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Details

Stereochemistry ACHIRAL
Molecular Formula C16H20N4O2.ClH.H2O
Molecular Weight 354.832
Optical Activity UNSPECIFIED
Defined Stereocenters 3 / 3
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ITASETRON HYDROCHLORIDE MONOHYDRATE

SMILES

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

InChI

InChIKey=UZOZFPGVCIJZKM-NXNLNBCESA-N
InChI=1S/C16H20N4O2.ClH.H2O/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);1H;1H2/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

Molecular Formula H2O
Molecular Weight 18.0153
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

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

Description
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.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
3.8 nM [Ki]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Secondary
Unknown

Approved Use

Unknown
Secondary
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Effect of DAU 6215, a novel 5-HT3 receptor antagonist, on scopolamine-induced amnesia in the rat in a spatial learning task.
1994 Jan
Patents

Sample Use Guides

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 15:56:46 GMT 2023
Edited
by admin
on Fri Dec 15 15:56:46 GMT 2023
Record UNII
904R36XZAJ
Record Status Validated (UNII)
Record Version
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Name Type Language
ITASETRON HYDROCHLORIDE MONOHYDRATE
Common Name English
1H-BENZIMIDAZOLE-1-CARBOXAMIDE, 2,3-DIHYDRO-N-(8-METHYL-8-AZABICYCLO(3.2.1)OCT-3-YL)-2-OXO-, MONOHYDROCHLORIDE, MONOHYDRATE, ENDO-
Common Name English
ITASETRON HYDROCHLORIDE HYDRATE
JAN  
Common Name English
U-98079A
Code English
ITASETRON HYDROCHLORIDE HYDRATE [JAN]
Common Name English
Code System Code Type Description
EPA CompTox
DTXSID30160727
Created by admin on Fri Dec 15 15:56:46 GMT 2023 , Edited by admin on Fri Dec 15 15:56:46 GMT 2023
PRIMARY
FDA UNII
904R36XZAJ
Created by admin on Fri Dec 15 15:56:46 GMT 2023 , Edited by admin on Fri Dec 15 15:56:46 GMT 2023
PRIMARY
CAS
138602-61-6
Created by admin on Fri Dec 15 15:56:46 GMT 2023 , Edited by admin on Fri Dec 15 15:56:46 GMT 2023
PRIMARY
Related Record Type Details
ANHYDROUS->SOLVATE
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ACTIVE MOIETY