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

• ChemBase ID: 73242
• Molecular Formular: C17H21Cl2N3O3
• Molecular Mass: 386.27294
• Monoisotopic Mass: 385.09599691
• SMILES: c1c(c2c(cc1Cl)N(C(=O)CO2)C)C(=O)NC1C2CCN(C1)CC2.Cl
• Canonical SMILES: Clc1cc2N(C)C(=O)COc2c(c1)C(=O)NC1CN2CCC1CC2.Cl
• InChI: 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
• InChIKey: DBMKBKPJYAHLQP-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 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
• IUPAC Traditional name: azasetron hydrochloride
• Synonyms: 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; Azasetron Hydrochloride; Y-25130; Azasetron HCl

Database IDs

• CAS Number: 123040-16-4; 123040-69-7
• PubChem SID: 162038162
• PubChem CID: 115000

CALCULATED PROPERTIES

• Acid pKa: 13.510593
• H Acceptors: 4
• H Donor: 1
• LogD (pH = 5.5): -1.5089439
• LogD (pH = 7.4): 0.19647564
• Log P: 0.67269003
• Molar Refractivity: 90.6912 cm^3
• Polarizability: 34.724697 Å^3
• Polar Surface Area: 61.88 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Water
• Apperance: White to Off-White Solid
• Melting Point: 290-296°C

Safety Information

• Storage Condition: -20°C; Hygroscopic, -20°C Freezer, Under inert atmosphere

Pharmacology Properties

• Target: 5-HT Receptor; Serotonin receptor

Product Information

• Salt Data: HCl

DETAILS

Selleck Chemicals - S2018

Research Area: Cancer
Biological Activity:
Y-25130 hydrochloride is a selective and potent 5-HT3 antagonist with a Ki of 2.9 nM. [1] Y-25130 hydrochloride is a hydrochloride salt form of Y-25130.Y-25130 prevents the emesis induced by the combined treatment of doxorubicin and cyclophosphamide in ferrets. The antiemetic effect of Y-25130 is more potent than that of metoclopramide, almost the same as that of granisetron and less potent than that of ondansetron. The antiemetic effect of Y-25130 on cisplatin-induced emesis in ferrets is very similar to that of ondansetron. In conclusion, Y-25130 is an orally active antiemetic compound against cisplatin and doxorubicin/cyclophosphamide- induced emeses. Addtionally, Y-25130 reveals low affinity for histamine H1 receptors with an IC50 of 4.4 μM. However, Y-25130 could not reveal any affinities for the other receptors (5-HT1A, 5-HT2, dopamine D1, dopamine D2, alpha 1-adrenoceptor, alpha 2-adrenoceptor, muscarine and benzodiazepine) even at a 10 μM concentration. In the isolated rabbit heart, Y-25130 antagonizes the indirect sympathomimetic responses to 5-HT (pA2 value = 10.06). [2]References on Y-25130 HCl[1] Jpn J Pharmacol., 1993, 63(3):377-83[2] Jpn J Pharmacol., 1992, 59(4):443-8

Toronto Research Chemicals - A802800

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

REFERENCES

• Sato N, et al. Jpn J Pharmacol. 1992; 59(4):443-8.
• Sato, N., et al.: Japan J. Pharmacol., 59, 443 (1992)
• Haga, K., et al.: Japan J. Pharmacol., 63, 377 (1993)