Protirelin

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
Thumb
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

Pharmacology
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Contraindications & Blackbox Warnings
Contraindications
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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
AThyrotropin Releasing Hormone Receptor
ligand
Humans
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
Adverseeffects
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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.
DrugInteraction
AcalabrutinibThe therapeutic efficacy of Protirelin can be decreased when used in combination with Acalabrutinib.
AcebutololThe risk or severity of adverse effects can be increased when Acebutolol is combined with Protirelin.
AcetohexamideThe therapeutic efficacy of Acetohexamide can be decreased when used in combination with Protirelin.
AfatinibThe therapeutic efficacy of Protirelin can be decreased when used in combination with Afatinib.
AldesleukinThe therapeutic efficacy of Protirelin can be decreased when used in combination with Aldesleukin.
AlectinibThe therapeutic efficacy of Protirelin can be decreased when used in combination with Alectinib.
Aminosalicylic acidThe therapeutic efficacy of Protirelin can be decreased when used in combination with Aminosalicylic acid.
AmphetamineThe risk or severity of adverse effects can be increased when Amphetamine is combined with Protirelin.
AvapritinibThe therapeutic efficacy of Protirelin can be decreased when used in combination with Avapritinib.
AxitinibThe therapeutic efficacy of Protirelin can be decreased when used in combination with Axitinib.
Interactions
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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

Products2
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Brand Name Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
Relefact Trh Inj 0.2mg/mlLiquid.2 mg / mLIntravenousHoechst Canada Inc.1976-12-311996-08-29Canada flag
Relefact Trh Injection 200mcg/mlLiquid200 mcg / mLIntravenousHoechst Roussel Canada Inc.1993-12-311999-08-11Canada flag
Relefact Trh Injection 200mcg/mlLiquid200 mcg / mLIntravenousOdan Laboratories Ltd1997-05-28Not applicableCanada flag
Thyrotropin Releasing Hormone TRHSolution500 ug/1mLIntravenousAnazao Health Corporation2012-06-19Not applicableUS flag
Unapproved/Other Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
Thyrotropin Releasing Hormone TRHProtirelin (500 ug/1mL)SolutionIntravenousAnazao Health Corporation2012-06-19Not applicableUS flag

Categories

ATC Codes
V04CJ02 — Protirelin
Drug Categories
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)-N-[(2S)-1-[(2S)-2-carbamoylpyrrolidin-1-yl]-3-(1H-imidazol-5-yl)-1-oxopropan-2-yl]-5-oxopyrrolidine-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
Human Metabolome Database
HMDB0060080
KEGG Drug
D00176
KEGG Compound
C03958
PubChem Compound
638678
PubChem Substance
347827851
ChemSpider
554166
BindingDB
50072394
RxNav
10580
ChEBI
35940
ChEMBL
CHEMBL1472
ZINC
ZINC000004096261
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
Wikipedia
Protirelin

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
3CompletedTreatmentRespiratory Distress Syndrome1
2CompletedDiagnosticHealthy Subjects (HS) / Pituitary Diseases / Thyroid Diseases1
2TerminatedSupportive CareCancer Related Fatigue1
1RecruitingDiagnosticThyroid Cancers1
Not AvailableCompletedOtherSubclinical Hypothyroidisms1
Not AvailableCompletedTreatmentRespiratory Distress Syndrome1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
FormRouteStrength
LiquidIntravenous.2 mg / mL
LiquidIntravenous200 mcg / mL
SolutionIntravenous500 ug/1mL
Injection, solutionIntravenous
Prices
Not Available
Patents
Not Available

Properties

State
Not Available
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility4.18 mg/mLALOGPS
logP-2.3ALOGPS
logP-3.3ChemAxon
logS-1.9ALOGPS
pKa (Strongest Acidic)11.15ChemAxon
pKa (Strongest Basic)6.74ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area150.28 Å2ChemAxon
Rotatable Bond Count6ChemAxon
Refractivity89.76 m3·mol-1ChemAxon
Polarizability35.13 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted ADMET Features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Targets

Drugtargets2
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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 on November 30, 2015 19:10 / Updated on October 19, 2021 07:39