Identification
- Generic Name
- Pimagedine
- DrugBank Accession Number
- DB05383
- Background
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.
- Type
- Small Molecule
- Groups
- Investigational
- Structure
Structure for Pimagedine (DB05383)
- Weight
- Average: 74.0851
Monoisotopic: 74.059246212 - Chemical Formula
- CH6N4
- Synonyms
- Aminate base
- Aminoguanidine
- Guanyl hydrazine
- Hydrazinecarboximidamide
- Monoaminoguanidine
- Pimagedine
Pharmacology
- Indication
Investigated for use/treatment in diabetic kidney disease.
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Prevent Adverse Drug Events TodayTap into our Clinical API for life-saving information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events with our Clinical API- Pharmacodynamics
Not 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.
Target Actions Organism ANitric oxide synthase, inducible inhibitordownregulatorHumans UAldose reductase Not Available Humans UMetalloproteinase inhibitor 3 Not Available Humans AAmiloride-sensitive amine oxidase [copper-containing] inhibitorHumans - Absorption
Not Available
- Volume of distribution
Not Available
- Protein binding
Not Available
- Metabolism
- Not Available
- Route of elimination
Not Available
- Half-life
Not Available
- Clearance
Not Available
- Adverse Effects
Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.- Toxicity
Not Available
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">
- Not Available
Interactions
- Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Drug Interaction Integrate drug-drug
interactions in your softwareAmantadine The serum concentration of Amantadine can be increased when it is combined with Pimagedine. Choline The serum concentration of Choline can be increased when it is combined with Pimagedine. Choline salicylate The serum concentration of Choline salicylate can be increased when it is combined with Pimagedine. Cisplatin The serum concentration of Cisplatin can be increased when it is combined with Pimagedine. Clofarabine The serum concentration of Clofarabine can be increased when it is combined with Pimagedine. - Food Interactions
- Not Available
Products
Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.- Product Ingredients
Ingredient UNII CAS InChI Key Pimagedine hydrochloride A2Z7G2RGAH 1937-19-5 UBDZFAGVPPMTIT-UHFFFAOYSA-N
Categories
- Drug Categories
- Chemical TaxonomyProvided by Classyfire
- Description
- This 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.
- Kingdom
- Organic compounds
- Super Class
- Organic nitrogen compounds
- Class
- Organonitrogen compounds
- Sub Class
- Guanidines
- Direct Parent
- Guanidines
- Alternative Parents
- Hydrazones / Organopnictogen compounds / Hydrocarbon derivatives
- Substituents
- Aliphatic acyclic compound / Guanidine / Hydrazone / Hydrocarbon derivative / Organopnictogen compound
- Molecular Framework
- Aliphatic acyclic compounds
- External Descriptors
- one-carbon compound, guanidines (CHEBI:40618)
- Affected organisms
- Not Available
Chemical Identifiers
- UNII
- SCQ4EZQ113
- CAS number
- 79-17-4
- InChI Key
- HAMNKKUPIHEESI-UHFFFAOYSA-N
- InChI
- InChI=1S/CH6N4/c2-1(3)5-4/h4H2,(H4,2,3,5)
- IUPAC Name
- N-aminoguanidine
- SMILES
- NNC(N)=N
References
- General References
- External Links
- PubChem Compound
- 2146
- PubChem Substance
- 175426990
- ChemSpider
- 2061
- BindingDB
- 50207159
- 1311670
- ChEBI
- 40618
- ChEMBL
- CHEMBL225304
- ZINC
- ZINC000008034829
- PDBe Ligand
- AGU
- Wikipedia
- Pimagedine
- PDB Entries
- 2nos / 5neq / 5ny8
Clinical Trials
- Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
Phase Status Purpose Conditions Count 1 Completed Basic Science Diabetic Retinopathy (DR) 1 1 Completed Prevention Endotoxaemia 1 Not Available Completed Treatment Asthma 1 Not Available Completed Treatment Chronic Obstructive Pulmonary Disease (COPD) 1
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
- Not Available
- Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
- Not Available
- Predicted Properties
Property Value Source Water Solubility 8.36 mg/mL ALOGPS logP -1.8 ALOGPS logP -1.5 Chemaxon logS -0.95 ALOGPS pKa (Strongest Basic) 12.01 Chemaxon Physiological Charge 1 Chemaxon Hydrogen Acceptor Count 4 Chemaxon Hydrogen Donor Count 4 Chemaxon Polar Surface Area 87.92 Å2 Chemaxon Rotatable Bond Count 0 Chemaxon Refractivity 40.84 m3·mol-1 Chemaxon Polarizability 6.88 Å3 Chemaxon Number of Rings 0 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter No Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.9153 Blood Brain Barrier + 0.8347 Caco-2 permeable - 0.5826 P-glycoprotein substrate Non-substrate 0.7501 P-glycoprotein inhibitor I Non-inhibitor 0.9597 P-glycoprotein inhibitor II Non-inhibitor 0.9903 Renal organic cation transporter Non-inhibitor 0.8183 CYP450 2C9 substrate Non-substrate 0.8968 CYP450 2D6 substrate Non-substrate 0.8024 CYP450 3A4 substrate Non-substrate 0.8143 CYP450 1A2 substrate Non-inhibitor 0.9045 CYP450 2C9 inhibitor Non-inhibitor 0.913 CYP450 2D6 inhibitor Non-inhibitor 0.9231 CYP450 2C19 inhibitor Non-inhibitor 0.944 CYP450 3A4 inhibitor Non-inhibitor 0.9056 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.9771 Ames test Non AMES toxic 0.5884 Carcinogenicity Carcinogens 0.5 Biodegradation Not ready biodegradable 0.9842 Rat acute toxicity 2.5602 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9236 hERG inhibition (predictor II) Non-inhibitor 0.9791
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 116.16322 predictedDeepCCS 1.0 (2019) [M+H]+ 118.055145 predictedDeepCCS 1.0 (2019) [M+Na]+ 125.37755 predictedDeepCCS 1.0 (2019)
Targets
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- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- InhibitorDownregulator
- 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 ...
- Gene Name
- NOS2
- Uniprot ID
- P35228
- Uniprot Name
- Nitric oxide synthase, inducible
- Molecular Weight
- 131116.3 Da
References
- Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
- 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. [Article]
- 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. [Article]
- Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [Article]
- Valente E, Assis MC, Alvim IM, Pereira GM, Plotkowski MC: Pseudomonas aeruginosa induces apoptosis in human endothelial cells. Microb Pathog. 2000 Dec;29(6):345-56. doi: 10.1006/mpat.2000.0400. [Article]
- Tomita M, Maeda M, Maezawa H, Usami N, Kobayashi K: Bystander cell killing in normal human fibroblasts is induced by synchrotron X-ray microbeams. Radiat Res. 2010 Mar;173(3):380-5. doi: 10.1667/RR1995.1. [Article]
- Draisma A, Dorresteijn MJ, Bouw MP, van der Hoeven JG, Pickkers P: The role of cytokines and inducible nitric oxide synthase in endotoxemia-induced endothelial dysfunction. J Cardiovasc Pharmacol. 2010 Jun;55(6):595-600. doi: 10.1097/FJC.0b013e3181da774b. [Article]
- Tassiopoulos AK, Hakim TS, Finck CM, Pedoto A, Hodell MG, Landas SK, McGraw DJ: Neutrophil sequestration in the lung following acute aortic occlusion starts during ischaemia and can be attenuated by tumour necrosis factor and nitric oxide blockade. Eur J Vasc Endovasc Surg. 1998 Jul;16(1):36-42. doi: 10.1016/s1078-5884(98)80089-0. [Article]
- Eslami SM, Moradi MM, Ghasemi M, Dehpour AR: Anticonvulsive Effects of Licofelone on Status Epilepticus Induced by Lithium-pilocarpine in Wistar Rats: a Role for Inducible Nitric Oxide Synthase. J Epilepsy Res. 2016 Dec 31;6(2):51-58. doi: 10.14581/jer.16011. eCollection 2016 Dec. [Article]
- Zamboni DS, Rabinovitch M: Phagocytosis of apoptotic cells increases the susceptibility of macrophages to infection with Coxiella burnetii phase II through down-modulation of nitric oxide production. Infect Immun. 2004 Apr;72(4):2075-80. doi: 10.1128/IAI.72.4.2075-2080.2004. [Article]
- Vera Y, Erkkila K, Wang C, Nunez C, Kyttanen S, Lue Y, Dunkel L, Swerdloff RS, Sinha Hikim AP: Involvement of p38 mitogen-activated protein kinase and inducible nitric oxide synthase in apoptotic signaling of murine and human male germ cells after hormone deprivation. Mol Endocrinol. 2006 Jul;20(7):1597-609. doi: 10.1210/me.2005-0395. Epub 2006 Feb 9. [Article]
- Saarinen M, Ekman P, He Q, Ikeda M, Virtala M, Yu DTY, Arvilommi H, Granfors K: Elimination of Salmonella enterica serotype enteritidis in intestinal epithelial cells by mechanisms other than nitric oxide. J Med Microbiol. 2002 Jan;51(1):13-19. doi: 10.1099/0022-1317-51-1-13. [Article]
- Wang J, Kalhor A, Lu S, Crawford R, Ni JD, Xiao Y: iNOS expression and osteocyte apoptosis in idiopathic, non-traumatic osteonecrosis. Acta Orthop. 2015 Feb;86(1):134-41. doi: 10.3109/17453674.2014.960997. Epub 2014 Sep 5. [Article]
- Butterworth KT, McGarry CK, Trainor C, O'Sullivan JM, Hounsell AR, Prise KM: Out-of-field cell survival following exposure to intensity-modulated radiation fields. Int J Radiat Oncol Biol Phys. 2011 Apr 1;79(5):1516-22. doi: 10.1016/j.ijrobp.2010.11.034. Epub 2011 Jan 27. [Article]
- Farhad AR, Razavi F, Razavi SM, Saatchi M, Manshaei M: Histological assessment of the local effect of different concentrations of aminoguanidine hydrochloride on bone healing in rats. Dent Res J (Isfahan). 2021 Aug 18;18:63. eCollection 2021. [Article]
- Scalise ML, Amaral MM, Reppetti J, Damiano AE, Ibarra C, Sacerdoti F: Cytotoxic effects of Shiga toxin-2 on human extravillous trophoblast cell lines. Reproduction. 2019 Mar;157(3):297-304. doi: 10.1530/REP-18-0581. [Article]
- Farhad AR, Razavi SM, Nejad PA: The use of aminoguanidine, a selective inducible nitric oxide synthase inhibitor, to evaluate the role of nitric oxide on periapical healing. Dent Res J (Isfahan). 2011 Oct;8(4):197-202. doi: 10.4103/1735-3327.86038. [Article]
- Matsumoto H, Hayashi S, Hatashita M, Ohnishi K, Shioura H, Ohtsubo T, Kitai R, Ohnishi T, Kano E: Induction of radioresistance by a nitric oxide-mediated bystander effect. Radiat Res. 2001 Mar;155(3):387-96. doi: 10.1667/0033-7587(2001)155[0387:iorban]2.0.co;2. [Article]
- Deng T, Xu K, Zhang L, Zheng X: Dynamic determination of Ox-LDL-induced oxidative/nitrosative stress in single macrophage by using fluorescent probes. Cell Biol Int. 2008 Nov;32(11):1425-32. doi: 10.1016/j.cellbi.2008.08.013. Epub 2008 Aug 20. [Article]
- MacAllister RJ, Whitley GS, Vallance P: Effects of guanidino and uremic compounds on nitric oxide pathways. Kidney Int. 1994 Mar;45(3):737-42. doi: 10.1038/ki.1994.98. [Article]
- Mahattanadul S, Reanmongkol W, Yano S, Panichayupakaranant P, Phdoongsombut N, Tungsinmunkong K: Preventive and curative effects of curcumin on the development of gastric inflammatory diseases in rats. J Nat Med. 2006 Jul;60(3):191-197. doi: 10.1007/s11418-006-0035-5. Epub 2006 Apr 28. [Article]
- Farhad AR, Razavi SM, Rozati AR, Shekarchizade N, Manshaei M: Selective nitric oxide synthase inhibitor promotes bone healing. Dent Res J (Isfahan). 2017 Sep-Oct;14(5):306-313. doi: 10.4103/1735-3327.215965. [Article]
- Trainor C, Butterworth KT, McGarry CK, McMahon SJ, O'Sullivan JM, Hounsell AR, Prise KM: DNA damage responses following exposure to modulated radiation fields. PLoS One. 2012;7(8):e43326. doi: 10.1371/journal.pone.0043326. Epub 2012 Aug 17. [Article]
- Kind
- Protein
- Organism
- Humans
- 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
- Uniprot Name
- Aldose reductase
- Molecular Weight
- 35853.125 Da
- Kind
- Protein
- Organism
- Humans
- 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 remodeli...
- Gene Name
- TIMP3
- Uniprot ID
- P35625
- Uniprot Name
- Metalloproteinase inhibitor 3
- Molecular Weight
- 24144.83 Da
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Inhibitor
- General Function
- Zinc ion binding
- Specific Function
- Catalyzes the degradation of compounds such as putrescine, histamine, spermine, and spermidine, substances involved in allergic and immune responses, cell proliferation, tissue differentiation, tum...
- Gene Name
- AOC1
- Uniprot ID
- P19801
- Uniprot Name
- Amiloride-sensitive amine oxidase [copper-containing]
- Molecular Weight
- 85377.1 Da
References
- MARSHALL PB: Effect of sex hormones on the excretion of free histamine by male and female rats. Br J Pharmacol Chemother. 1961 Feb;16:50-8. doi: 10.1111/j.1476-5381.1961.tb00297.x. [Article]
- Gahl WA, Pitot HC: Reversal by aminoguanidine of the inhibition of proliferation of human fibroblasts by spermidine and spermine. Chem Biol Interact. 1978 Jul;22(1):91-8. doi: 10.1016/0009-2797(78)90152-7. [Article]
- IVY AC, IVY EK, KARVINEN E, LIN TM: Effect of an histaminase inhibitor (aminoguanidine) on the gastric secretory response to exogenous histamine. Am J Physiol. 1956 Aug;186(2):231-8. doi: 10.1152/ajplegacy.1956.186.2.231. [Article]
Transporters
- Kind
- Protein
- Organism
- Humans
- 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, creat...
- Gene Name
- SLC22A2
- Uniprot ID
- O15244
- Uniprot Name
- Solute carrier family 22 member 2
- Molecular Weight
- 62579.99 Da
References
- 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. [Article]
- 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. [Article]
Drug created at November 18, 2007 18:24 / Updated at June 28, 2022 02:24