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Dexibuprofen
Chemical compound
Chemical compound
| Field | Value |
|---|---|
| Watchedfields | changed |
| verifiedrevid | 443586803 |
| IUPAC_name | (2S)-2-[4-(2-methylpropyl)phenyl]propanoic acid |
| image | Dexibuprofen v2.svg |
| image_class | skin-invert-image |
| image2 | (S)-ibuprofen-3D-balls.png |
| width | 200px |
| width2 | 200px |
| tradename | Seractil, Deltaran, Ibusoft, Monactil |
| Drugs.com | |
| pregnancy_AU | |
| pregnancy_US | |
| legal_AU | |
| legal_CA | |
| legal_UK | |
| legal_US | |
| routes_of_administration | Oral |
| excretion | |
| CAS_number_Ref | |
| CAS_number | 51146-56-6 |
| ATC_prefix | M01 |
| ATC_suffix | AE14 |
| PubChem | 39912 |
| DrugBank_Ref | |
| ChemSpiderID_Ref | |
| ChemSpiderID | 36498 |
| UNII_Ref | |
| UNII | 671DKG7P5S |
| KEGG_Ref | |
| KEGG | D03715 |
| ChEBI_Ref | |
| ChEBI | 43415 |
| ChEMBL_Ref | |
| synonyms | S(+)Ibuprofen |
| ChEMBL | 175 |
| C | 13 |
| H | 18 |
| O | 2 |
| smiles | CC@@HC(=O)O |
| StdInChI_Ref | |
| StdInChI | 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-/m0/s1 |
| StdInChIKey_Ref | |
| StdInChIKey | HEFNNWSXXWATRW-JTQLQIEISA-N |
| Drugs.com = | elimination_half-life =
Dexibuprofen is a nonsteroidal anti-inflammatory drug (NSAID). It is the active dextrorotatory enantiomer of ibuprofen. Most ibuprofen formulations, as well as other drugs of the profen drug class, contain a racemic mixture of both isomers.
Dexibuprofen is a chiral switch of racemic ibuprofen. The chiral carbon in dexibuprofen is assigned an absolute configuration of (S) per the Cahn–Ingold–Prelog rules. Dexibuprofen is also called (S)-(+)-ibuprofen.
Ibuprofen is an α-arylpropionic acid used largely in the treatment of rheumatoid arthritis and widely used over-the counter drug for headache and minor pains. This drug has a chiral center and exists as a pair of enantiomers. (S)-Ibuprofen, the eutomer, is responsible for the desired therapeutic effect. The inactive (R)-enantiomer, the distomer, undergoes a unidirectional chiral inversion to give the active (S)-enantiomer, the former acting as a prodrug for the latter. That is, when the ibuprofen is administered as a racemate the distomer is converted in vivo into the eutomer while the latter is unaffected.
References
References
- (September 2008). "Chiral non-steroidal anti-inflammatory drugs--a review". Journal of the Indian Medical Association.
- (1966). "Specification of Molecular Chirality". Angewandte Chemie International Edition in English.
- (1956). "The specification of asymmetric configuration in organic chemistry". Experientia.
- {{Pubchem. 39912
- (January 1988). "The metabolic chiral inversion and dispositional enantioselectivity of the 2-arylpropionic acids and their biological consequences". Biochemical Pharmacology.
- (November 1983). "The metabolic chiral inversion of 2-arylpropionic acids--a novel route with pharmacological consequences". The Journal of Pharmacy and Pharmacology.
- (March 1976). "Pharmacological differences between the optical isomers of ibuprofen: evidence for metabolic inversion of the (-)-isomer". The Journal of Pharmacy and Pharmacology.
- (2005). "Enantioselective pharmacokinetics of ibuprofen and involved mechanisms". Drug Metabolism Reviews.
- "Dexibuprofen – Chiralpedia".
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