4881. Ibuprofen

Nomenclature

CAS number: 15687-27-1
α-Methyl-4-(2-methylpropyl)benzeneacetic acid; p-isobutylhydratropic acid; (±)-2-(4-isobutylphenyl)propionic acid; RD-13621; Advil (Wyeth); Brufen (Abbott); Brufort (Lampugnani); Dolgit (Dolorgiet); Dolocyl (Novartis); Epobron (Ono); Fenbid (Goldshield); Gynofug (Wolff); Ibumetin (Nycomed); Ibutop (Dolorgiet); Ipren (Pharmacia); Motrin (McNeil); Napacetin (Toyama); Novogent (Temmler); Nuprin (BMS); Nurofen (Boots); Opturem (Kade); Proflex (Novartis); Solufen (SMB); Tabalon (Teofarma); Urem (Kade).
C13H18O2; mol wt 206.28.
C 75.69%, H 8.80%, O 15.51%.

Description and references

Nonsteroidal anti-inflammatory drug (NSAID); activity resides primarily in the (S)-isomer. Prepn: J. S. Nicholson, S. S. Adams, GB 971700; eidem, US 3385886 (1964, 1968 both to Boots Pure Drug); T. Shiori, N. Kawai, J. Org. Chem. 43, 2936 (1978); J. T. Pinhey, B. A. Rowe, Tetrahedron Lett. 21, 965 (1980). Methods for resolution of enantiomers: R. Bhushan, J. Martens, Biomed. Chromatogr. 12, 309 (1998). HPLC determn in plasma: R. Canaparo et al., ibid. 14, 219 (2000). Pharmacology: S. S. Adams et al., Arch. Int. Pharmacodyn. Ther. 178, 115 (1969). Acute toxicity: G. Orzalesi et al., Arzneim.-Forsch. 27, 1006 (1977). Clinical trial for closure of patent ductus arteriosus: B. Van Overmeire et al., N. Engl. J. Med. 343, 674 (2000). Review of pharmacology and clinical experience: M. Busson et al., J. Int. Med. Res. 14, 53-62 (1986); of clinical pharmacokinetics and metabolism: N. M. Davies, Clin. Pharmacokinet. 34, 101-154 (1998).

Chemical structure

Properties

Colorless, crystalline stable solid, mp 75-77°. Relatively insol in water. Readily sol in most organic solvents. LD50 in male mice, rats (mg/kg): 495, 626 i.p.; 1255, 1050 orally (Orzalesi).

Derivative

Lysine salt.

Nomenclature

Arfen (Lisapharma); Imbun (Merckle).
C13H18O2.C6H14N2O2; mol wt 352.47.
C 64.74%, H 9.15%, O 18.16%, N 7.95%.

Derivative

S-Form l-lysine salt monohydrate.

Nomenclature

CAS number: 141505-32-0
Dexibuprofen lysine; MK-223.
C13H18O2.C6H14N2O2.H2O; mol wt 370.48.
C 61.60%, H 9.25%, O 21.59%, N 7.56%.

Therapeutic Category

Anti-inflammatory; analgesic; antipyretic.

Therapeutic Category (Veterinary)

Anti-inflammatory.

Keywords

Anti-inflammatory (Nonsteroidal); Arylpropionic Acid Derivatives; Analgesic; Non-opioids; Acetic/Propionic Acid Derivatives; Antipyretic