gadolinium(3+) ion trisodium 2-{[1-({2-[bis(carboxylatomethyl)amino]ethyl}(carboxylatomethyl)amino)-3-[(4,4-diphenylcyclohexyl phosphonato)oxy]propan-2-yl](carboxylatomethyl)amino}acetate hydrate

• ChemBase ID: 4442
• Molecular Formular: C33H40GdN3Na3O15P
• Molecular Mass: 975.874871
• Monoisotopic Mass: 976.11311507
• SMILES: C1CC(CCC1OP(=O)([O-])OCC(CN(CCN(CC(=O)[O-])CC(=O)[O-])CC(=O)[O-])N(CC(=O)[O-])CC(=O)[O-])(c1ccccc1)c1ccccc1.O.[Na+].[Na+].[Na+].[Gd+3]
• Canonical SMILES: [O-]C(=O)CN(C(CN(CC(=O)[O-])CCN(CC(=O)[O-])CC(=O)[O-])COP(=O)(OC1CCC(CC1)(c1ccccc1)c1ccccc1)[O-])CC(=O)[O-].O.[Na+].[Na+].[Na+].[Gd+3]
• InChI: InChI=1S/C33H44N3O14P.Gd.3Na.H2O/c37-28(38)18-34(15-16-35(19-29(39)40)20-30(41)42)17-26(36(21-31(43)44)22-32(45)46)23-49-51(47,48)50-27-11-13-33(14-12-27,24-7-3-1-4-8-24)25-9-5-2-6-10-25;;;;;/h1-10,26-27H,11-23H2,(H,37,38)(H,39,40)(H,41,42)(H,43,44)(H,45,46)(H,47,48);;;;;1H2/q;+3;3*+1;/p-6
• InChIKey: PIZALBORPSCYJU-UHFFFAOYSA-H

NAMES AND DATABASE IDS

Names

• IUPAC name: gadolinium(3+) ion trisodium 2-{[1-({2-[bis(carboxylatomethyl)amino]ethyl}(carboxylatomethyl)amino)-3-[(4,4-diphenylcyclohexyl phosphonato)oxy]propan-2-yl](carboxylatomethyl)amino}acetate hydrate
• IUPAC Traditional name: gadolinium(3+) tripotassium 2-{[1-({2-[bis(carboxylatomethyl)amino]ethyl}(carboxylatomethyl)amino)-3-[(4,4-diphenylcyclohexyl phosphonato)oxy]propan-2-yl](carboxylatomethyl)amino}acetate hydrate
• Brand Name: Vasovist
• Synonyms: Gadofosveset trisodium

Database IDs

• CAS Number: 193901-90-5
• PubChem SID: 160967874
• PubChem CID: 23724913

CALCULATED PROPERTIES

• Acid pKa: 0.7821476
• H Acceptors: 15
• H Donor: 0
• LogD (pH = 5.5): -9.864648
• LogD (pH = 7.4): -16.179766
• Log P: -1.1778207
• Molar Refractivity: 241.5531 cm^3
• Polarizability: 69.67652 Å^3
• Polar Surface Area: 268.96 Å^2
• Rotatable Bonds: 23
• Lipinski's Rule of Five: false

DETAILS

DrugBank - DB06705

• Drug Groups: approved
• Description: Gadofosveset trisodium is an intravenous contrast agent used with magnetic resonance angiography(MRA), which is a non-invasive way of imaging blood vessels. The agent allows for the vascular system to be imaged more clearly by the MRA. In this way, gadofosveset trisodium is used to help diagnose certain disorders of the heart and blood vessels.
• Indication: Gadofosveset trisodium is used as a contrast agent in magnetic resonance angiography (MRA) to evaluate aortoiliac occlusive disease (AIOD) in adults with known or suspected peripheral vascular disease.
• Pharmacology: In human studies, gadofosveset substantially shortened blood T1 values for up to 4 hours after intravenous bolus injection. Relaxivity in plasma was measured to be 33.4 to 45.7 mM^-1s^-1 (0.47 T) over the dose range of up to 0.05 mmol/kg.
• Toxicity: Gadolinium-based contrast agents increase the risk for nephrogenic systemic fibrosis (NSF) in patients with acute or chronic severe renal insufficiency (glomerular filtration rate < 30 mL/min/1.73m2).
• Affected Organisms: Humans and other mammals
• Biotransformation: Gadofosveset does not undergo measurable metabolism.
• Half Life: The mean half-life of the distribution phase is 0.48 ± 0.11 hours and the mean half-life of the elimination phase is 16.3 ± 2.6 hours.
• Protein Binding: At 0.05, 0.5, 1 and 4 hours after injection of 0.03 mmol/kg the plasma protein binding of gadofosveset ranges from 79.8 to 87.4%.
• Elimination: Gadofosveset is eliminated primarily in the urine with approximately 83.5% of an injected dose excreted in the urine over 14 days. Ninety-four percent (94%) of urinary excretion occurs in the first 72 hours. A small portion of gadofosveset dose is recovered in feces (approximately 4.7%).
• Distribution: 48 ± 16 mL/kg
• Clearance: 6.57 ± 0.97 mL/h/kg following the administration of 0.03 mmol/kg.
• External Links: Wikipedia; Drugs.com