Details
Stereochemistry | ACHIRAL |
Molecular Formula | C6H4N2O6 |
Molecular Weight | 200.1058 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
OC1=CC(=CC(=C1O)[N+]([O-])=O)[N+]([O-])=O
InChI
InChIKey=VDCDWNDTNSWDFJ-UHFFFAOYSA-N
InChI=1S/C6H4N2O6/c9-5-2-3(7(11)12)1-4(6(5)10)8(13)14/h1-2,9-10H
DescriptionSources: https://www.ncbi.nlm.nih.gov/pubmed/3181288
Sources: https://www.ncbi.nlm.nih.gov/pubmed/3181288
3,5-Dinitrocatechol (OR-486) is a selective inhibitor of catechol O-methyl transferase (COMT). COMT is an enzyme that plays a major role in catechol neurotransmitter deactivation. Inhibition of COMT can increase neurotransmitter levels, which provides a means of treatment for Parkinson's disease, schizophrenia, and depression.
CNS Activity
Sources: https://www.ncbi.nlm.nih.gov/pubmed/3181288
Curator's Comment: Known to be CNS penetrant in rat. Human data not available.
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: P21964 Gene ID: 1312.0 Gene Symbol: COMT Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/3181288 |
12.0 nM [IC50] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
PubMed
Title | Date | PubMed |
---|---|---|
Effects of tolcapone upon soluble and membrane-bound brain and liver catechol-O-methyltransferase. | 1999 Mar 6 |
|
Role of adenosine in drug-induced catatonia in mice. | 2002 Aug |
|
Characterization of catechol glucuronidation in rat liver. | 2002 Feb |
|
Quercetin metabolism in the lens: role in inhibition of hydrogen peroxide induced cataract. | 2002 Jul 1 |
|
Quercetin potentiates L-Dopa reversal of drug-induced catalepsy in rats: possible COMT/MAO inhibition. | 2003 Jun |
|
Molecular modeling and metabolic studies of the interaction of catechol-O-methyltransferase and a new nitrocatechol inhibitor. | 2003 Mar |
|
Catecholamines block the antimitogenic effect of estradiol on human coronary artery smooth muscle cells. | 2004 Aug |
|
Cytochromes 1A1/1B1- and catechol-O-methyltransferase-derived metabolites mediate estradiol-induced antimitogenesis in human cardiac fibroblast. | 2005 Jan |
|
Redox properties of novel antioxidant 5,8-Dihydroxycoumarin: implications for its prooxidant cytotoxicity. | 2005 Nov-Dec |
|
Quantitative structure-activity relationships in prooxidant cytotoxicity of polyphenols: role of potential of phenoxyl radical/phenol redox couple. | 2005 Sep 15 |
|
(-)-Epicatechin elevates nitric oxide in endothelial cells via inhibition of NADPH oxidase. | 2007 Aug 3 |
|
Crystal structures of human 108V and 108M catechol O-methyltransferase. | 2008 Jun 27 |
|
Inhibitors of catechol-O-methyltransferase sensitize mice to pain. | 2010 Dec |
Sample Use Guides
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/3181288
in rat: orally administered OR-486 (3,5-DINITROCATECHOL) were more effective in reducing the formation of 3-O-methyldopa from levodopa than was the levodopa-carbidopa treatment alone. These results indicate that OR-486 is effective and long-lasting inhibitors of COMT activity.
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/3181288
Two novel COMT inhibitors, OR-462 and OR-486 (3,5-DINITROCATECHOL), were highly effective (IC50 = 18 and 12 nM, respectively) and selective in inhibiting COMT activity in vitro. Tyrosine hydroxylase was not inhibited until micromolar concentrations of these compounds were used: the IC50 values for OR-462 and OR-486 were 10 and 14 microM, respectively.
Name | Type | Language | ||
---|---|---|---|---|
|
Systematic Name | English | ||
|
Systematic Name | English | ||
|
Code | English | ||
|
Systematic Name | English | ||
|
Common Name | English | ||
|
Systematic Name | English | ||
|
Systematic Name | English | ||
|
Code | English | ||
|
Systematic Name | English |
Code System | Code | Type | Description | ||
---|---|---|---|---|---|
|
DTXSID00227391
Created by
admin on Sat Dec 16 04:48:46 GMT 2023 , Edited by admin on Sat Dec 16 04:48:46 GMT 2023
|
PRIMARY | |||
|
VK0VA22GY2
Created by
admin on Sat Dec 16 04:48:46 GMT 2023 , Edited by admin on Sat Dec 16 04:48:46 GMT 2023
|
PRIMARY | |||
|
7659-29-2
Created by
admin on Sat Dec 16 04:48:46 GMT 2023 , Edited by admin on Sat Dec 16 04:48:46 GMT 2023
|
PRIMARY | |||
|
3870203
Created by
admin on Sat Dec 16 04:48:46 GMT 2023 , Edited by admin on Sat Dec 16 04:48:46 GMT 2023
|
PRIMARY | |||
|
DB02105
Created by
admin on Sat Dec 16 04:48:46 GMT 2023 , Edited by admin on Sat Dec 16 04:48:46 GMT 2023
|
PRIMARY |
SUBSTANCE RECORD