4328. Gadoteridol

Nomenclature

CAS number: 120066-54-8
[10-(2-Hydroxypropyl)-1,4,7,10-tetraazacyclododecane-1,4,7-triacetato(3)-N1,N4,N7,N10,O1,O4,O7,O10]gadolinium; 10-(2-hydroxypropyl)-1,4,7,10-tetraazacyclododecane-1,4,7-triacetic acid gadolinium complex; gadolinium(III) 1,4,7-tris(carboxymethyl)-10-(2′-hydroxypropyl)-1,4,7,10-tetraazacyclododecane; Gd(HP-DO3A); SQ-32692.
C17H29GdN4O7; mol wt 558.68.
C 36.55%, H 5.23%, Gd 28.15%, N 10.03%, O 20.05%.

Description and references

Nonionic, low-osmolar paramagnetic gadolinium (III) chelate. Prepn: M. F. Tweedle et al., EP 292689; eidem, US 4885363 (1988, 1989 both to Squibb); D. D. Dischino et al., Inorg. Chem. 30, 1265 (1991). Biodistribution: P. Wedeking et al., Magn. Reson. Imaging 10, 641 (1992). RIA determn in biological fluids: M. D. Ogan et al., J. Pharm. Sci. 82, 475 (1993). Toxicological studies: R. A. Soltys, Invest. Radiol. 27, Suppl. 1, S7 (1992). Symposium on physicochemical properties, pharmacokinetics and clinical use in neurological disease: ibid. 1-63. Comprehensive description: K. Kumar et al., Anal. Profiles Drug Subs. Excip. 24, 209-241 (1996).

Chemical structure

Properties

White solid obtained as an aggregate clump of fine needle-like microcrystals from methanol/acetone, mp >225°. Hydrophilic. At pH 7, log P (octanol/water): 3.68; (butanol/water): 1.98. Soly (mg/ml): water 737, methanol 119, isopropanol 41, dimethylformamide 10.1, acetonitrile 6.1, methylene chloride 5.2, ethyl acetate 0.5, acetone 0.4, hexane 0.2, toluene 0.3. uv max (water): 274 nm (am 2.5).

Derivative

Gadoteridol injection.

Nomenclature

ProHance (BMS).

Properties

Osmolality (37°): 630 mOsM/kg water. Viscosity (cP): 2.0 (20°), 1.3 (37°). d25 1.140. LD50 in mice, rats (mmol/kg): 11-14, >10 i.v. (Soltys).

Therapeutic Category

Diagnostic aid (MRI contrast agent).

Keywords

Diagnostic Aid (MRI Contrast Agent)