Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | 2CH6N4.H2O.H2O4S |
| Molecular Weight | 264.264 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
O.NNC(N)=N.NNC(N)=N.OS(O)(=O)=O
InChI
InChIKey=QZGJQDYPEHOKPI-UHFFFAOYSA-N
InChI=1S/2CH6N4.H2O4S.H2O/c2*2-1(3)5-4;1-5(2,3)4;/h2*4H2,(H4,2,3,5);(H2,1,2,3,4);1H2
| 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 | H2O |
| Molecular Weight | 18.0153 |
| 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
PubMed
| Title | Date | PubMed |
|---|---|---|
| Involvement of nitric oxide on the peritoneal neutrophil influx induced by staphylococcal enterotoxin B in mouse. | 2001-09 |
|
| Inhibition of salivary secretion by lipopolysaccharide: possible role of prostaglandins. | 2001-08 |
|
| Histamine N-methyltransferase regulates histamine-induced phosphoinositide hydrolysis in guinea pig cerebellum. | 2001-07-27 |
|
| Glyoxal and methylglyoxal trigger distinct signals for map family kinases and caspase activation in human endothelial cells. | 2001-07-01 |
|
| Inducible nitric oxide synthase knockout mice exhibit resistance to the multiple organ failure induced by zymosan. | 2001-07 |
|
| 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. | 2001-07 |
|
| Advanced glycosylation end products stimulate collagen mRNA synthesis in mesangial cells mediated by protein kinase C and transforming growth factor-beta. | 2001-07 |
|
| Endotoxin-induced vascular hyporesponsiveness in rat aorta: in vitro effect of aminoguanidine. | 2001-07 |
|
| Nitric oxide-dependent apoptosis in ovarian carcinoma cell lines. | 2001-07 |
|
| Pharmacological inhibition of diabetic retinopathy: aminoguanidine and aspirin. | 2001-07 |
|
| Regulation of murine airway responsiveness by endothelial nitric oxide synthase. | 2001-07 |
|
| Involvement of nitric oxide in pollen-induced biphasic nasal blockage in sensitised guinea pigs. | 2001-06-29 |
|
| Neuroprotective effect of aminoguanidine on transient focal ischaemia in the rat brain. | 2001-06-29 |
|
| Combination of inflammatory cytokines increases nitrite and nitrate levels in the paraventricular nucleus of conscious rats. | 2001-06-29 |
|
| Minimal amidine structure for inhibition of nitric oxide biosynthesis. | 2001-06-15 |
|
| TNF-alpha controls intracellular mycobacterial growth by both inducible nitric oxide synthase-dependent and inducible nitric oxide synthase-independent pathways. | 2001-06-01 |
|
| Potentiation of 3-hydroxyglutarate neurotoxicity following induction of astrocytic iNOS in neonatal rat hippocampal cultures. | 2001-06 |
|
| Induction of nitric oxide production by bovine mammary epithelial cells and blood leukocytes. | 2001-06 |
|
| Differential cardiovascular responses to blockade of nNOS or iNOS in rostral ventrolateral medulla of the rat. | 2001-06 |
|
| ONO-1714, a new inducible nitric oxide synthase inhibitor, attenuates diaphragmatic dysfunction associated with cerulein-induced pancreatitis in rats. | 2001-06 |
|
| Amyloid beta-peptide induces nitric oxide production in rat hippocampus: association with cholinergic dysfunction and amelioration by inducible nitric oxide synthase inhibitors. | 2001-06 |
|
| Spontaneous and receptor-controlled soluble guanylyl cyclase activity in anterior pituitary cells. | 2001-06 |
|
| Temporal variation in endotoxin-induced vascular hyporeactivity in a rat mesenteric artery organ culture model. | 2001-06 |
|
| Glucose-modified proteins modulate essential functions and apoptosis of polymorphonuclear leukocytes. | 2001-06 |
|
| Advanced glycation: an important pathological event in diabetic and age related ocular disease. | 2001-06 |
|
| Erythrocyte deformability is a nitric oxide-mediated factor in decreased capillary density during sepsis. | 2001-06 |
|
| Potent and selective inhibition of the human Na+/H+ exchanger isoform NHE1 by a novel aminoguanidine derivative T-162559. | 2001-05-18 |
|
| Role of nitric oxide on the increased vascular permeability and neutrophil accumulation induced by staphylococcal enterotoxin B into the mouse paw. | 2001-05-15 |
|
| Crystallographic studies on endothelial nitric oxide synthase complexed with nitric oxide and mechanism-based inhibitors. | 2001-05-08 |
|
| The effect of advanced glycation end-products and aminoguanidine on TNFalpha production by rat peritoneal macrophages. | 2001-05-02 |
|
| Protective role of nitric oxide in indomethacin-induced gastric ulceration by a mechanism independent of gastric acid secretion. | 2001-05 |
|
| Mechanisms of diabetic vasculopathy: an overview. | 2001-05 |
|
| Peroxynitrite mediates cytokine-induced IL-8 gene expression and production by human leukocytes. | 2001-05 |
|
| Effect of aminoguanidine, a nitric oxide synthase inhibitor, on ocular infection with herpes simplex virus in Balb/c mice. | 2001-05 |
|
| Role of inducible nitric oxide synthase in the pulmonary vascular response to birth-related stimuli in the ovine fetus. | 2001-04-13 |
|
| Synthesis and biological activity of aminoguanidine and diaminoguanidine analogues of the antidiabetic/antiobesity agent 3-guanidinopropionic acid. | 2001-04-12 |
|
| Synthesis and biological activity of analogues of the antidiabetic/antiobesity agent 3-guanidinopropionic acid: discovery of a novel aminoguanidinoacetic acid antidiabetic agent. | 2001-04-12 |
|
| Two different NO-dependent mechanisms account for the low virulence of a non-mycelial morphological mutant of Candida albicans. | 2001-04 |
|
| Glycation cross-links inhibit matrix metalloproteinase-2 activation in vascular smooth muscle cells cultured on collagen lattice. | 2001-04 |
|
| Role of nitric oxide in the secondary expansion of a cortical brain lesion from cold injury. | 2001-04 |
|
| Ethanol effects on nitric oxide production in cerebral pial cultures. | 2001-04 |
|
| Aminoguanidinium(2+) aminoguanidinium(1+) hexachloroantimonate(III) at 295 and 92 K. | 2001-04 |
|
| Inducible nitric oxide synthase (iNOS) activity promotes ischaemic skin flap survival. | 2001-04 |
|
| Effects of aminoguanidine and desferrioxamine on some vascular and biochemical changes associated with streptozotocin-induced hyperglycaemia in rats. | 2001-03 |
|
| Isolation and characterization of glyoxal-arginine modifications. | 2001-03 |
|
| Nitric oxide is involved in the immunomodulating activities of acidic polysaccharide from Panax ginseng. | 2001-03 |
|
| Inhibitors of advanced glycation end product-associated protein cross-linking. | 2001-02-14 |
|
| Role of nitric oxide and renal nerves in the renal responses to acute volume expansion in anaesthetized rats. | 2001-01 |
|
| Effect of aminoguanidine and copper(II) ions on the formation of advanced glycosylation end products. In vitro study on human serum albumin. | 2001 |
|
| Delayed healing of gastric ulcers in adjuvant arthritis rats: role of acid secretion and basic fibroblast growth factor. | 2001 |
Patents
| Substance Class |
Chemical
Created
by
admin
on
Edited
Mon Mar 31 20:42:36 GMT 2025
by
admin
on
Mon Mar 31 20:42:36 GMT 2025
|
| Record UNII |
23IO5B0K8J
|
| Record Status |
Validated (UNII)
|
| Record Version |
|
-
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Preferred Name | English | ||
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Common Name | English |
| Code System | Code | Type | Description | ||
|---|---|---|---|---|---|
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5959-63-7
Created by
admin on Mon Mar 31 20:42:36 GMT 2025 , Edited by admin on Mon Mar 31 20:42:36 GMT 2025
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23IO5B0K8J
Created by
admin on Mon Mar 31 20:42:36 GMT 2025 , Edited by admin on Mon Mar 31 20:42:36 GMT 2025
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PRIMARY | |||
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90479166
Created by
admin on Mon Mar 31 20:42:36 GMT 2025 , Edited by admin on Mon Mar 31 20:42:36 GMT 2025
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| Related Record | Type | Details | ||
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PARENT -> SALT/SOLVATE |
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ANHYDROUS->SOLVATE |
| Related Record | Type | Details | ||
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ACTIVE MOIETY |