ITASETRON

Details

Stereochemistry	ACHIRAL
Molecular Formula	C16H20N4O2
Molecular Weight	300.3556
Optical Activity	UNSPECIFIED
Defined Stereocenters	3 / 3
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

[H][C@]12CC[C@]([H])(C[C@@H](C1)NC(=O)N3C(=O)NC4=CC=CC=C34)N2C

InChI

InChIKey=RWXRJSRJIITQAK-ZSBIGDGJSA-N

InChI=1S/C16H20N4O2/c1-19-11-6-7-12(19)9-10(8-11)17-15(21)20-14-5-3-2-4-13(14)18-16(20)22/h2-5,10-12H,6-9H2,1H3,(H,17,21)(H,18,22)/t10-,11+,12-

HIDE SMILES / InChI

Molecular Formula	C16H20N4O2
Molecular Weight	300.3556
Charge	0
Count

Stereochemistry	EPIMERIC
Additional Stereochemistry	No
Defined Stereocenters	2 / 3
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/10378635
Curator's Comment: description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/8891590

DAU 6215 (Itasetron) is a selective 5-hydroxytryptamine3 (5-HT3) antagonist, which was developed by Boehringer Ingelheim. And was investigated for treatment the nausea and vomiting induced by chemotherapy, it was confirmed that this drug possessed antiemetic properties. Also was discovered, that chronic treatment with itasetron significantly improved retention abilities of the aged rats in this memory test. However, development of itasetron was terminated.

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/1695682	Antagonist 2778		3.8 nM [Ki]

Conditions

Condition	Modality	Highest Phase	Product
Nausea 63 Sources: https://www.ncbi.nlm.nih.gov/pubmed/10378635	Secondary	Phase III 656	Unknown Approved Use Unknown
Vomiting 38 Sources: https://www.ncbi.nlm.nih.gov/pubmed/10378635	Secondary	Phase III 656	Unknown Approved Use Unknown
Age-related memory degeneration 3 Sources: https://www.ncbi.nlm.nih.gov/pubmed/8891590	Primary	Preclinical	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
DAU 6215, a novel 5-HT3-receptor antagonist, selectively antagonizes scopolamine-induced deficit in a passive-avoidance task, but not scopolamine-induced hypermotility in rats.	1993 Sep	7903377
Effect of DAU 6215, a novel 5-HT3 receptor antagonist, on scopolamine-induced amnesia in the rat in a spatial learning task.	1994 Jan	8115433

Patents

Sample Use Guides

In Vivo Use Guide

Nausea and vomiting: itasetron hydrochloride is effective in the dose range 35-280 microg/kg in preventing cisplatin-induced emesis.

Route of Administration: Intravenous

In Vitro Use Guide

DA 6215 (Itasetron ) has been synthesized and evaluated for 5-HT3 antagonistic activity in a radioligand binding assay. DA 6215 showed a Ki = 3.8 nM in the binding test

Substance Class	Chemical Created by `admin` on `Fri Dec 15 16:26:15 GMT 2023` Edited by `admin` on `Fri Dec 15 16:26:15 GMT 2023`
Record UNII	00S0D0OEKR
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

ITASETRON

Official Name

English

2-Oxo-N-1αH,5αH-tropan-3α-yl-1-benzimidazoline-1-carboxamide

Systematic Name

English

ITASETRON [USAN]

Common Name

English

1H-BENZIMIDAZOLE-1-CARBOXAMIDE, 2,3-DIHYDRO-N-(8-METHYL-8-AZABICYCLO(3.2.1)OCT-3-YL)-2-OXO, ENDO-

Systematic Name

English

DAU-6215CL

Code

English

ITASETRON [MI]

Common Name

English

DAU6215CL

Code

English

itasetron [INN]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C94726