MANGAFODIPIR

US Previously Marketed

Details

Stereochemistry	ACHIRAL
Molecular Formula	C22H26N4O14P2.Mn.4H
Molecular Weight	691.3776
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

[H+].[H+].[H+].[H+].[Mn++].CC1=NC=C(COP([O-])([O-])=O)C(CN(CCN(CC([O-])=O)CC2=C(COP([O-])([O-])=O)C=NC(C)=C2O)CC([O-])=O)=C1O

InChI

InChIKey=QDQFSBKXQQZVTB-UHFFFAOYSA-L

InChI=1S/C22H32N4O14P2.Mn/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/p-2

HIDE SMILES / InChI

Molecular Formula	H
Molecular Weight	1.0079
Charge	1
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Molecular Formula	Mn
Molecular Weight	54.938
Charge	2
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Molecular Formula	C22H26N4O14P2
Molecular Weight	632.4078
Charge	-6
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: http://www.ema.europa.eu/docs/en_GB/document_library/EPAR_-_Scientific_Discussion/human/000137/WC500036332.pdf
Curator's Comment: description was created based on several sources, including https://clinicaltrials.gov/ct2/show/NCT00727922 | https://clinicaltrials.gov/ct2/show/NCT00966563 | https://www.drugs.com/cons/mangafodipir-intravenous.html | https://www.drugbank.ca/drugs/DB06796 | https://www.ncbi.nlm.nih.gov/pubmed/27533964

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. Mangafodipir is a manganese (Mn2+) chelate with the ligand fodipir (dipyridoxyl diphosphate or DPDP). Mangafodipir trisodium is metabolised (dephosphorylated) and partially transmetallated (manganese exchanged for zinc) after intravenous administration. Manganese that is released from mangafodipir is taken up by hepatocytes thereby increasing the SI of normal liver tissue. This may result in an improvement of the detection of liver metastases, which usually have no hepatocytes. The metabolites of fodipir are renally excreted, whilst the biliary route mainly excretes manganese. Mangafodipir was withdrawn from the US market in 2003 and the European market in 2012.

CNS Activity

Originator

Approval Year

Conditions

Condition	Modality	Highest Phase	Product
Cancer 592 Sources: https://clinicaltrials.gov/ct2/show/NCT00727922	Diagnostic	Withdrawn	TESLASCAN Approved Use Unknown Launch Date 1997
Myocardial Infarction 2 Sources: https://clinicaltrials.gov/ct2/show/NCT00966563	Diagnostic	Phase II 1132	TESLASCAN Approved Use Unknown Launch Date 1997
Colon cancer 62 Sources: https://clinicaltrials.gov/ct2/show/NCT00671996	Diagnostic	Phase II 1132	TESLASCAN Approved Use Unknown Launch Date 1997
Hepatocellular carcinoma 83 Sources: http://www.ema.europa.eu/docs/en_GB/document_library/EPAR_-_Scientific_Discussion/human/000137/WC500036332.pdf	Diagnostic	Approved 8429	TESLASCAN Approved Use Unknown Launch Date 1997

C_max

Value	Dose	Analyte	Population
38.3 μM EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/9245963/	5 μmol/kg single, intravenous dose: 5 μmol/kg route of administration: Intravenous experiment type: SINGLE co-administered:	MANGANESE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
37.9 μM EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/9245963/	10 μmol/kg single, intravenous dose: 10 μmol/kg route of administration: Intravenous experiment type: SINGLE co-administered:	MANGANESE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
78.8 μM EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/9245963/	10 μmol/kg single, intravenous dose: 10 μmol/kg route of administration: Intravenous experiment type: SINGLE co-administered:	MANGANESE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
14.1 μM EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/9245963/	5 μmol/kg single, intravenous dose: 5 μmol/kg route of administration: Intravenous experiment type: SINGLE co-administered:	MANGANESE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
26.4 μM EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/9245963/	5 μmol/kg single, intravenous dose: 5 μmol/kg route of administration: Intravenous experiment type: SINGLE co-administered:	FODIPIR plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
38.6 μM EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/9245963/	10 μmol/kg single, intravenous dose: 10 μmol/kg route of administration: Intravenous experiment type: SINGLE co-administered:	FODIPIR plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
85.2 μM EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/9245963/	10 μmol/kg single, intravenous dose: 10 μmol/kg route of administration: Intravenous experiment type: SINGLE co-administered:	FODIPIR plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
61.1 μM EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/9245963/	10 μmol/kg single, intravenous dose: 10 μmol/kg route of administration: Intravenous experiment type: SINGLE co-administered:	FODIPIR plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN

AUC

Value	Dose	Analyte	Population
11.5 μM × h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/9245963/	5 μmol/kg single, intravenous dose: 5 μmol/kg route of administration: Intravenous experiment type: SINGLE co-administered:	MANGANESE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
26 μM × h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/9245963/	10 μmol/kg single, intravenous dose: 10 μmol/kg route of administration: Intravenous experiment type: SINGLE co-administered:	MANGANESE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
27.6 μM × h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/9245963/	10 μmol/kg single, intravenous dose: 10 μmol/kg route of administration: Intravenous experiment type: SINGLE co-administered:	MANGANESE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
8.89 μM × h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/9245963/	5 μmol/kg single, intravenous dose: 5 μmol/kg route of administration: Intravenous experiment type: SINGLE co-administered:	MANGANESE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
43.7 μM × h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/9245963/	5 μmol/kg single, intravenous dose: 5 μmol/kg route of administration: Intravenous experiment type: SINGLE co-administered:	FODIPIR plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
47.8 μM × h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/9245963/	10 μmol/kg single, intravenous dose: 10 μmol/kg route of administration: Intravenous experiment type: SINGLE co-administered:	FODIPIR plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
96 μM × h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/9245963/	10 μmol/kg single, intravenous dose: 10 μmol/kg route of administration: Intravenous experiment type: SINGLE co-administered:	FODIPIR plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
96.8 μM × h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/9245963/	10 μmol/kg single, intravenous dose: 10 μmol/kg route of administration: Intravenous experiment type: SINGLE co-administered:	FODIPIR plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN

T_1/2

Value	Dose	Analyte	Population
8 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/9245963/	5 μmol/kg single, intravenous dose: 5 μmol/kg route of administration: Intravenous experiment type: SINGLE co-administered:	MANGANESE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
8 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/9245963/	10 μmol/kg single, intravenous dose: 10 μmol/kg route of administration: Intravenous experiment type: SINGLE co-administered:	MANGANESE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
8 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/9245963/	10 μmol/kg single, intravenous dose: 10 μmol/kg route of administration: Intravenous experiment type: SINGLE co-administered:	MANGANESE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
8 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/9245963/	5 μmol/kg single, intravenous dose: 5 μmol/kg route of administration: Intravenous experiment type: SINGLE co-administered:	MANGANESE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
121 min EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/9245963/	5 μmol/kg single, intravenous dose: 5 μmol/kg route of administration: Intravenous experiment type: SINGLE co-administered:	FODIPIR plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
112 min EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/9245963/	10 μmol/kg single, intravenous dose: 10 μmol/kg route of administration: Intravenous experiment type: SINGLE co-administered:	FODIPIR plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
117 min EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/9245963/	10 μmol/kg single, intravenous dose: 10 μmol/kg route of administration: Intravenous experiment type: SINGLE co-administered:	FODIPIR plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
113 min EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/9245963/	10 μmol/kg single, intravenous dose: 10 μmol/kg route of administration: Intravenous experiment type: SINGLE co-administered:	FODIPIR plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN

Doses

Dose	Population	Adverse events
0.5 mL/kg single, intravenous Recommended Dose: 0.5 mL/kg Route: intravenous Route: single Dose: 0.5 mL/kg Sources: https://www.ema.europa.eu/en/documents/product-information/teslascan-epar-product-information_en.pdf	unhealthy Health Status: unhealthy Condition: Liver lesions Sources: https://www.ema.europa.eu/en/documents/product-information/teslascan-epar-product-information_en.pdf	Other AEs: Hypersensitivity reaction, Urticaria... Other AEs: Hypersensitivity reaction (rare) Urticaria (rare) Anaphylactoid reaction (rare) Sources: https://www.ema.europa.eu/en/documents/product-information/teslascan-epar-product-information_en.pdf
5 umol/kg single, intravenous Recommended Dose: 5 umol/kg Route: intravenous Route: single Dose: 5 umol/kg Sources: https://pubmed.ncbi.nlm.nih.gov/10931579	unhealthy n = 546 Health Status: unhealthy Condition: Liver lesions Sex: M+F Population Size: 546 Sources: https://pubmed.ncbi.nlm.nih.gov/10931579	Disc. AE: Nausea, Vomiting... AEs leading to discontinuation/dose reduction: Nausea (grade 1) Vomiting (grade 1) Pharyngitis (grade 1) Pruritus (grade 2) Nausea (grade 3, 0.18%) Vomiting (grade 3, 0.18%) Sources: https://pubmed.ncbi.nlm.nih.gov/10931579

AEs

AE	Significance	Dose	Population
Anaphylactoid reaction	rare	0.5 mL/kg single, intravenous Recommended Dose: 0.5 mL/kg Route: intravenous Route: single Dose: 0.5 mL/kg Sources: https://www.ema.europa.eu/en/documents/product-information/teslascan-epar-product-information_en.pdf	unhealthy Health Status: unhealthy Condition: Liver lesions Sources: https://www.ema.europa.eu/en/documents/product-information/teslascan-epar-product-information_en.pdf
Hypersensitivity reaction	rare	0.5 mL/kg single, intravenous Recommended Dose: 0.5 mL/kg Route: intravenous Route: single Dose: 0.5 mL/kg Sources: https://www.ema.europa.eu/en/documents/product-information/teslascan-epar-product-information_en.pdf	unhealthy Health Status: unhealthy Condition: Liver lesions Sources: https://www.ema.europa.eu/en/documents/product-information/teslascan-epar-product-information_en.pdf
Urticaria	rare	0.5 mL/kg single, intravenous Recommended Dose: 0.5 mL/kg Route: intravenous Route: single Dose: 0.5 mL/kg Sources: https://www.ema.europa.eu/en/documents/product-information/teslascan-epar-product-information_en.pdf	unhealthy Health Status: unhealthy Condition: Liver lesions Sources: https://www.ema.europa.eu/en/documents/product-information/teslascan-epar-product-information_en.pdf
Nausea	grade 1 Disc. AE	5 umol/kg single, intravenous Recommended Dose: 5 umol/kg Route: intravenous Route: single Dose: 5 umol/kg Sources: https://pubmed.ncbi.nlm.nih.gov/10931579	unhealthy n = 546 Health Status: unhealthy Condition: Liver lesions Sex: M+F Population Size: 546 Sources: https://pubmed.ncbi.nlm.nih.gov/10931579
Pharyngitis	grade 1 Disc. AE	5 umol/kg single, intravenous Recommended Dose: 5 umol/kg Route: intravenous Route: single Dose: 5 umol/kg Sources: https://pubmed.ncbi.nlm.nih.gov/10931579	unhealthy n = 546 Health Status: unhealthy Condition: Liver lesions Sex: M+F Population Size: 546 Sources: https://pubmed.ncbi.nlm.nih.gov/10931579
Vomiting	grade 1 Disc. AE	5 umol/kg single, intravenous Recommended Dose: 5 umol/kg Route: intravenous Route: single Dose: 5 umol/kg Sources: https://pubmed.ncbi.nlm.nih.gov/10931579	unhealthy n = 546 Health Status: unhealthy Condition: Liver lesions Sex: M+F Population Size: 546 Sources: https://pubmed.ncbi.nlm.nih.gov/10931579
Pruritus	grade 2 Disc. AE	5 umol/kg single, intravenous Recommended Dose: 5 umol/kg Route: intravenous Route: single Dose: 5 umol/kg Sources: https://pubmed.ncbi.nlm.nih.gov/10931579	unhealthy n = 546 Health Status: unhealthy Condition: Liver lesions Sex: M+F Population Size: 546 Sources: https://pubmed.ncbi.nlm.nih.gov/10931579
Nausea	grade 3, 0.18% Disc. AE	5 umol/kg single, intravenous Recommended Dose: 5 umol/kg Route: intravenous Route: single Dose: 5 umol/kg Sources: https://pubmed.ncbi.nlm.nih.gov/10931579	unhealthy n = 546 Health Status: unhealthy Condition: Liver lesions Sex: M+F Population Size: 546 Sources: https://pubmed.ncbi.nlm.nih.gov/10931579
Vomiting	grade 3, 0.18% Disc. AE	5 umol/kg single, intravenous Recommended Dose: 5 umol/kg Route: intravenous Route: single Dose: 5 umol/kg Sources: https://pubmed.ncbi.nlm.nih.gov/10931579	unhealthy n = 546 Health Status: unhealthy Condition: Liver lesions Sex: M+F Population Size: 546 Sources: https://pubmed.ncbi.nlm.nih.gov/10931579

Sourcing

Vendor/Aggregator	ID	URL
ChemIDplus	155319918	https://chem.nlm.nih.gov/chemidplus/id/0155319918
EPA DSSTox	DTXSID70894993	https://comptox.epa.gov/dashboard/DTXSID70894993
PubChem	76967443	https://pubchem.ncbi.nlm.nih.gov/compound/76967443

PubMed

Title	Date	PubMed
Mangafodipir as a cardioprotective adjunct to reperfusion therapy: a feasibility study in patients with ST-segment elevation myocardial infarction.	2015 Jan	27533964

Patents

Sample Use Guides

In Vivo Use Guide

Dose, 5-10 µmol/kg b.w.

Route of Administration: Intravenous

In Vitro Use Guide

MnDPDP (Mangafodipir) relax phenylephrine precontracted bovine mesenteric artery strips in a concentration- dependent manner. Bovine arteries from the branch of the superior mesenteric artery were obtained from a local slaughter-house within 30 mm of slaughter. Specimens were immersed in a Krebs’ buffer solution, dissected free from surrounding tissues, opened longitudinally and cut into strips approximately 5 mm wide. In some arterial strips the endothelial cells were removed by gently rubbing the intimal surface with a wooden stick for 30 to 60 sec. When the arterial strips had reached a steady state of contraction, MnDPDP (Mangafodipir) were added to the organ baths, at concentrations of 0.1 to 1000 ı.tM. ACh was used as a positive control. EDRF-independent effects were examined by using arterial strips minus endothelium.

Substance Class	Chemical Created by `admin` on `Sat Dec 16 05:04:50 GMT 2023` Edited by `admin` on `Sat Dec 16 05:04:50 GMT 2023`
Record UNII	N02W67RKJS
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

MANGAFODIPIR

Official Name

English

Mangafodipir [WHO-DD]

Common Name

English

mangafodipir [INN]

Common Name

English

HEXAHYDROGEN (OC-6-13)-((N,N'-ETHYLENEBIS(N-((3-HYDROXY-5-(HYDROXYMETHYL)-2-METHYL-4-PYRIDYL)METHYL)GLYCINE) 5,5'-BIS(PHOSPHATO))(8-))MANGANATE(6-)

Common Name

English

MANGAFODIPIR [VANDF]

Common Name

English

MANGAFODIPIR [MI]

Common Name

English

Classification Tree Code System Code

NDF-RT

N0000175862