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Compound Detail

CHEMBL485

CODEINE
💊 Approved Drug
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💊 Approved Drug
COc1ccc2c3c1O[C@H]1[C@@H](O)C=C[C@H]4[C@@H](C2)N(C)CC[C@@]341
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL485
Name CODEINE
Phase Approved
Structure Type MOL
InChI Key OROGSEYTTFOCAN-DNJOTXNNSA-N
Therapeutic ✓ Yes

Known Names

Codeine Codeine monohydrate Codeinum Codeinum monohydricum Dea no. 9050 IDS-NC-005(SECT.-2)
7
Targets
23
Activities
3
Assay Types
16
PK Parameters
20
Publications
6
Known Names
8
Indications

Molecular Properties

299.4
MW (Da)
1.50
ALogP
4
HBA
1
HBD
41.9
PSA (Ų)
0.80
QED
0
Ro5 Violations
1
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 1952
Availability Withdrawn
Chirality Single Enantiomer

Routes of Administration

Oral

Flags

Black Box Warning Withdrawn Natural Product
USAN Year 1987

Extended Properties

Molecular Formula C18H21NO3
MW 299.37
Aromatic Rings 1
Heavy Atoms 22
NP-Likeness 2.27

Indications

Cough Pain Myopia Toothache Neck Pain Osteoarthritis Anemia, Sickle Cell Constipation

ATC Classification

N02AA59
codeine, combinations excl. psycholeptics
Level 1: NERVOUS SYSTEM
Level 2: ANALGESICS
N02AA79
codeine, combinations with psycholeptics
Level 1: NERVOUS SYSTEM
Level 2: ANALGESICS
R05DA04
codeine
Level 1: RESPIRATORY SYSTEM
Level 2: COUGH AND COLD PREPARATIONS

Drug Warnings

Withdrawn
drug misuse
misuse and abuse
Country: Malaysia; Bangladesh   Year: 1985
Withdrawn
drug misuse
Liability for addiction and misuse
Country: Malaysia; Bangladesh   Year: 1985
Withdrawn
drug misuse
Liability for addiction and misuse
Country: Malaysia; Bangladesh   Year: 1985

Activity Summary

IC50 14 meas. best 6.98
Ki 5 meas. best 6.14
EC50 4 meas. best 5.21

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Mu-type opioid receptor
CHEMBL233
 IC50 6.98 6.98 105.0 1
Mu-type opioid receptor
CHEMBL233
 Ki 6.14 5.67 727.0 2
Rattus norvegicus
CHEMBL376
 IC50 5.58 5.12 2600.0 2
Unchecked
CHEMBL612545
 IC50 5.37 5.025 4320.0 2
Mu-type opioid receptor
CHEMBL233
 EC50 5.21 5.21 6100.0 1
Mas-related G-protein coupled receptor member X2
CHEMBL5849
 EC50 5.17 5.085 6760.8 2
Unchecked
CHEMBL612545
 Ki 5.16 5.16 6900.0 1
Opioid receptor
CHEMBL2095192
 IC50 5.0 5.0 10000.0 1
Kappa-type opioid receptor
CHEMBL237
 IC50 4.82 4.82 15000.0 1
Kappa-type opioid receptor
CHEMBL237
 Ki 4.59 4.59 25411.0 1
Unchecked
CHEMBL612545
 EC50 4.46 4.46 34700.0 1
Delta-type opioid receptor
CHEMBL236
 Ki 4.28 4.28 52207.0 1

Pharmacokinetic Data

Parameter Value Units Species
CL 15.0 mL.min-1.kg-1 Homo sapiens
CL 15.0 mL.min-1.kg-1 Homo sapiens
CL 8.35 mL.min-1.g-1 Rattus norvegicus
CL 11.95 mL.min-1.g-1 Rattus norvegicus
CL 18.65 mL.min-1.g-1 Rattus norvegicus
CL 31.11 mL.min-1.g-1 Rattus norvegicus
CL 47.97 mL.min-1.g-1 Rattus norvegicus
F 79.0 % Homo sapiens
F 55.0 % Homo sapiens
Fu 0.93 - Homo sapiens
Fu 0.7 - Homo sapiens
Fu 0.95 - Rattus norvegicus
Fu 0.62 - Rattus norvegicus
MRT 3.9 hr Homo sapiens
T1/2 4.0 hr Homo sapiens
Vd 3.2 L.kg-1 Rattus norvegicus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Mu-type opioid receptor IC50 = 105.0 nM 6.98 In vitro binding affinity against cloned human Opioid receptor mu 1 expressed in... 12502358
Mu-type opioid receptor Ki = 727.0 nM 6.14 Displacement of [3H]diprenorphine from recombinant mu opioid receptor expressed ... 18311899
Rattus norvegicus IC50 = 2600.0 nM 5.58 Concentration of drug required to inhibit the stereospecific binding of [3H]-nal... 6325691
Unchecked IC50 = 4320.0 nM 5.37 Inhibition of UDP-glucuronosyltransferase in Sprague-Dawley rat liver microsomes... 24183585
Mu-type opioid receptor EC50 = 6100.0 nM 5.21 Activation of human mu opioid receptor expressed in HEK293a cells co-expressing ... 17616524
Mu-type opioid receptor Ki = 6300.0 nM 5.2 Displacement of [3H]naloxone from human mu poioid receptor expressed in HEK293 c... 17616524
Mas-related G-protein coupled receptor member X2 EC50 = 6760.83 nM 5.17 Agonist activity at MRGPRX2 (unknown origin) expressed in HTLA cells assessed as... 28288109
Unchecked Ki = 6900.0 nM 5.16 Inhibition of UDP-glucuronosyltransferase in Sprague-Dawley rat liver microsomes... 24183585
Mas-related G-protein coupled receptor member X2 EC50 = 10000.0 nM 5.0 Agonist activity at N-terminal Flag-tagged human MRGPRX2 receptor expressed in t... 28288109
Opioid receptor IC50 = 10000.0 nM 5.0 Concentration required to inhibit [3H]naltrexone binding to Opioid receptors 6292420
Kappa-type opioid receptor IC50 = 15000.0 nM 4.82 In vitro binding affinity against cloned human Opioid receptor kappa 1 expressed... 12502358
Unchecked IC50 = 20910.0 nM 4.68 Inhibition of UDP-glucuronosyltransferase in Sprague-Dawley rat hepatocytes asse... 24183585
Rattus norvegicus IC50 = 22000.0 nM 4.66 Concentration of drug required to inhibit the stereospecific binding of [3H]nalo... 6325691
Kappa-type opioid receptor Ki = 25411.0 nM 4.59 Displacement of [3H]diprenorphine from recombinant kappa opioid receptor express... 18311899
Unchecked EC50 = 34700.0 nM 4.46 Displacement of 3.0 nM [3H]etorphine from opioid receptor in rat cerebrum 17962026
Delta-type opioid receptor Ki = 52207.0 nM 4.28 Displacement of [3H]diprenorphine from recombinant delta opioid receptor express... 18311899

Literature References

PubMed DOI Target Context # Activities
24183585 10.1016/j.bmc.2013.09.062 Unchecked 16
15646539 10.1016/s0399-8320(04)95062-2 Unchecked 11
15646539 10.1016/s0399-8320(04)95062-2 NON-PROTEIN TARGET 8
24183585 10.1016/j.bmc.2013.09.062 Liver microsome 5
19764786 10.1021/jm901036q Plasma 4
37468498 10.1038/s41467-023-40064-9 Cannabinoid receptor 1 4
8893832 10.1021/jm960073m No relevant target 4
37468498 10.1038/s41467-023-40064-9 Alpha-1A adrenergic receptor 4
6708055 10.1021/jm00370a019 Mus musculus 4
15781124 10.1016/j.pharmthera.2004.10.013 UDP-glucuronosyltransferase 2B7 4
28288109 10.1038/nchembio.2334 Mas-related G-protein coupled receptor member X2 4
18426954 10.1124/dmd.108.020479 ADMET 4
10836148 10.1146/annurev.pharmtox.40.1.581 UDP-glucuronosyltransferase 2B7 4
31597043 10.1021/acs.jmedchem.9b01301 Solute carrier family 22 member 1 4
12540239 10.1021/jm020067s Unchecked 3
37468498 10.1038/s41467-023-40064-9 Alpha-2A adrenergic receptor 3
8386248 10.1021/jm00056a010 Mus musculus 3
21149540 10.1124/dmd.110.035998 Brain 3
17616524 10.1074/jbc.m703272200 Mu-type opioid receptor 3
1433169 10.1021/jm00098a001 Monkey 3

Data from ChEMBL 36 via Core Engine