Details
Stereochemistry | ACHIRAL |
Molecular Formula | CH6N4 |
Molecular Weight | 74.0851 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
NNC(N)=N
InChI
InChIKey=HAMNKKUPIHEESI-UHFFFAOYSA-N
InChI=1S/CH6N4/c2-1(3)5-4/h4H2,(H4,2,3,5)
Pimagedine is a nucleophilic hydrazine. It was shown to inhibit diamine oxidase (histaminase), which catalyzes the oxidative deamination of diamines histamine and putrescine. Pimagedine was also reported to inhibit nitric oxide synthase (NOS) based on its structural similarity to the NOS substrate L-arginine. Although pimagedine affects constitutive NOS (cNOS) isoform, it has been demonstrated to be a relatively selective inhibitor of the inducible NOS (iNOS) isoform. Pimagedine was shown to stabilize S-adenosylmethionine decarboxylase (SAMDC). Pimagedine (aminoguanidine HCl) has been shown to be an effective agent in reducing the severity of the structural and functional alterations associated with experimental diabetic nephropathy. But clinical trial of pimagedine to prevent progression of diabetic nephropathy was terminated early due to safety concerns and apparent lack of efficacy.
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
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Target ID: CHEMBL3464 Sources: https://www.ncbi.nlm.nih.gov/pubmed/7682510 |
5.4 µM [IC50] | ||
Target ID: CHEMBL3048 Sources: https://www.ncbi.nlm.nih.gov/pubmed/7682510 |
160.0 µM [IC50] | ||
Target ID: CHEMBL4648 Sources: https://www.ncbi.nlm.nih.gov/pubmed/2124566 |
PubMed
Title | Date | PubMed |
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Suppression of flavin-containing monooxygenase by overproduced nitric oxide in rat liver. | 1999 Sep |
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Glycation amplifies lipoprotein(a)-induced alterations in the generation of fibrinolytic regulators from human vascular endothelial cells. | 2000 Jun |
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Glycation cross-links inhibit matrix metalloproteinase-2 activation in vascular smooth muscle cells cultured on collagen lattice. | 2001 Apr |
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Comparison of cardiac and regional hemodynamic responses to N-methyl-L-arginine and aminoguanidine infusions in conscious pigs. | 2001 Apr |
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Carbon monoxide from heme catabolism protects against hepatobiliary dysfunction in endotoxin-treated rat liver. | 2001 Apr |
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Synthesis and biological activity of aminoguanidine and diaminoguanidine analogues of the antidiabetic/antiobesity agent 3-guanidinopropionic acid. | 2001 Apr 12 |
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Antioxidants, vitamin C and dithiothreitol, activate membrane-bound guanylate cyclase in PC12 cells. | 2001 Feb |
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Transport and metabolism of agmatine in rat hepatocyte cultures. | 2001 Feb |
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Mechanisms of circulatory and intestinal barrier dysfunction during whole body hyperthermia. | 2001 Feb |
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Renoprotective effects of a novel inhibitor of advanced glycation. | 2001 Jan |
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Differential roles of iNOS and nNOS at rostral ventrolateral medulla during experimental endotoxemia in the rat. | 2001 Jan |
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Expression of intercellular adhesion molecule-1 induced by high glucose concentrations in human aortic endothelial cells. | 2001 Jan 5 |
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Endotoxin-induced vascular hyporesponsiveness in rat aorta: in vitro effect of aminoguanidine. | 2001 Jul |
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Glyoxal and methylglyoxal trigger distinct signals for map family kinases and caspase activation in human endothelial cells. | 2001 Jul 1 |
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Protective role of nitric oxide in indomethacin-induced gastric ulceration by a mechanism independent of gastric acid secretion. | 2001 May |
Patents
Sample Use Guides
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/11922864
150 or 300 mg b.i.d.
Route of Administration:
Oral
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NCI_THESAURUS |
C29574
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100000081949
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CHEMBL225304
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201-183-1
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40618
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DTXSID5040964
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C84059
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DB05383
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SUB09835MIG
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7088
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1311670
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C004479
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m1708
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2146
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79-17-4
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SCQ4EZQ113
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PIMAGEDINE
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ACTIVE MOIETY
SALT/SOLVATE (PARENT)
SALT/SOLVATE (PARENT)
SALT/SOLVATE (PARENT)