Gadofosveset

Gadofosveset trisodium
Clinical data
Trade names	Vasovist, Ablavar
Routes of; administration	Intravenous
ATC code	V08CA11 (WHO) ;
Legal status
Legal status	US: WARNINGRx-only;
Identifiers
	IUPAC name Trisodium 2-{[(2R)-2-[bis(2-oxido-2-oxoethyl)amino]-3-[(4,4-diphenylcyclohexyl)oxy-oxidophosphoryl]oxypropyl]-[2-[bis(2-oxido-2-oxoethyl)amino]ethyl]amino}acetate;
CAS Number	211570-55-7 ; 193901-90-5 (anhydrous);
PubChem CID	158440;
DrugBank	DB06705;
ChemSpider	139381;
UNII	XM33Q67UVH;
KEGG	D08005 ;
Chemical and physical data
Formula	C33H40GdN3Na3O15P
Molar mass	975.88 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES [Gd+3].[Na+].[Na+].[Na+].[O-]C(=O)CN(CC([O-])=O)CCN(CC([O-])=O)C[C@@H](N(CC([O-])=O)CC([O-])=O)COP([O-])(=O)OC3CCC(c1ccccc1)(c2ccccc2)CC3.O;
	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/t26-;;;;;/m1...../s1; Key:PIZALBORPSCYJU-QSQMUHTISA-H;

Gadofosveset (trade names Vasovist, Ablavar) is a gadolinium-based MRI contrast agent. It was used as the trisodium salt monohydrate form.^[2]^[3] It acts as a blood pool agent by binding to human serum albumin. The manufacturer (Lantheus Medical) discontinued production in 2017 due to poor sales.^[4]

Gadofosveset consists of a gadolinium cation bound to the chelating agent fosveset. It facilitates high-resolution magnetic resonance angiography.^[5] Ferumoxytol (trade names Feraheme, Rienso), an intravenous iron-replacement therapy, has been shown to potentially be superior to gadofosveset as a blood pool agent for MR venography in pediatric patients.^[6]

References

^ "FDA-sourced list of all drugs with black box warnings (Use Download Full Results and View Query links.)". nctr-crs.fda.gov. FDA. Retrieved 22 Oct 2023.
^ DailyMed: Vasovist
^ Drugs.com: Ablavar
^ Bell D, Morgan M. "Gadofosveset trisodium". Radiopaedia. radiopaedia.org. Retrieved 2018-08-28.
^ Sabach AS, Bruno M, Kim D, Mulholland T, Lee L, Kaura S, Lim RP (June 2013). "Gadofosveset trisodium: abdominal and peripheral vascular applications". AJR. American Journal of Roentgenology. 200 (6): 1378–86. doi:10.2214/AJR.12.8991. PMID 23701079.
^ Shahrouki P, Khan SN, Yoshida T, Iskander PJ, Ghahremani S, Finn JP (March 2022). "High-resolution three‑dimensional contrast‑enhanced magnetic resonance venography in children: comparison of gadofosveset trisodium with ferumoxytol". Pediatric Radiology. 52 (3): 501–512. doi:10.1007/s00247-021-05225-2. PMC 8857136. PMID 34936018.

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[FDA-AllBoxedWarnings-1] "FDA-sourced list of all drugs with black box warnings (Use Download Full Results and View Query links.)". nctr-crs.fda.gov. FDA. Retrieved 22 Oct 2023.

[2] DailyMed: Vasovist

[3] Drugs.com: Ablavar

[4] Bell D, Morgan M. "Gadofosveset trisodium". Radiopaedia. radiopaedia.org. Retrieved 2018-08-28.

[pmid23701079-5] Sabach AS, Bruno M, Kim D, Mulholland T, Lee L, Kaura S, Lim RP (June 2013). "Gadofosveset trisodium: abdominal and peripheral vascular applications". AJR. American Journal of Roentgenology. 200 (6): 1378–86. doi:10.2214/AJR.12.8991. PMID 23701079.

[6] Shahrouki P, Khan SN, Yoshida T, Iskander PJ, Ghahremani S, Finn JP (March 2022). "High-resolution three‑dimensional contrast‑enhanced magnetic resonance venography in children: comparison of gadofosveset trisodium with ferumoxytol". Pediatric Radiology. 52 (3): 501–512. doi:10.1007/s00247-021-05225-2. PMC 8857136. PMID 34936018.

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Clinical data

Trade names	Vasovist, Ablavar
Routes of administration	Intravenous
ATC code	V08CA11 (WHO)
Legal status
Legal status	US: WARNING^[1]Rx-only
Identifiers
IUPAC name Trisodium 2-{[(2R)-2-[bis(2-oxido-2-oxoethyl)amino]-3-[(4,4-diphenylcyclohexyl)oxy-oxidophosphoryl]oxypropyl]-[2-[bis(2-oxido-2-oxoethyl)amino]ethyl]amino}acetate
CAS Number	211570-55-7^Y 193901-90-5 (anhydrous)
PubChem CID	158440
DrugBank	DB06705
ChemSpider	139381
UNII	XM33Q67UVH
KEGG	D08005^Y
Chemical and physical data
Formula	C₃₃H₄₀GdN₃Na₃O₁₅P
Molar mass	975.88 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES [Gd+3].[Na+].[Na+].[Na+].[O-]C(=O)CN(CC([O-])=O)CCN(CC([O-])=O)C[C@@H](N(CC([O-])=O)CC([O-])=O)COP([O-])(=O)OC3CCC(c1ccccc1)(c2ccccc2)CC3.O
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/t26-;;;;;/m1...../s1 Key:PIZALBORPSCYJU-QSQMUHTISA-H