U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

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
(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

Targets

Primary TargetPharmacologyConditionPotency
Target ID: Prostaglandin synthetase system
8.6 mM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
PubMed

PubMed

TitleDatePubMed
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

Single dose is 300 mg
Route of Administration: Oral
The concentrations of (R)-Ibuprofen that inhibited lactate dehydrogenase efflux by 50% with respect to control samples (IC50) is 38.02 uM.
Name Type Language
IBUPROFEN, (-)-
Common Name English
R-(-)-P-ISOBUTYLHYDRATROPIC ACID
Common Name English
(-)-.ALPHA.-METHYL-4-(2-METHYLPROPYL)BENZENEACETIC ACID
Systematic Name English
(.ALPHA.R)-.ALPHA.-METHYL-4-(2-METHYLPROPYL)BENZENEACETIC ACID
Common Name English
BENZENEACETIC ACID, .ALPHA.-METHYL-4-(2-METHYLPROPYL)-, (.ALPHA.R)-
Systematic Name English
IBUPROFEN, (R)-
Common Name English
(R)-(-)-IBUPROFEN
Common Name English
(R)-2-(4-ISOBUTYLPHENYL)PROPANOIC ACID
Systematic Name English
BENZENEACETIC ACID, .ALPHA.-METHYL-4-(2-METHYLPROPYL)-, (R)-
Systematic Name English
L-IBUPROFEN
Common Name English
(R)-IBUPROFEN
Common Name English
(-)-IBUPROFEN
Common Name English
(-)-IBUPROPHEN
Common Name English
Code System Code Type Description
FDA UNII
99W8H60N62
Created by admin on Sat Dec 16 08:46:00 GMT 2023 , Edited by admin on Sat Dec 16 08:46:00 GMT 2023
PRIMARY
CHEBI
47835
Created by admin on Sat Dec 16 08:46:00 GMT 2023 , Edited by admin on Sat Dec 16 08:46:00 GMT 2023
PRIMARY
PUBCHEM
114864
Created by admin on Sat Dec 16 08:46:00 GMT 2023 , Edited by admin on Sat Dec 16 08:46:00 GMT 2023
PRIMARY
CAS
51146-57-7
Created by admin on Sat Dec 16 08:46:00 GMT 2023 , Edited by admin on Sat Dec 16 08:46:00 GMT 2023
PRIMARY