use Guide
The concentrations of (R)-Ibuprofen that inhibited lactate dehydrogenase efflux by 50% with respect to control samples (IC50) is 38.02 uM.
Substance Class Chemical
Record UNII
99W8H60N62
Record Status Validated (UNII)
Record Version