9045. Taltirelin
Nomenclature
CAS number: 103300-74-9
N-[[(4S)-Hexahydro-1-methyl-2,6-dioxo-4-primidinyl]carbonyl]-l-histidyl-l-prolinamide; (S)-N-(1-methyl-4,5-dihydroorotyl)-l-histidyl-l-prolinamide. C17H23N7O5; mol wt 405.41.
C 50.36%, H 5.72%, N 24.18%, O 19.73%.
Description and references
Analog of thyrotropin releasing hormone TRH, q.v., with pronounced CNS activity. Prepn: H. Sugano et al., EP 168042; eidem, US 4665056 (1986, 1987 both to Tanabe Seiyaku): M. Suzuki et al., J. Med. Chem. 33, 2130 (1990). Radioimmunoassay determn in plasma and urine: S. Morikawa et al., J. Pharm. Biomed. Anal. 16, 1267 (1998). CNS pharmacology: M. Yamamura et al., Jpn. J. Pharmacol. 53, 451 (1990). Effect on motor neuron survival: Y. Iwasaki et al., Neurol. Res. 19, 613 (1997). Review of pharmacology, toxicology, and clinical trials: K. Kinoshita et al., CNS Drug Rev. 4, 25-41 (1998).
Properties
Crystals from water as the hemiheptahydrate, mp 72-75°. [α]25D 13.6° (c = 1 in water).Derivative
Tetrahydrate.Nomenclature
CAS number: 201677-75-0
TA-0910; Ceredist (Tanabe Seiyaku). C17H21N7O5.4H2O; mol wt 475.45.
C 42.94%, H 6.15%, N 20.62%, O 30.29%.
Properties
White, odorless crystals, bp 72-75°. Sol in water, acetic acid, ethanol. Slightly sol in methanol, acetonitrile. [α]23D 13.6°. LD50 in mice, rats (mg/kg): >5000, >5000 orally; in mice, male, female rats (mg/kg): >2000, 799, 946 i.v. (Kinoshita).Therapeutic Category
In treatment of spinocerebellar degeneration.