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Compound Detail

CHEMBL1472

PROTIRELIN
💊 Approved Drug
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💊 Approved Drug
NC(=O)[C@@H]1CCCN1C(=O)[C@H](Cc1c[nH]cn1)NC(=O)[C@@H]1CCC(=O)N1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL1472
Name PROTIRELIN
Phase Approved
Structure Type BOTH
InChI Key XNSAINXGIQZQOO-SRVKXCTJSA-N
Therapeutic ✓ Yes

Known Names

5-oxo-pro-his-pro-nh2 A-38579 ABBOTT-38579 Lopremone NSC-760113 Protirelin Protirelin tartrate Protirelin, synthetic Protirelina Protireline Relefact trh SYNTHETIC TRH +9 more
5
Targets
25
Activities
3
Assay Types
4
PK Parameters
20
Publications
21
Known Names
2
Indications
1
Mechanisms

Molecular Properties

362.4
MW (Da)
-1.81
ALogP
5
HBA
4
HBD
150.3
PSA (Ų)
0.47
QED
0
Ro5 Violations
6
Rot. Bonds

Drug Information

Molecule Type Protein
First Approval 1976
Availability Discontinued
Chirality Single Enantiomer

Routes of Administration

Parenteral

Flags

Natural Product
USAN Stem -relin
USAN Year 1974

Extended Properties

Molecular Formula C16H22N6O4
MW 362.39
Aromatic Rings 1
Heavy Atoms 26
NP-Likeness -0.41

Mechanism of Action

Mechanism Action Type Target Direct Efficacy
Thyrotropin-releasing hormone receptor agonist AGONIST Thyrotropin-releasing hormone receptor ✓ ✓

Indications

Respiratory Distress Syndrome Neoplasms

ATC Classification

V04CJ02
protirelin
Level 1: VARIOUS
Level 2: DIAGNOSTIC AGENTS

Activity Summary

EC50 12 meas. best 9.31
Ki 7 meas. best 8.0
IC50 6 meas. best 8.59

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Thyrotropin-releasing hormone receptor
CHEMBL2467
 EC50 9.31 8.994 0.5 5
Thyrotropin-releasing hormone receptor 2
CHEMBL3600274
 EC50 9.3 9.03 0.5 3
Thyrotropin-releasing hormone receptor
CHEMBL2467
 IC50 8.59 8.085 2.6 2
Thyrotropin-releasing hormone receptor
CHEMBL1810
 EC50 8.52 8.52 3.0 1
Thyrotropin-releasing hormone receptor 2
CHEMBL3875
 EC50 8.52 8.52 3.0 2
Thyrotropin-releasing hormone receptor
CHEMBL4553
 EC50 8.52 8.52 3.0 1
Thyrotropin-releasing hormone receptor 2
CHEMBL3600274
 IC50 8.15 8.15 7.0 2
Thyrotropin-releasing hormone receptor
CHEMBL2467
 Ki 8.0 7.82 10.0 2
Thyrotropin-releasing hormone receptor 2
CHEMBL3875
 Ki 8.0 8.0 10.0 2
Thyrotropin-releasing hormone receptor
CHEMBL1810
 Ki 7.7 7.7 20.0 1
Thyrotropin-releasing hormone receptor
CHEMBL4553
 Ki 7.7 7.535 20.0 2
Thyrotropin-releasing hormone receptor 2
CHEMBL3875
 IC50 4.64 4.64 23000.0 1

Pharmacokinetic Data

Parameter Value Units Species
T1/2 0.1833 hr Rattus norvegicus
T1/2 0.2667 hr Rattus norvegicus
T1/2 0.05 hr Homo sapiens
T1/2 0.03333 hr Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Thyrotropin-releasing hormone receptor EC50 = 0.49 nM 9.31 Ability to activate thyroliberin endocrine receptor (TRH-R) using AtT-20 mouse p... 9873682
Thyrotropin-releasing hormone receptor 2 EC50 = 0.5 nM 9.3 Agonist activity at mouse TRH-R2 expressed in HEK293 cells assessed as Ca2+ rele... 26854379
Thyrotropin-releasing hormone receptor 2 EC50 = 0.52 nM 9.28 Agonist activity at mouse TRH-R2 expressed in HEK293 cells assessed as induction... 26216015
Thyrotropin-releasing hormone receptor EC50 = 0.68 nM 9.17 Effective concentration required to activate TRH-R receptor in AtT-20 mouse pitu... 8648595
Thyrotropin-releasing hormone receptor EC50 = 1.0 nM 9.0 Agonist activity at mouse TRH-R1 expressed in HEK293 cells assessed as induction... 26216015
Thyrotropin-releasing hormone receptor EC50 = 1.0 nM 9.0 Agonist activity at mouse TRH-R1 expressed in HEK293 cells assessed as Ca2+ rele... 26854379
Thyrotropin-releasing hormone receptor IC50 = 2.6 nM 8.59 Displacement of [3H]-1-MeHis-TRH from mouse TRH-R1 expressed in HEK293 cells inc... 26216015
Thyrotropin-releasing hormone receptor EC50 = 3.0 nM 8.52 Agonist activity at TRHR1 expressed in HEK293EM cells assessed as activation pot... 17035026
Thyrotropin-releasing hormone receptor 2 EC50 = 3.0 nM 8.52 Agonist activity at TRHR2 expressed in HEK293EM cells assessed as activation pot... 17035026
Thyrotropin-releasing hormone receptor EC50 = 3.0 nM 8.52 Signaling (activation) potency for thyrotropin releasing hormone receptor 1 expr... 16162016
Thyrotropin-releasing hormone receptor 2 EC50 = 3.0 nM 8.52 Signaling (activation) potency for thyrotropin releasing hormone receptor 2 expr... 16162016
Thyrotropin-releasing hormone receptor 2 EC50 = 3.1 nM 8.51 Agonist activity at mouse TRH-R2 expressed in HEK293 cells assessed as IP1 forma... 26854379
Thyrotropin-releasing hormone receptor EC50 = 3.2 nM 8.49 Agonist activity at mouse TRH-R1 expressed in HEK293 cells assessed as IP1 forma... 26854379
Thyrotropin-releasing hormone receptor 2 IC50 = 7.0 nM 8.15 Displacement of [3H]-1-MeHis-TRH from mouse TRH-R2 expressed in HEK293 cells inc... 26216015
Thyrotropin-releasing hormone receptor 2 IC50 = 7.0 nM 8.15 Displacement of [3H]-Me-His-TRH from mouse TRH-R2 expressed in HEK293 cells prei... 26854379
Thyrotropin-releasing hormone receptor Ki = 10.0 nM 8.0 Binding affinity against TRH-R receptor in AtT-20 mouse pituitary tumor cells 8648595
Thyrotropin-releasing hormone receptor 2 Ki = 10.0 nM 8.0 Inhibitory constant against thyrotropin releasing hormone receptor 2 expressed i... 16162016
Thyrotropin-releasing hormone receptor 2 Ki = 10.0 nM 8.0 Displacement of [3H]N(1)-Me-His-TRH from TRHR2 17035026
Thyrotropin-releasing hormone receptor Ki = 20.0 nM 7.7 Inhibitory constant against thyrotropin releasing hormone receptor 1 expressed i... 16162016
Thyrotropin-releasing hormone receptor Ki = 20.0 nM 7.7 Displacement of [3H]N(1)-Me-His-TRH from TRHR1 17035026

Literature References

PubMed DOI Target Context # Activities
1676757 10.1021/jm00111a014 Mus musculus 15
- 10.6019/CHEMBL4689842 HEK-293T 10
7636847 10.1021/jm00015a009 Mus musculus 9
- 10.6019/CHEMBL4689842 U2OS 9
- 10.6019/CHEMBL4689842 Fibroblast 8
26854379 10.1016/j.ejmech.2016.01.038 Thyrotropin-releasing hormone receptor 7
26216015 10.1016/j.bmc.2015.07.022 Plasma 4
10649973 10.1021/jm980333v Mus musculus 4
- 10.1016/0960-894X(96)00478-7 Mus musculus 4
1676756 10.1021/jm00111a013 Mus musculus 4
17498958 10.1016/j.bmc.2007.04.042 Caco-2 3
26854379 10.1016/j.ejmech.2016.01.038 Thyrotropin-releasing hormone receptor 2 3
3091831 10.1021/jm00159a015 Rattus norvegicus 3
2115588 10.1021/jm00170a014 Rattus norvegicus 3
15537357 10.1021/jm020531t ADMET 3
15537357 10.1021/jm020531t No relevant target 3
26854379 10.1016/j.ejmech.2016.01.038 Unchecked 3
6429332 10.1021/jm00372a006 Rattus norvegicus 2
8648595 10.1021/jm960053k Thyrotropin-releasing hormone receptor 2
26216015 10.1016/j.bmc.2015.07.022 Thyrotropin-releasing hormone receptor 2

Data from ChEMBL 36 via Core Engine