U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ABSOLUTE
Molecular Formula C14H20N2
Molecular Weight 216.322
Optical Activity UNSPECIFIED
Defined Stereocenters 2 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of CIPRALISANT

SMILES

CC(C)(C)CCC#C[C@@H]1C[C@H]1C2=CNC=N2

InChI

InChIKey=CVKJAXCQPFOAIN-VXGBXAGGSA-N
InChI=1S/C14H20N2/c1-14(2,3)7-5-4-6-11-8-12(11)13-9-15-10-16-13/h9-12H,5,7-8H2,1-3H3,(H,15,16)/t11-,12-/m1/s1

HIDE SMILES / InChI

Molecular Formula C14H20N2
Molecular Weight 216.322
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 2 / 2
E/Z Centers 0
Optical Activity UNSPECIFIED

Cipralisant (GT-2331) is an H3-receptor ligand developed by Gliatech in the late 1990s. The drug exhibits complex pharmacology: it behaves as an antagonist in a guinea pig jejunum contraction assay and mouse disogenia model, as a partial agonist in a rat brain synaptosome model, and as a full agonist at recombinant H3 receptors. In preclinical models, cipralisant enhanced wakefulness and improved learning in developmental rat models. In 2000 cipralisant was investigated in the clinical trials for the treatment of attention-deficit hyperactivity disorder, but due to the bankruptcy of Gliatech the development of the drug was discontinued.

Approval Year

PubMed

PubMed

TitleDatePubMed
Differential in vivo effects of H3 receptor ligands in a new mouse dipsogenia model.
2002 Jun
Characteristics of recombinantly expressed rat and human histamine H3 receptors.
2002 Oct 18
G protein-dependent pharmacology of histamine H3 receptor ligands: evidence for heterogeneous active state receptor conformations.
2005 Jul
Patents

Patents

Substance Class Chemical
Created
by admin
on Fri Dec 15 16:04:40 GMT 2023
Edited
by admin
on Fri Dec 15 16:04:40 GMT 2023
Record UNII
309713XSKW
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
CIPRALISANT
INN  
INN  
Official Name English
(-)-GT-2331
Code English
cipralisant [INN]
Common Name English
1H-IMIDAZOLE, 5-((1R,2R)-2-(5,5-DIMETHYL-1-HEXYN-1-YL)CYCLOPROPYL)-
Systematic Name English
GT-2331
Code English
CIPRALISANT, (-)-
Common Name English
5-((1R,2R)-2-(5,5-DIMETHYL-1-HEXYN-1-YL)CYCLOPROPYL)-1H-IMIDAZOLE
Systematic Name English
Classification Tree Code System Code
NCI_THESAURUS C1509
Created by admin on Fri Dec 15 16:04:40 GMT 2023 , Edited by admin on Fri Dec 15 16:04:40 GMT 2023
Code System Code Type Description
NCI_THESAURUS
C76618
Created by admin on Fri Dec 15 16:04:40 GMT 2023 , Edited by admin on Fri Dec 15 16:04:40 GMT 2023
PRIMARY
EPA CompTox
DTXSID501318142
Created by admin on Fri Dec 15 16:04:40 GMT 2023 , Edited by admin on Fri Dec 15 16:04:40 GMT 2023
PRIMARY
PUBCHEM
6450823
Created by admin on Fri Dec 15 16:04:40 GMT 2023 , Edited by admin on Fri Dec 15 16:04:40 GMT 2023
PRIMARY
ChEMBL
CHEMBL278462
Created by admin on Fri Dec 15 16:04:40 GMT 2023 , Edited by admin on Fri Dec 15 16:04:40 GMT 2023
PRIMARY
INN
8145
Created by admin on Fri Dec 15 16:04:40 GMT 2023 , Edited by admin on Fri Dec 15 16:04:40 GMT 2023
PRIMARY
WIKIPEDIA
CIPRALISANT
Created by admin on Fri Dec 15 16:04:40 GMT 2023 , Edited by admin on Fri Dec 15 16:04:40 GMT 2023
PRIMARY
SMS_ID
300000034124
Created by admin on Fri Dec 15 16:04:40 GMT 2023 , Edited by admin on Fri Dec 15 16:04:40 GMT 2023
PRIMARY
CAS
213027-19-1
Created by admin on Fri Dec 15 16:04:40 GMT 2023 , Edited by admin on Fri Dec 15 16:04:40 GMT 2023
PRIMARY
FDA UNII
309713XSKW
Created by admin on Fri Dec 15 16:04:40 GMT 2023 , Edited by admin on Fri Dec 15 16:04:40 GMT 2023
PRIMARY
Related Record Type Details
TARGET->LIGAND
SALT/SOLVATE -> PARENT
Related Record Type Details
ACTIVE MOIETY