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

CHEMBL33986

BUTORPHANOL
💊 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
Oc1ccc2c(c1)[C@@]13CCCC[C@@]1(O)[C@@H](C2)N(CC1CCC1)CC3
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL33986
Name BUTORPHANOL
Phase Approved
Structure Type MOL
InChI Key IFKLAQQSCNILHL-QHAWAJNXSA-N
Therapeutic ✓ Yes

Known Names

Butorfanol Butorphanol LEVO-BC-2627
3
Targets
21
Activities
3
Assay Types
6
PK Parameters
20
Publications
3
Known Names
2
Indications

Molecular Properties

327.5
MW (Da)
3.37
ALogP
3
HBA
2
HBD
43.7
PSA (Ų)
0.88
QED
0
Ro5 Violations
2
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 1978
Availability Prescription
Chirality Single Enantiomer

Routes of Administration

Parenteral Topical

Flags

Black Box Warning Natural Product
USAN Stem -orphan-
USAN Year 1974

Extended Properties

Molecular Formula C21H29NO2
MW 327.47
Aromatic Rings 1
Heavy Atoms 24
NP-Likeness 1.33

Indications

Pain Anxiety

ATC Classification

N02AF01
butorphanol
Level 1: NERVOUS SYSTEM
Level 2: ANALGESICS

Activity Summary

Ki 13 meas. best 9.92
IC50 5 meas. best 7.85
EC50 3 meas. best 8.54

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Mu-type opioid receptor
CHEMBL233
 Ki 9.92 9.7314 0.1 7
Kappa-type opioid receptor
CHEMBL237
 Ki 9.92 9.8333 0.1 3
Kappa-type opioid receptor
CHEMBL237
 EC50 8.54 8.54 2.9 1
Mu-type opioid receptor
CHEMBL233
 EC50 8.48 8.48 3.3 2
Delta-type opioid receptor
CHEMBL236
 Ki 7.92 7.92 12.0 3
Mu-type opioid receptor
CHEMBL233
 IC50 7.85 7.61 14.0 5

Pharmacokinetic Data

Parameter Value Units Species
CL 41.0 mL.min-1.kg-1 Homo sapiens
CL 41.0 mL.min-1.kg-1 Homo sapiens
Fu 0.18 - Homo sapiens
Fu 0.17 - Homo sapiens
MRT 5.3 hr Homo sapiens
T1/2 4.8 hr Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Kappa-type opioid receptor Ki = 0.12 nM 9.92 Displacement of [3H]U69593 from human kappa opioid receptor expressed in CHO cel... 18674902
Mu-type opioid receptor Ki = 0.12 nM 9.92 Displacement of [3H]DAMGO form human mu opioid receptor expressed in CHO cells 19027293
Kappa-type opioid receptor Ki = 0.12 nM 9.92 Displacement of [3H]U69563 from human kappa-opioid receptor expressed in CHO cel... 21482470
Mu-type opioid receptor Ki = 0.19 nM 9.72 Opioid Receptor Binding Assay: The Ki (binding affinity) for μ opioid receptors ... -
Mu-type opioid receptor Ki = 0.19 nM 9.72 Opioid Receptor Binding Assay: The Ki (binding affinity) for μ opioid receptors ... -
Mu-type opioid receptor Ki = 0.19 nM 9.72 Opioid Receptor Binding Assay: The Ki (binding affinity) for opioid receptors wa... -
Mu-type opioid receptor Ki = 0.19 nM 9.72 Opioid Receptor Binding Assay: The Ki (binding affinity) for opioid receptors wa... -
Mu-type opioid receptor Ki = 0.22 nM 9.66 Displacement of [3H]DAMGO from human mu-opioid receptor expressed in CHO cells a... 21482470
Kappa-type opioid receptor Ki = 0.22 nM 9.66 Displacement of [3H]U69593 form human kappa opioid receptor expressed in CHO cel... 19027293
Mu-type opioid receptor Ki = 0.22 nM 9.66 Displacement of [3H]DAMGO from human mu opioid receptor expressed in CHO cell me... 18674902
Kappa-type opioid receptor EC50 = 2.9 nM 8.54 Activity at human cloned kappa opioid receptor expressed in CHO cells by [35S]GT... 19027293
Mu-type opioid receptor EC50 = 3.3 nM 8.48 Opioid Receptor Binding Assay: The Ki (binding affinity) for opioid receptors wa... -
Mu-type opioid receptor EC50 = 3.3 nM 8.48 Opioid Receptor Binding Assay: The Ki (binding affinity) for opioid receptors wa... -
Delta-type opioid receptor Ki = 12.0 nM 7.92 Displacement of [3H]Naltindole from human delta opioid receptor expressed in CHO... 18674902
Delta-type opioid receptor Ki = 12.0 nM 7.92 Displacement of [3H]Naltrindole form human delta opioid receptor expressed in CH... 19027293
Delta-type opioid receptor Ki = 12.0 nM 7.92 Displacement of [3H]naltrindole from human delta-opioid receptor expressed in CH... 21482470
Mu-type opioid receptor IC50 = 14.0 nM 7.85 Activity at human cloned mu opioid receptor expressed in CHO cells assessed as i... 19027293
Mu-type opioid receptor IC50 = 28.0 nM 7.55 Opioid Receptor Binding Assay: The Ki (binding affinity) for μ opioid receptors ... -
Mu-type opioid receptor IC50 = 28.0 nM 7.55 Opioid Receptor Binding Assay: The Ki (binding affinity) for opioid receptors wa... -
Mu-type opioid receptor IC50 = 28.0 nM 7.55 Opioid Receptor Binding Assay: The Ki (binding affinity) for opioid receptors wa... -

Literature References

PubMed DOI Target Context # Activities
16472241 10.2174/1570163043334794 Hepatotoxicity 18
22194678 10.1371/journal.pcbi.1002310 Hepatotoxicity 14
19027293 10.1016/j.bmcl.2008.10.134 Kappa-type opioid receptor 5
19027293 10.1016/j.bmcl.2008.10.134 Mu-type opioid receptor 4
18426954 10.1124/dmd.108.020479 ADMET 4
16134 10.1021/jm00215a012 Rattus norvegicus 3
18674902 10.1016/j.bmcl.2008.07.054 Unchecked 3
660584 10.1021/jm00203a003 Mus musculus 3
37468498 10.1038/s41467-023-40064-9 Nuclear receptor subfamily 1 group I member 2 3
16134 10.1021/jm00215a012 Mus musculus 2
26948801 10.1016/j.drudis.2016.02.015 Homo sapiens 2
- 10.6019/CHEMBL4651402 SARS-CoV-2 2
6767032 10.1021/jm00176a013 Rattus norvegicus 2
660584 10.1021/jm00203a003 Rattus norvegicus 2
7192744 10.1021/jm00186a025 Rattus norvegicus 2
22931300 10.1021/tx300075j Cytochrome P450 3A4 2
19445515 10.1021/jm900403j Homo sapiens 2
22931300 10.1021/tx300075j Liver microsomes 2
19027293 10.1016/j.bmcl.2008.10.134 Unchecked 2
14971904 10.1021/jm030408h ADMET 2

Data from ChEMBL 36 via Core Engine