Gadobenic acid: Difference between revisions

Gadobenic acid
Clinical data
Trade names	Multihance
Other names	gadobenate dimeglumine (USAN US)
AHFS/Drugs.com	Professional Drug Facts
ATC code	V08CA08 (WHO) ;
Legal status
Legal status	CA: ℞-only; UK: POM (Prescription only); US: ℞-only;
Identifiers
	IUPAC name dihydrogen [(±)-4-carboxy-5,8,11-tris(carboxymethyl)-1-phenyl-2-oxa-5,8,11-triazatridecan-13-oato(5−)]gadolinate(2−).;
CAS Number	113662-23-0 ;
PubChem CID	105124;
DrugBank	DB00743 ;
ChemSpider	94843 ;
UNII	15G12L5X8K;
KEGG	D08018 ;
ChEMBL	ChEMBL1200571 ;
CompTox Dashboard (EPA)	DTXSID00921145 ;
Chemical and physical data
Formula	C22H28GdN3O11
Molar mass	667.73 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES [H+].[H+].[Gd+3].[O-]C(=O)CN(CC([O-])=O)CCN(CC([O-])=O)CCN(CC([O-])=O)C(C([O-])=O)COCc1ccccc1;
	InChI InChI=1S/C22H31N3O11.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;/h1-5,17H,6-15H2,(H,26,27)(H,28,29)(H,30,31)(H,32,33)(H,34,35);/q;+3/p-3 ; Key:MXZROTBGJUUXID-UHFFFAOYSA-K ;
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Gadobenic acid (INN, brand name Multihance) is a complex of gadolinium with the ligand BOPTA. In the form of the methylglucamine salt meglumine gadobenate (INNm) or gadobenate dimeglumine (USAN), it is used as a gadolinium-based MRI contrast medium.^[4]

BOPTA is a derivative of DTPA in which one terminal carboxyl group, –C(O)OH is replaced by -C–O–CH₂C₆H₅. Thus gadobenic acid is closely related to gadopentetic acid. BOPTA itself was first synthesized in 1995.^[5] In the "gadobenate" ion gadolinium ion is 9-coordinate with BOPTA acting as an 8-coordinating ligand. The ninth position is occupied by a water molecule, which exchanges rapidly with water molecules in the immediate vicinity of the strongly paramagnetic complex, providing a mechanism for MRI contrast enhancement. ¹³⁹La NMR studies on the diamagnetic La-BOPTA²⁻ complex suggest that the Gd complex maintains in solution the same kind of coordination as found, by X-ray crystallography, in the solid state for Gd-BOPTA disodium salt.^[5]

References

^ "Product monograph brand safety updates". Health Canada. 7 July 2016. Retrieved 1 April 2024.
^ "Multihance, 0.5 M solution for injection - Summary of Product Characteristics (SmPC)". (emc). 14 August 2019. Retrieved 29 August 2021.
^ "Multihance- gadobenate dimeglumine injection, solution". DailyMed. Retrieved 29 August 2021.
^ Sweetman, Sean C., ed. (2009). "Contrast Media". Martindale: The Complete Drug Reference (36th ed.). London: Pharmaceutical Press. p. 1478. ISBN 978-0-85369-840-1.
^ ^a ^b Uggeri F, Aime S, Anelli PL, Botta M, Brocchetta M, de Haeen C, Ermondi G, Grandi M, Paoli P (1995). "Novel Contrast Agents for Magnetic Resonance Imaging. Synthesis and Characterization of the Ligand BOPTA and Its Ln(III) Complexes (Ln = Gd, La, Lu). X-ray Structure of Disodium (TPS-9-145337286-C-S)-[4-Carboxy-5,8,11-tris(carboxymethyl)-1-phenyl-2-oxa- 5,8,11-triazatridecan-13-oato(5-)]gadolinate(2-) in a Mixture with Its Enantiomer". Inorganic Chemistry. 34 (3): 633–643. doi:10.1021/ic00107a017. ISSN 0020-1669.

This pharmacology-related article is a stub. You can help Wikipedia by expanding it.

[1] "Product monograph brand safety updates". Health Canada. 7 July 2016. Retrieved 1 April 2024.

[2] "Multihance, 0.5 M solution for injection - Summary of Product Characteristics (SmPC)". (emc). 14 August 2019. Retrieved 29 August 2021.

[3] "Multihance- gadobenate dimeglumine injection, solution". DailyMed. Retrieved 29 August 2021.

[Martindale-4] Sweetman, Sean C., ed. (2009). "Contrast Media". Martindale: The Complete Drug Reference (36th ed.). London: Pharmaceutical Press. p. 1478. ISBN 978-0-85369-840-1.

[UggeriAime1995-5] Uggeri F, Aime S, Anelli PL, Botta M, Brocchetta M, de Haeen C, Ermondi G, Grandi M, Paoli P (1995). "Novel Contrast Agents for Magnetic Resonance Imaging. Synthesis and Characterization of the Ligand BOPTA and Its Ln(III) Complexes (Ln = Gd, La, Lu). X-ray Structure of Disodium (TPS-9-145337286-C-S)-[4-Carboxy-5,8,11-tris(carboxymethyl)-1-phenyl-2-oxa- 5,8,11-triazatridecan-13-oato(5-)]gadolinate(2-) in a Mixture with Its Enantiomer". Inorganic Chemistry. 34 (3): 633–643. doi:10.1021/ic00107a017. ISSN 0020-1669.

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+{{Short description|Complex of gadolinium by a chelating agent derived from DTPA}}
 {{Drugbox
 | Verifiedfields = changed
+| Watchedfields = changed
-| verifiedrevid = 396139572
+| verifiedrevid = 477395679
-| IUPAC_name        = 2-[2-[2-[bis(2-oxido-2-oxoethyl)amino]ethyl-(2-oxido-2-oxoethyl)amino]ethyl-
+| image = Structure of Gadobenic acid.png
-(2-oxido-2-oxoethyl)amino]-3-phenylmethoxypropanoate;
+| USAN = gadobenate dimeglumine
-gadolinium(+3) cation
-| image             = Gadobenic acid.png
+<!--Clinical data-->
-| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
+| tradename = Multihance
+| Drugs.com = {{drugs.com|ppa|gadobenate-dimeglumine}}
+| pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X -->
+| pregnancy_category =
+| routes_of_administration =
+| ATC_prefix = V08
+| ATC_suffix = CA08
+| legal_AU = <!-- S2, S3, S4, S5, S6, S7, S8, S9 or Unscheduled-->
+| legal_CA = Rx-only
+| legal_CA_comment = <ref>{{cite web  | title=Product monograph brand safety updates | website=[[Health Canada]] | date=7 July 2016 | url=https://www.canada.ca/en/health-canada/services/drugs-health-products/drug-products/drug-product-database/label-safety-assessment-update/product-monograph-brand-safety-updates.html | access-date=1 April 2024}}</ref>
+| legal_UK = POM
+| legal_UK_comment = <ref>{{cite web | title=Multihance, 0.5 M solution for injection - Summary of Product Characteristics (SmPC) | website=(emc) | date=14 August 2019 | url=https://www.medicines.org.uk/emc/product/1388/smpc | access-date=29 August 2021}}</ref>
+| legal_US = Rx-only
+| legal_US_comment = <ref>{{cite web | title=Multihance- gadobenate dimeglumine injection, solution | website=DailyMed | url=https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=59077a3e-5f03-4342-ae24-856267545631 | access-date=29 August 2021}}</ref>
+| legal_status =
+<!--Pharmacokinetic data-->
+| bioavailability =
+| protein_bound =
+| metabolism =
+| elimination_half-life =
+| excretion =
+<!--Identifiers-->
+| CAS_number_Ref = {{cascite|changed|??}}
+| CAS_number = 113662-23-0
+| PubChem = 105124
+| DrugBank_Ref = {{drugbankcite|changed|drugbank}}
+| DrugBank = DB00743
+| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}
 | ChemSpiderID = 94843
 | UNII_Ref = {{fdacite|correct|FDA}}
 | UNII = 15G12L5X8K
+| KEGG_Ref = {{keggcite|correct|kegg}}
-| InChI = 1/C22H31N3O11.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;/h1-5,17H,6-15H2,(H,26,27)(H,28,29)(H,30,31)(H,32,33)(H,34,35);/q;+3/p-3
+| KEGG = D08018
+| ChEMBL_Ref = {{ebicite|changed|EBI}}
+| ChEMBL = 1200571
+<!--Chemical data-->
+| IUPAC_name = dihydrogen [(±)-4-carboxy-5,8,11-tris(carboxymethyl)-1-phenyl-2-oxa-5,8,11-triazatridecan-13-oato(5−)]gadolinate(2−).
+| C=22 | H=28 | Gd=1 | N=3 | O=11
 | smiles = [H+].[H+].[Gd+3].[O-]C(=O)CN(CC([O-])=O)CCN(CC([O-])=O)CCN(CC([O-])=O)C(C([O-])=O)COCc1ccccc1
+| StdInChI_Ref = {{stdinchicite|changed|chemspider}}
-| InChIKey = MXZROTBGJUUXID-DFZHHIFOAJ
-| CASNo_Ref = {{cascite|correct|CAS}}
-| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
 | StdInChI = 1S/C22H31N3O11.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;/h1-5,17H,6-15H2,(H,26,27)(H,28,29)(H,30,31)(H,32,33)(H,34,35);/q;+3/p-3
-| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
+| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}
 | StdInChIKey = MXZROTBGJUUXID-UHFFFAOYSA-K
-| CAS_number        = 113662-23-0
-| ATC_prefix        = V08
-| ATC_suffix        = CA08
-| PubChem           = 105124
-| DrugBank          =
-| KEGG_Ref = {{keggcite|changed|kegg}}
-| KEGG = D08018
-| C=22|H=28|Gd=1|N=3|O=11
-| molecular_weight  = 667.72 g/mol
-| bioavailability   =
-| protein_bound     =
-| metabolism        =
-| elimination_half-life =
-| excretion         =
-| pregnancy_AU      =  <!-- A / B1 / B2 / B3 / C / D / X -->
-| pregnancy_US      =  <!-- A / B            / C / D / X -->
-| pregnancy_category=
-| legal_AU =  <!-- S2, S3, S4, S5, S6, S7, S8, S9 or Unscheduled-->
-| legal_CA =  <!-- Schedule I, II, III, IV, V, VI, VII, VIII -->
-| legal_UK =  <!-- GSL, P, POM, CD, or Class A, B, C -->
-| legal_US =  <!-- OTC / Rx-only / Schedule I, II, III, IV, V -->
-| legal_status      =
-| routes_of_administration =
 }}
+'''Gadobenic acid''' ([[International Nonproprietary Name|INN]], brand name '''Multihance''') is a complex of [[gadolinium]] with the [[ligand]] BOPTA. In the form of the [[meglumine|methylglucamine]] salt '''meglumine gadobenate''' ([[International Nonproprietary Name|INNm]]) or '''gadobenate dimeglumine''' ([[United States Adopted Name|USAN]]), it is used as a [[gadolinium-based MRI contrast medium]].<ref name=Martindale>{{Cite book|editor=Sweetman, Sean C. |chapter=Contrast Media|title=[[Martindale: The Complete Drug Reference]] |edition=36th |year=2009 |pages=1478|publisher=Pharmaceutical Press |location=London|isbn=978-0-85369-840-1}}</ref>
-'''Gadobenic acid''' is a molecule used as a [[contrast medium]]. A common formulation of it is ''gadobenate dimeglumine''.
+BOPTA is a derivative of [[DTPA]] in which one terminal [[Carboxylic acid|carboxyl group]], –C(O)OH is replaced by -C–O–CH<sub>2</sub>C<sub>6</sub>H<sub>5</sub>. Thus gadobenic acid is closely related to [[gadopentetic acid]]. BOPTA itself was first synthesized in 1995.<ref name="UggeriAime1995">{{cite journal|vauthors = Uggeri F, Aime S, Anelli PL, Botta M, Brocchetta M, de Haeen C, Ermondi G, Grandi M, Paoli P|title=Novel Contrast Agents for Magnetic Resonance Imaging. Synthesis and Characterization of the Ligand BOPTA and Its Ln(III) Complexes (Ln = Gd, La, Lu). X-ray Structure of Disodium (TPS-9-145337286-C-S)-[4-Carboxy-5,8,11-tris(carboxymethyl)-1-phenyl-2-oxa- 5,8,11-triazatridecan-13-oato(5-)]gadolinate(2-) in a Mixture with Its Enantiomer|journal = Inorganic Chemistry|volume = 34|issue = 3|year = 1995|pages = 633–643|issn = 0020-1669|doi = 10.1021/ic00107a017}}</ref> In the "gadobenate" ion gadolinium ion is 9-[[Coordinate covalent bond|coordinate]] with BOPTA acting as an 8-coordinating ligand. The ninth position is occupied by a water molecule, which exchanges rapidly with water molecules in the immediate vicinity of the strongly [[paramagnetic]] complex, providing a mechanism for [[Magnetic resonance imaging|MRI contrast enhancement]]. <sup>139</sup>La NMR studies on the diamagnetic La-BOPTA<sup>2−</sup> complex suggest that the Gd complex maintains in solution the same kind of [[Coordination complex|coordination]] as found, by [[X-ray crystallography]], in the [[Solid-state chemistry|solid state]] for Gd-BOPTA disodium salt.<ref name="UggeriAime1995"/>
+==References==
-{{pharmacology-stub}}
+{{reflist}}
 {{Contrast media}}
+{{Portal bar | Medicine}}
-[[Category:Radiocontrast agents]]
+[[Category:MRI contrast agents]]
-[[Category:Gadolinium compounds]]
+[[Category:Organogadolinium compounds]]
+{{pharmacology-stub}}