Drug General Information
Drug ID
D0O3IT
Former ID
DCL000151
Drug Name
L-NMMA
Synonyms
Targinina; Targinine; Targininum; Tilarginina; Tilargininum; Acetic acid; Tilarginine Acetate; Tilarginine acetate [USAN]; ANO 1020; M 7033; M1365; L-Monomethylarginine; N-Monomethyl-L-arginine; NG-Methyl-L-arginine acetate salt; NG-Monomethyl-L-arginine acetate; NG-Monomethyl-L-arginine acetate salt; NG-monomethyl-L-argine; Ngamma-Monomethyl-L-arginine; Nomega-Me-L-Arg; Nomega-Methyl-L-arginine Acetate; Nomega-Methyl-L-arginine acetate salt; Nomega-Monomethyl-L-arginine Acetate; N(G)-Methyl-L-arginine acetate; N-omega-monomethyl-L-arginine; N5-(Methylamidino)-L-ornithine acetate salt; NG-Me-L-Arg, AcOH; NG-Monomethyl-L-arginine, Monoacetate Salt; L-Ornithine, N5-[imino(methylamino)methyl]-[CAS]; N(5)-(methylamidino)-L-ornithine; N(5)-(metilamidino)-L-ornitina; N(5)-[imino(methylamino)methyl]-L-ornithine; N5-(Imino(methylamino)methyl)-L-ornithine monoacetate; N5-(N-methylcarbamimidoyl)-L-ornithine; N(5)-(N-methylcarbamimidoyl)-L-ornithine; Acide (2S)-2-amino-5-(3-methylguanidino)pentanoique; L-Ornithine, N5-(imino(methylamino)methyl)-, monoacetate; N5-(n-methylcarbamimidoyl)-l-ornithineacetate(1:1); (2S)-2-amino-5-(N'-methylcarbamimidamido)pentanoic acid; (2S)-2-amino-5-[(N'-methylcarbamimidoyl)amino]pentanoic acid; (2S)-2-amino-5-{[imino(methylamino)methyl]amino}pentanoic acid; 546C88
Drug Type
Small molecular drug
Indication Angina pectoris [ICD9: 413; ICD10:I20] Discontinued in Phase 2 [545605]
Company
Cayman
Structure
Download
2D MOL

3D MOL

Formula
C7H16N4O2
Canonical SMILES
CN=C(N)NCCCC(C(=O)O)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
InChIKey
NTNWOCRCBQPEKQ-YFKPBYRVSA-N
CAS Number
CAS 64-19-7
PubChem Compound ID
PubChem Substance ID
ChEBI ID
ChEBI:28229
SuperDrug ATC ID
G01AD02; S02AA10
Target and Pathway
Target(s) Nitric-oxide synthase, endothelial Target Info Inhibitor [537513], [537560], [537561]
BioCyc Pathway Citrulline-nitric oxide cycle
KEGG Pathway Arginine and proline metabolism
Metabolic pathways
Calcium signaling pathway
cGMP-PKG signaling pathway
HIF-1 signaling pathway
Sphingolipid signaling pathway
PI3K-Akt signaling pathway
VEGF signaling pathway
Platelet activation
Estrogen signaling pathway
Oxytocin signaling pathway
NetPath Pathway Wnt Signaling Pathway
PANTHER Pathway Angiogenesis
Endothelin signaling pathway
Interleukin signaling pathway
PI3 kinase pathway
VEGF signaling pathway
Pathway Interaction Database Plasma membrane estrogen receptor signaling
Validated transcriptional targets of AP1 family members Fra1 and Fra2
Angiopoietin receptor Tie2-mediated signaling
Thromboxane A2 receptor signaling
SHP2 signaling
VEGFR1 specific signals
Signaling events mediated by VEGFR1 and VEGFR2
PAR1-mediated thrombin signaling events
Reactome ROS production in response to bacteria
Tetrahydrobiopterin (BH4) synthesis, recycling, salvage and regulation
eNOS activation
Nitric oxide stimulates guanylate cyclase
VEGFR2 mediated vascular permeability
WikiPathways ACE Inhibitor Pathway
EGF/EGFR Signaling Pathway
Myometrial Relaxation and Contraction Pathways
JAK/STAT
Corticotropin-releasing hormone
AGE/RAGE pathway
Endothelin Pathways
Leptin signaling pathway
Effects of Nitric Oxide
Metabolism of nitric oxide
Angiogenesis
References
Ref 545605Trusted, scientifically sound profiles of drug programs, clinical trials, safety reports, and company deals, written by scientists. Springer. 2015. Adis Insight (drug id 800003882)
Ref 537513Post-resuscitation NOS inhibition does not improve hemodynamic recovery of hypoxic newborn pigs. Intensive Care Med. 2009 Jun 24.
Ref 537560Gonadal hormones decrease temporomandibular joint kappa-mediated antinociception through a down-regulation in the expression of kappa opioid receptors in the trigeminal ganglia. Eur J Pharmacol. 2009Jun 28.
Ref 537561Gender is related to alterations of renal endothelial function in type 2 diabetes. Nephrol Dial Transplant. 2009 Jun 30.

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