CAS 113662-23-0|gadolinium(3+) bis(N-methyl-D(-)-glucamine) 8-(carboxylatomethyl)-5,11-bis(carboxymethyl)-1-phenyl-2-oxa-5,8,11-triazatridecane-4,13-dioate|Multihance Multipack|Gd-BOPTA|Gd-BOPTA/Dim...

General Information

Structure

Molecular Formula

C₃₆H₆₂GdN₅O₂₁

Molecular Mass

1058.14838

Exact Mass

1058.31783203

Charge

InChI

InChI=1S/C22H31N3O11.2C7H17NO5.Gd/c26-18(27)10-23(6-7-24(11-19(28)29)12-20(30)31)8-9-25(13-21(32)33)17(22(34)35)15-36-14-16-4-2-1-3-5-16;2*1-8-2-4(10)6(12)7(13)5(11)3-9;/h1-5,17H,6-15H2,(H,26,27)(H,28,29)(H,30,31)(H,32,33)(H,34,35);2*4-13H,2-3H2,1H3;/q;;;+3/p-3/t;2*4-,5+,6+,7+;/m.00./s1

InChIKey

OCDAWJYGVOLXGZ-VPVMAENOSA-K

Canonic Smiles

OC(=O)CN(C(C(=O)[O-])COCc1ccccc1)CCN(CC(=O)[O-])CCN(CC(=O)O)CC(=O)[O-].CNC[C@@H]([C@H]([C@@H]([C@@H](CO)O)O)O)O.CNC[C@@H]([C@H]([C@@H]([C@@H](CO)O)O)O)O.[Gd+3]

Isomeric Smiles

[Gd+3].O[C@@H]([C@H](O)[C@H](O)CO)[C@@H](O)CNC.O[C@@H]([C@H](O)[C@H](O)CO)[C@@H](O)CNC.O(CC(N(CCN(CCN(CC(=O)O)CC(=O)[O-])CC(=O)[O-])CC(=O)O)C(=O)[O-])Cc1ccccc1

Calculated Properties

JChem

Acid pKa

0.085447945

H Acceptors

H Donor

LogD (pH = 5.5)

-10.03401

LogD (pH = 7.4)

-15.980204

Log P

-4.1383862

Molar Refractivity

154.362

Polarizability

47.59504

Polar Surface Area

213.94

Rotatable Bonds

Lipinski's Rule of Five

false

Data Source

Academic Data

Data Source

Names and Identifiers

IUPAC Traditional name

gadolinium(3+) bis(N-methyl-D(-)-glucamine) 8-(carboxylatomethyl)-5,11-bis(carboxymethyl)-1-phenyl-2-oxa-5,8,11-triazatridecane-4,13-dioate

Brand Name

Multihance MultipackGd-BOPTAGd-BOPTA/DimegMultihance

IUPAC name

gadolinium(3+) ion bis((2R,3R,4R,5S)-6-(methylamino)hexane-1,2,3,4,5-pentol) 8-(carboxylatomethyl)-5,11-bis(carboxymethyl)-1-phenyl-2-oxa-5,8,11-triazatridecane-4,13-dioate

Synonyms

Gadobenate DimeglumineGadobenic acid

Names and Identifiers

Registration numbers

PubChem SID

46506805160964086

PubChem CID

6918204

CAS Number

113662-23-0

Registration numbers

Properties

No Data Available

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Related Proteins

No Data Available

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Molecular Spectra

No Data Available

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Molecule Details

DrugBank

DB00743

Drug Groups

approved

Description

Gadobenate Dimeglumine is an MRI contrast agent used primarily for MR imaging of the liver. It can also be used for visualizing the CNS and heart. In contrast to conventional extracellular fluid contrast agents, gadobenate dimeglumine is characterized by a weak and transient binding capacity to serum proteins. This binding leads to an increased relaxivity of gadobenate dimeglumine and, consequently, to a considerably increased signal intensity over that of other agents.

Indication

Gadobenate Dimeglumine is an MRI contrast agent used primarily for MR imaging of the liver. It can also be used for MRI of the heart, as well as and central nervous system in adults to visualize lesions with abnormal brain vascularity or abnormalities in the blood brain barrier, the brain, spine, or other associated tissues.

Pharmacology

Gadobenate dimeglumine shares the pharmacokinetic properties of the ECF contrast agent gadopentetate dimeglumine; however, gadobenate differs in that is also selectively taken-up by hepatocytes and excreted via the bile (up to 5% of dose). The elimination half-life of gadobenate dimeglumine is approximately 1 hour. It is not metabolized.

Toxicity

Gadolinium-based radiocontrast agents like gadobenate dimeglumine are cytotoxic to renal cells. The toxic effects include apoptosis, cellular energy failure, disruption of calcium homeostasis, and disturbance of tubular cell polarity, and are thought to be linked to oxidative stress.

Affected Organisms

Humans and other mammals

Biotransformation

Not metabolized.

Half Life

1 hour

Protein Binding

Plasma protein binding is low, weak, and transient.

Elimination

Gadobenate ion is eliminated predominately via the kidneys, with 78% to 96% of an administered dose recovered in the urine.

Clearance

* 0.093 +/- 0.010 L/hr/kg [healthy male subjects receiving 3 single-dose IV administration with doses from 0.005-0.4 mmol/kg]

References

• de Haen C, Cabrini M, Akhnana L, Ratti D, Calabi L, Gozzini L: Gadobenate dimeglumine 0.5 M solution for injection (MultiHance) pharmaceutical formulation and physicochemical properties of a new magnetic resonance imaging contrast medium. J Comput Assist Tomogr. 1999 Nov;23 Suppl 1:S161-8. [Pubmed]

• Morana G, Salviato E, Guarise A: Contrast agents for hepatic MRI. Cancer Imaging. 2007 Oct 1;7 Spec No A:S24-7. [Pubmed]

• Vogl TJ, Pegios W, McMahon C, Balzer J, Waitzinger J, Pirovano G, Lissner J: Gadobenate dimeglumine--a new contrast agent for MR imaging: preliminary evaluation in healthy volunteers. AJR Am J Roentgenol. 1992 Apr;158(4):887-92. [Pubmed]

• Kirchin MA, Pirovano GP, Spinazzi A: Gadobenate dimeglumine (Gd-BOPTA). An overview. Invest Radiol. 1998 Nov;33(11):798-809. [Pubmed]

• Clement O, Siauve N, Cuenod CA, Vuillemin-Bodaghi V, Leconte I, Frija G: Mechanisms of action of liver contrast agents: impact for clinical use. J Comput Assist Tomogr. 1999 Nov;23 Suppl 1:S45-52. [Pubmed]

Molecule Details

References

PubChem Literature

From Data Sources

• Kirchin MA, Pirovano GP, Spinazzi A: Gadobenate dimeglumine (Gd-BOPTA). An overview. Invest Radiol. 1998 Nov;33(11):798-809. Pubmed

• Morana G, Salviato E, Guarise A: Contrast agents for hepatic MRI. Cancer Imaging. 2007 Oct 1;7 Spec No A:S24-7. Pubmed

References

Bioactivity

PubChem BioAssay

Bioactivity

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General Information

Calculated Properties

• RDKit

• JChem

Data Source

• Academic Data

Names and Identifiers

• IUPAC Traditional name

• Brand Name

• IUPAC name

• Synonyms

Registration numbers

• PubChem SID

• PubChem CID

• CAS Number

• DrugBank

• PubChem Literature

• From Data Sources

Bioactivity

• PubChem BioAssay

IUPAC Traditional name

gadolinium(3+) bis(N-methyl-D(-)-glucamine) 8-(carboxylatomethyl)-5,11-bis(carboxymethyl)-1-phenyl-2-oxa-5,8,11-triazatridecane-4,13-dioate

Brand Name

Multihance MultipackGd-BOPTAGd-BOPTA/DimegMultihance

IUPAC name

gadolinium(3+) ion bis((2R,3R,4R,5S)-6-(methylamino)hexane-1,2,3,4,5-pentol) 8-(carboxylatomethyl)-5,11-bis(carboxymethyl)-1-phenyl-2-oxa-5,8,11-triazatridecane-4,13-dioate

Synonyms

Gadobenate DimeglumineGadobenic acid

PubChem SID

46506805160964086

CAS Number

113662-23-0

From Data Sources

• Kirchin MA, Pirovano GP, Spinazzi A: Gadobenate dimeglumine (Gd-BOPTA). An overview. Invest Radiol. 1998 Nov;33(11):798-809. Pubmed

• Morana G, Salviato E, Guarise A: Contrast agents for hepatic MRI. Cancer Imaging. 2007 Oct 1;7 Spec No A:S24-7. Pubmed

DrugBank

DB00743

Drug Groups

approved

Description

Indication

Pharmacology

Toxicity

Affected Organisms

Humans and other mammals

Biotransformation

Not metabolized.

Half Life

1 hour

Protein Binding

Plasma protein binding is low, weak, and transient.

Elimination

Gadobenate ion is eliminated predominately via the kidneys, with 78% to 96% of an administered dose recovered in the urine.

Clearance

* 0.093 +/- 0.010 L/hr/kg [healthy male subjects receiving 3 single-dose IV administration with doses from 0.005-0.4 mmol/kg]

References

• Morana G, Salviato E, Guarise A: Contrast agents for hepatic MRI. Cancer Imaging. 2007 Oct 1;7 Spec No A:S24-7. [Pubmed]

• Kirchin MA, Pirovano GP, Spinazzi A: Gadobenate dimeglumine (Gd-BOPTA). An overview. Invest Radiol. 1998 Nov;33(11):798-809. [Pubmed]

Molecule

ID:623