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Nedocromil

Product Name
Nedocromil
CAS No.
69049-73-6
Chemical Name
Nedocromil
Synonyms
Rapitil;FPL-59002;NedocroMi;NEDOCROMIL;Nedocromilo;FPL-59002KP;Nedocromilum;Tilarin:Tilade;Nedocromilum [latin];Nedocromil USP/EP/BP
CBNumber
CB9122310
Molecular Formula
C19H17NO7
Formula Weight
371.34
MOL File
69049-73-6.mol
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Nedocromil Property

Melting point:
298-300° (dec)
Boiling point:
645.5±55.0 °C(Predicted)
Density 
1.472±0.06 g/cm3(Predicted)
storage temp. 
Sealed in dry,2-8°C
solubility 
DMSO: soluble2mg/mL, clear (warmed)
pka
2.19±0.40(Predicted)
form 
Solid
color 
white to beige
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Safety

Hazard Codes 
Xi
Risk Statements 
36
Safety Statements 
26
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Warning
Hazard statements

H319Causes serious eye irritation

Precautionary statements

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

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N-Bromosuccinimide Price

ChemScene
Product number
CS-2323
Product name
Nedocromil
Purity
98.86%
Packaging
5mg
Price
$96
Updated
2021/12/16
ChemScene
Product number
CS-2323
Product name
Nedocromil
Purity
98.86%
Packaging
10mg
Price
$180
Updated
2021/12/16
American Custom Chemicals Corporation
Product number
API0006233
Product name
NEDOCROMIL
Purity
95.00%
Packaging
5MG
Price
$235.4
Updated
2021/12/16
Biorbyt Ltd
Product number
orb181296
Product name
Nedocromil
Purity
>98%
Packaging
100mg
Price
$690.2
Updated
2021/12/16
Biorbyt Ltd
Product number
orb181296
Product name
Nedocromil
Purity
>98%
Packaging
250mg
Price
$1356.6
Updated
2021/12/16
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Nedocromil Chemical Properties,Usage,Production

Description

Nedocromil sodium acts mainly by inhibiting the release of inflammatory mediators. It has a stabilizing action on mast cells similar to that of DSCG. Nedocromil is capable of inhibiting chloride ion flux in mast cells, epithelial cells, and neurons. This feature may explain why it can prevent responses such as mast cell degranulation and neuronal activation . Nedocromil is given by inhalation in the prophylactic control of asthma and rhinitis .

Originator

Alocril,Allergan,USA

Uses

Antiallergic (prophylactic).

Definition

ChEBI: Nedocromil is a dicarboxylic acid and an organic heterotricyclic compound. It has a role as a non-steroidal anti-inflammatory drug, an anti-asthmatic drug and an anti-allergic agent. It is a conjugate acid of a nedocromil(2-).

Manufacturing Process

4,6-Dioxo-10-propyl-4H,6H-pyrano[3,2-]quinoline-2,8-dicarbxylic acid disodium salt was prepared in 8 steps
1. 4-Acetamido-2-allylacetophenone
4-Acetamido-2-hydroxyacetophenone (19.3 g), allyl bromide (12.1 ml) and hydrous potassium carbonate (21.5 g) were stirred in dry dimethylformamide (250 ml) at room temperature for 24 hours. The reaction mixture was poured into water and the product was extracted with ethyl acetate. The organic solution was then washed well with water dried over magnesium sulphate and evaporated to dryness. The sub-title product was obtained as buff coloured solid (20.5 g). The structure of the product was confirmed by NMR and mass spectroscopy.
2. 4-Acetamido-3-allyl-2-hydroxyacetophenone
The above allyl ether (18.4 g) was heated at 200-210°C for 4 hours. 17.1 g of the thermally rearranged sub- title product was obtained as a brown solid. Again the structure was confirmed by NMR and mass spectroscopy.
3. 4-Acetamido-2-hydroxy-3-propyl acetophenone
The product of step 2 (17 g) was dissolved in glacial acetic acid and hydrogenated in the presence of Adams catalyst until hydrogen uptake had ceased. The catalyst was filtered off through a keiselguhr filter and the filtrate was evaporated to leave 13.0 g of almost colorless solid. The mass and NMR spectra confirmed the structure of product.
4. Ethyl-7-acetamido-4-oxo-8-propyl-4H-l-benzopyran-2-carboxylate
A mixture of diethyl oxalate (19.3 g; 17.9 ml) and the above product of step 3 (12.4 g) in dry ethanol (100 ml) was added to a stirred solution of sodium ethoxide in ethanol (prepared by dissolving sodium (6.1 g) in dry ethanol (200 ml)). The reaction mixture was refluxed for 3 hours and then poured into dilute hydrochloric acid and chloroform. The chloroform layer was separated, washed with water and dried. The solvent was evaporated to leave a brown solid which was dissolved in ethanol (300 ml) containing concentrated hydrochloric acid (3 ml) and the whole was refluxed for 1 hour. The reaction mixture was poured into water and the product was extracted into ethyl acetate which was washed with water and dried. The solvent was evaporated to leave 10 g of a sticky solid which had mass and NMR spectra consistent with the expected product.
5. Ethyl 7-amino-4-oxo-8-propyl-4H-1-benzopyran-2-carboxylate
A solution of the amide of step 4 (10 g) in ethanol (300 ml), containing concentrated hydrochloric acid (5 ml), was refluxed for 8 hours. The reaction mixture was diluted with water and extracted into ethyl acetate. The extract was washed with water, dried and the solvent was evaporated to leave a dark brown semi-solid. This was chromatographed on a silica gel column, using ether as eluant to give 4.8 g of the required product whose structure was confirmed by mass and NMR spectral evidence; mp 84-87°C.
6.8-Ethoxycarbonyl-2-methoxycarbonyl-4,6-dioxo-10-propyl-4H,6Hpyrano[3.2-g]quinoline
The amino benzopyran of step 5 (2.0 g) and dimethyl acetylene dicarboxylate (1.24 g; 1.01 ml) were refluxed in ethanol (30 ml) for 26 hours. The reaction mixture was cooled to 0°C and the insoluble yellow-brown solid was collected by filtration and washed with a little ethanol and dried to give 2.0 g of a product which was a mixture of maleic and fumaric esters obtained by Michael addition of the amine to the acetylene. This mixture of esters (2.0 g) was treated with polyphosphoric acid (30 ml) and heated on the steam bath with stirring for 20 minutes. The reaction mixture was then poured onto ice and stirred with ethyl acetate. The organic layer was separated, washed with water and dried. The solvent was evaporated to leave 1.6 g of a yellow orange solid. Recrystallisation of this solid from ethyl acetate gave the required product as fluffy orange needles, mp 187°-188°C.
7. 4,6-Dioxo-10-propyl-4H,6H-pyrano[3.2-g]quinoline-2,8-dicarboxylic acid
The above bis ester (2.5 g) was refluxed with sodium bicarbonate (1.64 g) in ethanol (100 ml) and water (50 ml) for 1.5 hours. The whole was poured into water and acidified to precipitate a gelatinous solid. This was collected by filtration, refluxed with ethanol and the product was separated by centrifugation (1.4 g), mp 303°-304°C dec. The structure of the product was confirmed by mass and NMR evidence.
8. Disodium 4,6-dioxo-10-propyl-4H,6H-pyrano[3,2-g]quinoline-2,8- dicarboxylate
The bis acid from step 6 (1.35 g) and sodium bicarbonate (0.661 g) in water (150 ml) were warmed and stirred until a clear solution was obtained. This solution was filtered and the filtrate was freeze dried to give 1.43 g of the required disodium salt.

Therapeutic Function

Antiallergic, Anti-asthmatic

Clinical Use

Nedocromil is a chromone analogue also used by inhalation as an aerosol, primarily in the prophylaxis of asthma and reversible obstructive airway disease. It inhibits release of allergic mediators, and it is effective in a broad range of patients. An ophthalmic solution is available for the treatment of seasonal and perennial allergic conjunctivitis. Other structurally related compounds are not currently available in the United States but are available in other markets.

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Nedocromil Suppliers

Shanghai Boyle Chemical Co., Ltd.
Tel
Fax
86-21-57758967
Email
sales@boylechem.com
Country
China
ProdList
2922
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LGM Pharma
Tel
1-(800)-881-8210
Fax
615-250-9817
Email
inquiries@lgmpharma.com
Country
United States
ProdList
2123
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70
NCE Biomedical Co.,Ltd.
Tel
4000-027-021 |24 +86-13986109188 | +86-15623472865 | +81-08033611988
Fax
+86-27-87599188
Country
China
ProdList
1493
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Shanghai T&W Pharmaceutical Co., Ltd.
Tel
+86 21 61551611
Fax
+86 21 50676805
Country
China
ProdList
9891
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58
Jiangsu Aikon Biopharmaceutical R&D co.,Ltd.
Tel
025-66099280 17798518460
Fax
(1)02557626880
Email
cfzhang@aikonchem.com
Country
China
ProdList
19915
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Haoyuan Chemexpress Co., Ltd.
Tel
021-58950125
Fax
(86) 21-58955996
Email
info@chemexpress.com
Country
China
ProdList
7552
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61
MedChemexpress LLC
Tel
021-58955995
Fax
609-228-5909
Email
sales@medchemexpress.cn
Country
United States
ProdList
4861
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58
Guangzhou Isun Pharmaceutical Co., Ltd
Tel
020-39119399 18927568969
Fax
020-39119999
Email
isunpharm@qq.com
Country
China
ProdList
4428
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55
Qingdao Kingway Pharmtech Co., Ltd.
Tel
0532-87118899
Fax
0532-84117788
Email
sales@kingwaypharm.com
Country
China
ProdList
119
Advantage
56
GIHI CHEMICALS CO.,LTD
Tel
0086-571-86217390
Fax
0086-571-86217391
Email
Sales@gihichem.com
Country
China
ProdList
860
Advantage
58
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View Lastest Price from Nedocromil manufacturers

Wuhan Nutra Biotechnology Co.,Ltd
Product
Nedocromil 69049-73-6
Price
US $150.00-0.00/g
Min. Order
1g
Purity
98%+
Supply Ability
100kgs
Release date
2021-05-19
Dideu Industries Group Limited
Product
Nedocromil 69049-73-6
Price
US $1.10/g
Min. Order
1g
Purity
99.9%
Supply Ability
100 Tons Min
Release date
2021-05-28

69049-73-6, NedocromilRelated Search:


  • NEDOCROMIL
  • FPL-59002
  • FPL-59002KP
  • Rapitil
  • Tilarin:Tilade
  • 101626-68-0 (Calcium salt (1:1))
  • 4H-Pyrano(3,2-G)quinoline-2,8-dicarboxylic acid, 9-ethyl-6,9-dihydro-4,6-dioxo-10-propyl-
  • 69049-74-7 (Di-hydrochloride salt)
  • 9-Ethyl-6,9-dihydro-4,6-dioxo-10-propyl-4H-pyrano(3,2-G)chinolin-2,8-dicarbonsaeure
  • Nedocromilo
  • Nedocromilo [spanish]
  • Nedocromilum
  • Nedocromilum [latin]
  • 9-ethyl-4,6-dioxo-10-propyl-6,9-dihydro-4H-pyrano[3,2-g]quinoline-2,8-dicarboxylic acid
  • NedocroMi
  • 9-Ethyl-6,9-dihydro-4,6-dioxo-10-propyl-4H-pyrano[3,2-g]quinoline-2,8-dicarboxylic acid
  • Nedocromil USP/EP/BP
  • Nedocromil,Prostaglandin Receptor,Inhibitor,inhibit,Leukotriene Receptor,FPL59002,FPL-59002,Histamine Receptor
  • 69049-73-6
  • C19H17NO7