6258. Montelukast

Nomenclature

CAS number: 158966-92-8
1-[[[(1R)-1-[3-[(1E)-2-(7-Chloro-2-quinolinyl)ethenyl]phenyl]-3-[2-(1-hydroxy-1-methylethyl)phenyl]propyl]thio]methyl]cyclopropaneacetic acid.
C35H36ClNO3S; mol wt 586.18.
C 71.71%, H 6.19%, Cl 6.05%, N 2.39%, O 8.19%, S 5.47%.

Description and references

Selective cysteinyl leukotriene type 1 (Cys-LT1) receptor antagonist. Prepn: M. L. Belley et al., EP 480717; eidem, US 5565473 (1992, 1996 both to Merck Frosst); M. Labelle et al., Bioorg. Med. Chem. Lett. 5, 283 (1995). Pharmacological profile: T. R. Jones et al., Can. J. Physiol. Pharmacol. 73, 191 (1995). LC determn in human plasma: R. D. Amin et al., J. Pharm. Biomed. Anal. 13, 155 (1995). Clinical trial in pediatric asthma: B. Knorr et al., J. Am. Med. Assoc. 279, 1181 (1998). Review of pharmacology and clinical applications in asthma and allergy: Z. Diamant, A. P. Sampson, J. Drug Eval. Respir. Med. 1, 53-88 (2002). Review of clinical experience in allergic rhinitis: J. A. Lagos, G. D. Marshall, Ther. Clin. Risk Manage. 3, 327-332 (2007); and asthma: A. Nayak, R. B. Langdon, Drugs 67, 887-901 (2007).

Chemical structure

Derivative

Monosodium salt.

Nomenclature

CAS number: 151767-02-1
MK-476; Singulair (Merck & Co.).
C35H35ClNNaO3S; mol wt 608.17.
C 69.12%, H 5.80%, Cl 5.83%, N 2.30%, Na 3.78%, O 7.89%, S 5.27%.

Properties

Hygroscopic, white to off-white powder. Freely sol in ethanol, methanol, water. Practically insol in acetonitrile.

Therapeutic Category

Antiasthmatic; antiallergic.

Keywords

Antiasthmatic (Nonbronchodilator); Leukotriene Antagonist; Antiallergic