2590. Cromolyn

Nomenclature

CAS number: 16110-51-3
5,5′-[(2-Hydroxy-1,3-propanediyl)bis(oxy)]bis[4-oxo-4H-1-benzopyran-2-carboxylic acid]; 5,5′-[(2-hydroxytrimethylene)dioxy]bis(4-oxo-4H-1-benzopyran-2-carboxylic acid); 5,5′-(2-hydroxytrimethylenedioxy)bis(4-oxochromene-2-carboxylic acid); 1,3-bis(2-carboxychromon-5-yloxy)-2-hydroxypropane; 1,3-di(2-carboxy-4-oxochromen-5-yloxy)propan-2-ol; cromoglycic acid.
C23H16O11; mol wt 468.37.
C 58.98%, H 3.44%, O 37.58%.

Description and references

Chromone complex which blocks mast cell degranulation. Prepn: NL 6603997; C. Fitzmaurice, T. B. Lee, US 3419578 (1966, 1968 both to Fisons). Metabolism: M. J. Ashton et al., Toxicol. Appl. Pharmacol. 26, 319 (1973). Mechanism of action: T. C. Theoharides et al., Science 207, 80 (1980); R. G. Alvarez et al., Agents Actions 11, 94 (1981). Toxicology in primates: J. E. Beach et al., Toxicol. Appl. Pharmacol. 57, 367 (1981). Clinical study in allergic conjunctivitis: G. A. Friday et al., Am. J. Ophthalmol. 95, 169 (1983). Review of pharmacology and clinical use: G. G. Shapiro, P. Konig, Pharmacotherapy 5, 156-170 (1985). Review: J. S. G. Cox in Pharmacological and Biochemical Properties of Drug Substances vol. 1, M. E. Goldberg, Ed. (Am. Pharm. Assoc., Washington, DC, 1977) pp 277-310; W. Storms, M. A. Kaliner, J. Asthma 42, 79-89 (2005).

Chemical structure

Properties

mp 241-242° (dec).

Derivative

Monohydrate.

Properties

Colorless crystals from ethanol + ether, mp 216-217° (dec).

Derivative

Disodium salt.

Nomenclature

CAS number: 15826-37-6
Cromolyn sodium; disodium cromoglycate; DSCG; FPL-670; Alloptrex (Fabre); Allergocrom (Ursapharm); Colimune (Sanofi-Aventis); Cromabak (Théa); Cromadoses (Théa); Cromedil (Europhta); Cromogen (Ivax); Cromoptic (Chauvin); Duracroman (Merck KGaA); Gastrofrenal (Sigma-Tau); Hay-Crom (Ivax); Intal (Sanofi-Aventis); Intercron (Zambon); Lomudal (Sanofi-Aventis); Lomupren (Sanofi-Aventis); Lomusol (Sanofi-Aventis); Multicrom (Menarini); Nalcrom (Sanofi-Aventis); Nalcron (Sanofi-Aventis); Nasalcrom (Pharmacia & Upjohn); Ophtacalm (Chauvin); Opticrom (Sanofi-Aventis); Rynacrom (Sanofi-Aventis); Vividrin (Mann).
C23H14Na2O11; mol wt 512.33.
C 53.92%, H 2.75%, Na 8.97%, O 34.35%.

Properties

Hygroscopic. Freely sol in water (100 mg/ml at 20°). Practically insol in chloroform and alcohol. LD50 in mice, rats (mg/kg): >8000 orally (Cox).

Therapeutic Category

Antiasthmatic; antiallergic.

Therapeutic Category (Veterinary)

Antiallergic.

Keywords

Antiallergic; Antiasthmatic (Nonbronchodilator)