Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C5H12N4O3 |
Molecular Weight | 176.1738 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 1 / 1 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
N[C@@H](CCNC(=N)NO)C(O)=O
InChI
InChIKey=KOBHCUDVWOTEKO-VKHMYHEASA-N
InChI=1S/C5H12N4O3/c6-3(4(10)11)1-2-8-5(7)9-12/h3,12H,1-2,6H2,(H,10,11)(H3,7,8,9)/t3-/m0/s1
N(ω)-hydroxy-nor-L-arginine (nor-NOHA), an arginase inhibitor, has therapeutic potential in the treatment of cardiovascular and obstructive airway diseases. Nor-NOHA is a reversible, competitive arginase inhibitor. The affinity of nor-NOHA for the to the arginase active site was found in the nanomolar range. Nor-NOHA has proven to be one of the strongest arginase inhibitors. Inhibition by nor-NOHA is ten times more potent on arginase II than on arginase I. The pharmacokinetics of nor-NOHA is characterized by high bioavailability, close to 100% after multiple dose and rapid elimination resulting in t1/2 of 15–30 min after intravenous and intraperitoneal administration to rats. Arginase inhibition with Nor-NOHA increased circulating arginine levels and decreased hepatic damage during liver I/R injury. Arginase blockade represents a potentially novel strategy to combat hepatic I/R injury associated with liver transplantation. Nor-NOHA is under investigation in clinical trial NCT02009527 (Arginase inhibition in ischemia-reperfusion injury).
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL3232699 Sources: https://pubs.acs.org/doi/abs/10.1021/ja970285o |
0.5 µM [Ki] |
PubMed
Title | Date | PubMed |
---|---|---|
Liver I/R injury is improved by the arginase inhibitor, N(omega)-hydroxy-nor-L-arginine (nor-NOHA). | 2007 Feb |
|
Effect of arginase inhibition on ischemia-reperfusion injury in patients with coronary artery disease with and without diabetes mellitus. | 2014 |
|
Intracellular sources of ornithine for polyamine synthesis in endothelial cells. | 2016 Oct |
|
Attenuated cutaneous microvascular function in healthy young African Americans: Role of intradermal l-arginine supplementation. | 2018 Jul |
Sample Use Guides
In Vivo Use Guide
Sources: https://clinicaltrials.gov/ct2/show/NCT02009527
Ischemia-reperfusion Injury: 0.1 mg/ min i.a. for 20 min
Route of Administration:
Intra-arterial
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/27180260
Nor-NOHA inhibited arginase with an IC50 value of 10 uM for intact endothelial cells (EC). Nor-NOHA (0.5 mM) alone inhibited arginase activity in EC by 98 %, increased total cellular concentrations of arginine by 14 %, and decreased total cellular concentrations of ornithine, putrescine and spermidine by 17, 65 and 74 %, respectively.
Name | Type | Language | ||
---|---|---|---|---|
|
Common Name | English | ||
|
Code | English | ||
|
Common Name | English | ||
|
Systematic Name | English | ||
|
Common Name | English | ||
|
Systematic Name | English | ||
|
Common Name | English |
Code System | Code | Type | Description | ||
---|---|---|---|---|---|
|
446124
Created by
admin on Sat Dec 16 10:19:25 GMT 2023 , Edited by admin on Sat Dec 16 10:19:25 GMT 2023
|
PRIMARY | |||
|
U0F1149OFR
Created by
admin on Sat Dec 16 10:19:25 GMT 2023 , Edited by admin on Sat Dec 16 10:19:25 GMT 2023
|
PRIMARY | |||
|
189302-40-7
Created by
admin on Sat Dec 16 10:19:25 GMT 2023 , Edited by admin on Sat Dec 16 10:19:25 GMT 2023
|
PRIMARY | |||
|
DB02381
Created by
admin on Sat Dec 16 10:19:25 GMT 2023 , Edited by admin on Sat Dec 16 10:19:25 GMT 2023
|
PRIMARY |
ACTIVE MOIETY