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=C1C=C(Cl)C=C2C(=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 antagonist. 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 2849		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 8583	Serotone Approved Use It is an effective agent in the management of nausea and vomiting induced by cancer chemotherapy including cisplatin.

C_max

Value	Dose	Co-administered	Analyte	Population
904.8 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/9212995/	10 mg single, rectal dose: 10 mg route of administration: Rectal experiment type: SINGLE co-administered:		AZASETRON plasma	Oryctolagus cuniculus population: HEALTHY age: ADULT sex: MALE food status: FASTED
420.4 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/9212995/	10 mg single, oral dose: 10 mg route of administration: Oral experiment type: SINGLE co-administered:		AZASETRON plasma	Oryctolagus cuniculus population: HEALTHY age: ADULT sex: MALE food status: FASTED

AUC

Value	Dose	Analyte	Population
1152.3 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/21204117/	4 mg/kg single, intravenous dose: 4 mg/kg route of administration: Intravenous experiment type: SINGLE co-administered:	AZASETRON plasma	Oryctolagus cuniculus population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
1084.7 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/9212995/	10 mg single, rectal dose: 10 mg route of administration: Rectal experiment type: SINGLE co-administered:	AZASETRON plasma	Oryctolagus cuniculus population: HEALTHY age: ADULT sex: MALE food status: FASTED
124.7 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/9212995/	10 mg single, oral dose: 10 mg route of administration: Oral experiment type: SINGLE co-administered:	AZASETRON plasma	Oryctolagus cuniculus population: HEALTHY age: ADULT sex: MALE food status: FASTED

T_1/2

Value	Dose	Co-administered	Analyte	Population
4.3 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/21204117/	4 mg/kg single, intravenous dose: 4 mg/kg route of administration: Intravenous experiment type: SINGLE co-administered:		AZASETRON plasma	Oryctolagus cuniculus population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN

Doses

Dose	Population	Adverse events
10 mg single, intravenous Studied dose Dose: 10 mg Route: intravenous Route: single Dose: 10 mg Sources: https://pubmed.ncbi.nlm.nih.gov/20046519/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/20046519/	Other AEs: Headache, Dizziness... Other AEs: Headache (8%) Dizziness (8%) Constipation (2%) Myalgia (4%) Sources: https://pubmed.ncbi.nlm.nih.gov/20046519/
10 mg single, intravenous Studied dose Dose: 10 mg Route: intravenous Route: single Dose: 10 mg Sources: https://pubmed.ncbi.nlm.nih.gov/19775450/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/19775450/	Sources: https://pubmed.ncbi.nlm.nih.gov/19775450/

AEs

AE	Significance	Dose	Population
Constipation	2%	10 mg single, intravenous Studied dose Dose: 10 mg Route: intravenous Route: single Dose: 10 mg Sources: https://pubmed.ncbi.nlm.nih.gov/20046519/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/20046519/
Myalgia	4%	10 mg single, intravenous Studied dose Dose: 10 mg Route: intravenous Route: single Dose: 10 mg Sources: https://pubmed.ncbi.nlm.nih.gov/20046519/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/20046519/
Dizziness	8%	10 mg single, intravenous Studied dose Dose: 10 mg Route: intravenous Route: single Dose: 10 mg Sources: https://pubmed.ncbi.nlm.nih.gov/20046519/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/20046519/
Headache	8%	10 mg single, intravenous Studied dose Dose: 10 mg Route: intravenous Route: single Dose: 10 mg Sources: https://pubmed.ncbi.nlm.nih.gov/20046519/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/20046519/

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
inhibitor 2252 inducer 1087	inhibitor 2438	inhibitor 2507

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP1A2 2153 CYP2E1 1060 CYP2C19 2057 CYP19A1 429 MATE1 415	P-gp 2052

Drug as perpetrator

Target	Modality	Activity
CYP19A1 430	inhibitor 4027 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/2264#section=Biological-Test-Results Page: 3.0	inconclusive [IC50 7.4978 uM]
CYP1A2 2333	inhibitor 4027 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwzMzU2IiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDE1OTg2MDgifX0=	no [IC50 >10 uM]
CYP2C19 2141	inhibitor 4027 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwzNjIyIiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDE1OTg2MDgifX0=	no [IC50 >10 uM]
CYP2C9 2497	inhibitor 4027 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwzMzk3IiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDE1OTg2MDgifX0=	no [IC50 >10 uM]
CYP2D6 2546	inhibitor 4027 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwyODkiLCJ1c2VfY3VzdG9tX3F1ZXJ5Ijp0cnVlLCJzZWFyY2hfdGVybSI6IiIsInRleHRfZmlsdGVyIjoiQ0hFTUJMMTU5ODYwOCJ9fQ==	no [IC50 >10 uM]
CYP2E1 1146	inhibitor 4027 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkw1MjgxIiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDE1OTg2MDgifX0=	no [IC50 >10 uM]
CYP3A4 2633	inhibitor 4027 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwzNDAiLCJ1c2VfY3VzdG9tX3F1ZXJ5Ijp0cnVlLCJzZWFyY2hfdGVybSI6IiIsInRleHRfZmlsdGVyIjoiQ0hFTUJMMTU5ODYwOCJ9fQ==	no [IC50 >10 uM]
CYP3A4 2633	inducer 1966 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/2264#section=Biological-Test-Results Page: 136.0	no
MATE1 416	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/27418674/	no

Drug as victim

Target	Modality	Activity	Metabolite	Clinical evidence
P-gp 2052	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/9336314/	yes [Km 15000 uM]

PubMed

Title	Date	PubMed
Spinal cord mechanisms mediating behavioral hyperalgesia induced by neurokinin-1 tachykinin receptor activation in the rostral ventromedial medulla.	2010-12-29	20888891
Simple determination of azasetron in rat plasma by column-switching high-performance liquid chromatography.	2010-12	20945413
Africa/Canada: BAT director on aid board spurs boycott.	2010-06	20501491
Study of 5HT3 and HT4 receptor expression in HT29 cell line and human colon adenocarcinoma tissues.	2010-03	20187666
Y25130 hydrochloride, a selective 5HT3 receptor antagonist has potent antimitogenic and apoptotic effect on HT29 colorectal cancer cell line.	2010-03	20010428
Comparison of azasetron and ondansetron for preventing postoperative nausea and vomiting in patients undergoing gynecological laparoscopic surgery.	2010-01	20046519
Luminal Cholera Toxin Alters Motility in Isolated Guinea-Pig Jejunum via a Pathway Independent of 5-HT(3) Receptors.	2010	21048896
Palonosetron for the prevention of chemotherapy-induced nausea and vomiting: approval and efficacy.	2009-12-10	21188135
Receptor occupancy theory-based analysis of interindividual differences in antiemetic effects of 5-HT3 receptor antagonists.	2009-12	19967488
Clinical research of Olanzapine for prevention of chemotherapy-induced nausea and vomiting.	2009-09-23	19775450
Activation of serotonin 3 receptors changes in vivo auditory responses in the mouse inferior colliculus.	2009-05	19236912
Management of postoperative nausea and vomiting: focus on palonosetron.	2009-02	19436621
[Cost-effectiveness analysis of 5-HT3 receptor antagonist drugs in cancer chemotherapy].	2008-04	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].	2008-04	18379183
Laxative effect of agarwood leaves and its mechanism.	2008-02	18256503
Neuropsychotoxicity of abused drugs: effects of serotonin receptor ligands on methamphetamine- and cocaine-induced behavioral sensitization in mice.	2008-01	18198473
[Clinical efficacy of Bannaitong Mdicinal Tea combined with azasetron in preventing and treating chemotherapy induced gastrointestinal reaction].	2007-10	17990468
[Analysis of antiemetic effect of various dosage regimens of azasetron hydrochloride based on 5-HT3 receptor occupancy of serotonin].	2007-02	17268155
Effects of osemozotan, ritanserin and azasetron on cocaine-induced behavioral sensitization in mice.	2006-09	16962650
Effects of serotonin-3 receptor antagonists on cytochrome P450 activities in human liver microsomes.	2006-09	16946512
[Comparison of ramosetron and azasetron for prevention of acute and delayed cisplatin-induced emesis in lung cancer patients].	2006-05	16685162
5-HT receptor subtypes involved in the anxiogenic-like action and associated Fos response of acute fluoxetine treatment in rats.	2006-04	16521035
Blockade of 5-HT(3) receptor with MDL7222 and Y25130 reduces hydrogen peroxide-induced neurotoxicity in cultured rat cortical cells.	2005-12-05	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.	2005-09-27	16150439
5-Hydroxytryptamine modulates cytokine and chemokine production in LPS-primed human monocytes via stimulation of different 5-HTR subtypes.	2005-05	15802305
Membrane receptors involved in modulation of responses of spinal dorsal horn interneurons evoked by feline group II muscle afferents.	2005-01-19	15659594
Phase II study of cisplatin, ifosfamide, and irinotecan with rhG-CSF support in patients with stage IIIb and IV non-small-cell lung cancer.	2003-09-15	12966417
Serotonin regulates rhythmic whisking.	2003-07-17	12873389
[Nausea and vomiting].	2003-06	12806942
Second-line chemotherapy with combined irinotecan and low-dose cisplatin for patients with metastatic gastric carcinoma resistant to 5-fluorouracil.	2003-04-10	12684644
Pretreatment with serotonin 5-HT(3) receptor antagonists produces no observable blockade of long-term motor sensitization to cocaine in rats.	2003-02	12451437
The 5-HT3 antagonist Y-25130 blocks cocaine-induced lowering of ICSS reward thresholds in the rat.	2003-01	12479948
[Comparative clinical studies for head and neck cancer in Japan].	2002-09	12355935
Complex regional haemodynamic effects of anandamide in conscious rats.	2002-04	11959791
Effects of ondansetron, granisetron, ramosetron, and azasetron on human neutrophil functions.	2002	11961382
Changes in serotonin levels and 5-HT receptor activity in duodenum of streptozotocin-diabetic rats.	2001-09	11518692
Pharmacological comparison of human homomeric 5-HT3A receptors versus heteromeric 5-HT3A/3B receptors.	2001-08	11489465

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 `Mon Mar 31 18:32:47 GMT 2025` Edited by `admin` on `Mon Mar 31 18:32:47 GMT 2025`
Record UNII	77HC7URR9Z
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

AZASETRON [MI]

Preferred Name

English

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

ARAZASETRON, (±)-

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C267