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Details

Stereochemistry ABSOLUTE
Molecular Formula C7H16N4O2.C2H4O2
Molecular Weight 248.2795
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of TILARGININE ACETATE

SMILES

CC(O)=O.CNC(=N)NCCC[C@H](N)C(O)=O

InChI

InChIKey=IKPNWIGTWUZCKM-JEDNCBNOSA-N
InChI=1S/C7H16N4O2.C2H4O2/c1-10-7(9)11-4-2-3-5(8)6(12)13;1-2(3)4/h5H,2-4,8H2,1H3,(H,12,13)(H3,9,10,11);1H3,(H,3,4)/t5-;/m0./s1

HIDE SMILES / InChI

Description
Curator's Comment: description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/12620067 | https://www.ncbi.nlm.nih.gov/pubmed/12182860 | https://clinicaltrials.gov/ct2/show/NCT00112281

Tilarginine is L-N-monomethyl arginine (L -NMMA), a non-selective inhibitor of nitric oxide synthase (NOS), which has been studied in the treatment of septic shock and cardiogenic shock complicating myocardial infarction. Despite strong evidence that excessive nitric oxide (NO) production plays a pivotal role in the pathogenesis of septic shock and may contribute to the pathogenesis of cardiogenic shock complicating myocardial infarction, outcome studies in these two disorders have proved disappointing. Tilarginine therapy was associated with an excess mortality, particularly at doses > 5 mg/(kg h), in septic shock, whereas the effects of a lower dose (1 mg/(kg h)) in cardiogenic shock complicating myocardial infarction were neutral. The excess mortality in patients with septic shock was almost certainly the result of unfavorable hemodynamic changes induced by Tilarginine (decreased cardiac output, increased pulmonary vascular resistance and reduced tissue oxygen delivery) whereas the lack of benefit in patients with cardiogenic shock complicating myocardial infarction may have been because the dose of Tilarginine was too low.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
90.0 nM [IC50]
1000.0 nM [IC50]
540.0 nM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Expert opinion on tilarginine in the treatment of shock.
2008 Oct
Patents

Sample Use Guides

Tilarginine was given as an intravenous infusion starting with a dose of 2.5 mg/(kg h), which could be subsequently increased in an incremental manner up to a maximum dose of 20 mg/(kg h).
Route of Administration: Intravenous
L-NMMA (Tilarginine) was assayed for ability to inhibit NO production in human colorectal adenocarcinoma (DLD-1) cells preincubated with a cytokine cocktail. Cells were grown to confluence in 12-well plates. Cytokines or other agents were added to fresh media (1 mL/well). At 18-24-h postinduction, culture supernatants were harvested and stored at -20 C for nitrite analysis. Nitrite was measured spectrophotometrically using the Griess reagent
Name Type Language
TILARGININE ACETATE
USAN  
USAN  
Official Name English
ANO-1020
Code English
L-NMMA ACETATE
Common Name English
TARGININE ACETATE
Common Name English
NG-MONOMETHYL-L-ARGININE ACETATE
MI  
Common Name English
TILARGININE ACETATE [USAN]
Common Name English
(2S)-2-Amino-5-[(methylcarbamimidoyl)amino]pentanoic acid monoacetate
Systematic Name English
NG-METHYLARGININE ACETATE [MI]
Common Name English
L-ORNITHINE, N(SUP 5)-(IMINO(METHYLAMINO)METHYL)-, MONOACETATE
Common Name English
NG-METHYLARGININE ACETATE
MI  
Common Name English
NG-METHYL-L-ARGININE ACETATE SALT
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C29574
Created by admin on Fri Dec 15 17:20:50 GMT 2023 , Edited by admin on Fri Dec 15 17:20:50 GMT 2023
FDA ORPHAN DRUG 198804
Created by admin on Fri Dec 15 17:20:50 GMT 2023 , Edited by admin on Fri Dec 15 17:20:50 GMT 2023
EU-Orphan Drug EU/3/05/330
Created by admin on Fri Dec 15 17:20:50 GMT 2023 , Edited by admin on Fri Dec 15 17:20:50 GMT 2023
Code System Code Type Description
NCI_THESAURUS
C90899
Created by admin on Fri Dec 15 17:20:50 GMT 2023 , Edited by admin on Fri Dec 15 17:20:50 GMT 2023
PRIMARY
ChEMBL
CHEMBL256147
Created by admin on Fri Dec 15 17:20:50 GMT 2023 , Edited by admin on Fri Dec 15 17:20:50 GMT 2023
PRIMARY
CAS
53308-83-1
Created by admin on Fri Dec 15 17:20:50 GMT 2023 , Edited by admin on Fri Dec 15 17:20:50 GMT 2023
PRIMARY
DRUG BANK
DBSALT002593
Created by admin on Fri Dec 15 17:20:50 GMT 2023 , Edited by admin on Fri Dec 15 17:20:50 GMT 2023
PRIMARY
PUBCHEM
135242
Created by admin on Fri Dec 15 17:20:50 GMT 2023 , Edited by admin on Fri Dec 15 17:20:50 GMT 2023
PRIMARY
FDA UNII
2FL3530AF2
Created by admin on Fri Dec 15 17:20:50 GMT 2023 , Edited by admin on Fri Dec 15 17:20:50 GMT 2023
PRIMARY
EPA CompTox
DTXSID7045780
Created by admin on Fri Dec 15 17:20:50 GMT 2023 , Edited by admin on Fri Dec 15 17:20:50 GMT 2023
PRIMARY
USAN
QQ-44
Created by admin on Fri Dec 15 17:20:50 GMT 2023 , Edited by admin on Fri Dec 15 17:20:50 GMT 2023
PRIMARY
MESH
C092506
Created by admin on Fri Dec 15 17:20:50 GMT 2023 , Edited by admin on Fri Dec 15 17:20:50 GMT 2023
PRIMARY
MERCK INDEX
m7366
Created by admin on Fri Dec 15 17:20:50 GMT 2023 , Edited by admin on Fri Dec 15 17:20:50 GMT 2023
PRIMARY Merck Index
SMS_ID
100000177288
Created by admin on Fri Dec 15 17:20:50 GMT 2023 , Edited by admin on Fri Dec 15 17:20:50 GMT 2023
PRIMARY