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Compound Detail

CHEMBL1200395

ORPHENADRINE CITRATE
💊 Approved Drug
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💊 Approved Drug
Cc1ccccc1C(OCCN(C)C)c1ccccc1.O=C(O)CC(O)(CC(=O)O)C(=O)O
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL1200395
Name ORPHENADRINE CITRATE
Phase Approved
Structure Type MOL
InChI Key MMMNTDFSPSQXJP-UHFFFAOYSA-N
Therapeutic ✓ Yes
Parent Compound CHEMBL900
Active Moiety CHEMBL900

Known Names

Norflex NSC-757238 Orphenadrine (citrate) Orphenadrine citrate Orphenadrine citrate component of invagesic Orphenadrine citrate component of invagesic forte Orphenadrine citrate component of norgesic Orphenadrine citrate component of orphengesic Orphenadrine citrate component of orphengesic forte Orphenadrine dihydrogen citrate
1
Targets
2
Activities
1
Assay Types
0
PK Parameters
6
Publications
10
Known Names
1
Indications
4
Mechanisms

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 1959
Availability Prescription
Chirality Racemic

Routes of Administration

Oral Parenteral
USAN Stem -drine

Extended Properties

Molecular Formula C24H31NO8
MW 461.51
Aromatic Rings 2
Heavy Atoms 20
NP-Likeness -0.72

Mechanism of Action

Mechanism Action Type Target Direct Efficacy
Histamine H1 receptor antagonist ANTAGONIST Histamine H1 receptor ✓ ✓
Norepinephrine transporter inhibitor INHIBITOR Sodium-dependent noradrenaline transporter ✓ ✓
Glutamate [NMDA] receptor antagonist ANTAGONIST Glutamate [NMDA] receptor ✓ ✓
Sodium channel alpha subunit blocker BLOCKER Sodium channel alpha subunit ✓ ✓

Indications

Pain

ATC Classification

M03BC01
orphenadrine (citrate)
Level 1: MUSCULO-SKELETAL SYSTEM
Level 2: MUSCLE RELAXANTS

Activity Summary

IC50 2 meas. best 5.36

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Unchecked
CHEMBL612545
 IC50 5.36 5.045 4348.3 2

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Unchecked IC50 = 4348.34 nM 5.36 PubChem BioAssay. insulin secretion from INS-1E cells in the presence of 5 mM gl... -
Unchecked IC50 = 18680.48 nM 4.73 PubChem BioAssay. tonic K+ channel activity under 0.1 mM glucose conditions in I... -

Literature References

PubMed DOI Target Context # Activities
- 10.6019/CHEMBL4495565 SARS-CoV-2 2
20553011 10.1021/tx1000865 Hepatotoxicity 1
20843939 10.1124/dmd.110.035113 Hepatotoxicity 1
23571415 10.1124/mol.112.084152 Solute carrier organic anion transporter family member 1B3 1
23571415 10.1124/mol.112.084152 Solute carrier organic anion transporter family member 1B1 1
- 10.6019/CHEMBL4495564 Replicase polyprotein 1ab 1

Data from ChEMBL 36 via Core Engine