Identification

Name
Protirelin
Accession Number
DB09421
Type
Small Molecule
Groups
Approved, Investigational
Description

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.

Structure
Thumb
Synonyms
  • 5-oxo-L-prolyl-L-histidyl-L-prolinamide
  • L-pyroglutamyl-L-histidyl-L-prolineamide
  • Protirelin
  • 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
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Relefact Trh Inj 0.2mg/mlLiquid.2 mgIntravenousHoechst Canada Inc.1976-12-311996-08-29Canada
Relefact Trh Injection 200mcg/mlLiquid200 mcgIntravenousHoechst Roussel Canada Inc.1993-12-311999-08-11Canada
Relefact Trh Injection 200mcg/mlLiquid200 mcgIntravenousOdan Laboratories Ltd1997-05-28Not applicableCanada
Unapproved/Other Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
Thyrotropin Releasing Hormone TRHProtirelin (500 ug/1mL)SolutionIntravenousAnazao Health Corporation2012-06-19Not applicableUs
Categories
UNII
5Y5F15120W
CAS number
24305-27-9
Weight
Average: 362.3837
Monoisotopic: 362.170253222
Chemical Formula
C16H22N6O4
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

Pharmacology

Indication
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
AThyrotropin Releasing Hormone Receptor
ligand
Human
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
Toxicity
Not Available
Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteraction
(R)-warfarinProtirelin may increase the anticoagulant activities of (R)-warfarin.
(S)-WarfarinProtirelin may increase the anticoagulant activities of (S)-Warfarin.
3-isobutyl-1-methyl-7H-xanthineThe serum concentration of 3-isobutyl-1-methyl-7H-xanthine can be increased when it is combined with Protirelin.
4-hydroxycoumarinProtirelin may increase the anticoagulant activities of 4-hydroxycoumarin.
6-O-benzylguanineThe serum concentration of 6-O-benzylguanine can be increased when it is combined with Protirelin.
7-DeazaguanineThe serum concentration of 7-Deazaguanine can be increased when it is combined with Protirelin.
7,9-DimethylguanineThe serum concentration of 7,9-Dimethylguanine can be increased when it is combined with Protirelin.
8-azaguanineThe serum concentration of 8-azaguanine can be increased when it is combined with Protirelin.
8-chlorotheophyllineThe serum concentration of 8-chlorotheophylline can be increased when it is combined with Protirelin.
9-DeazaguanineThe serum concentration of 9-Deazaguanine can be increased when it is combined with Protirelin.
Food Interactions
Not Available

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
ChEBI
35940
ChEMBL
CHEMBL1472
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
Wikipedia
Protirelin
ATC Codes
V04CJ02 — Protirelin
AHFS Codes
  • 36:60.00 — Thyroid Function

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
2CompletedDiagnosticHealthy Volunteers / Pituitary Diseases / Thyroid Diseases1
2TerminatedSupportive CareCancer-Related Fatigue1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
FormRouteStrength
LiquidIntravenous.2 mg
LiquidIntravenous200 mcg
SolutionIntravenous500 ug/1mL
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

Taxonomy

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
Alpha-oligopeptide / Histidine or derivatives / N-acyl-alpha amino acid or derivatives / Proline or derivatives / Alpha-amino acid amide / Alpha-amino acid or derivatives / N-acylpyrrolidine / Pyrrolidine carboxylic acid or derivatives / Pyrrolidine-2-carboxamide / Pyrrolidone
show 21 more
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
tripeptide, peptide hormone (CHEBI:35940) / Thyrotropin-releasing hormone [KO:K05253] (C03958)

Targets

Kind
Protein
Organism
Human
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 12:10 / Updated on October 21, 2018 20:37