53882-12-5 Usage
Description
Lodoxamide, also known as Alomide, is an antiallergic drug that functions as a mast cell stabilizer. It is primarily used in the treatment of allergic conjunctivitis and is effective in reducing vascular permeability. Lodoxamide is a promising pharmaceutical candidate due to its ability to stabilize mast cells and alleviate allergic symptoms.
Uses
Used in Pharmaceutical Industry:
Lodoxamide is used as an antiallergic agent for the treatment of allergic conjunctivitis. It works by stabilizing mast cells, preventing the release of histamine and other inflammatory mediators, which in turn reduces the symptoms of allergic reactions.
Additionally, Lodoxamide is used to decrease vascular permeability, which can be beneficial in managing various conditions characterized by increased vascular permeability, such as inflammation and edema.
Brand Name:
Alomide (Alcon) is the brand name under which Lodoxamide is marketed, making it easily recognizable and accessible for patients seeking relief from allergic conjunctivitis and related symptoms.
Originator
Lodoxamide,Alcon,USA
Manufacturing Process
To a solution of 1.56 mole of stannous chloride dihydrate in 860 ml of
concentrated hydrochloric acid is added 0.2195 mole of 4-chloro-3,5-
dinitrobenzonitrile. The mixture is stirred at room temperature for 2 hours and
cooled to 0°C in an ice-salt bath. A cold solution of 50% sodium hydroxide is
added to the mixture until strongly basic. During the addition the temperature
is kept below 30°C.The precipitate is removed by filtration and extracted three
times with 400 ml of ethyl acetate. The extracts are combined and added to
the aqueous filtrate. The phases are shaken well for ten minutes and
separated. The organic phase is evaporated to dryness in vacuo. The solid
residue is recrystallized from ethanol-water. There is obtained 25.0 g (68%) of
4-chloro-3,5-diaminobenzonitrile, melting point 169-170°C.To a solution of 0.34 mole of 4-chloro-3,5-diaminobenzonitrile in 160 ml of dry
DMF is added 0.82 mole of triethylamine. The solution is cooled to 5°C andthere is added 0.82 mole of ethyloxalyl chloride dropwise, keeping the
temperature less than 15°C. The mixture is stirred for 1 hour and warmed to
room temperature. The mixture is stirred at room temperature for 24 hours.
The precipitate is removed by filtration and washed two times with ethyl
acetate. The filtrate and washes are combined and the ethyl acetate distilled
off in vacuo. The DMF solution is poured into 3 L of water. The semi-solid
residue is removed by filtration. The residue is recrystallized from ethanol.
There is obtained 72.4 g (58%) of diethyl N,N'-(2-chloro-5-cyano-mphenylene)dioxamate, melting point 177-179°C.A solution of 0.197 mole of diethyl (N,N'-(2-chloro-5-cyano-m-phenylene)
dioxamate in 750 ml of methylene chloride is extracted with 465 ml of 1 N
sodium hydroxide. The aqueous phase is separated and stirred for 20 min at
room temperature. The solution is acidified with dilute hydrochloric acid. The
precipitate is removed by filtration and washed with water. There is obtained
59.1 g (96%) of N,N'-(2-chloro-5-cyano-m-phenylene)dioxamic acid, melting
point 212°C (dec.).
Biochem/physiol Actions
Lodoxamide Tromethamine is a potent agonist of GPR35 in both human and rat, and an antiallergic mast cell stabilizer used clinically in the UK for treatment of allergic conjunctivitis.
Check Digit Verification of cas no
The CAS Registry Mumber 53882-12-5 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 5,3,8,8 and 2 respectively; the second part has 2 digits, 1 and 2 respectively.
Calculate Digit Verification of CAS Registry Number 53882-12:
(7*5)+(6*3)+(5*8)+(4*8)+(3*2)+(2*1)+(1*2)=135
135 % 10 = 5
So 53882-12-5 is a valid CAS Registry Number.
InChI:InChI=1/C11H6ClN3O6/c12-7-5(14-8(16)10(18)19)1-4(3-13)2-6(7)15-9(17)11(20)21/h1-2H,(H,14,16)(H,15,17)(H,18,19)(H,20,21)
53882-12-5Relevant articles and documents
Preparation method of lodoxamide tromethamine intermediate
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Paragraph 0033-0047, (2018/12/13)
The invention belongs to the technical field of medicine chemical engineering, and particularly discloses a preparation method of a lodoxamide tromethamine intermediate of lodoxamide. The method comprises the following steps of (1) dissolving 3,5-diamino-4-chlorobenzonitrile into an organic solvent to form a solution A; (2) dissolving oxalyl chloride into the organic solvent to form a solution B;(3) slowly dripping the solution A into the solution B; in the dripping process, controlling the temperature of the reaction liquid at -20 to 0 DEG C; after the reaction is completed, slowly drippinga certain amount of ice water into the reaction liquid; after the dripping is completed, continuously performing stirring for 0.5 to 1h; then, performing suction filtering; drying obtained filter caketo obtain lodoxamide. The reaction steps of the method are few; the operation is facilitated; the yield is greatly improved and can reach 90 percent or higher; meanwhile, the related impurities of the product lodoxamide are few; the product purity is high; the HPLC purity can reach 99.5 percent or higher; great significance is realized on the synthesis of the lodoxamide tromethamine medicine.
Cyano phenylene dioxamic molecules
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, (2008/06/13)
Compounds represented below SPC1 And pharmaceutical compositions thereof, the compositions including the non-substituted phenylene dioxamates are useful in the prophylactic treatment of sensitized mammals for allergy and all anaphylactic reactions of a reagin or non-reagin mediated nature.
