U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

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
Structure of PIMAGEDINE HEMISULFATE

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)

HIDE SMILES / InChI

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

Targets

Primary TargetPharmacologyConditionPotency
5.4 µM [IC50]
160.0 µM [IC50]
PubMed

PubMed

TitleDatePubMed
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
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
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

Patents

Sample Use Guides

150 or 300 mg b.i.d.
Route of Administration: Oral
Substance Class Chemical
Created
by admin
on Fri Dec 15 15:16:11 GMT 2023
Edited
by admin
on Fri Dec 15 15:16:11 GMT 2023
Record UNII
R13YB310MU
Record Status Validated (UNII)
Record Version
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Name Type Language
PIMAGEDINE HEMISULFATE
Common Name English
AMINOGUANIDINE HEMISULFATE
Common Name English
NSC-7888
Code English
BIS(AMINOGUANIDINIUM) SULFATE
Systematic Name English
HYDRAZINECARBOXIMIDAMIDE, SULFATE (2:1)
Systematic Name English
Code System Code Type Description
NSC
7888
Created by admin on Fri Dec 15 15:16:11 GMT 2023 , Edited by admin on Fri Dec 15 15:16:11 GMT 2023
PRIMARY
CAS
996-19-0
Created by admin on Fri Dec 15 15:16:11 GMT 2023 , Edited by admin on Fri Dec 15 15:16:11 GMT 2023
PRIMARY
PUBCHEM
2734952
Created by admin on Fri Dec 15 15:16:11 GMT 2023 , Edited by admin on Fri Dec 15 15:16:11 GMT 2023
PRIMARY
EPA CompTox
DTXSID0046016
Created by admin on Fri Dec 15 15:16:11 GMT 2023 , Edited by admin on Fri Dec 15 15:16:11 GMT 2023
PRIMARY
ECHA (EC/EINECS)
213-628-7
Created by admin on Fri Dec 15 15:16:11 GMT 2023 , Edited by admin on Fri Dec 15 15:16:11 GMT 2023
PRIMARY
FDA UNII
R13YB310MU
Created by admin on Fri Dec 15 15:16:11 GMT 2023 , Edited by admin on Fri Dec 15 15:16:11 GMT 2023
PRIMARY
Related Record Type Details
PARENT -> SALT/SOLVATE
SOLVATE->ANHYDROUS