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

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
Structure of PIMAGEDINE

SMILES

NNC(N)=N

InChI

InChIKey=HAMNKKUPIHEESI-UHFFFAOYSA-N
InChI=1S/CH6N4/c2-1(3)5-4/h4H2,(H4,2,3,5)

HIDE SMILES / InChI
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
Suppression of flavin-containing monooxygenase by overproduced nitric oxide in rat liver.
1999 Sep
Glycation amplifies lipoprotein(a)-induced alterations in the generation of fibrinolytic regulators from human vascular endothelial cells.
2000 Jun
Glycation cross-links inhibit matrix metalloproteinase-2 activation in vascular smooth muscle cells cultured on collagen lattice.
2001 Apr
Comparison of cardiac and regional hemodynamic responses to N-methyl-L-arginine and aminoguanidine infusions in conscious pigs.
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
Antioxidants, vitamin C and dithiothreitol, activate membrane-bound guanylate cyclase in PC12 cells.
2001 Feb
Transport and metabolism of agmatine in rat hepatocyte cultures.
2001 Feb
Mechanisms of circulatory and intestinal barrier dysfunction during whole body hyperthermia.
2001 Feb
Renoprotective effects of a novel inhibitor of advanced glycation.
2001 Jan
Differential roles of iNOS and nNOS at rostral ventrolateral medulla during experimental endotoxemia in the rat.
2001 Jan
Expression of intercellular adhesion molecule-1 induced by high glucose concentrations in human aortic endothelial cells.
2001 Jan 5
Endotoxin-induced vascular hyporesponsiveness in rat aorta: in vitro effect of aminoguanidine.
2001 Jul
Glyoxal and methylglyoxal trigger distinct signals for map family kinases and caspase activation in human endothelial cells.
2001 Jul 1
Protective role of nitric oxide in indomethacin-induced gastric ulceration by a mechanism independent of gastric acid secretion.
2001 May
Patents

Patents

Sample Use Guides

150 or 300 mg b.i.d.
Route of Administration: Oral
Name Type Language
PIMAGEDINE
INN   MART.   WHO-DD  
INN  
Official Name English
pimagedine [INN]
Common Name English
AMINOGUANIDINE [MI]
Common Name English
PIMAGEDINE [MART.]
Common Name English
AMINOGUANIDINE
MI  
Systematic Name English
HYDRAZINECARBOXIMIDAMIDE
Systematic Name English
Pimagedine [WHO-DD]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C29574
Created by admin on Fri Dec 15 16:02:44 GMT 2023 , Edited by admin on Fri Dec 15 16:02:44 GMT 2023
Code System Code Type Description
SMS_ID
100000081949
Created by admin on Fri Dec 15 16:02:44 GMT 2023 , Edited by admin on Fri Dec 15 16:02:44 GMT 2023
PRIMARY
ChEMBL
CHEMBL225304
Created by admin on Fri Dec 15 16:02:44 GMT 2023 , Edited by admin on Fri Dec 15 16:02:44 GMT 2023
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ECHA (EC/EINECS)
201-183-1
Created by admin on Fri Dec 15 16:02:44 GMT 2023 , Edited by admin on Fri Dec 15 16:02:44 GMT 2023
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CHEBI
40618
Created by admin on Fri Dec 15 16:02:44 GMT 2023 , Edited by admin on Fri Dec 15 16:02:44 GMT 2023
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EPA CompTox
DTXSID5040964
Created by admin on Fri Dec 15 16:02:44 GMT 2023 , Edited by admin on Fri Dec 15 16:02:44 GMT 2023
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NCI_THESAURUS
C84059
Created by admin on Fri Dec 15 16:02:44 GMT 2023 , Edited by admin on Fri Dec 15 16:02:44 GMT 2023
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DRUG BANK
DB05383
Created by admin on Fri Dec 15 16:02:44 GMT 2023 , Edited by admin on Fri Dec 15 16:02:44 GMT 2023
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EVMPD
SUB09835MIG
Created by admin on Fri Dec 15 16:02:44 GMT 2023 , Edited by admin on Fri Dec 15 16:02:44 GMT 2023
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INN
7088
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RXCUI
1311670
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MESH
C004479
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MERCK INDEX
m1708
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PRIMARY Merck Index
PUBCHEM
2146
Created by admin on Fri Dec 15 16:02:44 GMT 2023 , Edited by admin on Fri Dec 15 16:02:44 GMT 2023
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CAS
79-17-4
Created by admin on Fri Dec 15 16:02:44 GMT 2023 , Edited by admin on Fri Dec 15 16:02:44 GMT 2023
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FDA UNII
SCQ4EZQ113
Created by admin on Fri Dec 15 16:02:44 GMT 2023 , Edited by admin on Fri Dec 15 16:02:44 GMT 2023
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WIKIPEDIA
PIMAGEDINE
Created by admin on Fri Dec 15 16:02:44 GMT 2023 , Edited by admin on Fri Dec 15 16:02:44 GMT 2023
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