Details
Stereochemistry | ACHIRAL |
Molecular Formula | 2CH6N4.H2O4S |
Molecular Weight | 246.249 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
NNC(N)=N.NNC(N)=N.OS(O)(=O)=O
InChI
InChIKey=VKGQPUZNCZPZKI-UHFFFAOYSA-N
InChI=1S/2CH6N4.H2O4S/c2*2-1(3)5-4;1-5(2,3)4/h2*4H2,(H4,2,3,5);(H2,1,2,3,4)
Molecular Formula | CH6N4 |
Molecular Weight | 74.0851 |
Charge | 0 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
Molecular Formula | H2O4S |
Molecular Weight | 98.078 |
Charge | 0 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
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 |
---|---|---|---|
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 |
---|---|---|
Effect of aminoguanidine and copper(II) ions on the formation of advanced glycosylation end products. In vitro study on human serum albumin. | 2001 |
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Delayed healing of gastric ulcers in adjuvant arthritis rats: role of acid secretion and basic fibroblast growth factor. | 2001 |
|
Role of nitric oxide in the secondary expansion of a cortical brain lesion from cold injury. | 2001 Apr |
|
Ethanol effects on nitric oxide production in cerebral pial cultures. | 2001 Apr |
|
Aminoguanidinium(2+) aminoguanidinium(1+) hexachloroantimonate(III) at 295 and 92 K. | 2001 Apr |
|
Inducible nitric oxide synthase (iNOS) activity promotes ischaemic skin flap survival. | 2001 Apr |
|
Carbon monoxide from heme catabolism protects against hepatobiliary dysfunction in endotoxin-treated rat liver. | 2001 Apr |
|
The lung is the major site that produces nitric oxide to induce acute pulmonary oedema in endotoxin shock. | 2001 Apr |
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Down regulation of interleukin 1beta production in human osteoarthritic synovial tissue and cartilage cultures by aminoguanidine. | 2001 Apr |
|
Synthesis and biological activity of aminoguanidine and diaminoguanidine analogues of the antidiabetic/antiobesity agent 3-guanidinopropionic acid. | 2001 Apr 12 |
|
Role of inducible nitric oxide synthase in the pulmonary vascular response to birth-related stimuli in the ovine fetus. | 2001 Apr 13 |
|
Inhibition of salivary secretion by lipopolysaccharide: possible role of prostaglandins. | 2001 Aug |
|
Ramipril and aminoguanidine restore renal lysosomal processing in streptozotocin diabetic rats. | 2001 Feb |
|
Advanced glycation end-products: a review. | 2001 Feb |
|
Role of nitric oxide and renal nerves in the renal responses to acute volume expansion in anaesthetized rats. | 2001 Jan |
|
Amadori albumin and advanced glycation end-product formation in peritoneal dialysis using icodextrin. | 2001 Jan-Feb |
|
Differing effects of two nitric oxide synthase inhibitors on experimental colitis. | 2001 Jan-Feb |
|
Inducible nitric oxide synthase knockout mice exhibit resistance to the multiple organ failure induced by zymosan. | 2001 Jul |
|
Mechanisms of beta-cell death in response to double-stranded (ds) RNA and interferon-gamma: dsRNA-dependent protein kinase apoptosis and nitric oxide-dependent necrosis. | 2001 Jul |
|
Advanced glycosylation end products stimulate collagen mRNA synthesis in mesangial cells mediated by protein kinase C and transforming growth factor-beta. | 2001 Jul |
|
Endotoxin-induced vascular hyporesponsiveness in rat aorta: in vitro effect of aminoguanidine. | 2001 Jul |
|
Nitric oxide-dependent apoptosis in ovarian carcinoma cell lines. | 2001 Jul |
|
Regulation of murine airway responsiveness by endothelial nitric oxide synthase. | 2001 Jul |
|
Glyoxal and methylglyoxal trigger distinct signals for map family kinases and caspase activation in human endothelial cells. | 2001 Jul 1 |
|
Histamine N-methyltransferase regulates histamine-induced phosphoinositide hydrolysis in guinea pig cerebellum. | 2001 Jul 27 |
|
Differential cardiovascular responses to blockade of nNOS or iNOS in rostral ventrolateral medulla of the rat. | 2001 Jun |
|
ONO-1714, a new inducible nitric oxide synthase inhibitor, attenuates diaphragmatic dysfunction associated with cerulein-induced pancreatitis in rats. | 2001 Jun |
|
Temporal variation in endotoxin-induced vascular hyporeactivity in a rat mesenteric artery organ culture model. | 2001 Jun |
|
Advanced glycation: an important pathological event in diabetic and age related ocular disease. | 2001 Jun |
|
Erythrocyte deformability is a nitric oxide-mediated factor in decreased capillary density during sepsis. | 2001 Jun |
|
Minimal amidine structure for inhibition of nitric oxide biosynthesis. | 2001 Jun 15 |
|
Neuroprotective effect of aminoguanidine on transient focal ischaemia in the rat brain. | 2001 Jun 29 |
|
Combination of inflammatory cytokines increases nitrite and nitrate levels in the paraventricular nucleus of conscious rats. | 2001 Jun 29 |
|
Effects of aminoguanidine and desferrioxamine on some vascular and biochemical changes associated with streptozotocin-induced hyperglycaemia in rats. | 2001 Mar |
|
Isolation and characterization of glyoxal-arginine modifications. | 2001 Mar |
|
Nitric oxide is involved in the immunomodulating activities of acidic polysaccharide from Panax ginseng. | 2001 Mar |
|
Inhibition of nitric oxide synthesis by aminoguanidine increases intestinal damage in the acute phase of rat TNB-colitis. | 2001 Mar |
|
Protective effect of aminoguanidine upon capillary and submesothelial anionic sites. | 2001 Mar |
|
Mutagenesis of two acidic active site residues in human muscle creatine kinase: implications for the catalytic mechanism. | 2001 Mar 13 |
|
The timing of endothelin and nitric oxide inhibition affects survival in a mice model of septic shock. | 2001 Mar 2 |
|
Protective role of nitric oxide in indomethacin-induced gastric ulceration by a mechanism independent of gastric acid secretion. | 2001 May |
|
Mechanisms of diabetic vasculopathy: an overview. | 2001 May |
|
Peroxynitrite mediates cytokine-induced IL-8 gene expression and production by human leukocytes. | 2001 May |
|
Effect of aminoguanidine, a nitric oxide synthase inhibitor, on ocular infection with herpes simplex virus in Balb/c mice. | 2001 May |
|
COX-2-dependent delayed dilatation of cerebral arterioles in response to bradykinin. | 2001 May |
|
Alterations in spontaneous contractions in vitro after repeated inflammation of rat distal colon. | 2001 May |
|
Upregulation of iNOS by COX-2 in muscularis resident macrophage of rat intestine stimulated with LPS. | 2001 May |
|
Role of nitric oxide on the increased vascular permeability and neutrophil accumulation induced by staphylococcal enterotoxin B into the mouse paw. | 2001 May 15 |
|
Crystallographic studies on endothelial nitric oxide synthase complexed with nitric oxide and mechanism-based inhibitors. | 2001 May 8 |
|
Involvement of nitric oxide on the peritoneal neutrophil influx induced by staphylococcal enterotoxin B in mouse. | 2001 Sep |
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
Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Dec 15 15:16:11 GMT 2023
by
admin
on
Fri Dec 15 15:16:11 GMT 2023
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Record UNII |
R13YB310MU
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Record Status |
Validated (UNII)
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Record Version |
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996-19-0
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2734952
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DTXSID0046016
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213-628-7
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R13YB310MU
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Related Record | Type | Details | ||
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PARENT -> SALT/SOLVATE | |||
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SOLVATE->ANHYDROUS |