gadolinium(3+) ion bis((2R,3R,4R,5S)-6-(methylamino)hexane-1,2,3,4,5-pentol) 2-[bis({2-[(carboxylatomethyl)(carboxymethyl)amino]ethyl})amino]acetate

• ChemBase ID: 668
• Molecular Formular: C28H54GdN5O20
• Molecular Mass: 937.99986
• Monoisotopic Mass: 938.26031715
• 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-]C(=O)CN(CCN(CC(=O)O)CC(=O)[O-])CCN(CC(=O)O)CC(=O)[O-]
• Canonical SMILES: [O-]C(=O)CN(CCN(CC(=O)O)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]
• InChI: InChI=1S/C14H23N3O10.2C7H17NO5.Gd/c18-10(19)5-15(1-3-16(6-11(20)21)7-12(22)23)2-4-17(8-13(24)25)9-14(26)27;2*1-8-2-4(10)6(12)7(13)5(11)3-9;/h1-9H2,(H,18,19)(H,20,21)(H,22,23)(H,24,25)(H,26,27);2*4-13H,2-3H2,1H3;/q;;;+3/p-3/t;2*4-,5+,6+,7+;/m.00./s1
• InChIKey: LGMLJQFQKXPRGA-VPVMAENOSA-K

NAMES AND DATABASE IDS

Names

• IUPAC name: gadolinium(3+) ion bis((2R,3R,4R,5S)-6-(methylamino)hexane-1,2,3,4,5-pentol) 2-[bis({2-[(carboxylatomethyl)(carboxymethyl)amino]ethyl})amino]acetate
• IUPAC Traditional name: gadolinium(3+) H2dtpa bis(N-methyl-D(-)-glucamine)
• Brand Name: Gadopentetic Acid Dimeglumine Salt; Magnevist
• Synonyms: Gadopentetate dimeglumine

Database IDs

• CAS Number: 86050-77-3
• PubChem SID: 160964131; 46504878
• PubChem CID: 55466

CALCULATED PROPERTIES

• Acid pKa: 0.093708016
• H Acceptors: 13
• H Donor: 2
• LogD (pH = 5.5): -12.340177
• LogD (pH = 7.4): -17.896065
• Log P: -6.3702765
• Molar Refractivity: 118.9606 cm^3
• Polarizability: 33.801125 Å^3
• Polar Surface Area: 204.71 Å^2
• Rotatable Bonds: 28
• Lipinski's Rule of Five: false

DETAILS

DrugBank - DB00789

• Drug Groups: approved
• Description: A complex of gadolinium with a chelating agent, diethylenetriamine penta-acetic acid (DTPA see pentetic acid), that is given to enhance the image in cranial and spinal MRIs. (From Martindale, The Extra Pharmacopoeia, 30th ed, p706)
• Indication: For use with magnetic resonance imaging (MRI) in adults, and pediatric patients (2 years of age and older) to visualize lesions with abnormal vascularity in the brain (intracranial lesions), spine and associated tissues as well as lesions with abnormal vascularity in the head and neck. Also used to facilitate the visualization of lesions with abnormal vascularity in the body (excluding the heart).
• Affected Organisms: Humans and other mammals
• Biotransformation: No detectable biotransformation or decomposition.
• Half Life: Distribution half life 12 minutes, elimination half 100 minutes
• Elimination: Gadopentetate is exclusively eliminated in the urine with 83 ± 14% (mean ± SD) of the dose excreted within 6 hours and 91 ± 13% (mean ± SD) by 24 hours, post-injection.
• Distribution: * 266 ± 43 mL/kg
• Clearance: * 1.94 +/- 0.28 mL/min/kg [Normal subjects]
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