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Details

Stereochemistry ACHIRAL
Molecular Formula C28H40N4O5
Molecular Weight 512.641
Optical Activity UNSPECIFIED
Defined Stereocenters 2 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of UMESPIRONE

SMILES

CCCCN1C(=O)[C@H]2C(=O)N(CCCCN3CCN(CC3)C4=C(OC)C=CC=C4)C(=O)[C@@H](C1=O)C2(C)C

InChI

InChIKey=BXNRTMZZILHVNJ-ZRZAMGCNSA-N
InChI=1S/C28H40N4O5/c1-5-6-14-31-24(33)22-26(35)32(27(36)23(25(31)34)28(22,2)3)15-10-9-13-29-16-18-30(19-17-29)20-11-7-8-12-21(20)37-4/h7-8,11-12,22-23H,5-6,9-10,13-19H2,1-4H3/t22-,23+

HIDE SMILES / InChI

Molecular Formula C28H40N4O5
Molecular Weight 512.641
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 2 / 2
E/Z Centers 0
Optical Activity UNSPECIFIED

Umespirone [KC 9172, KC 7218] is a serotonin 1A receptor agonist that was undergoing phase I clinical trials with Solvay in the Netherlands as a potential treatment for anxiety and psychotic disorders. Umespirone prevented the behavioural consequences of withdrawal from diazepam. Umespirone also had an anxiolytic profile of action in the tests of rat social interaction and in the marmoset exposed to a human threat. Umespirone reduced the hyperactivity induced by the infusion of dopamine into the nucleus accumbens of rat. In radioligand binding assays umespirone demonstrated nanomolar affinity for the alpha 1-adrenoceptor and the 5-HT1A and dopamine D2 receptors.

Approval Year

PubMed

PubMed

TitleDatePubMed

Sample Use Guides

Healthy men: single doses of umespirone (20 mg and 80 mg)
Route of Administration: Oral
Substance Class Chemical
Created
by admin
on Fri Dec 15 15:48:37 UTC 2023
Edited
by admin
on Fri Dec 15 15:48:37 UTC 2023
Record UNII
FG0A3VRL5K
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
UMESPIRONE
INN  
INN  
Official Name English
3,7-DIAZABICYCLO(3.3.1)NONANE-2,4,6,8-TETRONE, 3-BUTYL-7-(4-(4-(2-METHOXYPHENYL)-1-PIPERAZINYL)BUTYL)-9,9-DIMETHYL-
Systematic Name English
N-BUTYL-N'-(4-(4-(O-METHOXYPHENYL)-1-PIPERAZINYL)BUTYL)-2,2-DIMETHYL-1,1,3,3-PROPANETETRACARBOXYLIC 1,3:1,3-DIIMIDE
Common Name English
umespirone [INN]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C29710
Created by admin on Fri Dec 15 15:48:37 UTC 2023 , Edited by admin on Fri Dec 15 15:48:37 UTC 2023
NCI_THESAURUS C28197
Created by admin on Fri Dec 15 15:48:37 UTC 2023 , Edited by admin on Fri Dec 15 15:48:37 UTC 2023
Code System Code Type Description
EPA CompTox
DTXSID30869480
Created by admin on Fri Dec 15 15:48:37 UTC 2023 , Edited by admin on Fri Dec 15 15:48:37 UTC 2023
PRIMARY
SMS_ID
100000076660
Created by admin on Fri Dec 15 15:48:37 UTC 2023 , Edited by admin on Fri Dec 15 15:48:37 UTC 2023
PRIMARY
FDA UNII
FG0A3VRL5K
Created by admin on Fri Dec 15 15:48:37 UTC 2023 , Edited by admin on Fri Dec 15 15:48:37 UTC 2023
PRIMARY
EVMPD
SUB11380MIG
Created by admin on Fri Dec 15 15:48:37 UTC 2023 , Edited by admin on Fri Dec 15 15:48:37 UTC 2023
PRIMARY
NCI_THESAURUS
C152798
Created by admin on Fri Dec 15 15:48:37 UTC 2023 , Edited by admin on Fri Dec 15 15:48:37 UTC 2023
PRIMARY
INN
6337
Created by admin on Fri Dec 15 15:48:37 UTC 2023 , Edited by admin on Fri Dec 15 15:48:37 UTC 2023
PRIMARY
ChEMBL
CHEMBL2107677
Created by admin on Fri Dec 15 15:48:37 UTC 2023 , Edited by admin on Fri Dec 15 15:48:37 UTC 2023
PRIMARY
MESH
C059363
Created by admin on Fri Dec 15 15:48:37 UTC 2023 , Edited by admin on Fri Dec 15 15:48:37 UTC 2023
PRIMARY
CAS
107736-98-1
Created by admin on Fri Dec 15 15:48:37 UTC 2023 , Edited by admin on Fri Dec 15 15:48:37 UTC 2023
PRIMARY
WIKIPEDIA
Umespirone
Created by admin on Fri Dec 15 15:48:37 UTC 2023 , Edited by admin on Fri Dec 15 15:48:37 UTC 2023
PRIMARY
PUBCHEM
70695676
Created by admin on Fri Dec 15 15:48:37 UTC 2023 , Edited by admin on Fri Dec 15 15:48:37 UTC 2023
PRIMARY
Related Record Type Details
ACTIVE MOIETY