CAS No 24305-27-9 , Protirelin

Title: TRH
CAS Registry Number: 24305-27-9
CAS Name: 5-Oxo-L-prolyl-L-histidyl-L-prolinamide
Synonyms: thyrotropin-releasing factor; thyrotropin releasing hormone; TRF; protirelin; lopremone (rescinded USAN); TSH-releasing factor; pyroglutamylhistidylprolinamide; thyroliberin
Trademarks: Antepan (Henning); Stimu-TSH (HMR); Thypinone (Abbott); Thyrefact (HMR)
Molecular Formula: C16H22N6O4
Molecular Weight: 362.38
Percent Composition: C 53.03%, H 6.12%, N 23.19%, O 17.66%
Literature References: A hypothalamic neurohormone which stimulates the release and synthesis of TSH, q.v., from the anterior pituitary via the hypophyseal portal system; the first of the hypothalamic regulatory hormones to be isolated, characterized, and synthesized. Isoln from bovine hypothalami: Schreiber et al., Experientia 18, 338 (1962); Schally et al., Endocrinology 78, 726 (1966). Purification from ovine hypothalami: Guillemin et al., C.R. Seances Acad. Sci. Ser. D 262, 2278 (1966). Isoln from porcine hypothalami and properties: Schally et al., Biochem. Biophys. Res. Commun. 25, 165 (1966); Schally et al., J. Biol. Chem. 244, 4077 (1969). Structural studies: Folkers et al., Biochem. Biophys. Res. Commun. 37, 123 (1969); Burgus et al., C.R. Seances Acad. Sci. Ser. D 269, 226 (1969). Identity of isolated TRH with synthetic tripeptide: Burgus et al., ibid. 1870; Bowers et al., Endocrinology 86, 573, 1143 (1970). Solubility: Burgus et al., Experientia 23, 417 (1967). Synthesis: Flouret, J. Med. Chem. 13, 843 (1970); Chang et al., ibid. 14, 481 (1971); E. Gross et al., Angew. Chem. Int. Ed. 12, 664 (1972); P. G. Pietta et al., J. Org. Chem. 39, 44 (1974). Review of synthetic methods: Rivier, Methods Enzymol. 37, 408 (1975). TRH is also believed to induce the secretion of the pituitary lactogenic hormone, prolactin, q.v.: Tasjian et al., Biochem. Biophys. Res. Commun. 43, 516 (1971); Bowers et al., ibid. 51, 512 (1973). It has been shown to block and reverse leukotriene-induced hypotension in the unanesthetized guinea pig: W. E. Lux et al., Nature 302, 822 (1983). Clinical studies: Hershman, N. Engl. J. Med. 290, 886 (1974). Reviews of TRH and other hypothalamic releasing hormones: Schally et al., Recent Prog. Horm. Res. 24, 497 (1968); Burgus, Guillemin, Annu. Rev. Biochem. 39, 499 (1970); Polypeptide Hormones, R. F. Beers, E. G. Bassett, Eds. (Raven Press, New York, 1980) pp 165-278.
Properties: Purified TRH is partially sol in chloroform, highly sol in absolute methanol. Completely insol in pyridine. Inactivated by diazotized sulfanilic acid (Pauly reagent) and by plasma, serum, or whole blood in vitro. Resists inactivation by proteolytic enzymes.
 
Derivative Type: Tartrate
CAS Registry Number: 54974-54-8
Trademarks: Irtonin (Takeda); Xantium (Cyanamid)
Line Formula: C16H22N6O4.xC4H6O6
 
Therap-Cat: Prohormone.
Keywords: Thyrotropic Hormone.