EBALZOTAN

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C19H30N2O2
Molecular Weight	318.4537
Optical Activity	UNSPECIFIED
Defined Stereocenters	1 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CCCN(C(C)C)[C@H]1COC2=C(C1)C(=CC=C2)C(=O)NC(C)C

InChI

InChIKey=UEAKCKJAKUFIQP-OAHLLOKOSA-N

InChI=1S/C19H30N2O2/c1-6-10-21(14(4)5)15-11-17-16(19(22)20-13(2)3)8-7-9-18(17)23-12-15/h7-9,13-15H,6,10-12H2,1-5H3,(H,20,22)/t15-/m1/s1

HIDE SMILES / InChI

Molecular Formula	C19H30N2O2
Molecular Weight	318.4537
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	1 / 1
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/11714872 | https://adisinsight.springer.com/drugs/800006909 | https://www.ncbi.nlm.nih.gov/pubmed/12904815

Ebalzotan is a selective serotonin (5-HT1A) receptor agonist, was chosen by Astra in the early 1990s as a candidate drug for the treatment of depression and anxiety. It has a modest affinity for the 5-HT(7). In vivo, ebalzotan induced all the typical effects of a 5-HT(1A) receptor agonist in rats: it decreased 5-HT synthesis (5-HTP accumulation) and 5-HT turnover (measured as the ratio of 5-hydroxyindoleacetic acid/5-HT), increased corticosterone secretion, induced the 5-HT(1A) syndrome (flat body posture and forepaw treading), inhibited the cage-leaving response, and caused hypothermia. Ebalzotan had been in phase I clinical trial for the treatment of major depressive disorder. However, this study was discontinued.

Approval Year

PubMed

Title	Date	PubMed
The pharmacological profile of (R)-3,4-dihydro-N-isopropyl-3-(N-isopropyl-N-propylamino)-2H-1-benzopyran-5-carboxamide, a selective 5-hydroxytryptamine(1A) receptor agonist.	2001 Dec	11714872
Logistics of process R&D: transforming laboratory methods to manufacturing scale.	2003 Aug	12904815
Synthesis of robalzotan, ebalzotan, and rotigotine precursors via the stereoselective multienzymatic cascade reduction of α,β-unsaturated aldehydes.	2013 May 17	23611252

Substance Class	Chemical Created by `admin` on `Fri Dec 15 15:29:14 UTC 2023` Edited by `admin` on `Fri Dec 15 15:29:14 UTC 2023`
Record UNII	WV4B56N49H
Record Status	`Validated (UNII)`
Record Version

Download

Name

Type

Language

EBALZOTAN

Official Name

English

(R)-N-ISOPROPYL-3-(ISOPROPYLPROPYLAMINO)-5-CHROMANCARBOXAMIDE

Systematic Name

English

ebalzotan [INN]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C1509