2842. Deaminooxytocin

Nomenclature

CAS number: 113-78-0
1-(3-Mercaptopropanoic acid)oxytocin; demoxytocin; desaminooxytocin; ODA-914; Sandopart (Novartis).
C43H65N11O12S2; mol wt 992.17.
C 52.05%, H 6.60%, N 15.53%, O 19.35%, S 6.46%.

Description and references

Highly potent analog of the posterior pituitary hormone oxytocin, q.v., differing in structure at the 1 position where the free amino group in the half-cystine residue is replaced by hydrogen. Synthesis and biological activity: du Vigneaud et al., J. Biol. Chem. 235, P.C. 64 (1960); Hope et al., ibid. 237, 1563 (1962); Takashima et al., J. Am. Chem. Soc. 90, 1323 (1968). Isoln and purifn: Ferrier et al., J. Biol. Chem. 240, 4264 (1965). Structure-activity correlation: Jarvis, du Vigneaud, Science 143, 545 (1964). Synthesis of d-isomer: G. Flouret, V. du Vigneaud, J. Med. Chem. 14, 556 (1971). Crystal structure analysis: S. P. Wood et al., Science 232, 633 (1986). Pharmacology and comparison with oxytocin: Chan, du Vigneaud, Endocrinology 71, 977 (1962). Review: Adv. Exp. Med. Biol. vol. 2, 53-104 (1968).

Chemical structure

Derivative

l-Isomer.

Properties

White plate-like crystals from water, mp 179° (Ferrier); 182-183° (Takashima). For amorphous powder; [α]D20 -88.3° (Ferrier); [α]D21 -107° (Hope); [α]D25 -95.1° (Takashima); all (c = 0.5 in 1N acetic acid). Anhydrous form is very hygroscopic.

Derivative

d-Isomer.

Properties

White, fluffy powder, [α]D20 +104° (c = 0.5 in 1N acetic acid).

Therapeutic Category

Oxytocic.

Keywords

Oxytocic