The cysteinyl leukotrienes (CysLTs), LTC4 and LTD4, are potent mediators of asthma and hypersensitivity. They induce bronchoconstriction, increase microvascular permeability, and are vasoconstrictors of coronary arteries. Their biological effects are transduced by a pair of G protein-coupled receptors, CysLT1 and CysLT2.1,2,3 Montelukast (sodium salt) is a potent, selective CysLT1 receptor antagonist sold under the trade name Singulair for the treatment of asthma as well as for the symptoms associated with allergic rhinitis.4,5,6,7 It binds to the human CysLT1 receptor with an IC50 of less than 5 nM with no appreciable binding to the CysLT2 receptor.1,2,3
1
Lynch, K.R., O'Neill, G.P., Liu, Q., et al. Characterization of the human cysteinyl leukotriene CysLT1 receptor. Nature399789-793(1999).
2
Heise, C.E., O'Dowd, B.F., Figueroa, D.J., et al. Characterization of the human cysteinyl leukotriene 2 receptor. J Biol Chem27530531-30536(2000).
3
Sarau, H.M., Ames, R.S., Chambers, J., et al. Identification, molecular cloning, expression, and characterization of a cysteinyl leukotriene receptor. Mol Pharmacol56657-663(1999).
4
Leff, J.A., Busse, W.W., Pearlman, D., et al. Montelukast, a leukotriene-receptor antagonist, for the treatment of mild asthma and exercise-induced brochoconstriction. N Engl J Med339147-152(1998).
5
Reiss, T.F., Chervinsky, P., Dockhorn, R.J., et al. Montelukast, a once-daily leukotriene receptor antagonist, in the treatment of chronic asthma. A multicenter, randomized, double-blind trial. Arch Intern Med1581213-1220(1998).
6
Reiss, T.F., Altman, L.C., Chervinsky, P., et al. Effects of montelukast (MK-0476), a new potent cysteinyl leukotriene (LTD4) receptor antagonist, in patients with chronic asthma. J Allergy Clin Immunol98528-534(1996).
7
Peters-Golden, M., and Henderson, W.R. The role of leukotrienes in allergic rhinitis. Ann Allergy Asthma Immunol94609-618(2005).
Synonyms
Singulair®
Formal Name
1-[[[(1R)-1-[3-(1E)-2-(7-chloro-2-quinolinyl)ethenyl]phenyl]-3-[2-(1-hydroxy-1-methylethyl)phenyl]propyl]thio]-methyl]-cyclopropaneacetic acid, monosodium salt
CAS Number
151767-02-1
Molecular Formula
C35H35ClNO3S · Na
Formula Weight
608.2
Formulation
A crystalline solid
Purity
>98%
λmax
212, 284, 328, 345, 359 nm
Stability
2 years
Storage
-20°C
Shipping
Room temperature
in continental US; may vary elsewhere
Lynch, K.R., O'Neill, G.P., Liu, Q., et al. Characterization of the human cysteinyl leukotriene CysLT1 receptor. Nature399789-793(1999).
Leff, J.A., Busse, W.W., Pearlman, D., et al. Montelukast, a leukotriene-receptor antagonist, for the treatment of mild asthma and exercise-induced brochoconstriction. N Engl J Med339147-152(1998).
Reiss, T.F., Altman, L.C., Chervinsky, P., et al. Effects of montelukast (MK-0476), a new potent cysteinyl leukotriene (LTD4) receptor antagonist, in patients with chronic asthma. J Allergy Clin Immunol98528-534(1996).
Peters-Golden, M., and Henderson, W.R. The role of leukotrienes in allergic rhinitis. Ann Allergy Asthma Immunol94609-618(2005).
Reiss, T.F., Chervinsky, P., Dockhorn, R.J., et al. Montelukast, a once-daily leukotriene receptor antagonist, in the treatment of chronic asthma. A multicenter, randomized, double-blind trial. Arch Intern Med1581213-1220(1998).
Sarau, H.M., Ames, R.S., Chambers, J., et al. Identification, molecular cloning, expression, and characterization of a cysteinyl leukotriene receptor. Mol Pharmacol56657-663(1999).
Heise, C.E., O'Dowd, B.F., Figueroa, D.J., et al. Characterization of the human cysteinyl leukotriene 2 receptor. J Biol Chem27530531-30536(2000).