Deaminooxytocin

Title: Deaminooxytocin
CAS Registry Number: 113-78-0
CAS Name: 1-(3-Mercaptopropanoic acid)oxytocin
Additional Names: demoxytocin; desaminooxytocin
Manufacturers' Codes: ODA-914
Trademarks: Sandopart (Novartis)
Molecular Formula: C43H65N11O12S2
Molecular Weight: 992.17
Percent Composition: C 52.05%, H 6.60%, N 15.53%, O 19.35%, S 6.46%
Literature 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).
Derivative Type: L-Isomer
Properties: White plate-like crystals from water, mp 179° (Ferrier); 182-183° (Takashima). For amorphous powder; [a]D20 -88.3° (Ferrier); [a]D21 -107° (Hope); [a]D25 -95.1° (Takashima); all (c = 0.5 in 1N acetic acid). Anhydrous form is very hygroscopic.
Melting point: mp 179° (Ferrier); 182-183° (Takashima)
Optical Rotation: [a]D20 -88.3° (Ferrier); [a]D21 -107° (Hope); [a]D25 -95.1° (Takashima)
Derivative Type: D-Isomer
Properties: White, fluffy powder, [a]D20 +104° (c = 0.5 in 1N acetic acid).
Optical Rotation: [a]D20 +104° (c = 0.5 in 1N acetic acid)
Therap-Cat: Oxytocic.
Keywords: Oxytocic.
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