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Y 25130

Y 25130 structure

CAS No:
123040-16-4
Formula:
C17H20ClN3O3.ClH
Chemical Name:
Y 25130
Synonyms:
2H-1,4-Benzoxazine-8-carboxamide,N-1-azabicyclo[2.2.2]oct-3-yl-6-chloro-3,4-dihydro-4-methyl-3-oxo-,hydrochloride (1:1);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;Y 25130;Azasetron hydrochloride;Serotone;(±)-6-Chloro-3,4-dihydro-4-methyl-3-oxo-N-(3-quinuclidinyl)-2H-1,4-benzoxazine-8-carboxamide hydrochloride;132004-84-3;141922-90-9
Categories:
Active Pharmaceutical Ingredients > Digestive System Drugs

Description

White to Off-White SolidNazasetron (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. 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.

Azasetron hydrochloride is a benzoxazine.

Y 25130 Basic Attributes

Molecular Weight：

386.27

Exact Mass：

385.096008

EC Number：

1308068-626-2

DSSTox ID：

DTXSID7045651

Characteristics

PSA：

61.9

Melting Point：

281 °C (decomp)

Flash Point：

291.2ºC

Storage Conditions：

Desiccate at -20°C

Toxicity：

LD50 in male, female rats (mg/kg): 135, 132 i.v. (Takagi)

Safety Information

wgk germany：

safety instructions：

S22-S24/25

Precautionary statement(s)：

P201, P202, P281, P308+P313, P405, P501

Hazard Statements：

H361

GHS Classification：

|Warning|H361 (100%): Suspected of damaging fertility or the unborn child [Warning Reproductive toxicity]|P201, P202, P281, P308+P313, P405, and P501|The GHS information provided by 1 company from 1 notification to the ECHA C&L Inventory.

Drug Information

MeSH：

Drugs that bind to but do not activate serotonin receptors, thereby blocking the actions of serotonin or SEROTONIN RECEPTOR AGONISTS. (See all compounds classified as Serotonin Antagonists.)|Drugs used to prevent NAUSEA or VOMITING. (See all compounds classified as Antiemetics.)

MeSH Entry Terms：

azasetron

Y 25130 Use and Manufacturing

Methods of Manufacturing

In a dry 250ml three-necked flask, 20.8g of azasetron and 150ml of absolute ethanol were added, and the mixture was heated to 55 ° C and stirred until completely dissolved. Concentrated hydrochloric acid pH adjusted to 2 ~ 3, 45 ° C reaction 2h, Cooled to room temperature for 2h, filtered, washed with cold ethanol, vacuum 105 ° C for 16h, 22.lg white powder, yield 96.3percent, 99.95percent purity [HPLC Figure 1, HPLC self-control method (18:82). The detection wavelength was set at 305 nm and the column temperature was set at 35 ° C. The mobile phase consisted of Luna5u C18 (2) 100A (250 mm X 4.6 mm X 5 μη) C; flow rate 1. Oml / min].3-aminoquinuclidine hydrochloride (12.0g, 0.06mol), sodium hydroxide (4.8g, 0.12mol) and water (100ml) in an ice-water bath and cooled to 2 stirred for 20min, added to the reaction solution obtained above in tetrahydrofuran stirred at room temperature 12h, the reaction completion was adjusted to 10percent hydrochloric acid pH 2 ~ 3, and concentrated under reduced pressure to remove tetrahydrofuran, ethyl acetate (30ml) and extracted 3 times, collecting the aqueous phase, the aqueous phase was adjusted to pH 8 with potassium carbonate 1-9, ethyl acetate (30ml) and extracted 3 times, the organic phases combined, dried, passed through gaseous hydrochloric acid, stirring the precipitated solid was suction filtered, the filter cake ethanol - water and recrystallized to give a white powdery solid 16.7g.(Yield 86.4percent)

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.

Computed Properties

Molecular Weight:386.3
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:4
Rotatable Bond Count:2
Exact Mass:385.0959969
Monoisotopic Mass:385.0959969
Topological Polar Surface Area:61.9
Heavy Atom Count:25
Complexity:523
Undefined Atom Stereocenter Count:1
Covalently-Bonded Unit Count:2
Compound Is Canonicalized:Yes