Mangafodipir (CHEM000969)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesTargets (5)XML
Record Information
Version1.0
Creation Date2009-06-19 21:58:21 UTC
Update Date2026-05-14 18:25:09 UTC
Accession NumberCHEM000969
Identification
Common NameMangafodipir
ClassSmall Molecule
DescriptionMangafodipir is a contrast agent delivered intravenously to enhance contrast in magnetic resonance imaging (MRI) of the liver. It has two parts, paramagnetic manganese (II) ions and the chelating agent fodipir (dipyridoxyl diphosphate, DPDP). Normal liver tissue absorbs the manganese more than abnormal or cancerous tissue. The manganese shortens the longitudinal relaxation time (called T1), making the normal tissue appear brighter in MRIs. This enhanced contrast allows lesions to be more easily identified. Acute toxicity studies in mice, rats and dogs using IV administration showed mangafodipir to have low to moderate toxicity. Repeat dose toxicity studies were conducted in rats, cynomologous monkeys and dogs. The liver and to a lesser extent the kidney were target organs of toxicity.
Contaminant Sources
  • T3DB toxins
Contaminant Type
  • Amine
  • Industrial/Workplace Toxin
  • Manganese Compound
  • Organic Compound
  • Organometallic
  • Pollutant
  • Synthetic Compound
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
TeslascanKegg
MN-DPDPMeSH
CalmangafodipirMeSH
Ca4MN(DPDP)5MeSH
Nycomed brand OF mangafodipir trisodiumMeSH
Manganese dipyridoxyl diphosphateMeSH
Manganese-DPDPMeSH
Mangafodipir trisodium, anhydrousMeSH
DPDPMeSH
N,N'-bis(pyridoxal-5-phosphate)ethylenediamine-N,n'-diacetic acidMeSH
Mangafodipir trisodiumMeSH
Chemical FormulaC22H27MnN4Na3O14P2
Average Molecular Mass757.323 g/mol
Monoisotopic Mass757.007 g/mol
CAS Registry Number140678-14-4
IUPAC Namemanganese(2+) ion 2-({2-[(carboxylatomethyl)({3-hydroxy-2-methyl-6-[(phosphonooxy)methyl]pyridin-4-yl}methyl)amino]ethyl}({3-hydroxy-2-methyl-6-[(phosphonooxy)methyl]pyridin-4-yl}methyl)amino)acetate
Traditional Namemanganese(2+) ion trisodium 2-({2-[(carboxylatomethyl)({5-[(hydrogen phosphonatooxy)methyl]-2-methyl-3-oxidopyridin-4-yl}methyl)amino]ethyl}({2-methyl-3-oxido-5-[(phosphonooxy)methyl]pyridin-4-yl}methyl)amino)acetate
SMILES[Na+].[Na+].[Na+].[Mn++].CC1=C([O-])C(CN(CCN(CC([O-])=O)CC2=C(COP(O)([O-])=O)C=NC(C)=C2[O-])CC([O-])=O)=C(COP(O)(O)=O)C=N1
InChI IdentifierInChI=1S/C22H32N4O14P2.Mn.3Na/c1-13-21(31)17(15(5-23-13)11-39-41(33,34)35)7-25(9-19(27)28)3-4-26(10-20(29)30)8-18-16(12-40-42(36,37)38)6-24-14(2)22(18)32;;;;/h5-6,31-32H,3-4,7-12H2,1-2H3,(H,27,28)(H,29,30)(H2,33,34,35)(H2,36,37,38);;;;/q;+2;3*+1/p-5
InChI KeyBENFPBJLMUIGGD-UHFFFAOYSA-I
Chemical Taxonomy
Description belongs to the class of organic compounds known as pyridoxamine 5'-phosphates. These are heterocyclic aromatic compounds containing a pyridoxamine that carries a phosphate group at the 5'-position.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassPyridines and derivatives
Sub ClassPyridoxamines
Direct ParentPyridoxamine 5'-phosphates
Alternative Parents
Substituents
  • Pyridoxamine 5'-phosphate
  • Alpha-amino acid
  • Alpha-amino acid or derivatives
  • Pyridinolate
  • Aralkylamine
  • Methylpyridine
  • Phosphoric acid ester
  • Alkyl phosphate
  • Organic phosphoric acid derivative
  • Dicarboxylic acid or derivatives
  • Heteroaromatic compound
  • Amino acid or derivatives
  • Tertiary amine
  • Tertiary aliphatic amine
  • Carboxylic acid salt
  • Amino acid
  • Azacycle
  • Organic alkali metal salt
  • Organic transition metal salt
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic nitrogen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organic zwitterion
  • Organic salt
  • Organic sodium salt
  • Hydrocarbon derivative
  • Organic oxide
  • Carbonyl group
  • Organopnictogen compound
  • Amine
  • Organic oxygen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External DescriptorsNot Available
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Mitochondrion
Biofluid LocationsNot Available
Tissue LocationsNot Available
Pathways
NameSMPDB LinkKEGG Link
ApoptosisNot Availablemap04210
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateLiquid
AppearanceLiquid
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility8.43 g/LALOGPS
logP0.88ALOGPS
logP-1.9ChemAxon
logS-2ALOGPS
pKa (Strongest Acidic)1.44ChemAxon
pKa (Strongest Basic)-6.4ChemAxon
Physiological Charge-5ChemAxon
Hydrogen Acceptor Count16ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area294.99 ŲChemAxon
Rotatable Bond Count17ChemAxon
Refractivity185.26 m³·mol⁻¹ChemAxon
Polarizability55.1 ųChemAxon
Number of Rings2ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0000000900-90d667d5611bc91eb5d8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-0000000900-90d667d5611bc91eb5d8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-0000000900-90d667d5611bc91eb5d8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0000000900-52c507de86c5c97a522aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-0000000900-52c507de86c5c97a522aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-0000000900-52c507de86c5c97a522aSpectrum
Toxicity Profile
Route of ExposureOral (2) ; inhalation (2)
Mechanism of ToxicityManganese is a cellular toxicant that can impair transport systems, enzyme activities, and receptor functions. It primarily targets the central nervous system, particularily the globus pallidus of the basal ganglia. It is believed that the manganese ion, Mn(II), enhances the autoxidation or turnover of various intracellular catecholamines, leading to increased production of free radicals, reactive oxygen species, and other cytotoxic metabolites, along with a depletion of cellular antioxidant defense mechanisms, leading to oxidative damage and selective destruction of dopaminergic neurons. In addition to dopamine, manganese is thought to perturbations other neurotransmitters, such as GABA and glutamate. In order to produce oxidative damage, manganese must first overwhelm the antioxidant enzyme manganese superoxide dismutase. The neurotoxicity of Mn(II) has also been linked to its ability to substitute for Ca(II) under physiological conditions. It can enter mitochondria via the calcium uniporter and inhibit mitochondrial oxidative phosphorylation. It may also inhibit the efflux of Ca(II), which can result in a loss of mitochondrial membrane integrity. Mn(II) has been shown to inhibit mitochondrial aconitase activity to a significant level, altering amino acid metabolism and cellular iron homeostasis. (2)
MetabolismMetabolism of organophosphates occurs principally by oxidation, by hydrolysis via esterases and by reaction with glutathione. Demethylation and glucuronidation may also occur. Oxidation of organophosphorus pesticides may result in moderately toxic products. In general, phosphorothioates are not directly toxic but require oxidative metabolism to the proximal toxin. The glutathione transferase reactions produce products that are, in most cases, of low toxicity. Paraoxonase (PON1) is a key enzyme in the metabolism of organophosphates. PON1 can inactivate some organophosphates through hydrolysis. PON1 hydrolyzes the active metabolites in several organophosphates insecticides as well as, nerve agents such as soman, sarin, and VX. The presence of PON1 polymorphisms causes there to be different enzyme levels and catalytic efficiency of this esterase, which in turn suggests that different individuals may be more susceptible to the toxic effect of organophosphate exposure.
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesMangafodipir is a contrast agent delivered intravenously to enhance contrast in magnetic resonance imaging (MRI) of the liver. (4)
Minimum Risk LevelChronic Inhalation: 0.0003 mg/m3 (1)
Health EffectsManganese mainly affects the nervous system and may cause behavioral changes and other nervous system effects, which include movements that may become slow and clumsy. This combination of symptoms when sufficiently severe is referred to as “manganism”. (2)
SymptomsManganese mainly affects the nervous system and may cause behavioral changes and other nervous system effects, which include movements that may become slow and clumsy. This combination of symptoms when sufficiently severe is referred to as “manganism”. (2)
TreatmentNot Available
Concentrations
Not Available
DrugBank IDDBSALT001330
HMDB IDNot Available
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkMangafodipir
Chemspider IDNot Available
ChEBI IDNot Available
PubChem Compound ID160036
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General ReferencesNot Available