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

N-1-azabicyclo[2.2.2]oct-3-yl-6-chloro-3,4-dihydro-4-methyl-3-oxo-2H-1,4-benzoxazine-8-carboxamide - Names and Identifiers

Name	Azasetron
Synonyms	Asasetron Nazasetron Azasetron Azasetron [superceded rn] 6-chloro-4-methyl-3-oxo-N-quinuclidin-4-yl-1,4-benzoxazine-8-carboxamide N-1-azabicyclo[2.2.2]oct-3-yl-6-chloro-3,4-dihydro-4-methyl-3-oxo-2H-1,4-benzoxazine-8-carboxamide 2H-1,4-Benzoxazine-8-carboxamide,N-1-azabicyclo[2.2.2]oct-3-yl-6-chloro-3,4-dihydro-4-methyl-3-oxo- N-(1-AZABICYCLO[2.2.2]OCT-3-YL)-6-CHLORO-4-METHYL-3-OXO 3,4-DIHYDRO-2H-1,4-BENZOXAZINE-8-CARBOXAMIDE (±)-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 2H-1,4-Benzoxazine-8-carboxamide, N-1-azabicyclo(2.2.2)oct-3-yl-6-chloro-3,4-dihydro-4-methyl-3-oxo-, monohydrochloride
CAS	123040-93-7 123040-95-9 123039-99-6
EINECS	1533716-785-6
InChI	InChI=1/C17H20ClN3O3/c1-20-13-9-11(18)8-12(15(13)24-10-14(20)22)16(23)19-17-2-5-21(6-3-17)7-4-17/h8-9H,2-7,10H2,1H3,(H,19,23)

N-1-azabicyclo[2.2.2]oct-3-yl-6-chloro-3,4-dihydro-4-methyl-3-oxo-2H-1,4-benzoxazine-8-carboxamide - Physico-chemical Properties

Molecular Formula	C17H21Cl2N3O3
Molar Mass	386.27294
Density	1.42g/cm³
Boling Point	550.4°C at 760 mmHg
Flash Point	286.6°C
Vapor Presure	3.68E-12mmHg at 25°C
Refractive Index	1.653
Use	Used as an antineoplastic agent

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

Open Data Verified Data

crystallization from an ethanolic solution of hydrogen chloride. Melting point 281 °c (decomposition). There is also crystallization from ethanol, melting point 305 ° C (decomposition).

Last Update：2024-01-02 23:10:35

N-1-azabicyclo[2.2.2]oct-3-yl-6-chloro-3,4-dihydro-4-methyl-3-oxo-2H-1,4-benzoxazine-8-carboxamide - Preparation Method

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methyl 5 monochloro-2-hydroxybenzoate was nitrated with nitric acid in sulfuric acid solution and then reduced to amine with iron powder and ammonium chloride in water. The resulting amine and Chloroacetyl Chloride are acylated and cyclized in a mixture of chloroform and water under the action of sodium bicarbonate, and the resulting compound is methylated with methyl iodide in the presence of dimethyl formamide and potassium carbonate, and then hydrolyzed to a carboxylic acid. Then, it is refluxed with thionyl chloride to form acyl chloride, and finally, it is condensed with 3-aminoquinine in chloroform containing N-methylmorpholine to obtain azasetron.

Last Update：2022-01-01 09:23:26

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

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It was jointly developed by Japan Yoshitomi Pharn Inc. and Japan Tobacco Co., Inc. and was first launched in Japan in 1994. For the 5 serotonin type 3 (5-HT3) receptor antagonist antiemetic drugs. It has potent and selective antagonism of the 5-HT3 receptor without dopamine receptor antagonism. It is suitable for the treatment of Nausea, Vomit and other gastrointestinal symptoms caused by anti-malignant tumor drugs.

Last Update：2022-01-01 09:23:27

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

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male rats, female rats intravenous injection LD50 (mg/kg):135, 132.

Last Update：2022-01-01 09:23:27

N-1-azabicyclo[2.2.2]oct-3-yl-6-chloro-3,4-dihydro-4-methyl-3-oxo-2H-1,4-benzoxazine-8-carboxamide - Reference Information

Use	use as antineoplastic agent

Last Update：2024-04-10 22:29:15

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

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

Azasetron

CAS: 123040-93-7;123040-95-9;123039-99-6

Molecular Formula: C17H21Cl2N3O3

N-1-azabicyclo[2.2.2]oct-3-yl-6-chloro-3,4-dihydro-4-methyl-3-oxo-2H-1,4-benzoxazine-8-carboxamide - Names and Identifiers

N-1-azabicyclo[2.2.2]oct-3-yl-6-chloro-3,4-dihydro-4-methyl-3-oxo-2H-1,4-benzoxazine-8-carboxamide - Physico-chemical Properties

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

Open Data Verified Data

N-1-azabicyclo[2.2.2]oct-3-yl-6-chloro-3,4-dihydro-4-methyl-3-oxo-2H-1,4-benzoxazine-8-carboxamide - Preparation Method

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

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

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N-1-azabicyclo[2.2.2]oct-3-yl-6-chloro-3,4-dihydro-4-methyl-3-oxo-2H-1,4-benzoxazine-8-carboxamide - Reference Information

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