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Details

Stereochemistry ABSOLUTE
Molecular Formula C14H20N2.C4H4O4
Molecular Weight 332.3942
Optical Activity UNSPECIFIED
Defined Stereocenters 2 / 2
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of CIPRALISANT MALEATE

SMILES

OC(=O)\C=C/C(O)=O.CC(C)(C)CCC#C[C@@H]1C[C@H]1C2=CNC=N2

InChI

InChIKey=QIQWRCNAPQJQLL-COALEZEGSA-N
InChI=1S/C14H20N2.C4H4O4/c1-14(2,3)7-5-4-6-11-8-12(11)13-9-15-10-16-13;5-3(6)1-2-4(7)8/h9-12H,5,7-8H2,1-3H3,(H,15,16);1-2H,(H,5,6)(H,7,8)/b;2-1-/t11-,12-;/m1./s1

HIDE SMILES / InChI

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

Molecular Formula C4H4O4
Molecular Weight 116.0722
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry
Defined Stereocenters 0 / 0
E/Z Centers 1
Optical Activity NONE

Description

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 Tue Oct 22 01:24:26 UTC 2019
Edited
by admin
on Tue Oct 22 01:24:26 UTC 2019
Record UNII
7ENI812SZS
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
CIPRALISANT MALEATE
USAN  
USAN  
Official Name English
PERCEPTIN
Brand Name English
GT-2331 MALEATE
Code English
4-((1R,2R)-2-(5,5-DIMETHYL-1-HEXYNYL)CYCLOPROPYL)IMIDAZOLE MALEATE (1:1)
Systematic Name English
1H-IMIDAZOLE, 4-((1R,2R)-2-(5,5-DIMETHYL-1-HEXYNYL)CYCLOPROPYL)-, (2Z)-2-BUTENEDIOATE (1:1)
Systematic Name English
CIPRALISANT MALEATE [USAN]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C1509
Created by admin on Tue Oct 22 01:24:26 UTC 2019 , Edited by admin on Tue Oct 22 01:24:26 UTC 2019
Code System Code Type Description
ChEMBL
CHEMBL278462
Created by admin on Tue Oct 22 01:24:26 UTC 2019 , Edited by admin on Tue Oct 22 01:24:26 UTC 2019
PRIMARY
CAS
223420-20-0
Created by admin on Tue Oct 22 01:24:26 UTC 2019 , Edited by admin on Tue Oct 22 01:24:26 UTC 2019
PRIMARY
PUBCHEM
6450822
Created by admin on Tue Oct 22 01:24:26 UTC 2019 , Edited by admin on Tue Oct 22 01:24:26 UTC 2019
PRIMARY
NCI_THESAURUS
C76885
Created by admin on Tue Oct 22 01:24:26 UTC 2019 , Edited by admin on Tue Oct 22 01:24:26 UTC 2019
PRIMARY
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PARENT -> SALT/SOLVATE
PARENT -> SALT/SOLVATE
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ACTIVE MOIETY