Ibuprofen
Structural Formula Vector Image
Title: Ibuprofen
CAS Registry Number: 15687-27-1
CAS Name: a-Methyl-4-(2-methylpropyl)benzeneacetic acid
Additional Names: p-isobutylhydratropic acid; (±)-2-(4-isobutylphenyl)propionic acid
Manufacturers' Codes: RD-13621
Trademarks: 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)
Molecular Formula: C13H18O2
Molecular Weight: 206.28
Percent Composition: C 75.69%, H 8.80%, O 15.51%
Literature 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).
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).
Melting point: mp 75-77°
Toxicity data: LD50 in male mice, rats (mg/kg): 495, 626 i.p.; 1255, 1050 orally (Orzalesi)
 
Derivative Type: Lysine salt
Trademarks: Arfen (Lisapharma); Imbun (Merckle)
Molecular Formula: C13H18O2.C6H14N2O2
Molecular Weight: 352.47
Percent Composition: C 64.74%, H 9.15%, O 18.16%, N 7.95%
 
Derivative Type: S-Form L-lysine salt monohydrate
CAS Registry Number: 141505-32-0
Additional Names: Dexibuprofen lysine
Manufacturers' Codes: MK-223
Molecular Formula: C13H18O2.C6H14N2O2.H2O
Molecular Weight: 370.48
Percent Composition: C 61.60%, H 9.25%, O 21.59%, N 7.56%
 
Therap-Cat: Anti-inflammatory; analgesic; antipyretic.
Therap-Cat-Vet: Anti-inflammatory.
Keywords: Anti-inflammatory (Nonsteroidal); Arylpropionic Acid Derivatives.

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