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Compound Detail

CHEMBL80

NALOXONE
💊 Approved Drug
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💊 Approved Drug
C=CCN1CC[C@]23c4c5ccc(O)c4O[C@H]2C(=O)CC[C@@]3(O)[C@H]1C5

Basic Information

ChEMBL ID CHEMBL80
Name NALOXONE
Phase Approved
Structure Type MOL
InChI Key UZHSEJADLWPNLE-GRGSLBFTSA-N
Therapeutic ✓ Yes

Known Names

Dbl naloxone Naloxona Naloxone NSC-70413
21
Targets
199
Activities
4
Assay Types
30
PK Parameters
20
Publications
4
Known Names
20
Indications

Molecular Properties

327.4
MW (Da)
1.30
ALogP
5
HBA
2
HBD
70.0
PSA (Ų)
0.80
QED
0
Ro5 Violations
2
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 1971
Availability OTC
Chirality Single Enantiomer

Routes of Administration

Oral Parenteral Topical

Flags

Natural Product
USAN Stem nal-
USAN Year 1963

Extended Properties

Molecular Formula C19H21NO4
MW 327.38
Aromatic Rings 1
Heavy Atoms 24
NP-Likeness 1.94

Indications

Constipation Chronic Pain Epilepsy Heroin Dependence Low Back Pain Morphine Dependence Mycosis Fungoides Opioid-Related Disorders Opioid-Related Disorders Osteoarthritis Pain Parkinson Disease Restless Legs Syndrome Sezary Syndrome Substance Withdrawal Syndrome Substance-Related Disorders Diabetes Mellitus, Type 1 Diabetic Neuropathies Feeding and Eating Disorders Hypogonadism

ATC Classification

A06AH04
naloxone
Level 1: ALIMENTARY TRACT AND METABOLISM
Level 2: DRUGS FOR CONSTIPATION
V03AB15
naloxone
Level 1: VARIOUS
Level 2: ALL OTHER THERAPEUTIC PRODUCTS

Activity Summary

Ki 113 meas. best 9.64
IC50 59 meas. best 8.85
Kd 21 meas. best 9.66
EC50 6 meas. best 8.82

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Mu-type opioid receptor
CHEMBL233
Kd 9.66 9.66 0.2 2
Mu-type opioid receptor
CHEMBL233
Ki 9.64 8.4631 0.2 26
Kappa-type opioid receptor
CHEMBL237
Ki 9.6 8.1756 0.2 16
Mu-type opioid receptor
CHEMBL270
Kd 9.4 8.74 0.4 3
Mu-type opioid receptor
CHEMBL4354
Ki 9.17 8.8067 0.7 9
Opioid receptor
CHEMBL2094129
Kd 9.0 7.905 1.0 2
Kappa-type opioid receptor
CHEMBL3614
Kd 9.0 8.675 1.0 2
Mu-type opioid receptor
CHEMBL270
Ki 8.97 8.5967 1.1 6
Unchecked
CHEMBL612545
Ki 8.96 7.9743 1.1 7
Opioid receptor
CHEMBL2094129
IC50 8.85 8.0583 1.4 6
Opioid receptor
CHEMBL2094129
EC50 8.82 8.82 1.5 1
Kappa-type opioid receptor
CHEMBL237
IC50 8.82 7.318 1.5 5
Opioid receptors; mu/kappa/delta
CHEMBL2095181
IC50 8.8 7.95 1.6 4
Mu-type opioid receptor
CHEMBL4354
Kd 8.73 8.615 1.9 2
Mu-type opioid receptor
CHEMBL233
IC50 8.73 7.618 1.9 15
Delta-type opioid receptor
CHEMBL269
Ki 8.62 7.8867 2.4 6
Mus musculus
CHEMBL375
Kd 8.53 8.53 3.0 1
Kappa-type opioid receptor
CHEMBL3952
Ki 8.51 8.0144 3.1 18
Mu-type opioid receptor
CHEMBL3041
IC50 8.3 8.3 5.0 1
Unchecked
CHEMBL612545
EC50 8.2 8.12 6.3 2
Rattus norvegicus
CHEMBL376
IC50 8.19 7.6367 6.4 3
Kappa-type opioid receptor
CHEMBL237
EC50 8.18 8.09 6.6 2
Mu-type opioid receptor
CHEMBL233
EC50 8.06 8.06 8.6 1
Opioid receptors; mu & kappa
CHEMBL2095156
IC50 8.05 7.475 9.0 2
Mu-type opioid receptor
CHEMBL4354
IC50 8.05 8.05 8.9 2
Rattus norvegicus
CHEMBL376
Kd 8.0 8.0 10.0 1
Mu-type opioid receptor
CHEMBL2858
Kd 7.99 7.99 10.2 1
C-C chemokine receptor type 5
CHEMBL3676
Kd 7.98 7.83 10.5 2
Mu-type opioid receptor
CHEMBL2858
IC50 7.81 7.81 15.4 1
Delta-type opioid receptor
CHEMBL236
Ki 7.8 7.2126 15.8 23
Delta-type opioid receptor
CHEMBL269
Kd 7.75 7.75 18.0 1
Kappa-type opioid receptor
CHEMBL3952
Kd 7.7 7.7 19.9 1
Unchecked
CHEMBL612545
IC50 7.64 7.64 23.0 1
Delta-type opioid receptor
CHEMBL3222
Kd 7.35 7.325 44.7 2
Kappa-type opioid receptor
CHEMBL3952
IC50 7.3 7.3 50.0 2
Delta-type opioid receptor
CHEMBL236
IC50 7.21 6.8436 62.0 11
Kappa-type opioid receptor
CHEMBL4329
Kd 6.9 6.9 125.9 1
Cytochrome b-245 heavy chain
CHEMBL1287627
IC50 5.71 5.71 1960.0 1
Cytochrome P450 2D6
CHEMBL289
IC50 5.7 5.7 2000.0 1

Pharmacokinetic Data

Parameter Value Units Species
AUC 117.0 ng.hr.mL-1 Canis lupus familiaris
AUC 122.0 ng.hr.mL-1 Canis lupus familiaris
CL 48.8 mL.min-1.kg-1 Rattus norvegicus
CL 42.5 mL.min-1.kg-1 Canis lupus familiaris
CL 25.0 mL.min-1.kg-1 Homo sapiens
CL 19.5 mL.min-1.kg-1 Homo sapiens
CL 23.0 mL.min-1.kg-1 Homo sapiens
CL 23.0 mL.min-1.kg-1 Homo sapiens
CL 19.3 mL.min-1.kg-1 Homo sapiens
CL 14.1 mL.min-1.kg-1 Homo sapiens
CL - mL.min-1.kg-1 Homo sapiens
CL 21.7 mL.min-1.kg-1 Homo sapiens
CL 0.292 mL.min-1.g-1 Homo sapiens
CL 0.675 mL.min-1.g-1 Homo sapiens
CL 2.22 mL.min-1.g-1 Homo sapiens
CL 0.01 mL.min-1.g-1 Homo sapiens
CL 0.14 mL.min-1.g-1 Homo sapiens
CL 0.402 mL.min-1.g-1 Homo sapiens
CL 14.2 mL.min-1.g-1 Homo sapiens
CL 0.502 mL.min-1.g-1 Homo sapiens
CL 52.7 mL.min-1.g-1 Homo sapiens
CL 10.9 mL.min-1.g-1 Homo sapiens
CL 55.6 mL.min-1.g-1 Homo sapiens
CL 10.0 mL.min-1.g-1 Homo sapiens
Cmax 131.35 nM Canis lupus familiaris
Cmax 598.69 nM Canis lupus familiaris
F 20.0 % Homo sapiens
F 2.0 % Homo sapiens
F 9.6 % Canis lupus familiaris
Fu 0.54 - Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Mu-type opioid receptor Kd = 0.2188 nM 9.66 Antagonist activity at mu opioid receptor expressed in CHO cells assessed as rel... 18207400
Mu-type opioid receptor Kd = 0.2188 nM 9.66 Antagonist activity against mu opioid receptor assessed as effect on endomorphin... 17266203
Mu-type opioid receptor Ki = 0.23 nM 9.64 Displacement of [3H]DAMGO from human mu-opioid receptor expressed in CHO cells a... 21482470
Kappa-type opioid receptor Ki = 0.25 nM 9.6 Displacement of [3H]U69563 from human kappa-opioid receptor expressed in CHO cel... 21482470
Mu-type opioid receptor Kd = 0.4 nM 9.4 Opioid receptor mu 1 affinity against the receptor site model site 1 (mu1) 3007760
Mu-type opioid receptor Ki = 0.5623 nM 9.25 Displacement of [3H]DPN from human recombinant mu-type opioid receptor expressed... 19527931
Mu-type opioid receptor Ki = 0.57 nM 9.24 Displacement of [125I]-IBOxyA from MOR-1 expressed in CHO cells 21621410
Mu-type opioid receptor Ki = 0.66 nM 9.18 Displacement of [3H]DAMGO form human mu opioid receptor expressed in CHO cells 19027293
Mu-type opioid receptor Ki = 0.68 nM 9.17 Displacement of [3H]DAMGO from mu opioid receptor in guinea pig brain membrane 17420073
Mu-type opioid receptor Ki = 0.68 nM 9.17 Affinity to mu-receptor, using [3H]DAMGO as radioligand in homogenates of guinea... 11495592
Mu-type opioid receptor Ki = 0.79 nM 9.1 Displacement of [3H]DAMGO from human opioid gamma receptor expressed in CHO cell... 17407276
Mu-type opioid receptor Ki = 0.98 nM 9.01 Displacement of [125I]OXY from human mu opioid receptor expressed in CHO cells 20055417
Mu-type opioid receptor Ki = 1.0 nM 9.0 Binding affinity to mu-opioid receptor (unknown origin) 32870011
Opioid receptor Kd = 1.0 nM 9.0 Displacement of [3H]-(-)-naloxone from opiate receptor in rat brain membrane 206698
Kappa-type opioid receptor Kd = 1.0 nM 9.0 Compound was evaluated for Opioid receptor kappa 1 affinity against the receptor... 3007760
Mu-type opioid receptor Ki = 1.07 nM 8.97 Displacement [3H]-naloxone from the Opioid receptor mu 1 isolated from rat brain... 2563773
Mu-type opioid receptor Ki = 1.1 nM 8.96 In vivo binding affinity against mu opioid receptor was measured by using labele... 7932535
Unchecked Ki = 1.1 nM 8.96 Binding affinity to Hartley Guinea pig brain MOR assessed as inhibition constant... 38156970
Kappa-type opioid receptor Ki = 1.1 nM 8.96 Displacement of [3H]U-69593 from human opioid kappa receptor expressed in CHO ce... 17407276
Mu-type opioid receptor Ki = 1.148 nM 8.94 Displacement of 2-((1E,3E,5E)-5-(1-Ethyl-3,3-dimethyl-5-sulfoindolin-2-ylidene)-... 26632862

Literature References

PubMed DOI Target Context # Activities
- 10.6019/CHEMBL3885881 Rattus norvegicus 388
- 10.5281/zenodo.13943903 ADMET 86
22275465 10.1124/dmd.111.043984 ADMET 18
22194678 10.1371/journal.pcbi.1002310 Hepatotoxicity 14
21051535 10.1124/dmd.110.034629 ADMET 9
22275465 10.1124/dmd.111.043984 Liver microsome 9
17389363 10.1073/pnas.0700295104 Mus musculus 7
28968087 10.1021/acs.jmedchem.7b01133 Canis familiaris 7
38810170 10.1021/acs.jmedchem.4c00333 Mu-type opioid receptor 6
17407276 10.1021/jm061327z Kappa-type opioid receptor 5
28288109 10.1038/nchembio.2334 Mas-related G-protein coupled receptor member X2 5
12747782 10.1021/jm020125+ Kappa-type opioid receptor 5
2536439 10.1021/jm00122a021 Mus musculus 4
10836148 10.1146/annurev.pharmtox.40.1.581 UDP-glucuronosyltransferase 2B7 4
17407276 10.1021/jm061327z Mu-type opioid receptor 4
8410999 10.1021/jm00072a002 Kappa-type opioid receptor 4
18426954 10.1124/dmd.108.020479 ADMET 4
6276546 10.1021/jm00344a005 Rattus norvegicus 4
3023611 10.1021/jm00161a023 Mus musculus 4
3007760 10.1021/jm00154a018 Opioid receptor 4

Data from ChEMBL 36 via Core Engine