Protirelin

Base Information

• Chemical Name: Protirelin
• CAS No.: 24305-27-9
• Deprecated CAS: 9015-91-2,22365-02-2,22365-17-9,77666-61-6,39422-15-6
• Molecular Formula: C16H22N6O4
• Molecular Weight: 362.388
• European Community (EC) Number: 246-143-4
• UNII: 5Y5F15120W
• DSSTox Substance ID: DTXSID0023533
• Nikkaji Number: J3.473H
• Wikipedia: Thyrotropin-releasing_hormone
• Wikidata: Q12910980
• NCI Thesaurus Code: C66495
• RXCUI: 10580
• Pharos Ligand ID: J8HXVC75UP3T
• Metabolomics Workbench ID: 49932
• ChEMBL ID: CHEMBL1472
• Mol file: 24305-27-9.mol

Synonyms:Abbott 38579;Abbott-38579;Abbott38579;Antepan;Hydrate, Proterelin Tartrate;Prem, TRH;Proterelin Tartrate;Proterelin Tartrate Hydrate;Protirelin;Protirelin Tartrate (1:1);Relefact TRH;Stimu TSH;Stimu-TSH;StimuTSH;Tartrate Hydrate, Proterelin;Thypinone;Thyroliberin;Thyroliberin TRH Merck;Thyrotropin Releasing Factor;Thyrotropin Releasing Hormone;Thyrotropin Releasing Hormone Tartrate;Thyrotropin-Releasing Factor;Thyrotropin-Releasing Hormone;Thyrotropin-Releasing Hormone Tartrate;TRH Ferring;TRH Prem;TRH, Relefact

Chemical Property of Protirelin

Chemical Property:

• Appearance/Colour: COA
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.615
• Boiling Point: 978.4 °C at 760 mmHg
• PKA: 13.05±0.20(Predicted)
• Flash Point: 545.5 °C
• PSA: 144.49000
• Density: 1.421 g/cm³
• LogP: -0.55120
• Storage Temp.: −20°C
• Solubility.: H2O: 10 mg/mL, clear, colorless
• XLogP3: -2.5
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 6
• Exact Mass: 362.17025320
• Heavy Atom Count: 26
• Complexity: 597

Purity/Quality:

98.0%min ^*data from raw suppliers

Thyrotropin Releasing Hormone ^*data from reagent suppliers

Safty Information:

• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: UVCB,Biological Agents -> Proteins
• Canonical SMILES: C1CC(N(C1)C(=O)C(CC2=CN=CN2)NC(=O)C3CCC(=O)N3)C(=O)N
• Isomeric SMILES: C1C[C@H](N(C1)C(=O)[C@H](CC2=CN=CN2)NC(=O)[C@@H]3CCC(=O)N3)C(=O)N
• Recent ClinicalTrials: Palm Tocotrienols in Chronic Hemodialysis (USA)
• Recent EU Clinical Trials: The Efficacy of TRH in Intensive Care patients; a dose finding study
• Biological functions: The Trh knockout mice show normal development, but exhibit tertiary hypothyroidism and hyperglycemia due to diminished insulin secretion. The Trh knockout mice show defects in cerebellar long-term depression and a motor learning deficit.The Trhr1 knockout mice exhibit central hypothyroidism showing a decrease in serum T3, T4, and PRL levels but not in serum TSH?levels. The Trhr1 knockout mice exhibit normal growth and development but displayed increased anxiety and depression levels. The Trhr2 knockout mice are euthyroid with normal serum TSH levels and exhibit normal development and growth. The mutant females exhibited moderately increased depression and reduced anxiety phenotypes.
• Description: The first hypothalamic hypophysiotropic neurohormone identified, TRH consists of the tripeptide pGlu-His-ProNH2. It stimulates the secretion ofthyroid-stimulating hormone (TSH), prolactin (PRL), and growth hormone (GH), and also functions as a neurotransmitter and neuromodulator.
• Uses: Thyrotropin-Releasing Hormone is a hypothalamic hypophysiotropic neuropeptide, which has the ability to stimulate the release of thyroid-stimulating hormone in mammals. It is proven that Thyrotropin-Releasing Hormone can be used to accelerate wound healing. prothyrotropin
• Indications: Thyrotropin-releasing hormone, or protirelin, consists of three amino acids. TRH (Relefact TRH) is used for tests to distinguish primary from secondary hypothyroidism.
• Clinical Use: TRH (200–500μg) administered intravenously to normal subjects causes a rise in TSH levels within 15–30min, resulting in an increase in T3 levels within 90–150min. In primary hypothyroidism, TSH hyperresponse to TRH occurs, with a typical elevation in the basal TSH levels. In secondary (pituitary) hypothyroidism, an impaired TSH response to TRH occurs, whereas in tertiary (hypothalamic) hypothyroidism normal or increased TSH response to TRH occurs. Protirelin is used to test the response of the anterior pituitary to TRH in people who may have medical conditions of thyroid function, including hyperthyroidism, Graves’ disease, and hypothyroidism. In addition, TRH has been used to assess the ability of the prolactin secretion in the pituitary.

Technology Process of Protirelin

There total 44 articles about Protirelin which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 81.0%

Gln-His-Pro-NH2 (28613-24-3) → Pyr-His-Pro-NH2 (24305-27-9)

Guidance literature:

With acetic acid; In 1,4-dioxane; at 40 ℃; for 12h;

DOI:10.1248/cpb.37.3125

Reference yield: 80.3%

(S)-2-[(S)-1-[3-(Adamantan-2-yloxymethyl)-3H-imidazol-4-ylmethyl]-2-((S)-2-carbamoyl-pyrrolidin-1-yl)-2-oxo-ethylcarbamoyl]-5-oxo-pyrrolidine-1-carboxylic acid tert-butyl ester (189179-52-0) → Pyr-His-Pro-NH2 (24305-27-9)

Guidance literature:

With trifluorormethanesulfonic acid; methyl-phenyl-thioether; 3-methyl-phenol; trifluoroacetic acid; for 1h; Ambient temperature;

DOI:10.1248/cpb.45.452

Reference yield: 76.0%

L-pyroglutamyl-2,5-dibromo-L-histidyl-L-prolineamide (83468-78-4) → Pyr-His-Pro-NH2 (24305-27-9)

Guidance literature:

With Amberlite IR 45 (acetate form); hydrogen; palladium on activated charcoal; Rh on carbon; In acetic acid; for 6h;

upstream raw materials:

Gln-His-Pro-NH₂

pyroglutamic acid 2,4,6-trichlorophenylester

Adpoc-His(Adpoc)-Pro-NH₂

Pyroglutamylhistidine

Downstream raw materials:

C₁₇H₂₁F₃N₆O₄

C₁₇H₂₁F₃N₆O₄

Refernces

• 1、 Kalir et al.. "-". . p. 55,58. Retrieved 1975.
• 2、 Kinoshita et al.. "-". . p. 2619,2622. Retrieved 1979.
• 3、 Mattalia,Bucciarelli. "A new improved synthesis of thyrotropin releasing hormone". . p. 874 - 875. Retrieved 1975.
• 4、 Kaur, Sarabjit,Bhararia, Avani,Sharma, Krishna K.,Mittal, Sherry,Jain, Rahul,Wangoo, Nishima,Sharma, Rohit K.. "Thyrotropin-releasing hormone loaded and chitosan engineered polymeric nanoparticles: Towards effective delivery of neuropeptides". . p. 5324 - 5332. Retrieved 2016.
• 5、 Okada, Yoshio,Wang, Jidong,Yamamoto, Takeshi,Yokoi, Toshio,Mu, Yu. "Amino acids and peptides. L. Development of a novel N(π)-protecting group for histidine, N(π)-2-adamantyloxymethylhistidine, and its application to peptide synthesis". . p. 452 - 456. Retrieved 1997.
• 6、 Glass,Schwartz,Walter. "Bridging of peptides to solid supports through the dinitrophenylene moiety. Bidirectional extension of peptide chains.". . p. 6209 - 6211. Retrieved 1972.
• 7、 Orlowski et al.. "-". . p. 3701,3704. Retrieved 1976.