Taltirelin: Difference between revisions

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{{Short description|Chemical compound}}
{{cs1 config|name-list-style=vanc|display-authors=6}}
{{Drugbox
{{Drugbox
| Verifiedfields = changed
| verifiedrevid = 443335021
| verifiedrevid = 448119630
| IUPAC_name = ''N''-{[(4''S'')-1-methyl-2,6-dioxohexahydropyrimidin-4-yl]carbonyl}-<small>L</small>-histidyl-<small>L</small>-prolinamide
| IUPAC_name = ''N''-{[(4''S'')-1-methyl-2,6-dioxohexahydropyrimidin-4-yl]carbonyl}-<small>L</small>-histidyl-<small>L</small>-prolinamide
| image = Talitirelin.png
| image = Talitirelin.png
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| metabolism =
| metabolism =
| elimination_half-life =
| elimination_half-life =
| excretion =
| excretion =


<!--Identifiers-->
<!--Identifiers-->
| IUPHAR_ligand = 2143
| CAS_number_Ref = {{cascite|correct|??}}
| CAS_number = 103300-74-9
| CAS_number = 103300-74-9
| CAS_supplemental = <br />{{CAS|201677-75-0}}
| CAS_supplemental = <br />{{CAS|201677-75-0}}
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| UNII_Ref = {{fdacite|correct|FDA}}
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = DOZ62MV6A5
| UNII = DOZ62MV6A5
| ChEBI = 135653
| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}
| ChemSpiderID = 102734


<!--Chemical data-->
<!--Chemical data-->
| chemical_formula =
| chemical_formula =
| C=17 | H=31 | N=7 | O=9
| C=17 | H=31 | N=7 | O=9
| molecular_weight = 477.46 g/mol
| smiles = CN1C(=O)C[C@H](NC1=O)C(=O)N[C@@H](CC2=CN=CN2)C(=O)N3CCC[C@H]3C(=O)N
| smiles = CN1C(=O)C[C@H](NC1=O)C(=O)N[C@@H](CC2=CN=CN2)C(=O)N3CCC[C@H]3C(=O)N
| synonyms = <small>(4''S'')-''N''-[(2''S'')-1-[(2''S'')-2-carbamoylpyrrolidin-1-yl]-3-(3''H''-imidazol-4-yl)-1-oxopropan-2-yl]-1-methyl-2,6-dioxo-1,3-diazinane-4-carboxamide</small>
| synonyms = <small>(4''S'')-''N''-[(2''S'')-1-[(2''S'')-2-carbamoylpyrrolidin-1-yl]-3-(3''H''-imidazol-4-yl)-1-oxopropan-2-yl]-1-methyl-2,6-dioxo-1,3-diazinane-4-carboxamide</small>
| StdInChI_Ref = {{stdinchicite|changed|chemspider}}
| StdInChI = 1S/C17H23N7O5/c1-23-13(25)6-10(22-17(23)29)15(27)21-11(5-9-7-19-8-20-9)16(28)24-4-2-3-12(24)14(18)26/h7-8,10-12H,2-6H2,1H3,(H2,18,26)(H,19,20)(H,21,27)(H,22,29)/t10-,11-,12-/m0/s1
| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}
| StdInChIKey = LQZAIAZUDWIVPM-SRVKXCTJSA-N
}}
}}


'''Taltirelin''' (marketed under the tradename '''Ceredist''') is a [[thyrotropin-releasing hormone]] (TRH) analog, which mimics the physiological actions of TRH, but with a much longer half-life and duration of effects,<ref name="pmid9608876">{{cite journal |author=Fukuchi I |title=Effects of taltirelin hydrate (TA-0910), a novel thyrotropin-releasing hormone analog, on in vivo dopamine release and turnover in rat brain |journal=Arzneimittelforschung |volume=48 |issue=4 |pages=353–9 |year=1998 |month=April |pmid=9608876 |doi= |url= |author-separator=, |author2=Asahi T |author3=Kawashima K |display-authors=3 |last4=Kawashima |first4=Y |last5=Yamamura |first5=M |last6=Matsuoka |first6=Y |last7=Kinoshita |first7=K}}</ref> and little development of tolerance following prolonged dosing.<ref>Asai H, Asahi T, Yamamura M, Yamauchi-Kohno R, Saito A. Lack of behavioral tolerance by repeated treatment with taltirelin hydrate, a thyrotropin-releasing hormone analog, in rats. ''Pharmacology, Biochemistry and Behaviour''. 2005 Dec;82(4):646-51. PMID 16368129</ref> It has [[nootropic]],<ref>Yamamura M, Suzuki M, Matsumoto K. Synthesis and pharmacological action of TRH analog peptide (Taltirelin). ''Nippon Yakurigaku Zasshi''. (Japanese). 1997 Oct;110 Suppl 1:33P-38P. PMID 9503402</ref> [[neuroprotective]]<ref>Urayama A, Yamada S, Kimura R, Zhang J, Watanabe Y. Neuroprotective effect and brain receptor binding of taltirelin, a novel thyrotropin-releasing hormone (TRH) analogue, in transient forebrain ischemia of C57BL/6J mice. ''Life Sciences''. 2002 Dec 20;72(4-5):601-7. PMID 12467901</ref> and [[analgesic]] effects,<ref>Tanabe M, Tokuda Y, Takasu K, Ono K, Honda M, Ono H. The synthetic TRH analogue taltirelin exerts modality-specific antinociceptive effects via distinct descending monoaminergic systems. ''British Journal of Pharmacology''. 2007 Feb;150(4):403-14. PMID 17220907</ref> and is primarily being researched for the treatment of [[Spinocerebellar ataxia]].
'''Taltirelin''' (marketed under the tradename '''Ceredist''') is a [[thyrotropin-releasing hormone]] (TRH) analog, which mimics the physiological actions of TRH, but with a much longer half-life and duration of effects,<ref name="pmid9608876">{{cite journal | vauthors = Fukuchi I, Asahi T, Kawashima K, Kawashima Y, Yamamura M, Matsuoka Y, Kinoshita K | title = Effects of taltirelin hydrate (TA-0910), a novel thyrotropin-releasing hormone analog, on in vivo dopamine release and turnover in rat brain | journal = Arzneimittel-Forschung | volume = 48 | issue = 4 | pages = 353–9 | date = April 1998 | pmid = 9608876 }}</ref> and little development of tolerance following prolonged dosing.<ref>{{cite journal | vauthors = Asai H, Asahi T, Yamamura M, Yamauchi-Kohno R, Saito A | title = Lack of behavioral tolerance by repeated treatment with taltirelin hydrate, a thyrotropin-releasing hormone analog, in rats | journal = Pharmacology, Biochemistry, and Behavior | volume = 82 | issue = 4 | pages = 646–51 | date = December 2005 | pmid = 16368129 | doi = 10.1016/j.pbb.2005.11.004 | s2cid = 29935657 }}</ref> It has [[nootropic]],<ref>{{cite journal | vauthors = Yamamura M, Suzuki M, Matsumoto K | title = [Synthesis and pharmacological action of TRH analog peptide (Taltirelin)] | journal = Nihon Yakurigaku Zasshi. Folia Pharmacologica Japonica | volume = 110 | pages = 33P–38P | date = October 1997 | issue = Suppl 1 | pmid = 9503402 | doi = 10.1254/fpj.110.supplement_33 | doi-access = free }}</ref> [[neuroprotective]]<ref>{{cite journal | vauthors = Urayama A, Yamada S, Kimura R, Zhang J, Watanabe Y | title = Neuroprotective effect and brain receptor binding of taltirelin, a novel thyrotropin-releasing hormone (TRH) analogue, in transient forebrain ischemia of C57BL/6J mice | journal = Life Sciences | volume = 72 | issue = 4–5 | pages = 601–7 | date = December 2002 | pmid = 12467901 | doi = 10.1016/S0024-3205(02)02268-3 }}</ref> and [[analgesic]] effects.<ref>{{cite journal | vauthors = Tanabe M, Tokuda Y, Takasu K, Ono K, Honda M, Ono H | title = The synthetic TRH analogue taltirelin exerts modality-specific antinociceptive effects via distinct descending monoaminergic systems | journal = British Journal of Pharmacology | volume = 150 | issue = 4 | pages = 403–14 | date = February 2007 | pmid = 17220907 | pmc = 2189720 | doi = 10.1038/sj.bjp.0707125 }}</ref>


Taltirelin is primarily being researched for the treatment of [[spinocerebellar ataxia]]; limited research has also been carried out with regard to other neurodegenerative disorders, e.g., [[spinal muscular atrophy]].<ref>{{cite journal | vauthors = Takeuchi Y, Miyanomae Y, Komatsu H, Oomizono Y, Nishimura A, Okano S, Nishiki T, Sawada T | title = Efficacy of thyrotropin-releasing hormone in the treatment of spinal muscular atrophy | journal = Journal of Child Neurology | volume = 9 | issue = 3 | pages = 287–9 | date = July 1994 | pmid = 7930408 | doi = 10.1177/088307389400900313 | s2cid = 41678161 }}</ref><ref>{{cite journal | vauthors = Tzeng AC, Cheng J, Fryczynski H, Niranjan V, Stitik T, Sial A, Takeuchi Y, Foye P, DePrince M, Bach JR | title = A study of thyrotropin-releasing hormone for the treatment of spinal muscular atrophy: a preliminary report | journal = American Journal of Physical Medicine & Rehabilitation | volume = 79 | issue = 5 | pages = 435–40 | year = 2000 | pmid = 10994885 | doi = 10.1097/00002060-200009000-00005 | s2cid = 20416253 }}</ref><ref>{{cite journal | vauthors = Kato Z, Okuda M, Okumura Y, Arai T, Teramoto T, Nishimura M, Kaneko H, Kondo N | title = Oral administration of the thyrotropin-releasing hormone (TRH) analogue, taltireline hydrate, in spinal muscular atrophy | journal = Journal of Child Neurology | volume = 24 | issue = 8 | pages = 1010–2 | date = August 2009 | pmid = 19666885 | doi = 10.1177/0883073809333535 | s2cid = 29321906 }}</ref>
==References==
{{Reflist}}
* {{ja icon}} [http://di.mt-pharma.co.jp/file/dc/cdt.pdf Ceredist セレジスト錠] (PDF) Mitsubishi Tanabe Pharma. October 2007.


==External links==
== References ==
{{Reflist}}
* {{ja icon}} [http://www.mt-pharma.co.jp Official Mitsubishi Tanabe Pharma Website]


== External links ==
{{Psychostimulants, agents used for ADHD and nootropics}}
* {{in lang|ja}} [http://di.mt-pharma.co.jp/file/dc/cdt.pdf Ceredist セレジスト錠] (PDF) Mitsubishi Tanabe Pharma. October 2007.


[[Category:Nootropics]]
[[Category:Nootropics]]