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Details

Stereochemistry RACEMIC
Molecular Formula C17H20ClN3O3.ClH
Molecular Weight 386.273
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of AZASETRON HYDROCHLORIDE

SMILES

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

InChI

InChIKey=DBMKBKPJYAHLQP-UHFFFAOYSA-N
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

HIDE SMILES / InChI
Molecular Formula ClH
Molecular Weight 36.461
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE
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
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

Unknown
139594
Targets

Targets

Primary TargetPharmacologyConditionPotency
Antagonist
2778
 9.27 null [pKi]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
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

PubMed

TitleDatePubMed
Pharmacological comparison of human homomeric 5-HT3A receptors versus heteromeric 5-HT3A/3B receptors.
2001 Aug
Changes in serotonin levels and 5-HT receptor activity in duodenum of streptozotocin-diabetic rats.
2001 Sep
Effects of ondansetron, granisetron, ramosetron, and azasetron on human neutrophil functions.
2002
Complex regional haemodynamic effects of anandamide in conscious rats.
2002 Apr
[Comparative clinical studies for head and neck cancer in Japan].
2002 Sep
Pretreatment with serotonin 5-HT(3) receptor antagonists produces no observable blockade of long-term motor sensitization to cocaine in rats.
2003 Feb
The 5-HT3 antagonist Y-25130 blocks cocaine-induced lowering of ICSS reward thresholds in the rat.
2003 Jan
Serotonin regulates rhythmic whisking.
2003 Jul 17
[Nausea and vomiting].
2003 Jun
Second-line chemotherapy with combined irinotecan and low-dose cisplatin for patients with metastatic gastric carcinoma resistant to 5-fluorouracil.
2003 May-Jun
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
Blockade of 5-HT(3) receptor with MDL7222 and Y25130 reduces hydrogen peroxide-induced neurotoxicity in cultured rat cortical cells.
2005 Dec 5
Membrane receptors involved in modulation of responses of spinal dorsal horn interneurons evoked by feline group II muscle afferents.
2005 Jan 19
5-Hydroxytryptamine modulates cytokine and chemokine production in LPS-primed human monocytes via stimulation of different 5-HTR subtypes.
2005 May
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
5-HT receptor subtypes involved in the anxiogenic-like action and associated Fos response of acute fluoxetine treatment in rats.
2006 Apr
[Comparison of ramosetron and azasetron for prevention of acute and delayed cisplatin-induced emesis in lung cancer patients].
2006 May
Effects of osemozotan, ritanserin and azasetron on cocaine-induced behavioral sensitization in mice.
2006 Sep
Effects of serotonin-3 receptor antagonists on cytochrome P450 activities in human liver microsomes.
2006 Sep
[Analysis of antiemetic effect of various dosage regimens of azasetron hydrochloride based on 5-HT3 receptor occupancy of serotonin].
2007 Feb
[Clinical efficacy of Bannaitong Mdicinal Tea combined with azasetron in preventing and treating chemotherapy induced gastrointestinal reaction].
2007 Oct
[Cost-effectiveness analysis of 5-HT3 receptor antagonist drugs in cancer chemotherapy].
2008 Apr
[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
Laxative effect of agarwood leaves and its mechanism.
2008 Feb
Neuropsychotoxicity of abused drugs: effects of serotonin receptor ligands on methamphetamine- and cocaine-induced behavioral sensitization in mice.
2008 Jan
Receptor occupancy theory-based analysis of interindividual differences in antiemetic effects of 5-HT3 receptor antagonists.
2009 Dec
Palonosetron for the prevention of chemotherapy-induced nausea and vomiting: approval and efficacy.
2009 Dec 10
Management of postoperative nausea and vomiting: focus on palonosetron.
2009 Feb
Activation of serotonin 3 receptors changes in vivo auditory responses in the mouse inferior colliculus.
2009 May
Clinical research of Olanzapine for prevention of chemotherapy-induced nausea and vomiting.
2009 Sep 23
Luminal Cholera Toxin Alters Motility in Isolated Guinea-Pig Jejunum via a Pathway Independent of 5-HT(3) Receptors.
2010
Simple determination of azasetron in rat plasma by column-switching high-performance liquid chromatography.
2010 Dec
Spinal cord mechanisms mediating behavioral hyperalgesia induced by neurokinin-1 tachykinin receptor activation in the rostral ventromedial medulla.
2010 Dec 29
Comparison of azasetron and ondansetron for preventing postoperative nausea and vomiting in patients undergoing gynecological laparoscopic surgery.
2010 Jan
Africa/Canada: BAT director on aid board spurs boycott.
2010 Jun
Study of 5HT3 and HT4 receptor expression in HT29 cell line and human colon adenocarcinoma tissues.
2010 Mar
Y25130 hydrochloride, a selective 5HT3 receptor antagonist has potent antimitogenic and apoptotic effect on HT29 colorectal cancer cell line.
2010 Mar
Patents

Patents

JP2006516977A
31
JPH0881374A
2

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
2BSS7XL60S
Record Status Validated (UNII)
Record Version
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Name Type Language
AZASETRON HYDROCHLORIDE
JAN   MART.   MI   WHO-DD  
Common Name English
AZASETRON HYDROCHLORIDE [JAN]
Common Name English
AZASETRON HCL
Common Name English
AZASETRON HYDROCHLORIDE [MART.]
Common Name English
Azasetron hydrochloride [WHO-DD]
Common Name English
AZASETRON HYDROCHLORIDE [MI]
Common Name English
ARAZASETRON HYDROCHLORIDE, (±)-
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C94726
Created by admin on Fri Dec 15 16:37:08 GMT 2023 , Edited by admin on Fri Dec 15 16:37:08 GMT 2023
Code System Code Type Description
CAS
123040-16-4
Created by admin on Fri Dec 15 16:37:08 GMT 2023 , Edited by admin on Fri Dec 15 16:37:08 GMT 2023
PRIMARY
SMS_ID
100000085347
Created by admin on Fri Dec 15 16:37:08 GMT 2023 , Edited by admin on Fri Dec 15 16:37:08 GMT 2023
PRIMARY
FDA UNII
2BSS7XL60S
Created by admin on Fri Dec 15 16:37:08 GMT 2023 , Edited by admin on Fri Dec 15 16:37:08 GMT 2023
PRIMARY
EPA CompTox
DTXSID00924358
Created by admin on Fri Dec 15 16:37:08 GMT 2023 , Edited by admin on Fri Dec 15 16:37:08 GMT 2023
PRIMARY
MERCK INDEX
m2163
Created by admin on Fri Dec 15 16:37:08 GMT 2023 , Edited by admin on Fri Dec 15 16:37:08 GMT 2023
PRIMARY Merck Index
NCI_THESAURUS
C77260
Created by admin on Fri Dec 15 16:37:08 GMT 2023 , Edited by admin on Fri Dec 15 16:37:08 GMT 2023
PRIMARY
EVMPD
SUB00639MIG
Created by admin on Fri Dec 15 16:37:08 GMT 2023 , Edited by admin on Fri Dec 15 16:37:08 GMT 2023
PRIMARY
CAS
141922-90-9
Created by admin on Fri Dec 15 16:37:08 GMT 2023 , Edited by admin on Fri Dec 15 16:37:08 GMT 2023
SUPERSEDED
PUBCHEM
115000
Created by admin on Fri Dec 15 16:37:08 GMT 2023 , Edited by admin on Fri Dec 15 16:37:08 GMT 2023
PRIMARY
ChEMBL
CHEMBL1598608
Created by admin on Fri Dec 15 16:37:08 GMT 2023 , Edited by admin on Fri Dec 15 16:37:08 GMT 2023
PRIMARY
Related Record Type Details
Structure of AZASETRON
PARENT -> SALT/SOLVATE
Related Record Type Details
Structure of AZASETRON
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