Cromolyn Disodium Salt

Cromolyn Disodium Salt Basic information
Description References
Product Name:Cromolyn Disodium Salt
Synonyms:disodium 5,5'-[(2-hydroxytrimethylene)dioxy]bis[4-oxo-4h-1-benzopyran-2-carboxylate];disodium 1,3-bis(2-carboxy-5-chromonyloxy)-2-propanol;CROMOGLYCATE SODIUM SALT;CROMOGLYCIC ACID SODIUM SALT;CROMOLYN SODIUM SALT;4h-1-benzopyran-2-carboxylicacid,5,5’-((2-hydroxytrimethylene)dioxy)bis(4-oxo;4H-1-Benzopyran-2-carboxylicacid,5,5’-[(2-hydroxy-1,3-propanediyl)bis(oxy)]bis[4-oxo-,disodiumsalt;4H-1-Benzopyran-2-carboxylicacid,5,5’-[(2-hydroxytrimethylene)dioxy]bis[4-oxo-,disodiumsalt
CAS:15826-37-6
MF:C23H17NaO11
MW:492.37
EINECS:239-926-7
Product Categories:INTAL;Other APIs;Intermediates & Fine Chemicals;Pharmaceuticals;Drug bulk;API
Mol File:15826-37-6.mol
Cromolyn Disodium Salt Structure
Cromolyn Disodium Salt Chemical Properties
Melting point 241-2420C (dec)
storage temp. 2-8°C
solubility Soluble in water, practically insoluble in ethanol (96 per cent).
form neat
color White to Off-White
Water Solubility Soluble in water to 100mg/ml
Merck 14,2590
Stability:Hygroscopyc
InChIKeyVLARUOGDXDTHEH-UHFFFAOYSA-L
CAS DataBase Reference15826-37-6(CAS DataBase Reference)
Safety Information
Hazard Codes Xi
Risk Statements 36/37/38
Safety Statements 26-36
RIDADR 3249
WGK Germany 2
RTECS DJ2380000
HazardClass 6.1(b)
PackingGroup III
HS Code 29329990
ToxicityLD50 in mice, rats (mg/kg): >8000 orally (Cox)
MSDS Information
ProviderLanguage
SigmaAldrich English
Cromolyn Disodium Salt Usage And Synthesis
DescriptionSodium cromoglycate is the sodium salt and common market from of cromoglicic acid, which is a synthetic compound, and as a mast cell stabilizer. It is capable of inhibiting the antigen-induced bronchospasms, and thus being used to treat the asthma and allergic rhinitis. It can also be applied as an ophthalmic solution for the treatment of conjunctivitis and systemic mastocytosis and ulcerative colitis. It is capable of inhibiting the degranulation of mast cells, further preventing the release of histamine and slow-reacting substance of anaphylaxis (SRS-A), the mediators of type I allergic reaction. It is also capable of inhibiting the release of inflammatory leukotrienes and inhibiting calcium influx.
Referenceshttps://www.drugbank.ca/drugs/DB01003
https://en.wikipedia.org/wiki/Cromoglicic_acid
Chemical PropertiesWhite Crystalline Powder
OriginatorIntal,Fisons,UK,1969
UsesAnti Asthamatic
Usesantiasthmatic, antiallergy
UsesChromone complex which blocks mast cell degranulation
IndicationsCromolyn sodium (Intal) is chemically related drugs called chromones that is used for the prophylaxis of mild or moderate asthma. It is administered by inhalation and has very good safety profiles, making them particularly useful in treating children.
DefinitionChEBI: An organic sodium salt that is the disodium salt of cromoglycic acid.
Manufacturing ProcessTo a solution of 970 parts of 2,6-dihydroxyacetophenone and 325 parts of epichlorohydrin in 1,500 parts of hot isopropanol was added, with stirring under reflux, a solution of 233 parts of 85% KOH in 2,500 parts of isopropanol and sufficient water (ca 100 parts) to dissolve the solid. The mixture was heated, with stirring, under reflux for 48 hours. Half the solvent was then distilled off and 5,000 parts of water were added. The mixture was cooled and the solid filtered off and washed with isopropanol and ether. It was then recrystallized from 12,500 parts of isopropanol to obtain a first crop of 380 parts and a second crop, after concentration, of 300 parts of 1,3-bis(2- acetyl-3-hydroxyphenoxy)-2hydroxypropane.
4.6 parts of 1,3-bis(2-acetyl-3-hydroxyphenoxy)-2-hydroxypropane were reacted with diethyl oxalate and the product cyclized to obtain 4.4 parts of pure diethyl ester of 1,3-bis(2-carboxychromon-5-yloxy)-2-hydroxypropane as pale yellow crystals melting between 180° and 182°C from a mixture of benzene and petrol, 4 parts of the diethyl ester of 1,3-bis(2-carboxychromon5-yloxy)-2-hydroxypropane were saponified with sodium hydroxide to obtain 3.2 parts of the disodium salt tetrahydrate as colorless crystals from aqueous alcohol.
Therapeutic FunctionBronchodilator
General DescriptionCromolyn sodium, disodium 1,3-bis(2-carboxychromon-5-yloxy)-2-hydroxypropane (Intal), isa hygroscopic, white, hydrated crystalline powder that is solublein water (1:10). It is tasteless at first but leaves a veryslightly bitter aftertaste. The pK of cromolyn is 2. It is availableas a solution for a nebulizer, an aerosol spray, a nasal solution,an ophthalmic solution, and an oral concentrate.
Nebulized and aerosol cromolyn has been used for prophylacticmanagement of bronchial asthma and prevention ofexercise-induced bronchospasm. Cromolyn nasal solution isused for the prevention and treatment of allergic rhinitis, andoral concentrate is used to treat the histaminic symptomsof mastocytosis (diarrhea, flushing, headaches, vomiting, urticaria,abdominal pain, nausea, and itching). Topical cromolyn(eye drops) is used to treat allergic conjunctivitis andkeratitis. In the treatment of asthma, cromolyn efficacy is manifestedby decreased severity of clinical symptoms, or need for concomitant therapy, or both. Long-term use is justified if thedrug significantly reduces the severity of asthma symptoms;permits a significant reduction in, or elimination of, steroiddosage; or improves management of those who have intolerableside effects to sympathomimetic agents or methylxanthines.For cromolyn to be effective, it must be administered atleast 30 minutes prior to antigen challenge and administered atregular intervals (see dosing information that follows). Wheninhaled, the powder does produce irritation in some patients.Also, overuse of cromolyn can result in tolerance.
Biochem/physiol ActionsCromolyn blocks the release of histamine and other pro-inflammatory mediators from mast cells.
Mechanism of actionThe precise mechanism or mechanisms whereby cromolyn sodium and nedocromil sodium exert their antiasthmatic activities is unknown. Early work suggested that these agents act by “stabilizing” mast cells, preventing mediator release. However, several other compounds exhibit greater potency for stabilization of mast cells yet possess no clinical efficacy in asthma.This suggests that the therapeutic activity of cromolyn sodium and nedocromil sodium in asthma is related to one or more other pharmacological mechanisms. Postulates include inhibitory effects on irritant receptors, nerves, plasma exudation, and inflammatory cells in general.
PharmacokineticsCromolyn sodium is a bischromone that contains the fundamental benzopyrone moiety of khellin. The two chromone rings are necessary for activity and must be coplanar, with a linking chain of no longer than six carbons. If one changes the linking chain to positions 8 and 8′, coplanarity cannot be maintained, and the compound loses all activity. Cromolyn sodium is poorly absorbed from the lungs (~8%), insignificantly from the eye (~0.07%), and by approximately 1% from the GI tract. What little that finds its way into systemic circulation is eliminated intact in the urine and the bile. For the treatment of asthma, cromolyn sodium is available as a solution for both intranasal and inhalation administration. There also is an oral concentrate (100 mg/5 mL), which is administered as a 200-mg dose given four times a day.
Clinical UseCromolyn sodium is used almost exclusively for the prophylactic treatment of mild to moderate asthma and should not be used for the control of acute bronchospasm. This agent is effective in about 60 to 70% of children and adolescents with asthma. Unfortunately, there is no reliable means to predict which patients will respond.It is less effective in older patients and in patients with severe asthma. It may take up to 4 to 6 weeks of treatment for cromolyn sodium to be effective in chronic asthma, but it is effective after a single dose in exercise-induced asthma. With respect to clinical efficacy, cromolyn sodium and nedocromil sodium do not differ in a substantial way.
Side effectsCromolyn sodium is the least toxic of available therapies for asthma. Adverse reactions are rare and generally minor. Those occurring in fewer than 1 in 10,000 patients include transient bronchospasm, cough or wheezing, dryness of throat, laryngeal edema, swollen parotid gland, angioedema, joint swelling and pain, dizziness, dysuria, nausea, headache, nasal congestion, rash, and urticaria.
storageStore at RT
Cromolyn Disodium Salt Preparation Products And Raw materials
Raw materialsIsopropyl alcohol-->Diethyl oxalate-->Epichlorohydrin-->Resorcinol-->2',6'-Dihydroxyacetophenone-->Diethyl cromoglycate-->Sodium hydroxide
Sodium Cromoglicate Impurity 13 Sodium Cromoglicate Impurity 7 Sodium Cromoglicate Impurity 9 Sodium cromoglicate impurity 6 Sodium cromoglicate impurity 3 Sodium Cromoglicate Impurity 14 Sodium Cromoglicate Impurity 8 Sodium Cromoglicate Impurity 10 Sodium cromoglicate impurity 5 Sodium cromoglicate impurity 4 5-HYDROXY-4-OXO-4H-CHROMENE-2-CARBOXYLIC ACID (E)-4-OXO-PENT-2-ENOIC ACID sodium Sodium Cromoglycate-d5 trans-3-Benzoylacrylic acid Centchroman 2-(2-HYDROXYETHOXY)BENZALDEHYDE 1,3-diphenoxypropane Cromolyn Sodium Sodium Cromoglicate

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