U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ABSOLUTE
Molecular Formula C7H16N4O2.C6H8O7
Molecular Weight 380.3511
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of TILARGININE CITRATE

SMILES

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

InChI

InChIKey=YKWLPIRSUICUFT-JEDNCBNOSA-N
InChI=1S/C7H16N4O2.C6H8O7/c1-10-7(9)11-4-2-3-5(8)6(12)13;7-3(8)1-6(13,5(11)12)2-4(9)10/h5H,2-4,8H2,1H3,(H,12,13)(H3,9,10,11);13H,1-2H2,(H,7,8)(H,9,10)(H,11,12)/t5-;/m0./s1

HIDE SMILES / InChI

Molecular Formula C7H16N4O2
Molecular Weight 188.2275
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 1 / 1
E/Z Centers 0
Optical Activity UNSPECIFIED

Molecular Formula C6H8O7
Molecular Weight 192.1235
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

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
Substance Class Chemical
Created
by admin
on Sat Dec 16 10:38:30 GMT 2023
Edited
by admin
on Sat Dec 16 10:38:30 GMT 2023
Record UNII
O529X01226
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
TILARGININE CITRATE
Common Name English
L-ORNITHINE, N5-(IMINO(METHYLAMINO)METHYL)-, 2-HYDROXY-1,2,3-PROPANETRICARBOXYLATE (1:1)
Systematic Name English
L-NG-MONOMETHYL ARGININE CITRATE
Common Name English
Code System Code Type Description
PUBCHEM
54584654
Created by admin on Sat Dec 16 10:38:30 GMT 2023 , Edited by admin on Sat Dec 16 10:38:30 GMT 2023
PRIMARY
FDA UNII
O529X01226
Created by admin on Sat Dec 16 10:38:30 GMT 2023 , Edited by admin on Sat Dec 16 10:38:30 GMT 2023
PRIMARY
DRUG BANK
DBSALT002084
Created by admin on Sat Dec 16 10:38:30 GMT 2023 , Edited by admin on Sat Dec 16 10:38:30 GMT 2023
PRIMARY
CAS
209913-88-2
Created by admin on Sat Dec 16 10:38:30 GMT 2023 , Edited by admin on Sat Dec 16 10:38:30 GMT 2023
PRIMARY
Related Record Type Details
PARENT -> SALT/SOLVATE
Related Record Type Details
ACTIVE MOIETY