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

Details

Stereochemistry ACHIRAL
Molecular Formula CH6N4.ClH
Molecular Weight 110.546
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of PIMAGEDINE HYDROCHLORIDE

SMILES

Cl.NNC(N)=N

InChI

InChIKey=UBDZFAGVPPMTIT-UHFFFAOYSA-N
InChI=1S/CH6N4.ClH/c2-1(3)5-4;/h4H2,(H4,2,3,5);1H

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 ClH
Molecular Weight 36.461
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
Glycation cross-links inhibit matrix metalloproteinase-2 activation in vascular smooth muscle cells cultured on collagen lattice.
2001 Apr
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
Inducible nitric oxide synthase (iNOS) activity promotes ischaemic skin flap survival.
2001 Apr
Comparison of cardiac and regional hemodynamic responses to N-methyl-L-arginine and aminoguanidine infusions in conscious pigs.
2001 Apr
N-Acetylaspartate, a marker of both cellular dysfunction and neuronal loss: its relevance to studies of acute brain injury.
2001 Apr
Carbon monoxide from heme catabolism protects against hepatobiliary dysfunction in endotoxin-treated rat liver.
2001 Apr
Synthesis and biological activity of aminoguanidine and diaminoguanidine analogues of the antidiabetic/antiobesity agent 3-guanidinopropionic acid.
2001 Apr 12
Synthesis and biological activity of analogues of the antidiabetic/antiobesity agent 3-guanidinopropionic acid: discovery of a novel aminoguanidinoacetic acid antidiabetic agent.
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
Antioxidants, vitamin C and dithiothreitol, activate membrane-bound guanylate cyclase in PC12 cells.
2001 Feb
Ramipril and aminoguanidine restore renal lysosomal processing in streptozotocin diabetic rats.
2001 Feb
Inhibitors of advanced glycation end product-associated protein cross-linking.
2001 Feb 14
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
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
Pharmacological inhibition of diabetic retinopathy: aminoguanidine and aspirin.
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
Induction of nitric oxide production by bovine mammary epithelial cells and blood leukocytes.
2001 Jun
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
Amyloid beta-peptide induces nitric oxide production in rat hippocampus: association with cholinergic dysfunction and amelioration by inducible nitric oxide synthase inhibitors.
2001 Jun
Spontaneous and receptor-controlled soluble guanylyl cyclase activity in anterior pituitary cells.
2001 Jun
Temporal variation in endotoxin-induced vascular hyporeactivity in a rat mesenteric artery organ culture model.
2001 Jun
Glucose-modified proteins modulate essential functions and apoptosis of polymorphonuclear leukocytes.
2001 Jun
Advanced glycation: an important pathological event in diabetic and age related ocular disease.
2001 Jun
Involvement of nitric oxide in pollen-induced biphasic nasal blockage in sensitised guinea pigs.
2001 Jun 29
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
Effect of LPS on the permeability of the blood-brain barrier to insulin.
2001 Mar 30
Synthesis of pyrrolo[2,1-f][1,2,4]triazine C-nucleosides. Isosteres of sangivamycin, tubercidin, and toyocamycin.
2001 Mar 9
The effect of advanced glycation end-products and aminoguanidine on TNFalpha production by rat peritoneal macrophages.
2001 Mar-Apr
Mechanisms of diabetic vasculopathy: an overview.
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
Potent and selective inhibition of the human Na+/H+ exchanger isoform NHE1 by a novel aminoguanidine derivative T-162559.
2001 May 18
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 15:12:35 GMT 2023
Edited
by admin
on Fri Dec 15 15:12:35 GMT 2023
Record UNII
A2Z7G2RGAH
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
PIMAGEDINE HYDROCHLORIDE
MART.   USAN   WHO-DD  
USAN  
Official Name English
Aminoguanidine monohydrochloride
Systematic Name English
NSC-760398
Code English
PIMAGEDINE HYDROCHLORIDE [MART.]
Common Name English
PIMAGEDINE HYDROCHLORIDE [USAN]
Common Name English
AMINOGUANIDINE HCL [INCI]
Common Name English
HYDRAZINECARBOXIMIDAMIDE, MONOHYDROCHLORIDE
Common Name English
PIMAGEDINE HCL
Common Name English
AMINOGUANIDINE HYDROCHLORIDE
MI  
Systematic Name English
Pimagedine hydrochloride [WHO-DD]
Common Name English
AMINOGUANIDINE HCL
INCI  
INCI  
Official Name English
GER-11
Code English
GUANIDINE, AMINO-, MONOHYDROCHLORIDE
Common Name English
HYDRAZINECARBOXIMIDAMIDE, HYDROCHLORIDE (1:1)
Systematic Name English
AMINOGUANIDINE HYDROCHLORIDE [MI]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C29574
Created by admin on Fri Dec 15 15:12:36 GMT 2023 , Edited by admin on Fri Dec 15 15:12:36 GMT 2023
Code System Code Type Description
EPA CompTox
DTXSID9044405
Created by admin on Fri Dec 15 15:12:36 GMT 2023 , Edited by admin on Fri Dec 15 15:12:36 GMT 2023
PRIMARY
RXCUI
1311669
Created by admin on Fri Dec 15 15:12:36 GMT 2023 , Edited by admin on Fri Dec 15 15:12:36 GMT 2023
PRIMARY RxNorm
DAILYMED
A2Z7G2RGAH
Created by admin on Fri Dec 15 15:12:36 GMT 2023 , Edited by admin on Fri Dec 15 15:12:36 GMT 2023
PRIMARY
NCI_THESAURUS
C76661
Created by admin on Fri Dec 15 15:12:36 GMT 2023 , Edited by admin on Fri Dec 15 15:12:36 GMT 2023
PRIMARY
NSC
760398
Created by admin on Fri Dec 15 15:12:36 GMT 2023 , Edited by admin on Fri Dec 15 15:12:36 GMT 2023
PRIMARY
ECHA (EC/EINECS)
217-707-7
Created by admin on Fri Dec 15 15:12:36 GMT 2023 , Edited by admin on Fri Dec 15 15:12:36 GMT 2023
PRIMARY
FDA UNII
A2Z7G2RGAH
Created by admin on Fri Dec 15 15:12:36 GMT 2023 , Edited by admin on Fri Dec 15 15:12:36 GMT 2023
PRIMARY
MESH
C004479
Created by admin on Fri Dec 15 15:12:36 GMT 2023 , Edited by admin on Fri Dec 15 15:12:36 GMT 2023
PRIMARY
PUBCHEM
2734687
Created by admin on Fri Dec 15 15:12:36 GMT 2023 , Edited by admin on Fri Dec 15 15:12:36 GMT 2023
PRIMARY PUBCHEM
USAN
EE-10
Created by admin on Fri Dec 15 15:12:36 GMT 2023 , Edited by admin on Fri Dec 15 15:12:36 GMT 2023
PRIMARY
ChEMBL
CHEMBL225304
Created by admin on Fri Dec 15 15:12:36 GMT 2023 , Edited by admin on Fri Dec 15 15:12:36 GMT 2023
PRIMARY
MERCK INDEX
m1708
Created by admin on Fri Dec 15 15:12:36 GMT 2023 , Edited by admin on Fri Dec 15 15:12:36 GMT 2023
PRIMARY Merck Index
CAS
1937-19-5
Created by admin on Fri Dec 15 15:12:36 GMT 2023 , Edited by admin on Fri Dec 15 15:12:36 GMT 2023
PRIMARY
DRUG BANK
DBSALT002490
Created by admin on Fri Dec 15 15:12:36 GMT 2023 , Edited by admin on Fri Dec 15 15:12:36 GMT 2023
PRIMARY
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ACTIVE MOIETY