6762. Octreotide

Nomenclature

CAS number: 83150-76-9
d-Phenylalanyl-l-cysteinyl-l-phenylalanyl-d-tryptophyl-l-lysyl-l-threonyl-N-[(1R,2R)-2-hydroxy-1-(hydroxymethyl)propyl]-l-cysteinamide cyclic (2→7)-disulfide; 1,2-dithia-5,8,11,14,17-pentaazacycloeicosane cyclic peptide deriv; SMS-201-995.
C49H66N10O10S2; mol wt 1019.24.
C 57.74%, H 6.53%, N 13.74%, O 15.70%, S 6.29%.

Description and references

Octapeptide analog of somatostatin, q.v. Prepn: W. Bauer, J. Pless, EP 29579; eidem, US 4395403 (1981, 1983 both to Sandoz); and pharmacology: W. Bauer et al., Life Sci. 31, 1133 (1982). Opiate antagonist properties: R. Maurer et al., Proc. Natl. Acad. Sci. USA 79, 4815 (1982). HPLC determn in pharmaceutical formulations: N. Kyaterekera et al., J. Pharm. Biomed. Anal. 21, 327 (1999). Inhibitory effect on human gastroenteropancreatic hormone secretion: M. E. Kraenzlin et al., Experientia 41, 738 (1985). Endocrine profile in humans: E. del Pozo et al., Acta Endocrinol. 111, 433 (1986). Clinical evaluation in acromegaly: G. Plewe et al., Lancet 2, 782 (1984); in autonomic neuropathy: R. D. Hoeldtke et al., ibid. 2, 602 (1986). Symposium on chemistry, pharmacology and clinical trials: Scand. J. Gastroenterol. 21, Suppl. 119, 1-274 (1986); on clinical evaluation in gastrointestinal endocrine tumors: Am. J. Med. 82, Suppl. 5B, 1-99 (1987). Review of therapeutic potential in liver tumors: E. A. Kouroumalis, Chemotherapy (Basel) 47, Suppl. 2, 150-161 (2001); of clinical use of long-acting release formulation in acromegaly: K. McKeage et al., Drugs 63, 2473-2499 (2003).

Chemical structure

Derivative

Acetate.

Nomenclature

CAS number: 79517-01-4
SMS-201-995ac; Longastatin (Italfarmaco); Sandostatin (Novartis).
C49H66N10O10S2.xC2H4O2.

Properties

[α]D20 -42° (c = 0.5 in 95% acetic acid).

Therapeutic Category

Gastric antisecretory agent. Treatment of acromegaly.

Keywords

Gastric Secretion Inhibitor; Growth Hormone Antagonist/Inhibitor; Somatostatin Analog