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Compound Detail

CHEMBL895

NALBUPHINE
💊 Approved Drug
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💊 Approved Drug
Oc1ccc2c3c1O[C@H]1[C@@H](O)CC[C@@]4(O)[C@@H](C2)N(CC2CCC2)CC[C@]314
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL895
Name NALBUPHINE
Phase Approved
Structure Type MOL
InChI Key NETZHAKZCGBWSS-CEDHKZHLSA-N
Therapeutic ✓ Yes

Known Names

Intapan Nalbufina Nalbuphine
3
Targets
42
Activities
3
Assay Types
11
PK Parameters
20
Publications
3
Known Names
3
Indications

Molecular Properties

357.4
MW (Da)
1.71
ALogP
5
HBA
3
HBD
73.2
PSA (Ų)
0.75
QED
0
Ro5 Violations
2
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 1979
Availability Prescription
Chirality Single Enantiomer

Routes of Administration

Parenteral

Flags

Black Box Warning Natural Product
USAN Stem nal-
USAN Year 1968

Extended Properties

Molecular Formula C21H27NO4
MW 357.45
Aromatic Rings 1
Heavy Atoms 26
NP-Likeness 1.87

Indications

Pain Delirium Idiopathic Pulmonary Fibrosis

ATC Classification

N02AF02
nalbuphine
Level 1: NERVOUS SYSTEM
Level 2: ANALGESICS

Activity Summary

Ki 19 meas. best 9.05
IC50 13 meas. best 9.0
EC50 10 meas. best 7.85

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Mu-type opioid receptor
CHEMBL233
 Ki 9.05 8.6056 0.9 9
Mu-type opioid receptor
CHEMBL233
 IC50 9.0 7.2178 1.0 9
Kappa-type opioid receptor
CHEMBL237
 Ki 8.66 7.93 2.2 5
Mu-type opioid receptor
CHEMBL233
 EC50 7.85 7.562 14.0 5
Kappa-type opioid receptor
CHEMBL237
 EC50 7.6 7.242 25.1 5
Kappa-type opioid receptor
CHEMBL237
 IC50 7.08 7.02 83.0 2
Delta-type opioid receptor
CHEMBL236
 Ki 6.62 6.408 240.0 5
Delta-type opioid receptor
CHEMBL236
 IC50 6.45 6.085 353.0 2

Pharmacokinetic Data

Parameter Value Units Species
AUC 169.1 g.hr Rattus norvegicus
AUC 11.3 hr.sec Rattus norvegicus
AUC 175.9 g.hr Rattus norvegicus
AUC 16.9 hr.sec Rattus norvegicus
CL 22.0 mL.min-1.kg-1 Homo sapiens
CL 22.0 mL.min-1.kg-1 Homo sapiens
F 20.0 % Homo sapiens
F 11.0 % Homo sapiens
Fu 0.5 - Homo sapiens
MRT 3.5 hr Homo sapiens
T1/2 3.7 hr Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Mu-type opioid receptor Ki = 0.89 nM 9.05 Displacement of [3H]DAMGO from human opioid gamma receptor expressed in CHO cell... 17407276
Mu-type opioid receptor Ki = 0.98 nM 9.01 Opioid Receptor Binding Assay: The Ki (binding affinity) for opioid receptors wa... -
Mu-type opioid receptor Ki = 0.98 nM 9.01 Opioid Receptor Binding Assay: The Ki (binding affinity) for opioid receptors wa... -
Mu-type opioid receptor Ki = 0.98 nM 9.01 Opioid Receptor Binding Assay: The Ki (binding affinity) for μ opioid receptors ... -
Mu-type opioid receptor IC50 = 1.0 nM 9.0 Binding affinity against mu-opiate receptor (human) using [3H]DAMGO radioligand 11585443
Mu-type opioid receptor Ki = 1.3 nM 8.89 Opioid Receptor Binding Assay: The Ki (binding affinity) for μ opioid receptors ... -
Mu-type opioid receptor Ki = 1.6 nM 8.8 Displacement of [3H]DAMGO from human mu opioid receptor expressed in CHO cells a... 19282177
Kappa-type opioid receptor Ki = 2.2 nM 8.66 Displacement of [3H]U-69593 from human opioid kappa receptor expressed in CHO ce... 17407276
Kappa-type opioid receptor Ki = 3.0 nM 8.52 Displacement of [3H]U69,593 from human kappa opioid receptor expressed in CHO ce... 19282177
Mu-type opioid receptor Ki = 9.925 nM 8.0 DRUGMATRIX: Opiate mu (OP3, MOP) radioligand binding (ligand: [3H] Diprenorphine... -
Mu-type opioid receptor EC50 = 14.0 nM 7.85 Agonist activity at human opioid gamma receptor expressed in CHO cells assessed ... 17407276
Mu-type opioid receptor Ki = 14.31 nM 7.84 Binding of PEG-Nalbuphine assays: Specific binding is determined by subtraction ... -
Mu-type opioid receptor Ki = 14.3 nM 7.84 Receptor Binding of PEG-Nalbuphine Conjugates: Briefly, the receptor binding aff... -
Mu-type opioid receptor EC50 = 21.0 nM 7.68 Functional Assay (GTPgammaS Binding): The EC50 and Imax for μ opioid receptors w... -
Mu-type opioid receptor IC50 = 24.0 nM 7.62 DRUGMATRIX: Opiate mu (OP3, MOP) radioligand binding (ligand: [3H] Diprenorphine... -
Kappa-type opioid receptor EC50 = 25.1 nM 7.6 GTPyS binding assay: Test compound and/or vehicle was preincubated with the cell... -
Kappa-type opioid receptor Ki = 25.9 nM 7.59 Receptor Binding of PEG-Nalbuphine Conjugates: Briefly, the receptor binding aff... -
Kappa-type opioid receptor EC50 = 27.0 nM 7.57 Agonist activity at human opioid kappa receptor expressed in CHO cells assessed ... 17407276
Kappa-type opioid receptor Ki = 29.95 nM 7.52 Binding of PEG-Nalbuphine assays: Specific binding is determined by subtraction ... -
Mu-type opioid receptor EC50 = 34.0 nM 7.47 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
31212133 10.1016/j.ejmech.2019.06.028 Rattus norvegicus 12
22204910 10.1016/j.bmcl.2011.11.128 Kappa-type opioid receptor 7
17407276 10.1021/jm061327z Mu-type opioid receptor 5
17407276 10.1021/jm061327z Kappa-type opioid receptor 5
19282177 10.1016/j.bmcl.2009.02.078 Kappa-type opioid receptor 5
19282177 10.1016/j.bmcl.2009.02.078 Mu-type opioid receptor 5
18426954 10.1124/dmd.108.020479 ADMET 4
30852084 10.1016/j.bmcl.2019.02.028 GroEL/GroES 4
10836148 10.1146/annurev.pharmtox.40.1.581 UDP-glucuronosyltransferase 2B7 3
- 10.6019/CHEMBL4651402 SARS-CoV-2 2
19445515 10.1021/jm900403j Homo sapiens 2
19282177 10.1016/j.bmcl.2009.02.078 Unchecked 2
22931300 10.1021/tx300075j Liver microsomes 2
22931300 10.1021/tx300075j Cytochrome P450 3A4 2
26948801 10.1016/j.drudis.2016.02.015 Homo sapiens 2
10891117 10.1021/jm0000564 ADMET 2
10891117 10.1021/jm0000564 No relevant target 2
38318365 10.1016/j.isci.2024.108907 Deoxynucleoside triphosphate triphosphohydrolase SAMHD1 2

Data from ChEMBL 36 via Core Engine