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
Pharmacological comparison of human homomeric 5-HT3A receptors versus heteromeric 5-HT3A/3B receptors.	2001 Aug	11489465
Changes in serotonin levels and 5-HT receptor activity in duodenum of streptozotocin-diabetic rats.	2001 Sep	11518692
[Comparative clinical studies for head and neck cancer in Japan].	2002 Sep	12355935
Pretreatment with serotonin 5-HT(3) receptor antagonists produces no observable blockade of long-term motor sensitization to cocaine in rats.	2003 Feb	12451437
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
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 serotonin-3 receptor antagonists on cytochrome P450 activities in human liver microsomes.	2006 Sep	16946512
[Clinical efficacy of Bannaitong Mdicinal Tea combined with azasetron in preventing and treating chemotherapy induced gastrointestinal reaction].	2007 Oct	17990468
Receptor occupancy theory-based analysis of interindividual differences in antiemetic effects of 5-HT3 receptor antagonists.	2009 Dec	19967488
Management of postoperative nausea and vomiting: focus on palonosetron.	2009 Feb	19436621
Spinal cord mechanisms mediating behavioral hyperalgesia induced by neurokinin-1 tachykinin receptor activation in the rostral ventromedial medulla.	2010 Dec 29	20888891

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 UTC 2023` Edited by `admin` on `Fri Dec 15 16:37:08 UTC 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