AZASETRON

Details

Stereochemistry	RACEMIC
Molecular Formula	C17H20ClN3O3
Molecular Weight	349.812
Optical Activity	( + / - )
Defined Stereocenters	0 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

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

InChI

InChIKey=WUKZPHOXUVCQOR-UHFFFAOYSA-N

InChI=1S/C17H20ClN3O3/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)

HIDE SMILES / InChI

Molecular Formula	C17H20ClN3O3
Molecular Weight	349.812
Charge	0
Count

Stereochemistry	RACEMIC
Additional Stereochemistry	No
Defined Stereocenters	0 / 1
E/Z Centers	0
Optical Activity	( + / - )

Description
Sources: http://www.torii.co.jp/en/ir/releases/20090113.html
Curator's Comment: description was created based on several sources, including: http://adisinsight.springer.com/drugs/800000557 | https://www.ncbi.nlm.nih.gov/pubmed/20010428 | https://www.ncbi.nlm.nih.gov/pubmed/12451437

Azasetron is an antiemetic drug. It acts as serotonin 3 receptor antagonists. It is currently used to prevent nausea and vomiting caused by cancer chemotherapy (including cisplatin chemotherapy). Also it was demonstrated that azasetron has potent antimitogenic and apoptotic effect on cancer cell line. It was preclinically tested to treat cocaine abuse.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Serotonin 3 (5-HT3) receptor 59 Target ID: CHEMBL2094132 Sources: https://www.ncbi.nlm.nih.gov/pubmed/8678501	Antagonist 2778		9.27 null [pKi]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Chemotherapy induced nausea and vomiting 10 Sources: http://www.torii.co.jp/en/ir/releases/20090113.html	Secondary		Approved 8429	Serotone Approved Use It is an effective agent in the management of nausea and vomiting induced by cancer chemotherapy including cisplatin.

PubMed

Title	Date	PubMed
Changes in serotonin levels and 5-HT receptor activity in duodenum of streptozotocin-diabetic rats.	2001 Sep	11518692
Effects of ondansetron, granisetron, ramosetron, and azasetron on human neutrophil functions.	2002	11961382
[Nausea and vomiting].	2003 Jun	12806942
Phase II study of cisplatin, ifosfamide, and irinotecan with rhG-CSF support in patients with stage IIIb and IV non-small-cell lung cancer.	2003 Sep 15	12966417
Blockade of 5-HT(3) receptor with MDL7222 and Y25130 reduces hydrogen peroxide-induced neurotoxicity in cultured rat cortical cells.	2005 Dec 5	16112139
Blockade of 5-HT(3) receptor with MDL 72222 and Y 25130 reduces beta-amyloid protein (25--35)-induced neurotoxicity in cultured rat cortical neurons.	2005 Sep 27	16150439
5-HT receptor subtypes involved in the anxiogenic-like action and associated Fos response of acute fluoxetine treatment in rats.	2006 Apr	16521035
[Comparison of ramosetron and azasetron for prevention of acute and delayed cisplatin-induced emesis in lung cancer patients].	2006 May	16685162
Effects of osemozotan, ritanserin and azasetron on cocaine-induced behavioral sensitization in mice.	2006 Sep	16962650
Effects of serotonin-3 receptor antagonists on cytochrome P450 activities in human liver microsomes.	2006 Sep	16946512
[Analysis of antiemetic effect of various dosage regimens of azasetron hydrochloride based on 5-HT3 receptor occupancy of serotonin].	2007 Feb	17268155
[Clinical efficacy of Bannaitong Mdicinal Tea combined with azasetron in preventing and treating chemotherapy induced gastrointestinal reaction].	2007 Oct	17990468
[Cost-effectiveness analysis of 5-HT3 receptor antagonist drugs in cancer chemotherapy].	2008 Apr	18408430
[Clinical evaluation of antiemetic effects of 5-hydroxytryptamine receptor type 3 (5HT3 receptor) antagonists based on changes in eating condition in cancer patients receiving chemotherapy].	2008 Apr	18379183
Laxative effect of agarwood leaves and its mechanism.	2008 Feb	18256503
Neuropsychotoxicity of abused drugs: effects of serotonin receptor ligands on methamphetamine- and cocaine-induced behavioral sensitization in mice.	2008 Jan	18198473
Receptor occupancy theory-based analysis of interindividual differences in antiemetic effects of 5-HT3 receptor antagonists.	2009 Dec	19967488
Palonosetron for the prevention of chemotherapy-induced nausea and vomiting: approval and efficacy.	2009 Dec 10	21188135
Management of postoperative nausea and vomiting: focus on palonosetron.	2009 Feb	19436621
Activation of serotonin 3 receptors changes in vivo auditory responses in the mouse inferior colliculus.	2009 May	19236912
Clinical research of Olanzapine for prevention of chemotherapy-induced nausea and vomiting.	2009 Sep 23	19775450
Luminal Cholera Toxin Alters Motility in Isolated Guinea-Pig Jejunum via a Pathway Independent of 5-HT(3) Receptors.	2010	21048896
Simple determination of azasetron in rat plasma by column-switching high-performance liquid chromatography.	2010 Dec	20945413
Spinal cord mechanisms mediating behavioral hyperalgesia induced by neurokinin-1 tachykinin receptor activation in the rostral ventromedial medulla.	2010 Dec 29	20888891
Comparison of azasetron and ondansetron for preventing postoperative nausea and vomiting in patients undergoing gynecological laparoscopic surgery.	2010 Jan	20046519
Africa/Canada: BAT director on aid board spurs boycott.	2010 Jun	20501491
Study of 5HT3 and HT4 receptor expression in HT29 cell line and human colon adenocarcinoma tissues.	2010 Mar	20187666
Y25130 hydrochloride, a selective 5HT3 receptor antagonist has potent antimitogenic and apoptotic effect on HT29 colorectal cancer cell line.	2010 Mar	20010428

Patents

Sample Use Guides

In Vivo Use Guide

Intravenous: The recommended adult dosage is 10 mg, administered once daily. If the efficacy is not sufficient, the same dose may be additionally administered. The total daily dosage should not exceed 20 mg. Oral: The recommended adult dosage is 10 mg, administered once daily. The dose may be appropriately adjusted, according to patient age and symptoms. The total daily dosage should not exceed 15 mg.

Route of Administration: Other

In Vitro Use Guide

The effect of 5-HT3 receptor agonists and antagonists on the hypoxia/hypoglycemia (ischemia)-induced decrease in CA1 field potential elicited by stimulation of Schaffer collaterals was investigated using rat hippocampal slices. Treatment with the 5-HT3 receptor antagonist Y-25130 (0.1-100 uM) produced dose-dependent neuroprotection against the ischemia-induced decrease. However, in normal non-ischemic solution these treatments did not significantly change the CA1 field potential. The magnitude of protection in the Y-25130-treated group (EC50, 1.8 uM) was about 20 times greater than that in the ketanserin-treated group (EC50, 33 uM).

Substance Class	Chemical Created by `admin` on `Fri Dec 15 16:37:08 GMT 2023` Edited by `admin` on `Fri Dec 15 16:37:08 GMT 2023`
Record UNII	77HC7URR9Z
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

AZASETRON

Official Name

English

(±)-6-CHLORO-3,4-DIHYDRO-4-METHYL-3-OXO-N-3-QUINUCLIDINYL-2H-1,4-BENZOXAZINE-8-CARBOXAMIDE

Systematic Name

English

Azasetron [WHO-DD]

Common Name

English

azasetron [INN]

Common Name

English

AZASETRON [MI]

Common Name

English

ARAZASETRON, (±)-

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C267