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Compound Detail

CHEMBL1630578

TIRILAZAD
🧪 Phase III
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🧪 Phase III
C[C@@H]1C[C@H]2[C@@H]3CCC4=CC(=O)C=C[C@]4(C)C3=CC[C@]2(C)[C@H]1C(=O)CN1CCN(c2cc(N3CCCC3)nc(N3CCCC3)n2)CC1

Basic Information

ChEMBL ID CHEMBL1630578
Name TIRILAZAD
Phase Phase III
Structure Type MOL
InChI Key RBKASMJPSJDQKY-RBFSKHHSSA-N

Known Names

Tirilazad U 74006 U-74006
14
Targets
26
Activities
3
Assay Types
0
PK Parameters
20
Publications
3
Known Names
1
Indications
1
Mechanisms

Molecular Properties

624.9
MW (Da)
5.46
ALogP
8
HBA
0
HBD
72.9
PSA (Ų)
0.39
QED
2
Ro5 Violations
6
Rot. Bonds

Drug Information

Molecule Type Small molecule
Chirality Single Enantiomer

Flags

Natural Product
USAN Year 1990

Extended Properties

Molecular Formula C38H52N6O2
MW 624.87
Aromatic Rings 1
Heavy Atoms 46
NP-Likeness 0.53

Mechanism of Action

Mechanism Action Type Target Direct Efficacy
Lipid peroxidation inhibitor - -

Indications

Spinal Cord Injuries

ATC Classification

N07XX01
tirilazad
Level 1: NERVOUS SYSTEM
Level 2: OTHER NERVOUS SYSTEM DRUGS

Activity Summary

IC50 16 meas. best 6.14
Ki 9 meas. best 6.42
EC50 1 meas. best 4.55

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
5-hydroxytryptamine receptor 2C
CHEMBL225
Ki 6.42 6.42 376.0 1
5-hydroxytryptamine receptor 2A
CHEMBL224
Ki 6.24 6.24 572.0 1
5-hydroxytryptamine receptor 2C
CHEMBL225
IC50 6.14 6.14 718.0 1
Tyrosine-protein kinase Fyn
CHEMBL1841
IC50 5.95 5.95 1116.0 1
Alpha-2C adrenergic receptor
CHEMBL1916
Ki 5.94 5.94 1148.0 1
Unchecked
CHEMBL612545
Ki 5.91 5.7167 1219.0 3
Unchecked
CHEMBL612545
IC50 5.87 5.68 1359.0 3
5-hydroxytryptamine receptor 2A
CHEMBL224
IC50 5.7 5.7 2002.0 1
Mitogen-activated protein kinase 14
CHEMBL260
IC50 5.13 5.13 7406.0 1
Alpha-2C adrenergic receptor
CHEMBL1916
IC50 5.1 5.1 7898.0 1
5-hydroxytryptamine receptor 2B
CHEMBL1833
Ki 4.93 4.93 11777.0 1
Histamine H2 receptor
CHEMBL1941
Ki 4.86 4.86 13884.0 1
Histamine H2 receptor
CHEMBL1941
IC50 4.85 4.85 14120.0 1
Beta-2 adrenergic receptor
CHEMBL210
Ki 4.81 4.81 15578.0 1
Tyrosine-protein kinase Lck
CHEMBL258
IC50 4.8 4.8 15786.0 1
Mitogen-activated protein kinase 3
CHEMBL3385
IC50 4.79 4.79 16262.0 1
Rattus norvegicus
CHEMBL376
IC50 4.75 4.75 18000.0 2
5-hydroxytryptamine receptor 2B
CHEMBL1833
IC50 4.73 4.73 18507.0 1
Epidermal growth factor receptor
CHEMBL203
IC50 4.69 4.69 20397.0 1
Beta-2 adrenergic receptor
CHEMBL210
IC50 4.64 4.64 22659.0 1
Trypanosoma cruzi
CHEMBL368
EC50 4.55 4.55 28000.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
5-hydroxytryptamine receptor 2C Ki = 376.0 nM 6.42 DRUGMATRIX: Serotonin (5-Hydroxytryptamine) 5-HT2C radioligand binding (ligand: ... -
5-hydroxytryptamine receptor 2A Ki = 572.0 nM 6.24 DRUGMATRIX: Serotonin (5-Hydroxytryptamine) 5-HT2A radioligand binding (ligand: ... -
5-hydroxytryptamine receptor 2C IC50 = 718.0 nM 6.14 DRUGMATRIX: Serotonin (5-Hydroxytryptamine) 5-HT2C radioligand binding (ligand: ... -
Tyrosine-protein kinase Fyn IC50 = 1116.0 nM 5.95 DRUGMATRIX: Protein Tyrosine Kinase, Fyn enzyme inhibition (substrate: Poly(Glu:... -
Alpha-2C adrenergic receptor Ki = 1148.0 nM 5.94 DRUGMATRIX: Adrenergic Alpha-2C radioligand binding (ligand: [3H] MK-912) -
Unchecked Ki = 1219.0 nM 5.91 DRUGMATRIX: Sodium Channel, Site 2 radioligand binding (ligand: [3H] Batrachotox... -
Unchecked IC50 = 1359.0 nM 5.87 DRUGMATRIX: Sodium Channel, Site 2 radioligand binding (ligand: [3H] Batrachotox... -
5-hydroxytryptamine receptor 2A IC50 = 2002.0 nM 5.7 DRUGMATRIX: Serotonin (5-Hydroxytryptamine) 5-HT2A radioligand binding (ligand: ... -
Unchecked Ki = 2427.0 nM 5.62 DRUGMATRIX: Calcium Channel Type L, Phenylalkylamine radioligand binding (ligand... -
Unchecked Ki = 2395.0 nM 5.62 DRUGMATRIX: Calcium Channel Type L, Benzothiazepine radioligand binding (ligand:... -
Unchecked IC50 = 2496.0 nM 5.6 DRUGMATRIX: Calcium Channel Type L, Phenylalkylamine radioligand binding (ligand... -
Unchecked IC50 = 2694.0 nM 5.57 DRUGMATRIX: Calcium Channel Type L, Benzothiazepine radioligand binding (ligand:... -
Mitogen-activated protein kinase 14 IC50 = 7406.0 nM 5.13 DRUGMATRIX: Protein Serine/Threonine Kinase, p38alpha enzyme inhibition (substra... -
Alpha-2C adrenergic receptor IC50 = 7898.0 nM 5.1 DRUGMATRIX: Adrenergic Alpha-2C radioligand binding (ligand: [3H] MK-912) -
5-hydroxytryptamine receptor 2B Ki = 11777.0 nM 4.93 DRUGMATRIX: Serotonin (5-Hydroxytryptamine) 5-HT2B radioligand binding (ligand: ... -
Histamine H2 receptor Ki = 13884.0 nM 4.86 DRUGMATRIX: Histamine H2 radioligand binding (ligand: [125I] Aminopotentidine) -
Histamine H2 receptor IC50 = 14120.0 nM 4.85 DRUGMATRIX: Histamine H2 radioligand binding (ligand: [125I] Aminopotentidine) -
Beta-2 adrenergic receptor Ki = 15578.0 nM 4.81 DRUGMATRIX: Adrenergic beta2 radioligand binding (ligand: [3H] CGP-12177) -
Tyrosine-protein kinase Lck IC50 = 15786.0 nM 4.8 DRUGMATRIX: Protein Tyrosine Kinase, LCK enzyme inhibition (substrate: Poly(Glu:... -
Mitogen-activated protein kinase 3 IC50 = 16262.0 nM 4.79 DRUGMATRIX: Protein Serine/Threonine Kinase, ERK1 enzyme inhibition (substrate: ... -

Literature References

PubMed DOI Target Context # Activities
15646539 10.1016/s0399-8320(04)95062-2 Unchecked 11
15646539 10.1016/s0399-8320(04)95062-2 NON-PROTEIN TARGET 8
2319560 10.1021/jm00166a010 Mus musculus 4
1447746 10.1021/jm00101a025 Mus musculus 4
37468498 10.1038/s41467-023-40064-9 Thromboxane A2 receptor 2
37468498 10.1038/s41467-023-40064-9 Prostaglandin G/H synthase 1 2
37468498 10.1038/s41467-023-40064-9 Alpha-1A adrenergic receptor 2
37468498 10.1038/s41467-023-40064-9 Muscarinic acetylcholine receptor M1 2
20547819 10.1128/aac.01777-09 Unchecked 1
20547819 10.1128/aac.01777-09 Trypanosoma cruzi 1
37468498 10.1038/s41467-023-40064-9 Voltage-gated inwardly rectifying potassium channel KCNH2 1
37468498 10.1038/s41467-023-40064-9 Sodium-dependent dopamine transporter 1
37468498 10.1038/s41467-023-40064-9 Estrogen receptor 1
37468498 10.1038/s41467-023-40064-9 Acetylcholinesterase 1
37468498 10.1038/s41467-023-40064-9 Sodium-dependent noradrenaline transporter 1
37468498 10.1038/s41467-023-40064-9 Sodium-dependent serotonin transporter 1
20547819 10.1128/aac.01777-09 ADMET 1
37468498 10.1038/s41467-023-40064-9 Mu-type opioid receptor 1
37468498 10.1038/s41467-023-40064-9 Amine oxidase [flavin-containing] A 1
1447746 10.1021/jm00101a025 Rattus norvegicus 1

Data from ChEMBL 36 via Core Engine