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Details

Stereochemistry ABSOLUTE
Molecular Formula C7H16N4O2
Molecular Weight 188.2275
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of TILARGININE

SMILES

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

InChI

InChIKey=NTNWOCRCBQPEKQ-YFKPBYRVSA-N
InChI=1S/C7H16N4O2/c1-10-7(9)11-4-2-3-5(8)6(12)13/h5H,2-4,8H2,1H3,(H,12,13)(H3,9,10,11)/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
INN   MART.  
INN  
Official Name English
L-NMMA
Code English
OMEGA-N-METHYLARGININE
Common Name English
NG-METHYLARGININE
MI  
Common Name English
NG-METHYLARGININE [MI]
Common Name English
TARGININE
Common Name English
(2S)-2-AMINO-5-((METHYLCARBAMIMIDOYL)AMINO)PENTANOIC ACID
Systematic Name English
N-METHYLARGININE
Systematic Name English
TILARGININE [MART.]
Common Name English
L-ORNITHINE, N(SUP 5)-(IMINO(METHYLAMINO)METHYL)-
Common Name English
NG-MONOMETHYL-L-ARGININE
Common Name English
tilarginine [INN]
Common Name English
.OMEGA.-N-METHYLARGININE
Common Name English
OMEGA-N-METHYLATED ARGININE
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C29574
Created by admin on Fri Dec 15 15:31:12 GMT 2023 , Edited by admin on Fri Dec 15 15:31:12 GMT 2023
Code System Code Type Description
DRUG BANK
DB11815
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PRIMARY
SMS_ID
100000177267
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PRIMARY
ChEMBL
CHEMBL312870
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PRIMARY
ChEMBL
CHEMBL256147
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PRIMARY
CAS
17035-90-4
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EVMPD
SUB10833MIG
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NCI_THESAURUS
C1178
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EPA CompTox
DTXSID3040560
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INN
7672
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PUBCHEM
132862
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WIKIPEDIA
Methylarginine
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MERCK INDEX
m7366
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PRIMARY Merck Index
FDA UNII
27JT06E6GR
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PRIMARY
CHEBI
28229
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PRIMARY