158966-92-8 Usage
Originator
Singulair,Merck Pharmaceutical,Canada
Uses
cardiostimulant,
Therapeutic Function
Anti-asthmatic
Mechanism of action
Montelukast was developed from other weakly antagonistic quinoline derivatives. A number of changes can be made to the structure without the loss of activity. These include changing the double bond between the two aromatic rings to an ether linkage, reducing the quinoline ring, changing the chlorine to a fluorine, and/or exchanging the sulfur for an amide group.
Pharmacokinetics
Montelukast is a high-affinity, selective antagonist of the cysLT1 receptor. It is rapidly absorbed orally, with a bioavailability of 64%. Montelukast is 99% bound to plasma proteins and is extensively metabolized in the liver by CYP3A4 and CYP2C9 to oxidated products. CYP3A4 oxidizes the sulfur and the C-21 benzylic carbon, whereas CYP2C9 is selectively responsible for the methyl hydroxylation.
Clinical Use
Leukotriene receptor antagonist:
Prophylaxis of asthma
Seasonal allergic rhinitis
Side effects
Montelukast did not demonstrate any significant adverse effects greater than placebo in clinical trials; however, because it is metabolized by the cytochrome P450 (CYP450) enzymes, its plasma levels should be monitored when coadministered with CYP450-inducing drugs, such as phenobarbital, rifampin, and phenytoin.
Drug interactions
Potentially hazardous interactions with other drugs
None known
Metabolism
Extensively metabolised in the liver by cytochrome P450
isoenzymes CYP3A4, CYP2A6, and CYP2C9.
Excreted principally in the faeces via the bile. Metabolites
have minimal therapeutic activity.
Check Digit Verification of cas no
The CAS Registry Mumber 158966-92-8 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 1,5,8,9,6 and 6 respectively; the second part has 2 digits, 9 and 2 respectively.
Calculate Digit Verification of CAS Registry Number 158966-92:
(8*1)+(7*5)+(6*8)+(5*9)+(4*6)+(3*6)+(2*9)+(1*2)=198
198 % 10 = 8
So 158966-92-8 is a valid CAS Registry Number.
InChI:InChI=1/C35H36ClNO3S/c1-34(2,40)30-9-4-3-7-25(30)13-17-32(41-23-35(18-19-35)22-33(38)39)27-8-5-6-24(20-27)10-15-29-16-12-26-11-14-28(36)21-31(26)37-29/h3-12,14-16,20-21,32,40H,13,17-19,22-23H2,1-2H3,(H,38,39)/t32-/m1/s1
158966-92-8Relevant articles and documents
Montelukast sodium intermediate compound
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Paragraph 0066; 0067, (2020/12/08)
The invention provides a novel montelukast sodium intermediate compound and a preparation method thereof. The intermediate compound is good in stability and convenient to store; the intermediate compound serves as a starting material of montelukast sodium, the synthesized montelukast sodium is high in yield and good in purity; and the structural formula of the intermediate compound is shown in thespecification,
The crystal manufacturing method [...]
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Paragraph 0056, (2017/12/27)
PROBLEM TO BE SOLVED: To provide a method for efficiently manufacturing dipropylamine 1-(((1(R)-(3-(2(E)-(7-chloro-2-quinolinyl)ethenyl)phenyl)-3-(2-(1-hydroxy-1-methylethyl)phenyl)propyl)thio)methylcyclopropaneacetate by reacting dipropylamine with a crude form of 1-(((1(R)-(3-(2(E)-(7-chloro-2-quinolinyl)ethenyl)phenyl)-3-(2-(1-hydroxy-1-methylethyl)phenyl)propyl)thio)methylcyclopropaneacetic acid.SOLUTION: When synthesizing dipropylamine 1-(((1(R)-(3-(2(E)-(7-chloro-2-quinolinyl)ethenyl)phenyl)-3-(2-(1-hydroxy-1-methylethyl)phenyl)propyl)thio)methylcyclopropaneacetate, a solvent mixture of butyl acetate and a hydrocarbon having 5-7 carbon atoms is used as a solvent, and crystals are deposited from a solution.
Asymmetric Catalysis with Iron-Salen Complexes
Shaw, Subrata,White, James D.
, p. 2768 - 2780 (2016/08/31)
Iron(III)-salen complexes based on a chiral cis-2,5-diaminobicyclo[2.2.2]octane scaffold are used as catalysts for a variety of stereo selective reactions. High enantio- and diastereoselectivities can be achieved with these catalysts in sulfa-Michael conjugate addition to acyclic α,β-unsaturated ketones, in regioselective δ-addition of thiols to acyclic α,β,γ,δ-unsaturated ketones, and in Conia-ene carbocyclization of alkynyl-substituted β-dicarbonyl compounds. The use of these chiral iron-salen complexes as catalysts provides a new method for conducting these three important reactions under environmentally sustainable conditions.