Protirelin (CED0003066)

Record Information

Version

1.0

Creation Date

2016-05-22 03:45:34 UTC

Update Date

2026-05-14 19:05:58 UTC

Accession Number

CHEM016853

Identification

Common Name

Protirelin

Class

Small Molecule

Description

Protirelin is an organic compound with the formula C16H22N6O4 and an average molecular weight of 362.38 g/mol. Protirelin belongs to the amino acids, peptides, and analogues, a subclass of carboxylic acids and derivatives within the organic compounds. It acts as a ligand of the thyrotropin-releasing hormone receptor (TRHR). In industrial applications, the compound is utilized as a softener and conditioner. It is found in two recorded sources: household cleaning and consumer products, specifically non electric simulated smoking devices, and healthcare, pharmaceuticals and veterinary products, where it is listed as an unclassified diagnostic agent. The recorded route of exposure for this compound is intravenous.

Contaminant Type

Not Available

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
L-Pyroglutamyl-L-histidyl-L-prolineamide	ChEBI
Thyroliberin	ChEBI
Thyrotropic releasing hormone	ChEBI
Thyrotropic-releasing factor	ChEBI
Thyrotropin-releasing factor	ChEBI
TRH	ChEBI
TSH-Releasing factor	ChEBI
TSH-Releasing hormone	ChEBI
Protirelin	Kegg
Relefact TRH	Kegg
Abbott brand OF protirelin	HMDB
Abbott-38579	HMDB
Antepan	HMDB
Aventis brand OF protirelin	HMDB
Novartis brand OF protirelin	HMDB
Proterelin tartrate	HMDB
Proterelin tartrate hydrate	HMDB
Protirelin abbott brand	HMDB
Protirelin aventis brand	HMDB
Stimu TSH	HMDB
Tartrate hydrate, proterelin	HMDB
Thypinone	HMDB
Abbott 38579	HMDB
Protirelin tartrate (1:1)	HMDB
TRH Ferring	HMDB
TRH Prem	HMDB
Thyrotropin-releasing hormone	HMDB
Thyrotropin-releasing hormone tartrate	HMDB
Abbott38579	HMDB
Ferring brand OF protirelin	HMDB
Henning berlin brand OF protirelin	HMDB
Hydrate, proterelin tartrate	HMDB
Merck brand OF protirelin	HMDB
Prem, TRH	HMDB
Protirelin ferring brand	HMDB
Protirelin merck brand	HMDB
Stimu-TSH	HMDB
Thyroliberin TRH merck	HMDB
Thyrotropin releasing factor	HMDB
Protirelin novartis brand	HMDB
StimuTSH	HMDB
TRH, Relefact	HMDB
Thyrotropin releasing hormone tartrate	HMDB
Thyrotropin releasing hormone	ChEBI

Chemical Formula

C₁₆H₂₂N₆O₄

Average Molecular Mass

362.384 g/mol

Monoisotopic Mass

362.170 g/mol

CAS Registry Number

24305-27-9

IUPAC Name

(2S)-N-[(2S)-1-[(2S)-2-carbamoylpyrrolidin-1-yl]-3-(1H-imidazol-5-yl)-1-oxopropan-2-yl]-5-oxopyrrolidine-2-carboxamide

Traditional Name

(2S)-N-[(2S)-1-[(2S)-2-carbamoylpyrrolidin-1-yl]-3-(3H-imidazol-4-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

InChI Identifier

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

InChI Key

XNSAINXGIQZQOO-SRVKXCTJSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as estrogens and derivatives. These are steroids with a structure containing a 3-hydroxylated estrane.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Estrane steroids

Direct Parent

Estrogens and derivatives

Alternative Parents

Substituents

Estrogen-skeleton
3-oxosteroid
Hydroxysteroid
Oxosteroid
17-hydroxysteroid
2-oxosteroid
Cyclic alcohol
Cyclic ketone
Ketone
Secondary alcohol
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Carbonyl group
Alcohol
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

Not Available

Biological Properties

Status

Detected and Not Quantified

Origin

Not Available

Cellular Locations

Not Available

Biofluid Locations

Not Available

Tissue Locations

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Organoleptic Effects

Not Available

Physical Properties

State

Not Available

Appearance

Not Available

Experimental Properties

Property	Value
Melting Point	Not Available
Boiling Point	Not Available
Solubility	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	4.18 g/L	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	35.13 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum	splash10-001i-9132000000-49fa8da4e6762d408997	Not Available	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum	Not Available	Not Available	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum	Not Available	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0ika-0196000000-afe7149844b51b017ffe	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0uxr-2890000000-b54b008a540dfef60574	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-06e9-4900000000-ee9272d8925098115bfd	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0uxr-1980000000-71c7b1b1167912a394e4	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-03di-0229000000-07452232680491a34370	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-03k9-4910000000-36df0cdebfe4ff6da0c5	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-00xs-0590000000-a869c0d113c010b718fa	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-03di-4900000000-4508511e6a002d601f08	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-00xs-1690000000-48f23b21f382fe83e1ec	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-03k9-7900000000-c0fe7f08cbc139f31fc5	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-02mj-1794000000-14f46bfee6df7d4a5a00	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0229-3960000000-af2ed02667f34a7fcac6	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-03di-0139000000-3e36ea4f46eaffc55495	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-00xs-0790000000-099b2f8d353b67c2e883	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0ika-2369000000-319ede954f3ced479d6e	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-001i-9582000000-bdc5d7fba5104a9bcfe8	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-00lr-9400000000-32c92be7b84a0dc3663b	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-03di-1129000000-e58ba2209f3459479f64	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-03di-6968000000-2fff001bc2b3c86f57d8	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0006-9411000000-a08e549b33f1b6a81063	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-03di-0009000000-696431d5c8a5cf963eca	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-044i-4439000000-6797de0104dd10461c61	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-03dj-9812000000-16c08d58395f971c0c3e	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-03di-0019000000-f097eb2b9e44187f9db3	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0006-9762000000-3dbee1b2272386f8656e	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0006-9400000000-b461be63e422ce2b4eff	Not Available	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, D₂O, predicted)	Not Available	Not Available	View Spectrum
1D NMR	¹H NMR Spectrum (1D, D₂O, predicted)	Not Available	Not Available	View Spectrum

Toxicity Profile

Mechanism of Toxicity

Not Available

Carcinogenicity (IARC Classification)

Not Available

Minimum Risk Level

Not Available

Symptoms

Not Available

Treatment

Not Available

Toxicity Values

Toxicity Value	Unit	Value Range	Organism	Dose Descriptor	Route of Exposure	Predicted or Experimental	Reference
2045.0	Log mg/kg	[1100:3600]	Rat	LD50	oral	predicted	Not Available

Health Effects

Health Effect	Relationship	Direction	Reference

Exposure Sources

Source ID	Source	Sector	Reference
411	Unclassified diagnostic agents	Healthcare, pharmaceuticals & veterinary products	Not Available
559	Non Electric Simulated Smoking Devices	Household cleaning & consumer products	Not Available
583	Anchoring Equipment	Marine, shipping & aquaculture	Not Available
584	Buoys	Marine, shipping & aquaculture	Not Available
643	Headwear	Textiles, leather & furnishings	Not Available

Pathways

1 pathway

Protirelin Drug Metabolism Action Pathway

Targets

Structure	Protein	UniProt ID	Organism	Relationship	Details
Click to view 3D structure	Thyrotropin-releasing hormone receptor	P21761	Mus musculus	Predicted (SEA)	0.0778492
Click to view 3D structure	Thyrotropin-releasing hormone receptor 2	A6IZR3	Rattus norvegicus	Predicted (SEA)	0.155698
Click to view 3D structure	Thyrotropin-releasing hormone receptor 2	Q9ERT1	Mus musculus	Predicted (SEA)	0.0778492
Click to view 3D structure	Thyrotropin-releasing hormone receptor	P34981	Humans	Predicted (SEA)	0.155698
Click to view 3D structure	Thyrotropin releasing hormone degrading enzyme	A0A287AP33	Sus scrofa	Predicted (SEA)	0.0778492
Click to view 3D structure	Thyrotropin-releasing hormone receptor	Q01717	Rattus norvegicus	Predicted (SEA)	0.155698
Click to view 3D structure	Type-1 angiotensin II receptor	P30556	Humans	Predicted (SEA)	54.1831
Click to view 3D structure	Mu-type opioid receptor	P33535	Rattus norvegicus	Predicted (SEA)	195.557
Click to view 3D structure	Mu-type opioid receptor	P97266	Cavia porcellus	Predicted (SEA)	191.976
Click to view 3D structure	Delta-type opioid receptor	P32300	Mus musculus	Predicted (SEA)	186.682
Click to view 3D structure	Delta-type opioid receptor	P33533	Rattus norvegicus	Predicted (SEA)	199.45
Click to view 3D structure	BTB/POZ domain-containing protein KCTD12	Q96CX2	Humans	Predicted (SEA)	65.1598
Click to view 3D structure	Aminopeptidase N	P15144	Humans	Predicted (SEA)	58.3869
Click to view 3D structure	Mu-type opioid receptor	P35372	Humans	Predicted (SEA)	322.996
Click to view 3D structure	3-hydroxy-3-methylglutaryl-coenzyme A reductase	P09610	Mesocricetus auratus	Predicted (SEA)	40.1702
Click to view 3D structure	Dipeptidyl peptidase 3	Q9NY33	Humans	Predicted (SEA)	57.297
Click to view 3D structure	Uncharacterized protein	F1N083	Bos taurus	Predicted (SEA)	61.5009
Click to view 3D structure	Leucyl-cystinyl aminopeptidase	Q9UIQ6	Humans	Predicted (SEA)	42.8171
Click to view 3D structure	Kappa-type opioid receptor	P41144	Cavia porcellus	Predicted (SEA)	231.524
Click to view 3D structure	Substance-P receptor	P14600	Rattus norvegicus	Predicted (SEA)	138.338
Click to view 3D structure	Apical membrane antigen 1	Q7KQK5	Plasmodium falciparum (isolate 3D7)	Predicted (SEA)	88.2032
Click to view 3D structure	Xaa-Pro dipeptidase	P12955	Humans	Predicted (SEA)	26.2352
Click to view 3D structure	Delta-type opioid receptor	P41143	Humans	Predicted (SEA)	384.186
Click to view 3D structure	Cytosol aminopeptidase	P28838	Humans	Predicted (SEA)	43.4399
Click to view 3D structure	Prothrombin	P00734	Humans	Predicted (SEA)	281.892