<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <id type="integer">1141</id>
  <title>T3D1137</title>
  <common-name>Mangafodipir</common-name>
  <description>Mangafodipir is an exogenous liquid compound with the formula C22H27MnN4Na3O14P2. Mangafodipir belongs to the pyridoxamines, a subclass of pyridines and derivatives within the organic compounds. With an average molecular weight of 757.32 g/mol, Mangafodipir is a heavy molecule. This compound is used as a magnetic resonance imaging (MRI) contrast agent delivered intravenously to enhance contrast in the liver. It consists of paramagnetic manganese (II) ions and the chelating agent fodipir (dipyridoxyl diphosphate, DPDP). Normal liver tissue absorbs manganese more than abnormal or cancerous tissue, which shortens the longitudinal relaxation time (T1) and makes normal tissue appear brighter, allowing lesions to be more easily identified.

Mangafodipir is recorded as being released from healthcare, pharmaceuticals and veterinary products, as well as household cleaning and consumer products and electrical and electronic equipment. It targets three proteins: cytoplasmic aconitate hydratase (ACO1), mitochondrial aconitate hydratase (ACO2), and the major prion protein (PRNP). Manganese inhibits aconitase, increasing citrate levels and disrupting the catalytic [4Fe-4S] cluster, which produces iron regulatory protein 1 and alters cellular iron homeostasis. Manganese also stabilizes iron regulatory protein 2 by competing for an iron-binding site. Additionally, manganese binds to the prion protein, displacing copper and altering its conformation and redox chemistry in a manner similar to prion disease.</description>
  <cas>140678-14-4</cas>
  <pubchem-id>160036</pubchem-id>
  <chemical-formula>C22H27MnN4Na3O14P2</chemical-formula>
  <weight>757.007260</weight>
  <appearance>Liquid</appearance>
  <melting-point></melting-point>
  <boiling-point></boiling-point>
  <density nil="true"/>
  <solubility></solubility>
  <specific-gravity nil="true"/>
  <flash-point nil="true"/>
  <vapour-pressure nil="true"/>
  <route-of-exposure>Oral (L228) ; inhalation (L228)</route-of-exposure>
  <target nil="true"/>
  <mechanism-of-toxicity>Manganese 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. (L228)</mechanism-of-toxicity>
  <metabolism>Metabolism 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.</metabolism>
  <toxicity></toxicity>
  <lethaldose></lethaldose>
  <carcinogenicity>No indication of carcinogenicity to humans (not listed by IARC).</carcinogenicity>
  <use-source>Mangafodipir is a contrast agent delivered intravenously to enhance contrast in magnetic resonance imaging (MRI) of the liver. (L231)</use-source>
  <min-risk-level>Chronic Inhalation: 0.0003 mg/m3 (L134)</min-risk-level>
  <health-effects>Manganese 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”. (L228)</health-effects>
  <symptoms>Manganese 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”. (L228)</symptoms>
  <treatment></treatment>
  <created-at type="dateTime">2009-06-19T21:58:21Z</created-at>
  <updated-at type="dateTime">2026-05-14T18:25:09Z</updated-at>
  <interacting-proteins>Alpha-2-macroglobulin (P01023) Serum albumin (P02768) Serotransferrin (P02787) Superoxide dismutase [Mn], mitochondrial (P04179) (L228) </interacting-proteins>
  <wikipedia></wikipedia>
  <uniprot-id></uniprot-id>
  <kegg-compound-id></kegg-compound-id>
  <omim-id></omim-id>
  <chebi-id></chebi-id>
  <biocyc-id></biocyc-id>
  <ctd-id></ctd-id>
  <stitch-id>Mangafodipir</stitch-id>
  <drugbank-id>DB06796</drugbank-id>
  <pdb-id></pdb-id>
  <actor-id></actor-id>
  <organism nil="true"/>
  <export type="boolean">true</export>
  <metabolizing-proteins nil="true"/>
  <transporting-proteins>Alpha-2-macroglobulin (P01023) 
Serum albumin (P02768) 
Serotransferrin (P02787) 
(L228) </transporting-proteins>
  <moldb-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</moldb-smiles>
  <moldb-formula>C22H27MnN4Na3O14P2</moldb-formula>
  <moldb-inchi>InChI=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</moldb-inchi>
  <moldb-inchikey>BENFPBJLMUIGGD-UHFFFAOYSA-I</moldb-inchikey>
  <moldb-average-mass type="decimal">757.3231</moldb-average-mass>
  <moldb-mono-mass type="decimal">757.007258277</moldb-mono-mass>
  <origin>Exogenous</origin>
  <state>Liquid</state>
  <logp></logp>
  <hmdb-id></hmdb-id>
  <chembl-id></chembl-id>
  <chemspider-id>140690</chemspider-id>
  <structure-image-file-name nil="true"/>
  <structure-image-content-type nil="true"/>
  <structure-image-file-size type="integer" nil="true"/>
  <structure-image-updated-at type="dateTime" nil="true"/>
  <biodb-id nil="true"/>
  <synthesis-reference></synthesis-reference>
  <structure-image-caption nil="true"/>
  <chemdb-id>CHEM000969</chemdb-id>
  <dsstox-id nil="true"/>
  <toxcast-id nil="true"/>
  <stoff-ident-origin nil="true"/>
  <stoff-ident-id nil="true"/>
  <susdat-id nil="true"/>
  <iupac>manganese(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</iupac>
  <moldb-polar-surface-area>294.99</moldb-polar-surface-area>
  <moldb-refractivity>185.26330000000002</moldb-refractivity>
  <moldb-polarizability>55.09741832997964</moldb-polarizability>
  <moldb-rotatable-bond-count>17</moldb-rotatable-bond-count>
  <moldb-acceptor-count>16</moldb-acceptor-count>
  <moldb-donor-count>3</moldb-donor-count>
  <moldb-pka-strongest-acidic>1.441270538958376</moldb-pka-strongest-acidic>
  <moldb-pka-strongest-basic>-6.387918922503165</moldb-pka-strongest-basic>
  <moldb-physiological-charge>-5</moldb-physiological-charge>
  <moldb-number-of-rings>2</moldb-number-of-rings>
  <moldb-alogps-logp>0.88</moldb-alogps-logp>
  <moldb-alogps-logs>-1.98</moldb-alogps-logs>
  <moldb-alogps-solubility>8.43e+00 g/l</moldb-alogps-solubility>
  <kingdom>Organic compounds</kingdom>
  <superklass>Organoheterocyclic compounds</superklass>
  <klass>Pyridines and derivatives</klass>
  <subklass>Pyridoxamines</subklass>
  <paper-count type="integer">185</paper-count>
  <sync-id>CED0010276</sync-id>
  <structure-inchikey>BENFPBJLMUIGGD-UHFFFAOYSA-I</structure-inchikey>
  <structure-fingerprint>a000000008008000000000000402800200020800000000000001000010008010000100000000000000020000000000000000000000000420000100000000000001000000000000000000000200000000001000010000000410400000040000100000000000000000040000000000000000000000000000000000000000000400000000000000000000000000000000200000400200000000000000008000002000000040000000800000000000000000800000000000000000001100000000000000800000000000000000000000000000820000000000020000000000010000a0000000040000000000400000001000000000000000000002000</structure-fingerprint>
  <structure-pattern-fingerprint>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</structure-pattern-fingerprint>
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</structure-pickle>
  <structure-indexed-at type="dateTime">2026-09-19T04:00:00Z</structure-indexed-at>
</compound>
