Identification
- Summary
Protirelin is a synthetic analogue of thyrotropin-releasing hormone that has been used during diagnostic tests to evaluate function of the thyroid gland.
- Brand Names
- Relefact Trh
- Generic Name
- Protirelin
- DrugBank Accession Number
- DB09421
- Background
Protirelin is the pharmaceutically available synthetic analogue of the endogenous peptide thyrotropin-releasing hormone (TRH). It is a tri-peptide tropic hormone, released by the hypothalamus, that stimulates the release of Thyroid Stimulating Hormone (TSH) and prolactin from the anterior pituitary.
Although not currently available in any FDA-approved product, protirelin is a component of the TRH Test where it is used to test the response of the anterior pituitary gland in conditions such as secondary hypothyroidism and acromegaly.
- Type
- Small Molecule
- Groups
- Approved, Investigational
- Structure
Structure for Protirelin (DB09421)
- Weight
- Average: 362.3837
Monoisotopic: 362.170253222 - Chemical Formula
- C16H22N6O4
- Synonyms
- 5-oxo-L-prolyl-L-histidyl-L-prolinamide
- L-pyroglutamyl-L-histidyl-L-prolineamide
- Protirelin
- Protirelina
- Thyroliberin
- Thyrotropic releasing hormone
- Thyrotropic-releasing factor
- Thyrotropin releasing hormone
- Thyrotropin-releasing factor
- TRH
- TSH-releasing factor
- TSH-releasing hormone
- External IDs
- A 38579
- A-38579
- A38579
Pharmacology
- Indication
Not Available
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Prevent Adverse Drug Events TodayTap into our Clinical API for life-saving information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events with our Clinical API- Pharmacodynamics
Not Available
- Mechanism of action
Target Actions Organism AThyrotropin Releasing Hormone Receptor ligandHumans - Absorption
Not Available
- Volume of distribution
Not Available
- Protein binding
Not Available
- Metabolism
- Not Available
- Route of elimination
Not Available
- Half-life
Not Available
- Clearance
Not Available
- Adverse Effects
Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.- Toxicity
Not Available
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs
- Not Available
Interactions
- Drug Interactions
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Drug Interaction Integrate drug-drug
interactions in your softwareAcalabrutinib The therapeutic efficacy of Protirelin can be decreased when used in combination with Acalabrutinib. Acebutolol The risk or severity of adverse effects can be increased when Acebutolol is combined with Protirelin. Acetohexamide The therapeutic efficacy of Acetohexamide can be decreased when used in combination with Protirelin. Afatinib The therapeutic efficacy of Protirelin can be decreased when used in combination with Afatinib. Aldesleukin The therapeutic efficacy of Protirelin can be decreased when used in combination with Aldesleukin. - Food Interactions
- Do not take with or immediately after a high-fat meal. Fatty food can disrupt the TSH assay by increasing lipid levels in the blood.
- Take with or without food. Take protirelin either after a low-fat meal or on an empty stomach.
Products
Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.- Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Relefact Trh Inj 0.2mg/ml Liquid .2 mg / mL Intravenous Hoechst Canada Inc. 1976-12-31 1996-08-29 Canada 
Relefact Trh Injection 200mcg/ml Liquid 200 mcg / mL Intravenous Hoechst Roussel Canada Inc. 1993-12-31 1999-08-11 Canada Relefact Trh Injection 200mcg/ml Liquid 200 mcg / mL Intravenous Odan Laboratories Ltd 1997-05-28 Not applicable Canada Thyrotropin Releasing Hormone TRH Solution 500 ug/1mL Intravenous Anazao Health Corporation 2012-06-19 Not applicable US 
- Unapproved/Other Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image Thyrotropin Releasing Hormone TRH Protirelin (500 ug/1mL) Solution Intravenous Anazao Health Corporation 2012-06-19 Not applicable US
Categories
- ATC Codes
- V04CJ02 — Protirelin
- Drug Categories
- Amino Acids, Peptides, and Proteins
- Diagnostic Agents
- Hormones
- Hormones, Hormone Substitutes, and Hormone Antagonists
- Hypothalamic Hormones
- Nerve Tissue Proteins
- Neuropeptides
- Oligopeptides
- Peptide Hormones
- Peptides
- Pituitary Hormone-Releasing Hormones
- Proteins
- Tests for Thyreoidea Function
- Thyroid Products
- Thyrotropin-Releasing Hormone
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as oligopeptides. These are organic compounds containing a sequence of between three and ten alpha-amino acids joined by peptide bonds.
- Kingdom
- Organic compounds
- Super Class
- Organic acids and derivatives
- Class
- Carboxylic acids and derivatives
- Sub Class
- Amino acids, peptides, and analogues
- Direct Parent
- Oligopeptides
- Alternative Parents
- Histidine and derivatives / N-acyl-alpha amino acids and derivatives / Proline and derivatives / Alpha amino acid amides / Pyrrolidinecarboxamides / N-acylpyrrolidines / Pyrrolidine-2-ones / Tertiary carboxylic acid amides / Imidazoles / Heteroaromatic compounds show 9 more
- Substituents
- 2-pyrrolidone / Alpha-amino acid amide / Alpha-amino acid or derivatives / Alpha-oligopeptide / Aromatic heteromonocyclic compound / Azacycle / Azole / Carbonyl group / Carboxamide group / Heteroaromatic compound show 21 more
- Molecular Framework
- Aromatic heteromonocyclic compounds
- External Descriptors
- tripeptide, peptide hormone (CHEBI:35940) / Thyrotropin-releasing hormone [KO:K05253] (C03958)
- Affected organisms
- Not Available
Chemical Identifiers
- UNII
- 5Y5F15120W
- CAS number
- 24305-27-9
- InChI Key
- XNSAINXGIQZQOO-SRVKXCTJSA-N
- InChI
- 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
- IUPAC Name
- (2S)-1-[(2S)-3-(1H-imidazol-5-yl)-2-{[(2S)-5-oxopyrrolidin-2-yl]formamido}propanoyl]pyrrolidine-2-carboxamide
- SMILES
- [H][C@@](CC1=CN=CN1)(NC(=O)[C@]1([H])CCC(=O)N1)C(=O)N1CCC[C@@]1([H])C(N)=O
References
- General References
- Not Available
- External Links
- Human Metabolome Database
- HMDB0060080
- KEGG Drug
- D00176
- KEGG Compound
- C03958
- PubChem Compound
- 638678
- PubChem Substance
- 347827851
- ChemSpider
- 554166
- BindingDB
- 50072394
- 10580
- ChEBI
- 35940
- ChEMBL
- CHEMBL1472
- ZINC
- ZINC000004096261
- RxList
- RxList Drug Page
- Drugs.com
- Drugs.com Drug Page
- Wikipedia
- Protirelin
Clinical Trials
- Clinical Trials
Phase Status Purpose Conditions Count 3 Completed Treatment Respiratory Distress Syndrome 1 2 Completed Diagnostic Healthy Volunteers (HV) / Pituitary Diseases / Thyroid Gland Diseases 1 2 Terminated Supportive Care Cancer Related Fatigue 1 1 Withdrawn Diagnostic Thyroid Cancer 1 Not Available Completed Other Subclinical Hypothyroidisms 1
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
Form Route Strength Liquid Intravenous .2 mg / mL Liquid Intravenous 200 mcg / mL Solution Intravenous 500 ug/1mL Injection, solution Intravenous 0.2 mg/ml - Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Not Available
- Experimental Properties
- Not Available
- Predicted Properties
Property Value Source Water Solubility 4.18 mg/mL ALOGPS logP -2.3 ALOGPS logP -3.3 Chemaxon logS -1.9 ALOGPS pKa (Strongest Acidic) 11.15 Chemaxon pKa (Strongest Basic) 6.74 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 5 Chemaxon Hydrogen Donor Count 4 Chemaxon Polar Surface Area 150.28 Å2 Chemaxon Rotatable Bond Count 6 Chemaxon Refractivity 89.76 m3·mol-1 Chemaxon Polarizability 35.03 Å3 Chemaxon Number of Rings 3 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter No Chemaxon Veber's Rule No Chemaxon MDDR-like Rule Yes Chemaxon - Predicted ADMET Features
- Not Available
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted GC-MS Spectrum - GC-MS Predicted GC-MS splash10-001i-9132000000-49fa8da4e6762d408997 Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS splash10-03di-0019000000-8683fca59090619a8f3c Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS splash10-03dj-1369000000-68d77940f3c600624884 Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS splash10-03xs-1029000000-e5733d134191b53e1144 Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS splash10-03dl-9777000000-42929516c7f278a8a794 Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS splash10-03km-8879000000-18cb8487122805e5a459 Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS splash10-0006-9543000000-b15e301d3b13cd3306eb Predicted 1H NMR Spectrum 1D NMR Not Applicable Predicted 13C NMR Spectrum 1D NMR Not Applicable - Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 195.2295537 predictedDarkChem Lite v0.1.0 [M-H]- 195.1755537 predictedDarkChem Lite v0.1.0 [M-H]- 195.4558537 predictedDarkChem Lite v0.1.0 [M-H]- 194.9333537 predictedDarkChem Lite v0.1.0 [M-H]- 169.62257 predictedDeepCCS 1.0 (2019) [M+H]+ 196.9620537 predictedDarkChem Lite v0.1.0 [M+H]+ 197.0363537 predictedDarkChem Lite v0.1.0 [M+H]+ 196.8338537 predictedDarkChem Lite v0.1.0 [M+H]+ 196.4101537 predictedDarkChem Lite v0.1.0 [M+H]+ 172.01813 predictedDeepCCS 1.0 (2019) [M+Na]+ 196.1325537 predictedDarkChem Lite v0.1.0 [M+Na]+ 196.4742537 predictedDarkChem Lite v0.1.0 [M+Na]+ 196.6208537 predictedDarkChem Lite v0.1.0 [M+Na]+ 196.0294537 predictedDarkChem Lite v0.1.0 [M+Na]+ 177.93068 predictedDeepCCS 1.0 (2019)
Targets
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- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Ligand
- General Function
- Receptor for thyrotropin-releasing hormone. This receptor is mediated by G proteins which activate a phosphatidylinositol-calcium second messenger system.
- Specific Function
- Thyrotropin-releasing hormone receptor activity
- Gene Name
- TRHR
- Uniprot ID
- P34981
- Uniprot Name
- Thyrotropin-releasing hormone receptor
- Molecular Weight
- 45084.415 Da
Drug created at November 30, 2015 19:10 / Updated at April 18, 2024 09:15