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Compound Detail

CHEMBL900

ORPHENADRINE
💊 Approved Drug
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💊 Approved Drug
Cc1ccccc1C(OCCN(C)C)c1ccccc1

Basic Information

ChEMBL ID CHEMBL900
Name ORPHENADRINE
Phase Approved
Structure Type MOL
InChI Key QVYRGXJJSLMXQH-UHFFFAOYSA-N
Therapeutic ✓ Yes

Known Names

Invagesic Mefenamine Mialgin Norgesic Orfenadrina Orphenadrin Orphenadrine Orphengesic
24
Targets
46
Activities
2
Assay Types
2
PK Parameters
20
Publications
8
Known Names
1
Indications

Molecular Properties

269.4
MW (Da)
3.66
ALogP
2
HBA
0
HBD
12.5
PSA (Ų)
0.79
QED
0
Ro5 Violations
6
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 1957
Availability Prescription
Chirality Racemic

Routes of Administration

Oral Parenteral

Flags

Natural Product
USAN Stem -drine

Extended Properties

Molecular Formula C18H23NO
MW 269.39
Aromatic Rings 2
Heavy Atoms 20
NP-Likeness -0.72

Indications

Low Back Pain

ATC Classification

M03BC51
orphenadrine, combinations
Level 1: MUSCULO-SKELETAL SYSTEM
Level 2: MUSCLE RELAXANTS

Activity Summary

IC50 27 meas. best 7.55
Ki 19 meas. best 7.77

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Muscarinic acetylcholine receptor M4
CHEMBL1821
Ki 7.77 7.77 17.0 1
Muscarinic acetylcholine receptor M5
CHEMBL2035
Ki 7.7 7.7 20.0 1
Muscarinic acetylcholine receptor M5
CHEMBL2035
IC50 7.55 7.55 28.0 1
Muscarinic acetylcholine receptor M1
CHEMBL216
Ki 7.44 7.44 36.0 1
Muscarinic acetylcholine receptor M3
CHEMBL245
Ki 7.43 7.43 37.0 1
Muscarinic acetylcholine receptor M4
CHEMBL1821
IC50 6.9 6.9 125.0 1
5-hydroxytryptamine receptor 2A
CHEMBL224
Ki 6.9 6.9 125.0 1
Muscarinic acetylcholine receptor M2
CHEMBL211
Ki 6.87 6.87 134.0 1
Histamine H1 receptor
CHEMBL231
Ki 6.84 6.84 144.0 1
Muscarinic acetylcholine receptor M1
CHEMBL216
IC50 6.83 6.83 148.0 1
Histamine H1 receptor
CHEMBL4701
IC50 6.79 6.79 162.2 1
Muscarinic acetylcholine receptor M3
CHEMBL245
IC50 6.76 6.76 175.0 1
Sodium-dependent serotonin transporter
CHEMBL228
Ki 6.61 6.61 243.0 1
5-hydroxytryptamine receptor 2C
CHEMBL225
Ki 6.55 6.55 280.0 1
Muscarinic acetylcholine receptor M2
CHEMBL211
IC50 6.42 6.42 376.0 1
Cytochrome P450 2D6
CHEMBL289
IC50 6.4 6.4 400.0 1
5-hydroxytryptamine receptor 2A
CHEMBL224
IC50 6.36 6.36 436.0 1
Sodium-dependent serotonin transporter
CHEMBL228
IC50 6.34 6.34 458.0 1
5-hydroxytryptamine receptor 6
CHEMBL3371
Ki 6.28 6.28 521.0 1
5-hydroxytryptamine receptor 2C
CHEMBL225
IC50 6.27 6.27 534.0 1
Alpha-2A adrenergic receptor
CHEMBL1867
Ki 6.09 6.09 809.0 1
Voltage-gated inwardly rectifying potassium channel KCNH2
CHEMBL240
IC50 6.07 6.07 851.1 1
Alpha-2B adrenergic receptor
CHEMBL1942
Ki 6.06 6.06 865.0 1
5-hydroxytryptamine receptor 6
CHEMBL3371
IC50 5.95 5.95 1121.0 1
Histamine H1 receptor
CHEMBL231
IC50 5.91 4.96 1241.0 2
Unchecked
CHEMBL612545
Ki 5.77 5.7033 1698.0 3
Unchecked
CHEMBL612545
IC50 5.76 5.595 1746.0 4
Alpha-2B adrenergic receptor
CHEMBL1942
IC50 5.72 5.72 1895.0 1
5-hydroxytryptamine receptor 2B
CHEMBL1833
Ki 5.67 5.67 2158.0 1
Alpha-2A adrenergic receptor
CHEMBL1867
IC50 5.67 5.67 2156.0 1
Solute carrier family 22 member 2
CHEMBL1743122
IC50 5.6 5.6 2500.0 1
Sodium-dependent noradrenaline transporter
CHEMBL222
Ki 5.58 5.58 2643.0 1
Sodium-dependent noradrenaline transporter
CHEMBL222
IC50 5.57 5.57 2666.0 1
5-hydroxytryptamine receptor 2B
CHEMBL1833
IC50 5.47 5.47 3391.0 1
Glutamate [NMDA] receptor
CHEMBL2094124
Ki 5.22 5.22 6000.0 1
Histamine H2 receptor
CHEMBL1941
Ki 5.17 5.17 6845.0 1
Histamine H2 receptor
CHEMBL1941
IC50 5.16 5.16 6961.0 1
Solute carrier family 22 member 1
CHEMBL5685
IC50 4.9 4.9 12600.0 1
Cytochrome P450 2C19
CHEMBL3622
IC50 4.62 4.62 24200.0 1
Multidrug and toxin extrusion protein 1
CHEMBL1743126
IC50 4.19 4.19 65000.0 1

Pharmacokinetic Data

Parameter Value Units Species
CL 150.0 uL.min-1.(10^6cells)-1 Rattus norvegicus
Cmax 310.0 nM Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Muscarinic acetylcholine receptor M4 Ki = 17.0 nM 7.77 DRUGMATRIX: Muscarinic M4 radioligand binding (ligand: [3H] N-Methylscopolamine) -
Muscarinic acetylcholine receptor M5 Ki = 20.0 nM 7.7 DRUGMATRIX: Muscarinic M5 radioligand binding (ligand: [3H] N-Methylscopolamine) -
Muscarinic acetylcholine receptor M5 IC50 = 28.0 nM 7.55 DRUGMATRIX: Muscarinic M5 radioligand binding (ligand: [3H] N-Methylscopolamine) -
Muscarinic acetylcholine receptor M1 Ki = 36.0 nM 7.44 DRUGMATRIX: Muscarinic M1 radioligand binding (ligand: [3H] N-Methylscopolamine) -
Muscarinic acetylcholine receptor M3 Ki = 37.0 nM 7.43 DRUGMATRIX: Muscarinic M3 radioligand binding (ligand: [3H] N-Methylscopolamine) -
5-hydroxytryptamine receptor 2A Ki = 125.0 nM 6.9 DRUGMATRIX: Serotonin (5-Hydroxytryptamine) 5-HT2A radioligand binding (ligand: ... -
Muscarinic acetylcholine receptor M4 IC50 = 125.0 nM 6.9 DRUGMATRIX: Muscarinic M4 radioligand binding (ligand: [3H] N-Methylscopolamine) -
Muscarinic acetylcholine receptor M2 Ki = 134.0 nM 6.87 DRUGMATRIX: Muscarinic M2 radioligand binding (ligand: [3H] N-Methylscopolamine) -
Histamine H1 receptor Ki = 144.0 nM 6.84 DRUGMATRIX: Histamine H1, Central radioligand binding (ligand: [3H] Pyrilamine) -
Muscarinic acetylcholine receptor M1 IC50 = 148.0 nM 6.83 DRUGMATRIX: Muscarinic M1 radioligand binding (ligand: [3H] N-Methylscopolamine) -
Histamine H1 receptor IC50 = 162.18 nM 6.79 Displacement of [3H]mepyramine from histamine H1 receptor in Sprague-Dawley rat ... 22793499
Muscarinic acetylcholine receptor M3 IC50 = 175.0 nM 6.76 DRUGMATRIX: Muscarinic M3 radioligand binding (ligand: [3H] N-Methylscopolamine) -
Sodium-dependent serotonin transporter Ki = 243.0 nM 6.61 DRUGMATRIX: Transporter, Serotonin (5-Hydroxytryptamine) (SERT) radioligand bind... -
5-hydroxytryptamine receptor 2C Ki = 280.0 nM 6.55 DRUGMATRIX: Serotonin (5-Hydroxytryptamine) 5-HT2C radioligand binding (ligand: ... -
Muscarinic acetylcholine receptor M2 IC50 = 376.0 nM 6.42 DRUGMATRIX: Muscarinic M2 radioligand binding (ligand: [3H] N-Methylscopolamine) -
Cytochrome P450 2D6 IC50 = 400.0 nM 6.4 DRUGMATRIX: CYP450, 2D6 enzyme inhibition (substrate: 3-Cyano-7-ethoxycoumarin) -
5-hydroxytryptamine receptor 2A IC50 = 436.0 nM 6.36 DRUGMATRIX: Serotonin (5-Hydroxytryptamine) 5-HT2A radioligand binding (ligand: ... -
Sodium-dependent serotonin transporter IC50 = 458.0 nM 6.34 DRUGMATRIX: Transporter, Serotonin (5-Hydroxytryptamine) (SERT) radioligand bind... -
5-hydroxytryptamine receptor 6 Ki = 521.0 nM 6.28 DRUGMATRIX: Serotonin (5-Hydroxytryptamine) 5-HT6 radioligand binding (ligand: [... -
5-hydroxytryptamine receptor 2C IC50 = 534.0 nM 6.27 DRUGMATRIX: Serotonin (5-Hydroxytryptamine) 5-HT2C radioligand binding (ligand: ... -

Literature References

PubMed DOI Target Context # Activities
- 10.5281/zenodo.13943903 ADMET 89
31158845 10.1038/s41586-019-1291-3 ADMET 57
22194678 10.1371/journal.pcbi.1002310 Hepatotoxicity 14
18694955 10.1128/aac.00661-08 NON-PROTEIN TARGET 8
21599003 10.1021/jm2001629 ADMET 5
20014752 10.1021/tx900326k Hepatotoxicity 3
37468498 10.1038/s41467-023-40064-9 Alpha-1A adrenergic receptor 2
18788725 10.1021/jm8003152 Solute carrier family 22 member 1 2
- 10.6019/CHEMBL4808148 Histone deacetylase 6 2
18027916 10.1021/jm070524a No relevant target 2
38318365 10.1016/j.isci.2024.108907 Deoxynucleoside triphosphate triphosphohydrolase SAMHD1 2
37468498 10.1038/s41467-023-40064-9 Muscarinic acetylcholine receptor M1 2
- 10.6019/CHEMBL4651402 SARS-CoV-2 2
22931300 10.1021/tx300075j Liver microsomes 2
22931300 10.1021/tx300075j Cytochrome P450 3A4 2
22328583 10.1124/dmd.111.043505 Cytochrome P450 2J2 2
37468498 10.1038/s41467-023-40064-9 Prostaglandin G/H synthase 1 2
37468498 10.1038/s41467-023-40064-9 Thromboxane A2 receptor 2
22793499 10.1021/jm300671m Histamine H1 receptor 2
26948801 10.1016/j.drudis.2016.02.015 Homo sapiens 2

Data from ChEMBL 36 via Core Engine