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Azasetron hydrochloride

Product Name
Azasetron hydrochloride
CAS No.
123040-16-4
Chemical Name
Azasetron hydrochloride
Synonyms
Y-25130;Serotone;AZASETRON;Y-25130HCl;AZASETRON HCL;PubChem CID 2264;Y-25130 HYDROCHLORIDE;Azasetron hydrochloride;Azasetron HCl (Y-25130);INTERMEDIATE OF AZASETRON HCL
CBNumber
CB8706748
Molecular Formula
C17H21Cl2N3O3
Formula Weight
386.27
MOL File
123040-16-4.mol
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Azasetron hydrochloride Property

Melting point:
281° (dec); mp 305° (dec) (Kawakita)
storage temp. 
Sealed in dry,Room Temperature
solubility 
Methanol (Slightly), Water (Slightly)
form 
White solid.
color 
White
CAS DataBase Reference
123040-16-4(CAS DataBase Reference)
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Safety

Toxicity
LD50 in male, female rats (mg/kg): 135, 132 i.v. (Takagi)
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Warning
Hazard statements

H361Suspected of damaging fertility or the unborn child

Precautionary statements

P201Obtain special instructions before use.

P202Do not handle until all safety precautions have been read and understood.

P281Use personal protective equipment as required.

P308+P313IF exposed or concerned: Get medical advice/attention.

P405Store locked up.

P501Dispose of contents/container to..…

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
SML2491
Product name
Azasetron hydrochloride
Purity
≥98% (HPLC)
Packaging
5mg
Price
$102
Updated
2024/03/01
Sigma-Aldrich
Product number
SML2491
Product name
Azasetron hydrochloride
Purity
≥98% (HPLC)
Packaging
25mg
Price
$411
Updated
2024/03/01
Cayman Chemical
Product number
28383
Product name
Azasetron (hydrochloride)
Packaging
10mg
Price
$97
Updated
2024/03/01
Cayman Chemical
Product number
28383
Product name
Azasetron (hydrochloride)
Packaging
100mg
Price
$625
Updated
2024/03/01
Cayman Chemical
Product number
28383
Product name
Azasetron (hydrochloride)
Packaging
25mg
Price
$218
Updated
2024/03/01
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Azasetron hydrochloride Chemical Properties,Usage,Production

Description

Nazasetron (azasetron) hydrochloride is the fourth in the class of highly potent 5- HT3 receptor antagonists to reach the market for prophylaxis of severe nausea and vomiting induced by cytotoxic chemotherapy and by total body X-radiation. In a study with 146 cancer patients suffering from emesis induced by cisplatin, nazasetron was reported to be markedly effective in 72% of subjects. Nazasetron is devoid of dopamine D2 receptor blocking activity and therefore is free of the extrapyrimidal side effects associated with other commonly used antiemetics such as metoclopramide and domperidone. Nazasetron has been reported to be potentially useful for the treatment of gastrointestinal motility dysfunction, such as gastric stasis, vomiting and irritable bowel syndrome.

Chemical Properties

White to Off-White Solid

Originator

Yoshitomi (Japan)

Uses

A 5-HT3 receptor antagonist. Used as an antiemetic.

Uses

Azasetron HCl is a selective 5-HT3 receptor antagonist with IC50 of 0.33 nM used in the management of nausea and vomiting induced by cancer chemotherapy.

Definition

ChEBI: Azasetron hydrochloride is a benzoxazine.

Manufacturing Process

To a solution of 2-(2-carboxy-4-chlorophenoxy)acetic acid in concentrated sulfuric acid is added dropwise a mixed liquid of fuming nitric acid and concentrated sulfuric acid under stirring with keeping at a temperature below 10°C. After the addition, the reaction mixture is stirred and poured into 10 L of ice-cold water. The precipitated crystals are collected by filtration, washed with 2 L of water four times and them dried to give 2-(2-carboxy-4-chloro-6- nitrophenoxy)acetic acid.
To a solution of ferrous sulfate heptahydrate in of hot water is added a solution of 2-(2-carboxy-4-chloro-6-nitrophenoxy)acetic acid and aqueous concentrated ammonia solution in water under stirring. After stirring, to the reaction mixture is twice added aqueous concentrated ammonia solution. While the reaction mixture becomes exothermic, stirring is continued. The resultant mixture is filtered through a celite layer under reduced pressure and washed with hot water twice. The filtrate is cooled and made acid with concentrated hydrochloric acid. The precipitated crystals are washed with water and dried to give 6-chloro-3,4-dihydro-3-oxo-2H-1,4-benzoxazine-8- carboxylic acid.
A mixture of 6-chloro-3,4-dihydro-3-oxo-2H-1,4-benzoxazine-8-carboxylic acid, methanol and concentrated sulfuric acid is refluxed under heating with stirring, and then cooled. The precipitated crystals are collected by filtration, washed with methanol and dried to give methyl 6-chloro-3,4-dihydro-3-oxo- 2H-1,4-benzoxazine-8-carboxylate, melting point 239°-241°C.
To a solution of methyl 6-chloro-3,4-dihydro-3-oxo-2H-1,4-benzoxazine-8-carboxylate in dimethylformamide is added potassium t-butoxide and solution stirred at room temperature. To the resultant solution is added dropwise a solution of methyl iodide in dimethylformainide under stirring. After the reaction solution is stirred, water is added thereto. The insoluble substance is collected by filtration, washed with water and dried to give methyl 6-chloro- 3,4-dihydro-4-methyl-3-oxo-2H-1,4-benzoxazine-8-carboxylate. A mixture of methyl 6-chloro-3,4-dihydro-4-methyl-3-oxo-2H-1,4- benzoxazine-8-carboxylate, ethanol and 4% aqueous potassium hydroxide solution is refluxed with heating. The resultant solution is cooled and water is added thereto followed by filtration. The filtrate is made acid with concentrated hydrochloric acid. The precipitated crystals are collected by filtration, washed with water and dried, and then recrystallized from ethanol to give 6-chloro-3,4-dihydro-4-methyl-3-oxo-2H-1,4-benzoxazine-8-carboxylic acid, melting point 241°-243°C.
A solution of 6-chloro-3,4-dihydro-4-methyl-3-oxo-2H-1,4-benzoxazine-8- carboxylic acid in tetrahydrofuran and dimethylformamide is cooled to below 0°C and triethylamine is added under stirring thereto. Further, ethyl chlorocarbonate is added and the mixture is stirred at room temperature. To the resultant mixture is added 3-amino-8-azabicyclo[3.2.1]octane and the mixture stirred. After completion of the reaction, aqueous sodium hydrogen carbonate and ethyl acetate are added. The organic layer is separated, washed with water and dried over magnesium sulfate. The solvent is distilled off to give 6-chloro-3,4-dihydro-4-methyl-N-(8-azabicyclo[3.2.1]oct-3-yl)-3- oxo-2H-1,4-benzoxazine-8-carboxamide. In practice it is usually used as hydrochloride.

brand name

Serotone

Therapeutic Function

Antiemetic

Biological Activity

A selective and potent 5-HT 3 antagonist (K i = 2.9 nM).

storage

Desiccate at -20°C

Azasetron hydrochloride Preparation Products And Raw materials

Raw materials

Preparation Products

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Azasetron hydrochloride Suppliers

Hubei kangen Pharmaceutical Chemical Co., Ltd
Tel
15337215803 15337215803
Fax
027-89771658
Email
3357312443@qq.com
Country
China
ProdList
232
Advantage
56
Shanghai Yu Ben Biotechnology Co., Ltd.
Tel
15502154572
Fax
-
Email
yuben012@sina.com
Country
China
ProdList
508
Advantage
58
Cool Pharm, Ltd
Tel
021-60455363 18019463053
Fax
50966098
Email
sales@coolpharm.com
Country
China
ProdList
12346
Advantage
58
J & K SCIENTIFIC LTD.
Tel
010-82848833 400-666-7788
Fax
86-10-82849933
Email
jkinfo@jkchemical.com
Country
China
ProdList
96815
Advantage
76
3B Pharmachem (Wuhan) International Co.,Ltd.
Tel
821-50328103-801 18930552037
Fax
86-21-50328109
Email
3bsc@sina.com
Country
China
ProdList
15839
Advantage
69
Zhejiang Jianfeng Haizhou Pharmaceutical Co., Ltd.
Tel
+86 (576) 88221016
Fax
+86 (576) 88811295
Country
China
ProdList
44
Advantage
60
Adamas Reagent, Ltd.
Tel
400-6009262 16621234537
Fax
021-64823266
Email
chenyj@titansci.com
Country
China
ProdList
14103
Advantage
59
LGM Pharma
Tel
1-(800)-881-8210
Fax
615-250-9817
Email
inquiries@lgmpharma.com
Country
United States
ProdList
2123
Advantage
70
Shanghai Hanhong Scientific Co.,Ltd.
Tel
021-54306202 13764082696
Email
info@hanhongsci.com
Country
China
ProdList
42958
Advantage
64
Chemsky(shanghai)International Co.,Ltd.
Tel
021-50135380
Email
shchemsky@sina.com
Country
China
ProdList
32321
Advantage
50
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View Lastest Price from Azasetron hydrochloride manufacturers

WUHAN FORTUNA CHEMICAL CO., LTD
Product
Azasetron hydrochloride 123040-16-4
Price
US $0.00/Kg/Bag
Min. Order
1KG
Purity
98%min
Supply Ability
100kg
Release date
2021-11-03
Henan Bao Enluo International TradeCo.,LTD
Product
Azasetron hydrochloride 123040-16-4
Price
US $10.00/kg
Min. Order
1kg
Purity
99%
Supply Ability
1000tons
Release date
2023-07-21
Dideu Industries Group Limited
Product
Azasetron hydrochloride 123040-16-4
Price
US $1.10/g
Min. Order
1g
Purity
99.9%
Supply Ability
100 Tons min
Release date
2021-08-04

123040-16-4, Azasetron hydrochlorideRelated Search:


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