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Mangafodipir

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Mangafodipir

Mangafodipir.png

 

 Mangafodipir
CAS : 118248-94-5 (free acid); 155319-91-8 (hexahydrogen)
CAS Name: (OC-6-13)-[[N,N¢-1,2-Ethanediylbis[N-[[3-(hydroxy-kO)-2-methyl-5-[(phosphonooxy)methyl]-4-pyridinyl]methyl]glycinato-kN,kO]](8-)]manganate(6-)
Add Names: manganese(II)-N,N¢-dipyridoxylethylenediamine-N,N¢-diacetate-5,5-bis(phosphonate); manganese dipyridoxal diphosphate; MnDPDP
Manufacturers’ Codes: S-095
 C22H24MnN4O14P2
 685.33
Percent Composition: C 38.56%, H 3.53%, Mn 8.02%, N 8.18%, O 32.68%, P 9.04%
Mangafodipir 3D sticks.png
Clinical data
AHFS/Drugs.com Micromedex Detailed Consumer Information
Pregnancy cat. Not to be used
Routes Intravenous infusion
Pharmacokinetic data
Bioavailability NA
Protein binding 27% (manganese)
Negligible (DPDP)
Half-life 20 minutes (manganese)
50 minutes (DPDP)
Excretion Renal and fecal (manganese)
Renal (DPDP)
Identifiers
ATC code V08CA05
PubChem CID 3086672
ChemSpider 2343239 Yes
UNII N02W67RKJS Yes
Chemical data
Formula C22H28MnN4O14P2 
Mol. mass 689.362 g/mol
Diagnostic Aid (MRI Contrast Agent)
Manganese dipyridoxal diphosphate trisodium salt, Mangafodipir trisodium, Win-59010-2, S-095, MnDPDP, Teslascan

Mangafodipir (sold under the brand name Teslascan as mangafodipir trisodium) 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 thechelating agent fodipir (dipyridoxyl diphosphate, DPDP). Normal liver tissue absorbs the manganese more than abnormal or cancerous tissue. The manganese shortens the longitudinal relaxation time (T1), making the normal tissue appear brighter in MRIs. This enhanced contrast allows lesions to be more easily identified.

 

The condensation of pyridoxal 5-phosphate (I) with ethylenediamine (II) in methanol by means of NaOH gives the corresponding diimine (III), which is reduced with hydrogen over Pt/C in methanol/water yielding the expected diamine (IV). The reaction of (IV) with bromoacetic acid (V) by means of NaOH in methanol/water affords the N,N’-diacetic acid derivative (VI), which is finally treated with MnCl2 in water containing NaOH.

References

Literature References:
Paramagnetic manganese (II) chelate designed as a tissue specific imaging agent taken up by normal liver parenchyma. Prepn: S. M. Rocklage, S. C. Quay, EP 290047; eidem, US 4933456 (1988, 1990 both to Salutar); idem et al.,Inorg. Chem. 28, 477 (1989).
Pharmacology, toxicity and image enhancement studies: G. Elizondo et al., Radiology 178, 73 (1991).
HPLC determn in plasma: K. G. Toft et al., J. Pharm. Biomed. Anal. 15, 973 (1997).
Series of articles on clinical studies, toxicology and physicochemical properties: Acta Radiol. 38, 626-789 (1997).
Review of use as contrast agent for liver lesion detection: N. M. Rofsky, J. P. Earls, MRI Clin. North Am. 4, 73-85 (1996).
Properties: LD50 i.v. in mice: 5.4 mmol/kg (Elizondo).
Toxicity data: LD50 i.v. in mice: 5.4 mmol/kg (Elizondo)
……………………………………
Mangafodipir Trisodium
Click to View Image

C22H27MnN4Na3O14P2 757.33
Trisodium trihydrogen (OC-6-13)-[[N,N¢-1,2-ethanediylbis[N-[[3-hydroxy-2-methyl-5-[(phosphonooxy)methyl]-4-pyridinyl]methyl]glycinato]](8-)] manganate(6-).
Trisodium trihydrogen (OC-6-13)-[[N,N¢-ethylenebis[N-[[3-hydroxy-5-(hydroxymethyl)-2-methyl-4-pyridyl]methyl]glycine] 5,5¢-bis(phosphato)](8-)]manganate(6-) [140678-14-4].

Derivative Type: Trisodium salt
CAS Registry Number: 140678-14-4
Additional Names: Magnafodipir trisodium
Manufacturers’ Codes: Win-59010
Trademarks: Teslascan (Nycomed)
Molecular Formula: C22H27MnN4Na3O14P2
Molecular Weight: 757.32
Percent Composition: C 34.89%, H 3.59%, Mn 7.25%, N 7.40%, Na 9.11%, O 29.58%, P 8.18%
Properties: Pale yellow, triclinic hygroscopic crystals. d 1.537. uv max (water): 220, 257, 319 nm (e 37600, 10300, 13400). Soly (g/ml): 0.4596 water, 0.0230 methanol, 0.0008 ethanol, 0.0006 acetone, 0.0011 chloroform. Log P (1-octanol:water) -5.62; (1-butanol: water) -3.68. Prepd as 0.01 mmol/ml aqueous infusion: bright yellow, clear soln, pH 7.5. Viscosity (mPa.s): 1.0 at 20°, 0.7 at 37°. Osmolality (37°): 290 mosmol/kg. d20 1.01 g/ml.
Log P: Log P (1-octanol:water) -5.62; (1-butanol: water) -3.68
Absorption maximum: uv max (water): 220, 257, 319 nm (e 37600, 10300, 13400)
Density: d 1.537; d20 1.01 g/ml
Therap-Cat: Diagnostic aid (MRI contrast agent).

Filed under: Uncategorized Tagged: Contrast agent, Diagnostic Aid (MRI Contrast Agent), Mangafodipir, manganese

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