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{{Short description|Complex of gadolinium by a chelating agent derived from DTPA}}
{{Drugbox
{{Drugbox
| Verifiedfields = changed
| IUPAC_name =
| Watchedfields = changed
| image =
| verifiedrevid = 477395679
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| CAS_number =
| image = Structure of Gadobenic acid.png
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| ATC_prefix = V08
| USAN = gadobenate dimeglumine
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| ATC_suffix = CA08

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| PubChem = 105124
<!--Clinical data-->
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| DrugBank =
| tradename = Multihance
| chemical_formula = C22H28GdN3O11
| Drugs.com = {{drugs.com|ppa|gadobenate-dimeglumine}}
| molecular_weight = 667.72122
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| pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X -->
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| bioavailability =
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| pregnancy_category =
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| protein_bound =
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| routes_of_administration =
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| metabolism =
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| ATC_prefix = V08
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| elimination_half-life =
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| ATC_suffix = CA08
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| excretion =

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| pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X -->
| pregnancy_US = <!-- A / B / C / D / X -->
| legal_AU = <!-- S2, S3, S4, S5, S6, S7, S8, S9 or Unscheduled-->
| legal_CA = Rx-only
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| pregnancy_category=
| 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_AU = <!-- S2, S3, S4, S5, S6, S7, S8, S9 or Unscheduled-->
| legal_UK = POM
| legal_CA = <!-- Schedule I, II, III, IV, V, VI, VII, VIII -->
| 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_UK = <!-- GSL, P, POM, CD, or Class A, B, C -->
| legal_US = <!-- OTC / Rx-only / Schedule I, II, III, IV, V -->
| 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 =
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<!--Pharmacokinetic data-->
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<!--Identifiers-->
| CAS_number_Ref = {{cascite|changed|??}}
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| CAS_number = 113662-23-0
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| PubChem = 105124
| DrugBank_Ref = {{drugbankcite|changed|drugbank}}
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| DrugBank = DB00743
| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}
| ChemSpiderID = 94843
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 15G12L5X8K
| KEGG_Ref = {{keggcite|correct|kegg}}
| 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}}
| 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|changed|chemspider}}
| StdInChIKey = MXZROTBGJUUXID-UHFFFAOYSA-K
}}
}}
'''Gadobenic acid''' is a molecule used as a [[contrast medium]].


'''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>
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{{pharmacology-stub}}

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==
{{reflist}}

{{Contrast media}}
{{Contrast media}}
{{Portal bar | Medicine}}

[[Category:MRI contrast agents]]
[[Category:Organogadolinium compounds]]


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Latest revision as of 06:01, 1 April 2024

Gadobenic acid
Clinical data
Trade namesMultihance
Other namesgadobenate dimeglumine (USAN US)
AHFS/Drugs.comProfessional Drug Facts
ATC code
Legal status
Legal status
Identifiers
  • dihydrogen [(±)-4-carboxy-5,8,11-tris(carboxymethyl)-1-phenyl-2-oxa-5,8,11-triazatridecan-13-oato(5−)]gadolinate(2−).
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC22H28GdN3O11
Molar mass667.73 g·mol−1
3D model (JSmol)
  • [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=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 ☒N
  • Key:MXZROTBGJUUXID-UHFFFAOYSA-K ☒N
 ☒NcheckY (what is this?)  (verify)

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

[edit]
  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.
  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.
  5. ^ 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.


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