Identification
NamePimagedine
Accession NumberDB05383  (EXPT00459, DB02533)
TypeSmall Molecule
GroupsInvestigational
Description

Pimagedine has been developed by Synvista Therapeutics, Inc for the treatment of diabetic kidney disease. It is an advanced glycation end product inhibitor which manages diabetic nephropathy, either alone or in combination with other therapies. It is beneficial in treating patients with diabetic nephropathy.

Structure
Thumb
Synonyms
Aminoguanidine
Hydrazinecarboximidamide
External IDs Not Available
Product Ingredients
IngredientUNIICASInChI KeyDetails
Pimagedine hydrochlorideA2Z7G2RGAH 1937-19-5UBDZFAGVPPMTIT-UHFFFAOYSA-NDetails
Approved Prescription ProductsNot Available
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International BrandsNot Available
Brand mixturesNot Available
CategoriesNot Available
UNIISCQ4EZQ113
CAS number79-17-4
WeightAverage: 74.0851
Monoisotopic: 74.059246212
Chemical FormulaCH6N4
InChI KeyHAMNKKUPIHEESI-UHFFFAOYSA-N
InChI
InChI=1S/CH6N4/c2-1(3)5-4/h4H2,(H4,2,3,5)
IUPAC Name
1-aminoguanidine
SMILES
NNC(N)=N
Pharmacology
Indication

Investigated for use/treatment in diabetic kidney disease.

Structured Indications Not Available
PharmacodynamicsNot Available
Mechanism of action

Pimagedine reportedly inhibits the formation of glycosylated proteins (advanced glycosylation end-products) and has other actions including inhibition of aldose reductase.

TargetKindPharmacological actionActionsOrganismUniProt ID
Nitric oxide synthase, inducibleProteinunknown
inhibitor
HumanP35228 details
Aldose reductaseProteinunknownNot AvailableHumanP15121 details
Metalloproteinase inhibitor 3ProteinunknownNot AvailableHumanP35625 details
Related Articles
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
MetabolismNot Available
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityNot Available
Affected organismsNot Available
PathwaysNot Available
Pharmacogenomic Effects/ADRs Not Available
Interactions
Drug Interactions Not Available
Food InteractionsNot Available
References
Synthesis ReferenceNot Available
General References
  1. Abdel-Rahman E, Bolton WK: Pimagedine: a novel therapy for diabetic nephropathy. Expert Opin Investig Drugs. 2002 Apr;11(4):565-74. [PubMed:11922864 ]
  2. Edelstein D, Brownlee M: Mechanistic studies of advanced glycosylation end product inhibition by aminoguanidine. Diabetes. 1992 Jan;41(1):26-9. [PubMed:1727735 ]
External Links
ATC CodesNot Available
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSNot Available
Clinical Trials
Clinical Trials
PhaseStatusPurposeConditionsCount
1CompletedPreventionEndotoxaemia1
1RecruitingBasic ScienceRetinopathy, Diabetic1
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
StateSolid
Experimental PropertiesNot Available
Predicted Properties
PropertyValueSource
Water Solubility8.36 mg/mLALOGPS
logP-1.8ALOGPS
logP-1.5ChemAxon
logS-0.95ALOGPS
pKa (Strongest Basic)12.01ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area87.92 Å2ChemAxon
Rotatable Bond Count0ChemAxon
Refractivity40.84 m3·mol-1ChemAxon
Polarizability6.88 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9153
Blood Brain Barrier+0.8347
Caco-2 permeable-0.5826
P-glycoprotein substrateNon-substrate0.7501
P-glycoprotein inhibitor INon-inhibitor0.9597
P-glycoprotein inhibitor IINon-inhibitor0.9903
Renal organic cation transporterNon-inhibitor0.8183
CYP450 2C9 substrateNon-substrate0.8968
CYP450 2D6 substrateNon-substrate0.8024
CYP450 3A4 substrateNon-substrate0.8143
CYP450 1A2 substrateNon-inhibitor0.9045
CYP450 2C9 inhibitorNon-inhibitor0.913
CYP450 2D6 inhibitorNon-inhibitor0.9231
CYP450 2C19 inhibitorNon-inhibitor0.944
CYP450 3A4 inhibitorNon-inhibitor0.9056
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9771
Ames testNon AMES toxic0.5884
CarcinogenicityCarcinogens 0.5
BiodegradationNot ready biodegradable0.9842
Rat acute toxicity2.5602 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9236
hERG inhibition (predictor II)Non-inhibitor0.9791
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Spectra
Mass Spec (NIST)Not Available
SpectraNot Available
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as guanidines. These are compounds containing a guanidine moiety, with the general structure (R1R2N)(R3R4N)C=N-R5.
KingdomOrganic compounds
Super ClassOrganic nitrogen compounds
ClassOrganonitrogen compounds
Sub ClassGuanidines
Direct ParentGuanidines
Alternative ParentsHydrazones / Organopnictogen compounds / Hydrocarbon derivatives
SubstituentsGuanidine / Hydrazone / Organopnictogen compound / Hydrocarbon derivative / Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptorsone-carbon compound, guanidines (CHEBI:40618 )

Targets

Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
inhibitor
General Function:
Tetrahydrobiopterin binding
Specific Function:
Produces nitric oxide (NO) which is a messenger molecule with diverse functions throughout the body. In macrophages, NO mediates tumoricidal and bactericidal actions. Also has nitrosylase activity and mediates cysteine S-nitrosylation of cytoplasmic target proteins such COX2. As component of the iNOS-S100A8/9 transnitrosylase complex involved in the selective inflammatory stimulus-dependent S-n...
Gene Name:
NOS2
Uniprot ID:
P35228
Molecular Weight:
131116.3 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
  3. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [PubMed:10592235 ]
  4. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
General Function:
Glyceraldehyde oxidoreductase activity
Specific Function:
Catalyzes the NADPH-dependent reduction of a wide variety of carbonyl-containing compounds to their corresponding alcohols with a broad range of catalytic efficiencies.
Gene Name:
AKR1B1
Uniprot ID:
P15121
Molecular Weight:
35853.125 Da
Kind
Protein
Organism
Human
Pharmacological action
unknown
General Function:
Protease binding
Specific Function:
Complexes with metalloproteinases (such as collagenases) and irreversibly inactivates them by binding to their catalytic zinc cofactor. May form part of a tissue-specific acute response to remodeling stimuli. Known to act on MMP-1, MMP-2, MMP-3, MMP-7, MMP-9, MMP-13, MMP-14 and MMP-15.
Gene Name:
TIMP3
Uniprot ID:
P35625
Molecular Weight:
24144.83 Da

Transporters

Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
inhibitor
General Function:
Quaternary ammonium group transmembrane transporter activity
Specific Function:
Mediates tubular uptake of organic compounds from circulation. Mediates the influx of agmatine, dopamine, noradrenaline (norepinephrine), serotonin, choline, famotidine, ranitidine, histamin, creatinine, amantadine, memantine, acriflavine, 4-[4-(dimethylamino)-styryl]-N-methylpyridinium ASP, amiloride, metformin, N-1-methylnicotinamide (NMN), tetraethylammonium (TEA), 1-methyl-4-phenylpyridiniu...
Gene Name:
SLC22A2
Uniprot ID:
O15244
Molecular Weight:
62579.99 Da
References
  1. Kimura N, Masuda S, Katsura T, Inui K: Transport of guanidine compounds by human organic cation transporters, hOCT1 and hOCT2. Biochem Pharmacol. 2009 Apr 15;77(8):1429-36. doi: 10.1016/j.bcp.2009.01.010. Epub 2009 Jan 29. [PubMed:19426682 ]
  2. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [PubMed:10592235 ]
Drug created on November 18, 2007 11:24 / Updated on June 21, 2017 17:27