MedKoo Cat#: 326811 | Name: Verlukast

Description:

WARNING: This product is for research use only, not for human or veterinary use.

Verlukast, also known as MK-0679, is a (R)-enantiomer of MK-571 and a potent and selective LTD4 receptor antagonist. Verlukast showed [3H]leukotriene D4 binding in guinea-pig (IC50 = 3.1 +/- 0.5 nM) and human (IC50 = 8.0 +/- 3.0 nM) lung homogenates and dimethyl sulfoxide differentiated U937 cell membrane preparations (IC50 = 10.7 +/- 1.6 nM) but is essentially inactive versus [3H]leukotriene C4 binding in guinea-pig lung homogenates (IC50 values of 19 and 33 microM). Verlukast was in clinical development for the treatment of asthma and related diseases. (last updated: 8/8/2016)

Chemical Structure

Verlukast
Verlukast
CAS#120443-16-5

Theoretical Analysis

MedKoo Cat#: 326811

Name: Verlukast

CAS#: 120443-16-5

Chemical Formula: C26H27ClN2O3S2

Exact Mass: 514.1152

Molecular Weight: 515.08

Elemental Analysis: C, 60.63; H, 5.28; Cl, 6.88; N, 5.44; O, 9.32; S, 12.45

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.
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Related CAS #
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Synonym
L 668,019; L 668019; L-668,019; MK 0679; MK 679; MK-679; R-(-)-MK 571; Verlukast.
IUPAC/Chemical Name
(R,E)-3-(((3-(2-(7-chloroquinolin-2-yl)vinyl)phenyl)((3-(dimethylamino)-3-oxopropyl)thio)methyl)thio)propanoic acid
InChi Key
AXUZQJFHDNNPFG-LHAVAQOQSA-N
InChi Code
InChI=1S/C26H27ClN2O3S2/c1-29(2)24(30)12-14-33-26(34-15-13-25(31)32)20-5-3-4-18(16-20)6-10-22-11-8-19-7-9-21(27)17-23(19)28-22/h3-11,16-17,26H,12-15H2,1-2H3,(H,31,32)/b10-6+/t26-/m1/s1
SMILES Code
O=C(O)CCS[C@H](C1=CC=CC(/C=C/C2=NC3=CC(Cl)=CC=C3C=C2)=C1)SCCC(N(C)C)=O
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>2 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 515.08 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
1: Nicoll-Griffith DA, Gupta N, Twa SP, Williams H, Trimble LA, Yergey JA. Verlukast (MK-0679) conjugation with glutathione by rat liver and kidney cytosols and excretion in the bile. Drug Metab Dispos. 1995 Oct;23(10):1085-93. PubMed PMID: 8654196. 2: Hsieh JY, Lin C, Matuszewski BK. Robotic sample preparation and high-performance liquid chromatographic analysis of verlukast in human plasma. J Chromatogr B Biomed Appl. 1994 Nov 18;661(2):307-12. PubMed PMID: 7894671. 3: Schwartz JI, Margolskee DJ, Bjornsson TD, Williams VC, Hsieh JY, Lin CC, Rogers JD. Oral pharmacokinetics and food interaction of the leukotriene D4 receptor antagonist verlukast. Br J Clin Pharmacol. 1993 Nov;36(5):464-6. PubMed PMID: 12959296; PubMed Central PMCID: PMC1364621. 4: Grossman SJ, Herold EG, Drey JM, Alberts DW, Umbenhauer DR, Patrick DH, Nicoll-Griffith D, Chauret N, Yergey JA. CYP1A1 specificity of Verlukast epoxidation in mice, rats, rhesus monkeys, and humans. Drug Metab Dispos. 1993 Nov-Dec;21(6):1029-36. PubMed PMID: 7905381. 5: Nicoll-Griffith DA, Chauret N, Yergey JA, Trimble LA, Favreau L, Zamboni R, Grossman SJ, Drey J, Herold E. Characterization of verlukast metabolites arising from an epoxide intermediate produced with hepatic microsomes from beta-naphthoflavone-treated rodents (P-4501A1). Drug Metab Dispos. 1993 Sep-Oct;21(5):861-7. PubMed PMID: 7902249. 6: Lammers JW, Van Daele P, Van den Elshout FM, Decramer M, Buntinx A, De Lepeleire I, Friedman B. Bronchodilator properties of an inhaled leukotriene D4 antagonist (verlukast--MK-0679) in asthmatic patients. Pulm Pharmacol. 1992 Jun;5(2):121-5. PubMed PMID: 1611229. 7: Nicoll-Griffith D, Yergey J, Trimble L, Williams H, Rasori R, Zamboni R. In vitro and in vivo biotransformations of the potent leukotriene D4 antagonist verlukast in the rat. Drug Metab Dispos. 1992 May-Jun;20(3):383-9. PubMed PMID: 1355712. 8: Jones TR, Zamboni R, Belley M, Champion E, Charette L, Ford-Hutchinson AW, Gauthier JY, Leger S, Lord A, Masson P, et al. Pharmacology of the leukotriene antagonist verlukast: the (R)-enantiomer of MK-571. Can J Physiol Pharmacol. 1991 Dec;69(12):1847-54. PubMed PMID: 1666333.