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

Canada 2 CHINA 134 Europe 1 Germany 2 India 4 Japan 1 South Korea 1 The Netherlands 1 United Kingdom 4 United States 30 Global 180

Hubei kangen Pharmaceutical Chemical Co., Ltd

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Cool Pharm, Ltd

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J & K SCIENTIFIC LTD.

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3B Pharmachem (Wuhan) International Co.,Ltd.

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Shanghai Hanhong Scientific Co.,Ltd.

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View Lastest Price from Azasetron hydrochloride manufacturers

Shaanxi Dideu Medichem Co. Ltd

Product: Azasetron hydrochloride 123040-16-4
Price: US $1.00-1.00/KG
Min. Order: 1g
Purity: 99%
Supply Ability: 50tons
Release date: 2020-05-06

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

123040-16-4, Azasetron hydrochlorideRelated Search:

Trimethyl-pyrazine METSULFURON METHYL Methyl salicylate Tribenuron methyl Methyl acetate Buflomedil hydrochloride Topotecan hydrochloride 1-AdaMantanethylaMine Thiophanate-methyl Tetramethylpyrazine Kresoxim-methyl Methyl AZASETRON HCL,Azasetron hydrochloride,Azasetron base,Azasetron hydrochloride Difluorochloromethane Tramadol hydrochloride Sibutramine hydrochloride Methyl bromide AZASETRON-D3, HYDROCHLORIDE

N-(1-Azabicyclo[2.2.2]octane-3-yl)-6-chloro-4-methyl-3-oxo-3,4-dihydro-2H-1,4-benzoxazine-8-carboxamide·hydrochloride

6-chloro-3-keto-4-methyl-N-quinuclidin-3-yl-1,4-benzoxazine-8-carboxamide hydrochloride

N-[(3S)-1-azoniabicyclo[2.2.2]octan-3-yl]-6-chloro-4-methyl-3-oxo-1,4-benzoxazine-8-carboxamide

N-{1-azabicyclo[2.2.2]octan-3-yl}-6-chloro-4-Methyl-3-oxo-3,4-dihydro-2H-1,4-benzoxazine-8-carboxaMide

Azastron hydrochloride injection

N-(1-Azabicyclo[2.2.2]oct-3-yl)-6-chloro-4-Methyl-3-oxo-3,4-dihydro-2H-1,4-benzoxazine-8-carboxaMide hydrochloride (1:1)

N-1-AZABICYCLO[2.2.2]-OCT-3-YL-6-CHLORO-3,4-DIHYDRO-4-METHYL-3-OXO-2H-1,4-BENZOXAZINE-8-CARBOXAMIDE, HYDROCHLORIDE

N-(1-AZABICYCLO[2.2.2]OCT-3-YL)-6-CHLORO-4-METHYL-3-OXO-3,4-DIHYDRO-2H-1,4-BENZOXAZINE-8-CARBOXAMIDE HCL

N-(1-AZABICYCLO[2.2.2]OCT-3-YL)-6-CHLORO-4-METHYL-3-OXO-3,4-DIHYDRO-2H-1,4-BENZOXAZINE-8-CARBOXAMIDE HYDROCHLORIDE

Y-25130 HYDROCHLORIDE

Y-25130

2h-1,4-benzoxazine-8-carboxamide,3,4-dihydro-n-1-azabicyclo(2.2.2)oct-3-yl-6-c

N-1-azabicyclo[2.2.2]oct-3-yl-6-chloro-3,4-dihydro-4-methyl-3-oxo-2H-1,4-benzoxazine-8-carboxamide, hydrochloride (1:1)

AZASETRON

AZASETRON HCL

N-(1-Azabicyclo[2,2,2]Oct-3-Yl)-6-Chloro-4-Methyl-3-Oxo-3,4-Dihydro-2h-1,4-Benzoxazine-8-Carboxamide HCl

Y-25130HCl

N-(1-Azabicyclo[2.2.2]oct-3-yl)-6-chloro-4-methyl-3-oxo-3,4-dihydro-2H-1,4-benzo

INTERMEDIATE OF AZASETRON HCL

Serotone

Azasetron hydrochloride

N-(1-Azabicyclo[2.2.2]octan-8-yl)-6-chloro-4-methyl-3-oxo-1,4-benzoxazine-8-carboxamide hydrochloride

Azasetron hydrochloride , CID 115000

PubChem CID 2264

Azasetron HCl (Y-25130)

N-{1-azabicyclo[2.2.2]octan-3-yl}-6-chloro-4-methyl-3-oxo-3,4-dihydro-2H-1,4-benzoxazine-8-carboxamide hydrochloride

6-Chloro-4-methyl-3-oxo-N-(quinuclidin-3-yl)-3,4-dihydro-2H-benzo[b][1,4]oxazine-8-carboxamide hydrochloride

123040-16-4

C17H21Cl2N3O3

Serotonin receptor

anti-emetic