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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, (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,
Montelukast sodium intermediate and preparation method and application thereof
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, (2017/08/31)
The invention relates to a series of novel compounds as shown in a formula (III) and a preparation method thereof. The invention also relates to an application of the novel compounds as shown in the formula (III) in synthesizing Montelukast sodium. The compounds as shown in the formula (III) are critical intermediates in the Montelukast sodium synthesizing process, and play a critical role of synthesizing the final target compound. The intermediate is stable in chemical property, the preparation process is mild in reaction condition, the yield is high, the optical purity is high, and the intermediate is suitable for large-scaled production. The formula is as shown in the description.
And Menlust sodium process for the preparation of intermediates
-
Paragraph 0032; 0047-0048, (2017/01/09)
The invention relates to a method suitable for preparing montelukast sodium and intermediate 2-(3(S)-(3-(2-(7-chlorine-2-quinolyl) vinyl) phenyl)-3-hydroxypropyl) phenyl)-2-propoxy) tetrahydropyrane (intermediate 3) of the montelukast sodium in a large scale. According to the method, 7-chloroquinaldine and 3-cyanobenzaldehyde are used as starting raw materials, 2-(3-(3-(2-(7-chlorine-2-quinolyl) vinyl) phenyl)-3-oxopropyl) phenyl)-2-propoxy) tetrahydropyrane (intermediate 2) is obtained by six steps of reaction, then intermediate 3 with ee more than 99% and yield more than 90% is obtained by chiral reduction, and the montelukast sodium with high optical purity and high chemical purity is obtained by the intermediate 3 through four steps of reaction.