13-04991. Indoprofen [Archived]

Nomenclature

CAS number: 31842-01-0
4-(1,3-Dihydro-1-oxo-2H-isoindol-2-yl)-α-methylbenzeneacetic acid; p-(1-oxo-2-isoindolinyl)hydratropic acid; 2-[4-(1-carboxyethyl)phenyl]-1-isoindolinone; 1-oxo-2-[p-[(α-methyl)carboxymethyl]phenyl]isoindoline; 2-[4-(1-oxo-2-isoindolinyl)phenyl]propionic acid; IPP; K-4277; Bor-Ind (Borromeo); Flosin (Erba); Flosint (Erba); Isindone (Erba); Praxis (Lisapharma); Reumofene (Von Boch).
C17H15NO3; mol wt 281.31.
C 72.58%, H 5.37%, N 4.98%, O 17.06%.

Description and references

Nonsteroidal anti-inflammatory agent. Prepn: BE 753600; R. W. J. Carney, G. de Stevens, US 4316850 (1970, 1982 both to Ciba); P. N. Giraldi et al., DE 2154525 (1972 to Carlo Erba), C.A. 77, 88292v (1972); G. Nannini et al., Arzneim.-Forsch. 23, 1090 (1973). Synthesis and resolution of enantiomers: F. Buzzetti et al., DE 2258088 (1974 to Carlo Erba), C.A. 81, 13382y (1974); T. Kametani et al., J. Heterocycl. Chem. 15, 369 (1978). Abs config: S. De Munari et al., Tetrahedron Lett. 21, 2273 (1980). Pharmacology: A. Buttinoni et al., Arzneim.-Forsch. 23, 1100 (1973). Absorption, excretion and metabolism: G. C. Goldaniga et al., ibid. 24, 1603 (1974); L. F. Chasseaud et al., ibid. 1606. GLC determn of enantiomers in plasma: G. P. Tosolini et al., J. Pharm. Sci. 63, 1072 (1974). Biological activity and toxicity data: A. Buttinoni et al., J. Pharm. Pharmacol. 35, 603 (1983).

Chemical structure

Properties

Colorless scales from ethanol, mp 213-214°. LD50 in rats (mg/kg): 58.66 i.v.; 60.83 orally (Buttinoni).

Derivative

(+)-Form.

Nomenclature

CAS number: 53086-13-8
Dexindoprofen; Nedius (Erba).

Properties

Colorless scales from isopropanol, mp 205-207°. [α]D20 +48° (c = 0.05 in DMSO). LD50 in rats (mg/kg): 31.98 i.v.; 33.75 orally (Buttinoni).

Derivative

()-Form.

Nomenclature

CAS number: 53086-14-9

Properties

Colorless scales from isopropanol, mp 205-207°. [α]D20 48° (c = 0.05 in DMSO). LD50 in rats (mg/kg): 555.39 i.v.; 538.02 orally (Buttinoni).

Therapeutic Category

Analgesic; anti-inflammatory.

Keywords

Anti-inflammatory (Nonsteroidal); Arylpropionic Acid Derivatives; Analgesic (Non-Narcotic)

Status

This monograph has been retired and is no longer subject to revision or update.