Taltirelin

Base Information

• Chemical Name: Taltirelin
• CAS No.: 103300-74-9
• Molecular Formula: C17H23N7O5
• Molecular Weight: 405.41
• UNII: DOZ62MV6A5
• DSSTox Substance ID: DTXSID0043763
• Nikkaji Number: J372.170A
• Wikipedia: Taltirelin
• Wikidata: Q7680336
• NCI Thesaurus Code: C77011
• Pharos Ligand ID: 67D426946DJP,67DYBSYZ5UXB
• Metabolomics Workbench ID: 144323
• ChEMBL ID: CHEMBL2107016
• Mol file: 103300-74-9.mol

Synonyms:(1-methyl-4,5-dihydroorotyl)-histidyl-prolinamide;TA 0910;TA-0910;taltirelin hydrate

Chemical Property of Taltirelin

Chemical Property:

• Melting Point: 72-75°
• Refractive Index: 1.611
• PKA: 9.32±0.40(Predicted)
• PSA: 170.59000
• Density: 1.447 g/cm³
• LogP: -0.85060
• Storage Temp.: Store at +4°C
• XLogP3: -3
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 6
• Exact Mass: 405.17606686
• Heavy Atom Count: 29
• Complexity: 714

Purity/Quality:

98% ^*data from raw suppliers

Taltirelin ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CN1C(=O)CC(NC1=O)C(=O)NC(CC2=CN=CN2)C(=O)N3CCCC3C(=O)N
• Isomeric SMILES: CN1C(=O)C[C@H](NC1=O)C(=O)N[C@@H](CC2=CN=CN2)C(=O)N3CCC[C@H]3C(=O)N
• Recent NIPH Clinical Trials: Taltirelin in obstructive sleep apnea
• 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.
• Uses: Taltirelin is a thyrotropin-releasing hormone analog. Analog of thyrotropin releasing hormone TRH, with pronounced CNS activity. Used in the treatment of spinocerebellar degeneration.