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,
Production of montelukast
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Paragraph 0009; 0019; 0023, (2017/08/02)
PROBLEM TO BE SOLVED: To provide a method of producing a montelukast with raw materials which are easy to handle and inexpensive and in simple reaction operations.SOLUTION: A method of producing a montelukast includes mixing a 1-(mercaptomethyl)cyclopropane acetic acid and an alcohol solution of a sodium methoxide and/or a sodium ethoxide in an aromatic hydrocarbon solvent, adding a reaction accelerator and then adding 2-(2-(3(S)-(3-(2-(7-chloro-2-quinolinyl)ethenyl)phenyl)-3-(methanesulfonyloxypropyl)phenyl)-2-propanol to the resultant disodium dianion solution to react them.
Preparation method of montelukast sodium intermediates
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Paragraph 0031; 0032; 0033, (2016/12/26)
The invention relates to a preparation method of montelukast sodium intermediates. The method comprises the steps that under the protection of inert gas, in solvent, nucleophilic substitution is conducted on a montelukast mother nucleus compound, replaced by various leaving groups, of secondary hydroxyl and various side chains respectively under the action of a catalyst, and various montelukast sodium intermediates are obtained. According to the preparation method of the montelukast sodium intermediates, new catalysts of 4-dimethylaminopyridine and 4-pyrrolidinopyridine are utilized, the reaction is mild in condition and rapid, the product is single, purification is easy and convenient, the obtained intermediates are high in optical purity and higher in yield, and the preparation method is more suitable for industrial production.