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Compound Detail

CHEMBL511142

BUPRENORPHINE
💊 Approved Drug
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💊 Approved Drug
CO[C@@]12CC[C@@]3(C[C@@H]1[C@](C)(O)C(C)(C)C)[C@H]1Cc4ccc(O)c5c4[C@@]3(CCN1CC1CC1)[C@H]2O5
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL511142
Name BUPRENORPHINE
Phase Approved
Structure Type MOL
InChI Key RMRJXGBAOAMLHD-CTAPUXPBSA-N
Therapeutic ✓ Yes

Known Names

Brixadi Bupeaze Buplast Buprenorfina Buprenorphin Buprenorphine BUPRENORPHINE COMPONENT OF ALKS-5461 Butec Butrans Buvidal Hapoctasin Panitaz +8 more
14
Targets
90
Activities
3
Assay Types
12
PK Parameters
20
Publications
20
Known Names
20
Indications
2
Mechanisms

Molecular Properties

467.6
MW (Da)
4.41
ALogP
5
HBA
2
HBD
62.2
PSA (Ų)
0.69
QED
0
Ro5 Violations
4
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 1981
Availability Prescription
Chirality Single Enantiomer

Routes of Administration

Parenteral Topical

Flags

Black Box Warning Natural Product
USAN Year 1976

Extended Properties

Molecular Formula C29H41NO4
MW 467.65
Aromatic Rings 1
Heavy Atoms 34
NP-Likeness 1.56

Mechanism of Action

Mechanism Action Type Target Direct Efficacy
Mu opioid receptor agonist AGONIST Mu-type opioid receptor ✓ ✓
Kappa opioid receptor agonist AGONIST Kappa-type opioid receptor ✓ ✓

Indications

Acute Pain Chronic Pain Drug Overdose Opioid-Related Disorders Opioid-Related Disorders Pain Substance-Related Disorders Substance-Related Disorders Back Pain Cocaine-Related Disorders Depressive Disorder Depressive Disorder, Major Heroin Dependence HIV Infections Intervertebral Disc Degeneration Low Back Pain Morphine Dependence Neonatal Abstinence Syndrome Neuralgia Osteoarthritis

ATC Classification

N02AE01
buprenorphine
Level 1: NERVOUS SYSTEM
Level 2: ANALGESICS
N07BC01
buprenorphine
Level 1: NERVOUS SYSTEM
Level 2: OTHER NERVOUS SYSTEM DRUGS
N07BC51
buprenorphine, combinations
Level 1: NERVOUS SYSTEM
Level 2: OTHER NERVOUS SYSTEM DRUGS

Drug Warnings

Black Box Warning
misuse
Country: United States
Black Box Warning
respiratory toxicity
Country: United States

Activity Summary

Ki 50 meas. best 10.4
EC50 25 meas. best 9.96
IC50 15 meas. best 9.39

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Kappa-type opioid receptor
CHEMBL237
 Ki 10.4 9.6209 0.0 11
Unchecked
CHEMBL612545
 Ki 10.1 9.3375 0.1 4
Mu-type opioid receptor
CHEMBL233
 Ki 10.05 9.2523 0.1 13
Mu-type opioid receptor
CHEMBL233
 EC50 9.96 8.8567 0.1 12
Mu-type opioid receptor
CHEMBL270
 Ki 9.89 9.8333 0.1 3
Kappa-type opioid receptor
CHEMBL237
 EC50 9.74 9.1433 0.2 3
Mu-type opioid receptor
CHEMBL270
 EC50 9.57 9.36 0.3 2
Mu-type opioid receptor
CHEMBL4354
 Ki 9.4 9.06 0.4 3
Opioid receptor
CHEMBL2094129
 IC50 9.39 9.375 0.4 2
Mu-type opioid receptor
CHEMBL233
 IC50 9.39 9.334 0.4 5
Delta-type opioid receptor
CHEMBL269
 Ki 9.32 9.32 0.5 2
Kappa-type opioid receptor
CHEMBL3952
 Ki 9.3 8.98 0.5 3
Delta-type opioid receptor
CHEMBL236
 EC50 9.07 9.07 0.8 1
Delta-type opioid receptor
CHEMBL236
 Ki 8.94 8.4857 1.1 7
Kappa-type opioid receptor
CHEMBL3952
 IC50 8.7 8.395 2.0 2
Kappa-type opioid receptor
CHEMBL237
 IC50 8.5 8.16 3.2 2
Mu-type opioid receptor
CHEMBL2858
 EC50 8.44 8.44 3.6 1
Cavia porcellus
CHEMBL369
 IC50 8.09 8.09 8.1 1
Kappa-type opioid receptor
CHEMBL3952
 EC50 7.68 7.68 21.0 1
Mu-type opioid receptor
CHEMBL4354
 EC50 7.68 7.68 21.0 1
Unchecked
CHEMBL612545
 EC50 7.68 7.68 21.0 1
Mus musculus
CHEMBL375
 IC50 7.67 7.67 21.1 1
Nociceptin receptor
CHEMBL2014
 EC50 7.27 6.68 53.4 3
Nociceptin receptor
CHEMBL2014
 Ki 7.11 6.89 77.0 4
Voltage-gated inwardly rectifying potassium channel KCNH2
CHEMBL240
 IC50 5.12 5.11 7585.8 2

Pharmacokinetic Data

Parameter Value Units Species
CL 19.0 mL.min-1.kg-1 Homo sapiens
CL 19.0 mL.min-1.kg-1 Homo sapiens
Fu 0.04 - Homo sapiens
Ke - - Cavia porcellus
Ke - - Mus musculus
Ke 15.0 nM Mus musculus
Ke 0.043 nM Mus musculus
Ke 0.004 nM Mus musculus
Ke 1.8 nM Cavia porcellus
Ke 0.14 nM Homo sapiens
MRT 4.9 hr Homo sapiens
T1/2 3.2 hr Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Kappa-type opioid receptor Ki = 0.04 nM 10.4 κ-Opioid Receptor Binding Assay: Radioligand dose displacement assays used 0.4 n... -
Kappa-type opioid receptor Ki = 0.04 nM 10.4 Antagonist activity at kappa opioid receptor (unknown origin) assessed as stimul... 29107424
Kappa-type opioid receptor Ki = 0.067 nM 10.17 Displacement of [3H]-diprenorphine from human KOR expressed in CHO cells 23438330
Kappa-type opioid receptor Ki = 0.07 nM 10.15 Binding affinity to human cloned kappa opioid receptor expressed in HEK293 cells... 24933507
Unchecked Ki = 0.08 nM 10.1 Binding affinity to monkey brain mu-opioid receptor 27299736
Kappa-type opioid receptor Ki = 0.089 nM 10.05 Displacement of [3H]diprenorphine from human kappa opioid receptor expressed in ... 25898137
Mu-type opioid receptor Ki = 0.09 nM 10.05 Binding affinity to human cloned mu opioid receptor expressed in CHO cells by ra... 24933507
Kappa-type opioid receptor Ki = 0.089 nM 10.05 Displacement of [3H]diprenorphine from recombinant human kappa opioid receptor e... 24761755
Mu-type opioid receptor EC50 = 0.11 nM 9.96 Activity at human cloned mu opioid receptor expressed in CHO cells by [35S]GTPga... 19027293
Mu-type opioid receptor Ki = 0.13 nM 9.89 Displacement of [3H]diprenorphine from rat mu opioid receptor expressed in rat C... 24761755
Mu-type opioid receptor Ki = 0.13 nM 9.89 Displacement of [3H]diprenorphine from rat mu opioid receptor expressed in rat C... 25898137
Kappa-type opioid receptor EC50 = 0.18 nM 9.74 Activity at human cloned kappa opioid receptor expressed in CHO cells by [35S]GT... 19027293
Mu-type opioid receptor Ki = 0.19 nM 9.72 Displacement of [3H]-diprenorphine from rat recombinant MOR expressed in rat C6 ... 23438330
Mu-type opioid receptor Ki = 0.21 nM 9.68 Displacement of [3H]DAMGO form human mu opioid receptor expressed in CHO cells 19027293
Mu-type opioid receptor EC50 = 0.27 nM 9.57 Agonist activity at rat recombinant MOR expressed in rat C6 cells assessed as st... 23438330
Mu-type opioid receptor EC50 = 0.3 nM 9.52 Opioid Receptor Binding Assay: The Ki (binding affinity) for μ opioid receptors ... -
Mu-type opioid receptor EC50 = 0.3 nM 9.52 Functional Assay (GTPgammaS Binding): The EC50 and Imax for μ opioid receptors w... -
Mu-type opioid receptor EC50 = 0.3 nM 9.52 Opioid Receptor Binding Assay: The Ki (binding affinity) for opioid receptors wa... -
Mu-type opioid receptor Ki = 0.3 nM 9.52 μ-Opioid Receptor Binding Assay: Radioligand dose-displacement binding assays fo... -
Mu-type opioid receptor Ki = 0.4 nM 9.4 Displacement of [3H]DAMGO from MOR in Hartley guinea pig membrane 23438330

Literature References

PubMed DOI Target Context # Activities
16472241 10.2174/1570163043334794 Hepatotoxicity 18
16650985 10.1016/j.bmcl.2006.02.017 Mus musculus 16
22194678 10.1371/journal.pcbi.1002310 Hepatotoxicity 14
15646539 10.1016/s0399-8320(04)95062-2 Unchecked 11
23438330 10.1021/jm301543e Kappa-type opioid receptor 9
15646539 10.1016/s0399-8320(04)95062-2 NON-PROTEIN TARGET 8
38810170 10.1021/acs.jmedchem.4c00333 Mu-type opioid receptor 7
8893832 10.1021/jm960073m No relevant target 6
23438330 10.1021/jm301543e Mu-type opioid receptor 6
19027293 10.1016/j.bmcl.2008.10.134 Kappa-type opioid receptor 5
24761755 10.1021/jm401964y Mu-type opioid receptor 5
19027293 10.1016/j.bmcl.2008.10.134 Mu-type opioid receptor 5
28288109 10.1038/nchembio.2334 Mas-related G-protein coupled receptor member X2 4
38810170 10.1021/acs.jmedchem.4c00333 Kappa-type opioid receptor 4
24063433 10.1021/jm4010829 Mu-type opioid receptor 4
17887741 10.1021/jm070255o Mu-type opioid receptor 4
18426954 10.1124/dmd.108.020479 ADMET 4
10836148 10.1146/annurev.pharmtox.40.1.581 UDP-glucuronosyltransferase 2B7 4
15781124 10.1016/j.pharmthera.2004.10.013 UDP-glucuronosyltransferase 1A1 4
10649968 10.1021/jm991165p Delta-type opioid receptor 3

Data from ChEMBL 36 via Core Engine