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Merck
CN

SML2491

Sigma-Aldrich

Azasetron hydrochloride

≥98% (HPLC)

Synonym(s):

6-Chloro-4-methyl-3-oxo-N-(quinuclidin-3-yl)-3,4-dihydro-2H-benzo[b][1,4]oxazine-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 hydrochloride, N-1-Azabicyclo[2.2.2]oct-3-yl-6-chloro-3,4-dihydro-4-methyl-3-oxo-2H-1,4-benzoxazine-8-carboxamide monohydrochloride, Y 25130, Y-25130, Y25130

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About This Item

Empirical Formula (Hill Notation):
C17H20ClN3O3 · HCl
CAS Number:
123040-16-4
Molecular Weight:
386.27
MDL number:
MFCD00209913
UNSPSC Code:
12352200
NACRES:
NA.54

Key Documents

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Assay

≥98% (HPLC)

form

powder

storage condition

desiccated

color

white to beige

solubility

H2O: 2 mg/mL, clear

storage temp.

2-8°C

SMILES string

CN1C(COC2=C(C=C(Cl)C=C12)C(NC3CN4CCC3CC4)=O)=O.Cl

InChI

1S/C17H20ClN3O3.ClH/c1-20-14-7-11(18)6-12(16(14)24-9-15(20)22)17(23)19-13-8-21-4-2-10(13)3-5-21;/h6-7,10,13H,2-5,8-9H2,1H3,(H,19,23);1H

InChI key

DBMKBKPJYAHLQP-UHFFFAOYSA-N

Biochem/physiol Actions

Azasetron (Y-25130) is an orally active, potent and selective 5-HT3 receptor antagonist (binding Ki = 0.33 nM against [3H]granisetron/rat small intestine, 2.9 nM against [3H]quipazine/rat cortex; little or no affinity toward H1,d5-HT1A/2, Dopamine D1/2, α1/α2 adrenoceptor, muscarinic receptors) with in vivo antiemetic efficacy (0.1-0.3 mg/kg i.v. & 0.1-1 mg/kg p.o.; dogs, ferrets). Y-25130 inhibits 5-HT-induced bradycardia in anesthetized rats (ED50 = 820 ng/kg i.v.), while concurrent intrahippocampal infusion (1.0 μg/side) prevents memory function impairment caused by muscarinic acetylcholine receptor antagonist scopolamine (3.2 μg/side), but not NMDA receptor antagonist CPP (32 ng/side).
Orally active, potent and selective 5-HT3 receptor antagonist with in vivo antiemetic efficacy.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
0000062025
0000062024
0000062025
0000055933

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A Ozaki et al.
Japanese journal of pharmacology, 80(1), 25-32 (1999-08-14)
5-Hydroxytryptamine3 (5-HT3)-receptor blocking activities of KB-R6933 (6-amino-5-chloro-1-isopropyl-2-(4-methyl-1-piperazinyl)-benzimidazole dimaleate) were assessed in vivo and in vitro. Intravenous administration of KB-R6933, granisetron, ondansetron and azasetron inhibited 5-HT-induced bradycardia (von Bezold-Jarisch reflex) in anesthetized rats, with ED50 values of 0.071, 0.71, 4.0 and
K Katayama et al.
Japanese journal of pharmacology, 73(4), 357-360 (1997-04-01)
The binding affinity of azasetron hydrochloride (azasetron) for the 5-hydroxytryptamine3 (5-HT3) receptor in a tissue preparation of rat small intestine was investigated by using [3H]granisetron as a radioligand. Scatchard analysis of specific [3H]granisetron binding revealed a single population of saturable
T Fukuda et al.
European journal of pharmacology, 196(3), 299-305 (1991-04-24)
Y-25130( (+/-)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) is a potent and selective 5-HT3 receptor antagonist free of dopamine receptor blocking activity. This compound was effective against emesis induced in animals by cytotoxic drugs or by total body X-radiation. When given prophylactically, the

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