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SML2905

Sigma-Aldrich

Rovatirelin

≥98% (HPLC)

Synonyme(s) :

1-{N-[(4S,5S)-(5-methyl-2-oxooxazolidine-4-yl)carbonyl]-3-(thiazol-4-yl)-l-alanyl}-(2R)-2-methylpyrrolidine

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About This Item

Formule empirique (notation de Hill):
C16H22N4O4S
Numéro CAS:
204386-76-5
Poids moléculaire :
366.44
Code UNSPSC :
12352200
Nomenclature NACRES :
NA.77

Niveau de qualité

100

Pureté

≥98% (HPLC)

Forme

powder

Couleur

white to beige

Solubilité

DMSO: 2 mg/mL, clear

Température de stockage

2-8°C

InChI

1S/C16H22N4O4S/c1-9-4-3-5-20(9)15(22)12(6-11-7-25-8-17-11)18-14(21)13-10(2)24-16(23)19-13/h7-10,12-13H,3-6H2,1-2H3,(H,18,21)(H,19,23)/t9-,10+,12+,13+/m1/s1

Clé InChI

WTXWDXWZGJGIHV-URBCHYCLSA-N

Actions biochimiques/physiologiques

Rovatirelin is an orally active and brain-penetrant thyrotropin-releasing hormone (TRH) mimetic with higher receptor affinity than taltirelin (Ki = 702 nM vs 3877 nM, repectively). Rovatirelin oral administration in rats (10 or 30 mg/kg p.o.) upregulates locus coeruleus (LC) c-Fos expression and medial prefrontal cortex (mPFC) extracellular noradrenaline (NA), being more potent than taltirelin in enhancing spontaneous firing activity of isolated rat LC noradrenergic neurons in vitro (10-1000 nM) and rat locomotor activity in vivo (10 or 30 mg/kg p.o.).

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Certificats d'analyse (COA)

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Naotake Kobayashi et al.
Journal of peptide science : an official publication of the European Peptide Society, 25(12), e3228-e3228 (2019-11-13)
We discovered the orally active thyrotropin-releasing hormone (TRH) mimetic: (4S,5S)-5-methyl-N-{(2S)-1-[(2R)-2-methylpyrrolidin-1-yl]-1-oxo-3-(1,3-thiazol-4-yl)propan-2-yl}-2-oxo-1,3-oxazolidine-4-carboxamide 1 (rovatirelin). The central nervous system (CNS) effect of rovatirelin after intravenous (iv) administration is 100-fold higher than that of TRH. As 1 has four asymmetric carbons in its molecule
Kaoru Kobayashi et al.
Xenobiotica; the fate of foreign compounds in biological systems, 49(1), 106-119 (2018-01-05)
1. The non-clinical pharmacokinetic profiles of rovatirelin, a novel thyrotropin-releasing hormone (TRH) analogue, were investigated in vivo and in vitro. 2. Rovatirelin orally administered to rats and dogs was rapidly absorbed and bioavailability was estimated to be 7.3 and 41.3%
Tomoyuki Ijiro et al.
European journal of pharmacology, 761, 413-422 (2015-07-06)
Rovatirelin ([1-[-[(4S,5S)-(5-methyl-2-oxo oxazolidin-4-yl) carbonyl]-3-(thiazol-4-yl)-l-alanyl]-(2R)-2-methylpyrrolidine) is a novel synthetic agent that mimics the actions of thyrotropin-releasing hormone (TRH). The aim of this study was to investigate the electrophysiological and pharmacological effects of rovatirelin on the central noradrenergic system and to compare
Kaoru Kobayshi et al.
Xenobiotica; the fate of foreign compounds in biological systems, 49(12), 1434-1446 (2019-02-13)
The mass balance, pharmacokinetics and metabolism of rovatirelin were characterised in healthy male subjects after a single oral dose of [14C]rovatirelin. [14C]Rovatirelin was steadily absorbed, and the peak concentrations of radioactivity and rovatirelin were observed in plasma at 5-6 h after
Naotake Kobayashi et al.
ACS omega, 3(10), 13647-13666 (2018-11-10)
We have explored orally effective thyrotropin-releasing hormone (TRH) mimetics, showing oral bioavailability and brain penetration by structure-activity relationship (SAR) study on the basis of in vivo antagonistic activity on reserpine-induced hypothermia in mice. By primary screening of the synthesized TRH

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