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Details

Stereochemistry ACHIRAL
Molecular Formula C19H17NO.C4H4O4
Molecular Weight 391.4165
Optical Activity UNSPECIFIED
Defined Stereocenters 0 / 0
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of OMIGAPIL MALEATE

SMILES

OC(=O)\C=C/C(O)=O.CN(CC#C)CC1=CC2=CC=CC=C2OC3=CC=CC=C13

InChI

InChIKey=SQAZQLMBEHYFJA-BTJKTKAUSA-N
InChI=1S/C19H17NO.C4H4O4/c1-3-12-20(2)14-16-13-15-8-4-6-10-18(15)21-19-11-7-5-9-17(16)19;5-3(6)1-2-4(7)8/h1,4-11,13H,12,14H2,2H3;1-2H,(H,5,6)(H,7,8)/b;2-1-

HIDE SMILES / InChI

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

Molecular Formula C19H17NO
Molecular Weight 275.3444
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description

Omigapil (CGP 3466 or TCH346) is a structurally related analog of R-(-)-deprenyl that exhibits virtually no monoamine oxidase type B inhibiting activity but is neuroprotective in the picomolar concentration range. It binds to glyceraldehyde-3-phosphate dehydrogenase (GAPDH) and at subnanomolar concentrations prevent the S-nitrosylation of GAPDH, inhibit GAPDH-Siah binding and prevent the nuclear translocation of GAPDH. Omigapil demonstrated promising potential in the treatment of Parkinson's disease and motoneuron disease in animal models, however, it did not show efficacy in clinical trials. Omigapil is in development for the treatment of congenital muscular dystrophy.

CNS Activity

Originator

Approval Year

PubMed

PubMed

TitleDatePubMed
CGP 3466B has no effect on disease course of (G93A) mSOD1 transgenic mice.
2004 Dec
Amyotrophic lateral sclerosis: a consensus viewpoint on designing and implementing a clinical trial.
2004 Jun
Clinical trials of neuroprotection for Parkinson's disease.
2004 Oct 12
Preclinical evidence for neuroprotection with monoamine oxidase-B inhibitors in Parkinson's disease.
2004 Oct 12
TCH346 as a neuroprotective drug in Parkinson's disease: a double-blind, randomised, controlled trial.
2006 Dec
The use of LC/MS, GC/MS, and LC/NMR hyphenated techniques to identify a drug degradation product in pharmaceutical development.
2006 Feb 24
High-resolution structure of human D-glyceraldehyde-3-phosphate dehydrogenase.
2006 Mar
Phase II/III randomized trial of TCH346 in patients with ALS.
2007 Aug 21
Post-translational protein modifications in type 1 diabetes: a role for the repair enzyme protein-L-isoaspartate (D-aspartate) O-methyltransferase?
2007 Mar
Targets for neuroprotection in Parkinson's disease.
2009 Jul
Patents

Patents

Sample Use Guides

In Vivo Use Guide
Phase II/III randomized trial of TCH346 in patients with ALS: Patients were randomly assigned in a double-blind fashion to receive either placebo or one of four doses of TCH346 (1.0, 2.5, 7.5, or 15 mg/day) administered orally once daily for at least 24 weeks.
Route of Administration: Oral
In Vitro Use Guide
1 nM omigapil (CGP 3466 protects) PAJU cells from toxicity mediated by GAPDH overexpression.
Substance Class Chemical
Created
by admin
on Mon Oct 21 20:45:37 UTC 2019
Edited
by admin
on Mon Oct 21 20:45:37 UTC 2019
Record UNII
3Q69BFZ4OP
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
OMIGAPIL MALEATE
Common Name English
CGP-3466B
Code English
TCH-346
Code English
DIBENZO(B,F)OXEPIN-10-YLMETHYL-METHYL-PROP-2-YNYL-AMINE MALEATE
Systematic Name English
N-(DIBENZ(B,F)OXEPIN-10-YLMETHYL)-N-METHYL-N-(2-PROPYNYL)AMINE MONOMALEIC ACID SALT
Common Name English
CGP 3466B
Common Name English
TCH346
Code English
Classification Tree Code System Code
EU-Orphan Drug EU/1/08/544
Created by admin on Mon Oct 21 20:45:37 UTC 2019 , Edited by admin on Mon Oct 21 20:45:37 UTC 2019
Code System Code Type Description
PUBCHEM
9821821
Created by admin on Mon Oct 21 20:45:37 UTC 2019 , Edited by admin on Mon Oct 21 20:45:37 UTC 2019
PRIMARY
CAS
200189-97-5
Created by admin on Mon Oct 21 20:45:37 UTC 2019 , Edited by admin on Mon Oct 21 20:45:37 UTC 2019
PRIMARY
Related Record Type Details
PARENT -> SALT/SOLVATE
PARENT -> SALT/SOLVATE
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ACTIVE MOIETY