Taltirelin | CAS#103300-74-9 | thyrotropin-releasing hormone analog

MedKoo Cat#: 597825 | Name: Taltirelin

Description:

WARNING: This product is for research use only, not for human or veterinary use.

Taltirelin is a thyrotropin-releasing hormone analog. Taltirelin alleviates mechanical allodynia through activation of descending monoaminergic neurons in persistent inflammatory pain.

Chemical Structure

Taltirelin

CAS#103300-74-9

Theoretical Analysis

MedKoo Cat#: 597825

Name: Taltirelin

CAS#: 103300-74-9

Chemical Formula: C17H23N7O5

Exact Mass: 405.1761

Molecular Weight: 405.41

Elemental Analysis: C, 50.36; H, 5.72; N, 24.18; O, 19.73

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.

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Related CAS #

No Data

Synonym

Taltirelin; TA 0910; TA-0910; TA0910; CCRIS 8513;

IUPAC/Chemical Name

(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

InChi Key

LQZAIAZUDWIVPM-SRVKXCTJSA-N

InChi Code

InChI=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

SMILES Code

O=C(N)[C@H]1N(C([C@H](CC2=CNC=N2)NC([C@H](CC(N3C)=O)NC3=O)=O)=O)CCC1

Appearance

Solid powder

Purity

>98% (or refer to the Certificate of Analysis)

Shipping Condition

Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition

Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility

Soluble in DMSO

Shelf Life

>3 years if stored properly

Drug Formulation

This drug may be formulated in DMSO

Stock Solution Storage

0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code

2934.99.03.00

More Info

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 405.41 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

1: Eto K, Kim SK, Nabekura J, Ishibashi H. Taltirelin, a thyrotropin-releasing hormone analog, alleviates mechanical allodynia through activation of descending monoaminergic neurons in persistent inflammatory pain. Brain Res. 2011 Sep 26;1414:50-7. doi: 10.1016/j.brainres.2011.07.065. Epub 2011 Aug 6. PubMed PMID: 21872219. 2: Ijiro T, Nakamura K, Ogata M, Inada H, Kiguchi S, Maruyama K, Nabekura J, Kobayashi M, Ishibashi H. Effect of rovatirelin, a novel thyrotropin-releasing hormone analog, on the central noradrenergic system. Eur J Pharmacol. 2015 Aug 15;761:413-22. doi: 10.1016/j.ejphar.2015.05.047. Epub 2015 Jul 2. PubMed PMID: 26142830. 3: Thirunarayanan N, Raaka BM, Gershengorn MC. Taltirelin is a superagonist at the human thyrotropin-releasing hormone receptor. Front Endocrinol (Lausanne). 2012 Oct 9;3:120. doi: 10.3389/fendo.2012.00120. eCollection 2012. PubMed PMID: 23087672; PubMed Central PMCID: PMC3466466. 4: Thirunarayanan N, Nir EA, Raaka BM, Gershengorn MC. Thyrotropin-releasing hormone receptor type 1 (TRH-R1), not TRH-R2, primarily mediates taltirelin actions in the CNS of mice. Neuropsychopharmacology. 2013 May;38(6):950-6. doi: 10.1038/npp.2012.256. Epub 2012 Dec 11. PubMed PMID: 23303050; PubMed Central PMCID: PMC3629383. 5: Asai H, Watanabe Y, Yamauchi-Kohno R, Doi O. Reversal of hemorrhagic shock in rats using the metabolically stable thyrotropin-releasing hormone analog taltirelin hydrate. J Recept Signal Transduct Res. 2011 Dec;31(6):416-22. doi: 10.3109/10799893.2011.625427. Epub 2011 Nov 1. PubMed PMID: 22044177. 6: Yamamura M, Suzuki M, Matsumoto K. [Synthesis and pharmacological action of TRH analog peptide (Taltirelin)]. Nihon Yakurigaku Zasshi. 1997 Oct;110 Suppl 1:33P-38P. Review. Japanese. PubMed PMID: 9503402. 7: 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. Br J Pharmacol. 2007 Feb;150(4):403-14. Epub 2007 Jan 15. PubMed PMID: 17220907; PubMed Central PMCID: PMC2189720. 8: Fukuchi I, Asahi T, Kawashima K, Kawashima Y, Yamamura M, Matsuoka Y, Kinoshita K. Effects of taltirelin hydrate (TA-0910), a novel thyrotropin-releasing hormone analog, on in vivo dopamine release and turnover in rat brain. Arzneimittelforschung. 1998 Apr;48(4):353-9. PubMed PMID: 9608876. 9: 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. Pharmacol Biochem Behav. 2005 Dec;82(4):646-51. Epub 2005 Dec 20. PubMed PMID: 16368129. 10: Imahie H, Kobayashi T, Imado N, Inui T, Ariyuki F, Asano Y. [Reproductive and developmental toxicity studies of taltirelin hydrate (1) fertility study in rats by oral administration]. J Toxicol Sci. 1997 Nov;22 Suppl 2:371-9. Japanese. PubMed PMID: 9430095. 11: Brown W. Taltirelin. Tanabe Seiyaku. IDrugs. 1999 Oct;2(10):1059-68. PubMed PMID: 16118715. 12: Imahie H, Kobayashi T, Nishida A, Imado N, Asano Y. [Reproductive and developmental toxicity studies of taltirelin hydrate (2) teratogenicity study in rats by oral administration]. J Toxicol Sci. 1997 Nov;22 Suppl 2:381-94. Japanese. PubMed PMID: 9430096. 13: Horimoto S, Mayumi T, Tagawa K, Yamakita H, Yoshikawa M. Determination of taltirelin, a new stable thyrotropin-releasing hormone analogue, in human plasma by high-performance liquid chromatography turbo-ionspray ionization tandem mass spectrometry. J Pharm Biomed Anal. 2002 Nov 7;30(4):1361-9. PubMed PMID: 12408927. 14: 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 Sci. 2002 Dec 20;72(4-5):601-7. PubMed PMID: 12467901. 15: Imahie H, Nishida A, Imado N, Asano Y. [Reproductive and developmental toxicity studies of taltirelin hydrate (3) teratogenicity study in rabbits by oral administration]. J Toxicol Sci. 1997 Nov;22 Suppl 2:395-403. Japanese. PubMed PMID: 9430097. 16: Nie C, Yang D, Liu N, Dong D, Xu J, Zhang J. Thyrotropin-releasing hormone and its analogs accelerate wound healing. J Surg Res. 2014 Jun 15;189(2):359-65. doi: 10.1016/j.jss.2014.03.004. Epub 2014 Mar 11. PubMed PMID: 24713470. 17: Urayama A, Yamada S, Hirano K, Deguchi Y, Kimura R. Brain receptor binding characteristics and pharmacokinetic-pharmacodynamic analysis of thyrotropin-releasing hormone analogues. Life Sci. 2001 Dec 28;70(6):647-57. PubMed PMID: 11833715. 18: Imahie H, Koguchi A, Kobayashi T, Asano Y. [Reproductive and developmental toxicity studies of taltirelin hydrate (4) perinatal and postnatal study in rats by oral administration]. J Toxicol Sci. 1997 Nov;22 Suppl 2:405-17. Japanese. PubMed PMID: 9430098. 19: Asai H, Kinoshita K, Yamamura M, Matsuoka Y. Diversity of thyrotropin-releasing hormone receptors in the pituitary and discrete brain regions of rats. Jpn J Pharmacol. 1999 Mar;79(3):313-7. PubMed PMID: 10230859. 20: Yamamura T, Nishimura T, Kuwamura Y, Inui T, Aughton P, Kawai Y. Oncogenicity studies of taltirelin tetrahydrate (TA-0910) by oral (GAVAGE) administration in CD-1 mice and CD rats. J Toxicol Sci. 1997 Nov;22 Suppl 2:419-30. PubMed PMID: 9430099.