Protirelin
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MedKoo CAT#: 328402

CAS#: 24305-27-9 (free base)

Description: Protirelin, also known as Thyrel TRH, is a thyrotropin-releasing hormone receptor used totreat hypothyroidism. Protirelin stimulates release of a hormone called thyroid-stimulating hormone, or TSH, from the anterior pituitary gland.


Chemical Structure

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Protirelin
CAS# 24305-27-9 (free base)

Theoretical Analysis

MedKoo Cat#: 328402
Name: Protirelin
CAS#: 24305-27-9 (free base)
Chemical Formula: C16H22N6O4
Exact Mass: 362.17
Molecular Weight: 362.390
Elemental Analysis: C, 53.03; H, 6.12; N, 23.19; O, 17.66

Price and Availability

Size Price Availability Quantity
50mg USD 225
250mg USD 750
1g USD 1950
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Related CAS #: 120876-23-5 (acetate)   24305-27-9 (free base)    

Synonym: Protirelin; Antepan; Hirtonin; A-38579; A 38579; A38579; Thyrel TRH

IUPAC/Chemical Name: (S)-N-((S)-1-((S)-2-carbamoylpyrrolidin-1-yl)-3-(1H-imidazol-4-yl)-1-oxopropan-2-yl)-5-oxopyrrolidine-2-carboxamide

InChi Key: XNSAINXGIQZQOO-SRVKXCTJSA-N

InChi Code: InChI=1S/C16H22N6O4/c17-14(24)12-2-1-5-22(12)16(26)11(6-9-7-18-8-19-9)21-15(25)10-3-4-13(23)20-10/h7-8,10-12H,1-6H2,(H2,17,24)(H,18,19)(H,20,23)(H,21,25)/t10-,11-,12-/m0/s1

SMILES Code: O=C(N)[C@H]1N(C([C@H](CC2=CNC=N2)NC([C@H](CC3)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: >2 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: 2934.99.9001

More Info:

Biological target:
In vitro activity:
In vivo activity:

Preparing Stock Solutions

The following data is based on the product molecular weight 362.39 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.

Recalculate based on batch purity %
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
Formulation protocol:
In vitro protocol:
In vivo protocol:

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1: Ohuchi K, Funato M, Kato Z, Seki J, Kawase C, Tamai Y, Ono Y, Nagahara Y, Noda Y, Kameyama T, Ando S, Tsuruma K, Shimazawa M, Hara H, Kaneko H. Established Stem Cell Model of Spinal Muscular Atrophy Is Applicable in the Evaluation of the Efficacy of Thyrotropin-Releasing Hormone Analog. Stem Cells Transl Med. 2016 Feb;5(2):152-63. doi: 10.5966/sctm.2015-0059. Epub 2015 Dec 18. PubMed PMID: 26683872; PubMed Central PMCID: PMC4729546.

2: Kaur S, Bhararia A, Sharma K, Mittal S, Jain R, Wangoo N, Sharma RK. Thyrotropin-Releasing Hormone Loaded and Chitosan Engineered Polymeric Nanoparticles: Towards Effective Delivery of Neuropeptides. J Nanosci Nanotechnol. 2016 May;16(5):5324-32. PubMed PMID: 27483926.

3: 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.

4: Kanasaki H, Oride A, Mijiddorj T, Kyo S. Role of thyrotropin-releasing hormone in prolactin-producing cell models. Neuropeptides. 2015 Dec;54:73-7. doi: 10.1016/j.npep.2015.08.001. Epub 2015 Aug 5. Review. PubMed PMID: 26297348.

5: Yamamoto A, Kawai M, Iwanaga K, Matsukura T, Niwa F, Hasegawa T, Heike T. Response to thyrotropin-releasing hormone stimulation tests in preterm infants with transient hypothyroxinemia of prematurity. J Perinatol. 2015 Sep;35(9):725-8. doi: 10.1038/jp.2015.67. Epub 2015 Jun 25. PubMed PMID: 26110495.

6: Zhang L, Kolaj M, Renaud LP. Intracellular postsynaptic cannabinoid receptors link thyrotropin-releasing hormone receptors to TRPC-like channels in thalamic paraventricular nucleus neurons. Neuroscience. 2015 Dec 17;311:81-91. doi: 10.1016/j.neuroscience.2015.10.015. Epub 2015 Oct 22. PubMed PMID: 26470810.

7: Meena CL, Thakur A, Nandekar PP, Sangamwar AT, Sharma SS, Jain R. Synthesis of CNS active thyrotropin-releasing hormone (TRH)-like peptides: Biological evaluation and effect on cognitive impairment induced by cerebral ischemia in mice. Bioorg Med Chem. 2015 Sep 1;23(17):5641-53. doi: 10.1016/j.bmc.2015.07.022. Epub 2015 Jul 17. PubMed PMID: 26216015.

8: Kelly JA, Boyle NT, Cole N, Slator GR, Colivicchi MA, Stefanini C, Gobbo OL, Scalabrino GA, Ryan SM, Elamin M, Walsh C, Vajda A, Goggin MM, Campbell M, Mash DC, O'Mara SM, Brayden DJ, Callanan JJ, Tipton KF, Della Corte L, Hunter J, O'Boyle KM, Williams CH, Hardiman O. First-in-class thyrotropin-releasing hormone (TRH)-based compound binds to a pharmacologically distinct TRH receptor subtype in human brain and is effective in neurodegenerative models. Neuropharmacology. 2015 Feb;89:193-203. doi: 10.1016/j.neuropharm.2014.09.024. Epub 2014 Sep 30. PubMed PMID: 25281210.

9: Goodale L, Frank N, Hermida P, D'Oench S. Evaluation of a thyrotropin-releasing hormone solution stored at room temperature for pituitary pars intermedia dysfunction testing in horses. Am J Vet Res. 2015 May;76(5):437-44. doi: 10.2460/ajvr.76.5.437. PubMed PMID: 25909376.

10: Waniek A, Hartlage-Rübsamen M, Höfling C, Kehlen A, Schilling S, Demuth HU, Roßner S. Identification of thyrotropin-releasing hormone as hippocampal glutaminyl cyclase substrate in neurons and reactive astrocytes. Biochim Biophys Acta. 2015 Jan;1852(1):146-55. doi: 10.1016/j.bbadis.2014.11.011. Epub 2014 Nov 18. PubMed PMID: 25446989.

11: Schuman ML, Peres Diaz LS, Landa MS, Toblli JE, Cao G, Alvarez AL, Finkielman S, Pirola CJ, García SI. Thyrotropin-releasing hormone overexpression induces structural changes of the left ventricle in the normal rat heart. Am J Physiol Heart Circ Physiol. 2014 Dec 1;307(11):H1667-74. doi: 10.1152/ajpheart.00494.2014. Epub 2014 Oct 3. PubMed PMID: 25281568.

12: Chen LM, Chen YC, Hsiao HP, Chen BH, Chao MC. Role of thyrotropin-releasing hormone test in re-evaluation of congenital hypothyroidism. Kaohsiung J Med Sci. 2014 Aug;30(8):383-9. doi: 10.1016/j.kjms.2014.04.005. Epub 2014 May 28. PubMed PMID: 25002375.

13: 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.

14: Horjales-Araujo E, Hellysaz A, Broberger C. Lateral hypothalamic thyrotropin-releasing hormone neurons: distribution and relationship to histochemically defined cell populations in the rat. Neuroscience. 2014 Sep 26;277:87-102. doi: 10.1016/j.neuroscience.2014.06.043. Epub 2014 Jun 30. PubMed PMID: 24993479.

15: Kolaj M, Zhang L, Renaud LP. L-type calcium channels and MAP kinase contribute to thyrotropin-releasing hormone-induced depolarization in thalamic paraventricular nucleus neurons. Am J Physiol Regul Integr Comp Physiol. 2016 Jun 1;310(11):R1120-7. doi: 10.1152/ajpregu.00082.2016. Epub 2016 Mar 23. PubMed PMID: 27009047; PubMed Central PMCID: PMC4935505.