Taltirelin

Synonym(s):(4S)-Hexahydro-1-methyl-2,6-dioxo-4-pyrimidinecarbonyl-L-histidyl-L-prolinamide;(S)-N-((S)-1-((S)-2-Carbamoylpyrrolidin-1-yl)-3-(1H-imidazol-4-yl)-1-oxopropan-2-yl)-1-methyl-2,6-dioxohexahydropyrimidine-4-carboxamide;(S)-N-[(Hexahydro-1-methyl-2,6-dioxo-4-pyrimidinyl)carbonyl]-L-histidyl-L-prolinamide;

CAS NO.：103300-74-9
Empirical Formula: C17H23N7O5
Molecular Weight: 405.41
MDL number: MFCD00894697
SAFETY DATA SHEET (SDS)
Update Date: 2024-07-02 08:55:04

What is Taltirelin?

Description

Taltirelin was marketed in Japan for the treatment of neurodegenerative diseases, in particular the improvement of ataxia due to spino-cerebellar degeneration (SCD); it is the first orally-active drug in this indication. This synthetic thyrotropin-releasing hormone (TRH) analog is prepared by condensation of (S)-1-methyl-4,5-dihydroorotic acid with L-histidyl-Lprolinamide. It was shown that the S-configuration for all 3 chiral centers is crucial for CNS activity. Taltirelin is a potent agonist of the TRH receptors that shows significant effects on the cerebral monoamine systems when administered i.p. in rats. As TRH at 10-fold higher doses, taltirelin has been found to increase the extracellular levels of dopamine and its metabolites (DOPAC and HVA) as well as precursors and/or metabolites of noradrenaline and serotonin in different areas of the rat brain. Taltirelin produced an anti-ataxic activity in the Rolling mouse Nagoya, an ataxic mutant mouse. In several clinical studies performed in patients suffering from various forms of SCD, taltirelin demonstrated a statistically significant increase in the global improvement of ataxic symptoms and other neurologic abnormalities.

Originator

Tanabe Seiyaku (Japan)

The Uses of Taltirelin

Taltirelin is a thyrotropin-releasing hormone analog.

The Uses of Taltirelin

Analog of thyrotropin releasing hormone TRH, with pronounced CNS activity. Used in the treatment of spinocerebellar degeneration.

What are the applications of Application

Taltirelin is a synthetic thyrotropin-releasing hormone analog

Definition

ChEBI: Taltirelin is an oligopeptide comprising of (4S)-1-methyl-2,6-dioxohexahydropyrimidine-4-carboxylic acid, L-histidine and L-prolinamide joined in sequence by peptide linkages. It is a thyrotropin-releasing hormone (TRH) analog. Its tetrahydrate form is approved in Japan for the treatment of spinal muscular atrophy. It has a role as a nootropic agent, a neuroprotective agent and an analgesic.

brand name

Ceredist

Biological Activity

Synthetic thyrotropin-releasing hormone (TRH) analog. Displays ~ 30-100-fold more potent CNS activity and ~ 50-fold weaker endocrine activity than TRH. Antinociceptive and neuroprotective.

Properties of Taltirelin

Melting point:	72-75°
alpha	25D -13.6° (c = 1 in water)
Density	1.447±0.06 g/cm3(Predicted)
storage temp.	Store at +4°C
form	Solid
pka	9.32±0.40(Predicted)
color	White to off-white
Water Solubility	Soluble to 50 mM in sterile water