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Compound Detail

CHEMBL1254682

LEVALLORPHAN
💊 Approved Drug
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💊 Approved Drug
C=CCN1CC[C@]23CCCC[C@H]2[C@H]1Cc1ccc(O)cc13
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL1254682
Name LEVALLORPHAN
Phase Approved
Structure Type MOL
InChI Key OZYUPQUCAUTOBP-QXAKKESOSA-N
Therapeutic ✓ Yes

Known Names

Levallorphan Levallorphane Levalorfano Naloxiphan
6
Targets
11
Activities
2
Assay Types
0
PK Parameters
20
Publications
4
Known Names

Molecular Properties

283.4
MW (Da)
3.64
ALogP
2
HBA
1
HBD
23.5
PSA (Ų)
0.84
QED
0
Ro5 Violations
2
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 1982
Availability Discontinued
Chirality Single Enantiomer

Routes of Administration

Parenteral

Flags

Natural Product
USAN Stem -orphan

Extended Properties

Molecular Formula C19H25NO
MW 283.41
Aromatic Rings 1
Heavy Atoms 21
NP-Likeness 1.17

Activity Summary

IC50 7 meas. best 9.27
Ki 4 meas. best 9.32

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Mu-type opioid receptor
CHEMBL233
 Ki 9.32 8.9933 0.5 3
Opioid receptor
CHEMBL2094129
 IC50 9.27 9.115 0.5 2
Mu-type opioid receptor
CHEMBL270
 IC50 9.2 9.2 0.6 1
Opioid receptors; mu & kappa
CHEMBL2095156
 IC50 9.17 8.88 0.7 2
Rattus norvegicus
CHEMBL376
 IC50 8.05 7.76 9.0 2
Acetylcholinesterase
CHEMBL4078
 Ki 4.92 4.92 12000.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Mu-type opioid receptor Ki = 0.48 nM 9.32 Displacement of [125I]-IBOxyA from MOR-1 expressed in CHO cells 21621410
Opioid receptor IC50 = 0.54 nM 9.27 Inhibition of [3H]naloxone binding to opioid receptor in presence of NaCl 2536439
Mu-type opioid receptor IC50 = 0.6341 nM 9.2 Displacement of [3H]-dihydromorphine from mu opioid receptor in rat cerebral cor... 21864951
Opioid receptors; mu & kappa IC50 = 0.67 nM 9.17 Inhibition of [3H]fluadom binding to opioid receptor 2536439
Opioid receptor IC50 = 1.1 nM 8.96 Inhibition of [3H]naloxone binding to opioid receptor in presence of NaCl 2536439
Mu-type opioid receptor Ki = 1.29 nM 8.89 Displacement of [125I]-IBNtxA from MOR-1 expressed in CHO cells 21621410
Mu-type opioid receptor Ki = 1.69 nM 8.77 Displacement of [125I]-IBNalA from MOR-1 expressed in CHO cells 21621410
Opioid receptors; mu & kappa IC50 = 2.6 nM 8.59 Inhibition of [3H]DADLE binding to opioid receptor 2536439
Rattus norvegicus IC50 = 9.0 nM 8.05 Concentration of drug required to inhibit the stereospecific binding of [3H]-nal... 6325691
Rattus norvegicus IC50 = 34.0 nM 7.47 Concentration of drug required to inhibit the stereospecific binding of [3H]nalo... 6325691
Acetylcholinesterase Ki = 12000.0 nM 4.92 Inhibition of electric eel AChE by Ellman's method 20580236

Literature References

PubMed DOI Target Context # Activities
28288109 10.1038/nchembio.2334 Mas-related G-protein coupled receptor member X2 5
21621410 10.1016/j.bmcl.2011.05.008 Mu-type opioid receptor 3
- 10.6019/CHEMBL4808148 Histone deacetylase 6 2
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
2536439 10.1021/jm00122a021 Opioid receptors; mu & kappa 2
2536439 10.1021/jm00122a021 Opioid receptor 2
6325691 10.1021/jm00371a012 Rattus norvegicus 2
20580236 10.1016/j.bmc.2010.05.071 Acetylcholinesterase 1
- 10.1101/2020.04.21.054387 SARS-CoV-2 1
10841799 10.1021/jm990968+ Mus musculus 1
37468498 10.1038/s41467-023-40064-9 D(1A) dopamine receptor 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
2536439 10.1021/jm00122a021 Opioid receptors; mu/kappa/delta 1
37468498 10.1038/s41467-023-40064-9 Sodium-dependent serotonin transporter 1

Data from ChEMBL 36 via Core Engine