3513. Edotreotide

Nomenclature

CAS number: 204318-14-9
N-[[4,7,10-Tris(carboxymethyl)-1,4,7,10-tetraazacyclododec-1-yl]acetyl]-d-phenylalanyl-l-cysteinyl-l-tyrosyl-d-tryptophyl-l-lysyl-l-threonyl-N-[(1R,2R)-2-hydroxy-1-(hydroxymethyl)propyl]-l-cysteinamide cyclic(2→7)-disulfide; (DOTA d-Phe1,Tyr3)octreotide; DOTATOC; SMT-487.
C65H92N14O18S2; mol wt 1421.64.
C 54.92%, H 6.52%, N 13.79%, O 20.26%, S 4.51%.

Description and references

Octapeptide analog of somatostatin, q.v. Designed for targeted radiotherapy vs somatostatin receptor-expressing tumors. Prepn: R. Albert et al., EP 714911; eidem, US 6183721 (1996, 2001 both to Novartis); idem, et al., Bioorg. Med. Chem. Lett. 8, 1207 (1998). Solution-phase synthesis: M. Schottelius et al., Tetrahedron Lett. 44, 2393 (2003). In vivo antineoplastic activity: B. Stolz et al., Eur. J. Nucl. Med. 25, 668 (1998). Receptor binding study: J. C. Reubi et al., ibid. 27, 273 (2000). Clinical pharmacokinetics: F. Jamar et al., Eur. J. Nucl. Med. Mol. Imaging 30, 510 (2003). Clinical evaluation in neuroendocrine tumors: C. Waldherr et al., J. Nucl. Med. 43, 610 (2002).

Chemical structure

Properties

Prepd as acetate. [α]22D -14.75° (c = 0.52 in 95% acetic acid).

Derivative

90Y chelate.

Nomenclature

CAS number: 322407-70-5
90Y-SMT-487; OctreoTher (Novartis).

Therapeutic Category

90Y chelate as antineoplastic.

Keywords

Somatostatin Analog

Edotreotide 90Y Chelate: Antineoplastic (Radiation Source)