Skip to main content
Free research Free research Free compound review with research home and workspace preview
Quick search ChEMBL 36
Compound Detail

CHEMBL592

LEVORPHANOL
💊 Approved Drug
Enter ChEMBL ID:
Free Research Context This compound will appear in recent viewed items on the research home for this browser.
Research home View demo workspace
💊 Approved Drug
CN1CC[C@]23CCCC[C@H]2[C@H]1Cc1ccc(O)cc13
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL592
Name LEVORPHANOL
Phase Approved
Structure Type MOL
InChI Key JAQUASYNZVUNQP-USXIJHARSA-N
Therapeutic ✓ Yes

Known Names

Aromarone IDS-NL-007 Levorfanol Levorphan Levorphanol RO 1-5431
15
Targets
50
Activities
3
Assay Types
2
PK Parameters
20
Publications
6
Known Names
1
Indications

Molecular Properties

257.4
MW (Da)
3.08
ALogP
2
HBA
1
HBD
23.5
PSA (Ų)
0.77
QED
0
Ro5 Violations
0
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 1991
Availability Prescription
Chirality Single Enantiomer

Routes of Administration

Oral Parenteral

Flags

Black Box Warning Natural Product
USAN Stem -orphan-

Extended Properties

Molecular Formula C17H23NO
MW 257.38
Aromatic Rings 1
Heavy Atoms 19
NP-Likeness 1.58

Indications

Pain

Activity Summary

Ki 31 meas. best 9.68
IC50 15 meas. best 9.89
EC50 4 meas. best 4.9

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Mu-type opioid receptor
CHEMBL233
 IC50 9.89 9.89 0.1 1
Mu-type opioid receptor
CHEMBL4354
 Ki 9.68 9.68 0.2 2
Mu-type opioid receptor
CHEMBL233
 Ki 9.68 9.68 0.2 7
Mu-type opioid receptor
CHEMBL2858
 Ki 9.52 9.52 0.3 1
Mu-type opioid receptor
CHEMBL4354
 IC50 9.22 8.495 0.6 2
Sigma non-opioid intracellular receptor 1
CHEMBL3465
 Ki 8.72 8.72 1.9 1
Kappa-type opioid receptor
CHEMBL237
 Ki 8.64 8.64 2.3 7
Kappa-type opioid receptor
CHEMBL3952
 Ki 8.64 8.64 2.3 2
Delta-type opioid receptor
CHEMBL236
 IC50 8.54 8.415 2.9 2
Kappa-type opioid receptor
CHEMBL237
 IC50 8.4 8.4 4.0 1
Delta-type opioid receptor
CHEMBL236
 Ki 8.38 8.38 4.2 9
Unchecked
CHEMBL612545
 IC50 8.1 8.1 8.0 1
Kappa-type opioid receptor
CHEMBL4329
 Ki 8.0 8.0 10.0 1
Mu-type opioid receptor
CHEMBL2858
 IC50 6.56 6.56 278.0 1
Glutamate NMDA receptor
CHEMBL1907608
 IC50 5.92 5.515 1200.0 2
Glutamate [NMDA] receptor
CHEMBL2094124
 IC50 5.6 5.585 2500.0 2
Solute carrier family 22 member 1
CHEMBL5685
 IC50 5.1 5.1 8000.0 1
Mas-related G-protein coupled receptor member X2
CHEMBL5849
 EC50 4.9 4.755 12589.2 4
Acetylcholinesterase
CHEMBL4078
 Ki 4.6 4.6 25000.0 1
Sodium channel alpha subunits; brain (Types I, II, III)
CHEMBL2096682
 IC50 4.6 4.6 25000.0 1

Pharmacokinetic Data

Parameter Value Units Species
Ke 0.127 nM Cavia porcellus
Ke 0.587 nM Mus musculus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Mu-type opioid receptor IC50 = 0.13 nM 9.89 In vitro binding affinity against cloned human Opioid receptor mu 1 expressed in... 12502358
Mu-type opioid receptor Ki = 0.21 nM 9.68 Inhibition of [3H]-DAMGO binding to Opioid receptor mu 1 of Chinese hamster ovar... 15055988
Mu-type opioid receptor Ki = 0.21 nM 9.68 Binding affinity to MOR (unknown origin) assessed as inhibition constant by radi... 36179400
Mu-type opioid receptor Ki = 0.21 nM 9.68 Displacement of [3H]-DAMGO from human mu opioid receptor expressed in CHO cells ... 22439881
Mu-type opioid receptor Ki = 0.21 nM 9.68 Displacement of [3H]DAMGO from human mu opioid receptor expressed in CHO cell me... 18674902
Mu-type opioid receptor Ki = 0.21 nM 9.68 Displacement of [3H]DAMGO from human mu opioid receptors expressed in CHO cell m... 17276685
Mu-type opioid receptor Ki = 0.21 nM 9.68 Displacement of [3H]DAMGO from human mu opioid receptor expressed in CHO cells 16392810
Mu-type opioid receptor Ki = 0.21 nM 9.68 Binding affinity towards Opioid receptor mu 1 in guinea pig brain membranes usin... 11591513
Mu-type opioid receptor Ki = 0.21 nM 9.68 Binding affinity against opioid receptor mu 1 using [3H]DAMGO as radioligand in ... 14695830
Mu-type opioid receptor Ki = 0.21 nM 9.68 Inhibitory activity against Opioid receptor mu 1 in chinese Hamster Ovary (CHO) ... 14613319
Mu-type opioid receptor Ki = 0.3 nM 9.52 Binding affinity for mouse opioid receptor mu 2549247
Mu-type opioid receptor IC50 = 0.6 nM 9.22 Inhibitory activity against opioid receptor mu of guinea pig brain using [3H]DAG... 2542556
Sigma non-opioid intracellular receptor 1 Ki = 1.9 nM 8.72 Binding affinity for mouse sigma opioid receptor 2549247
Kappa-type opioid receptor Ki = 2.3 nM 8.64 Displacement of [3H]U69593 from human kappa opioid receptor expressed in CHO cel... 18674902
Kappa-type opioid receptor Ki = 2.3 nM 8.64 Displacement of [3H]-U69,593 from human kappa opioid receptor expressed in CHO c... 22439881
Kappa-type opioid receptor Ki = 2.3 nM 8.64 Binding affinity to KOR (unknown origin) assessed as inhibition constant 36179400
Kappa-type opioid receptor Ki = 2.3 nM 8.64 Displacement of [3H]U69593 from human kappa opioid receptor expressed in CHO cel... 16392810
Kappa-type opioid receptor Ki = 2.3 nM 8.64 Binding affinity against opioid receptor kappa 1 using [3H]-U-69,593 as radiolig... 14695830
Kappa-type opioid receptor Ki = 2.3 nM 8.64 Inhibition of [3H]U-69593 binding to Opioid receptor kappa 1 of Chinese hamster ... 15055988
Kappa-type opioid receptor Ki = 2.3 nM 8.64 Inhibitory activity against Opioid receptor kappa 1 in chinese Hamster Ovary (CH... 14613319

Literature References

PubMed DOI Target Context # Activities
11425529 10.1016/s0960-894x(01)00262-1 Rattus norvegicus 6
28288109 10.1038/nchembio.2334 Mas-related G-protein coupled receptor member X2 6
2863378 10.1021/jm00147a009 Mus musculus 4
10836148 10.1146/annurev.pharmtox.40.1.581 UDP-glucuronosyltransferase 2B7 4
218009 10.1021/jm00188a008 Opioid receptor 4
31597043 10.1021/acs.jmedchem.9b01301 Solute carrier family 22 member 1 4
37468498 10.1038/s41467-023-40064-9 Alpha-2A adrenergic receptor 3
13215 10.1021/jm00211a010 No relevant target 3
6296388 10.1021/jm00354a008 Mu-type opioid receptor 3
18674902 10.1016/j.bmcl.2008.07.054 Unchecked 3
1433216 10.1021/jm00100a019 Glutamate NMDA receptor 3
1433216 10.1021/jm00100a019 Rattus norvegicus 3
37468498 10.1038/s41467-023-40064-9 Mu-type opioid receptor 2
2579237 10.1021/jm00381a019 Sodium channel alpha subunits; brain (Types I, II, III) 2
- 10.6019/CHEMBL4651402 SARS-CoV-2 2
1433216 10.1021/jm00100a019 Glutamate [NMDA] receptor 2
22439881 10.1021/jm3001086 Unchecked 2
6292420 10.1021/jm00352a037 Mus musculus 2
209185 10.1021/jm00205a002 Opioid receptors; mu/kappa/delta 2
2831361 10.1021/jm00398a007 Mu-type opioid receptor 2

Data from ChEMBL 36 via Core Engine