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Compound Detail

CHEMBL651

METHADONE
💊 Approved Drug
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💊 Approved Drug
CCC(=O)C(CC(C)N(C)C)(c1ccccc1)c1ccccc1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL651
Name METHADONE
Phase Approved
Structure Type MOL
InChI Key USSIQXCVUWKGNF-UHFFFAOYSA-N
Therapeutic ✓ Yes

Known Names

Amidone Diaminon Dl-methadone Dolophin Heptadone IDS-NM-002 Metadona Metasedin Methadone Phenadone Phy Symoron
12
Targets
13
Activities
3
Assay Types
27
PK Parameters
20
Publications
12
Known Names
20
Indications

Molecular Properties

309.4
MW (Da)
4.29
ALogP
2
HBA
0
HBD
20.3
PSA (Ų)
0.76
QED
0
Ro5 Violations
7
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 1947
Availability Prescription
Chirality Racemic

Routes of Administration

Oral Parenteral

Flags

Black Box Warning Natural Product

Extended Properties

Molecular Formula C21H27NO
MW 309.45
Aromatic Rings 2
Heavy Atoms 23
NP-Likeness -0.20

Indications

Pain Substance-Related Disorders Cancer Pain Chronic Pain Cocaine-Related Disorders Cocaine-Related Disorders Heroin Dependence HIV Infections Neoplasms Neuralgia Neuralgia, Postherpetic Opioid-Related Disorders Opioid-Related Disorders Renal Insufficiency, Chronic Scoliosis Neonatal Abstinence Syndrome Peripheral Nervous System Diseases Restless Legs Syndrome Hepatitis C Premature Birth

ATC Classification

N02AC52
methadone, combinations excl. psycholeptics
Level 1: NERVOUS SYSTEM
Level 2: ANALGESICS
N07BC02
methadone
Level 1: NERVOUS SYSTEM
Level 2: OTHER NERVOUS SYSTEM DRUGS

Activity Summary

IC50 7 meas. best 8.39
Ki 5 meas. best 7.89
EC50 1 meas. best 4.36

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Mu-type opioid receptor
CHEMBL233
 IC50 8.39 8.39 4.1 1
Mu-type opioid receptor
CHEMBL233
 Ki 7.89 7.89 13.0 1
Aldehyde oxidase 1
CHEMBL1641355
 Ki 7.52 7.52 30.0 1
Kappa-type opioid receptor
CHEMBL237
 IC50 6.29 6.29 512.0 1
Delta-type opioid receptor
CHEMBL236
 IC50 5.96 5.96 1090.0 1
D(3) dopamine receptor
CHEMBL234
 Ki 5.68 5.68 2110.0 1
ATP-dependent translocase ABCB1
CHEMBL4302
 IC50 5.12 5.12 7500.0 1
Voltage-gated inwardly rectifying potassium channel KCNH2
CHEMBL240
 IC50 5.01 5.01 9772.4 1
Cytochrome P450 2B6
CHEMBL4729
 Ki 5.0 5.0 10000.0 1
Unchecked
CHEMBL612545
 IC50 4.64 4.64 23000.0 1
D(4) dopamine receptor
CHEMBL219
 Ki 4.58 4.58 26200.0 1
Voltage-gated L-type calcium channel
CHEMBL2095229
 IC50 4.43 4.43 37400.0 1
Mas-related G-protein coupled receptor member X2
CHEMBL5849
 EC50 4.36 4.36 43651.6 1

Pharmacokinetic Data

Parameter Value Units Species
CL 1.7 mL.min-1.kg-1 Homo sapiens
CL 1.3 mL.min-1.kg-1 Homo sapiens
CL 1.7 mL.min-1.kg-1 Homo sapiens
CL 41.4 mL.min-1.kg-1 Canis lupus familiaris
CL 59.3 mL.min-1.kg-1 Rattus norvegicus
CL 1.4 mL.min-1.kg-1 Homo sapiens
CL 1.7 mL.min-1.kg-1 Homo sapiens
CL 29.4 mL.min-1.kg-1 Macaca
CL 0.3 ml/min Homo sapiens
CL 0.09 ml/min Homo sapiens
CL 0.08 ml/min Homo sapiens
CL 0.06 ml/min Homo sapiens
CL 0.7 ml/min Homo sapiens
CL 0.6 ml/min Homo sapiens
CL 0.5 ml/min Homo sapiens
CL 0.3 ml/min Homo sapiens
CL 14.33 mL.min-1.kg-1 Rattus norvegicus
CL 5.22 mL.min-1.kg-1 Rattus norvegicus
CL 0.006 mL.min-1.kg-1 Homo sapiens
CL 0.001 mL.min-1.kg-1 Homo sapiens
F 80.0 % Homo sapiens
Fu 0.11 - Homo sapiens
Fu 0.21 - Homo sapiens
Fu 0.21 - Homo sapiens
MRT 43.0 hr Homo sapiens
T1/2 31.0 hr Homo sapiens
T1/2 0.4167 hr Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Mu-type opioid receptor IC50 = 4.1 nM 8.39 Binding affinity against mu-opiate receptor (human) using [3H]DAMGO radioligand 11585443
Mu-type opioid receptor Ki = 13.0 nM 7.89 Displacement of [3H]DAMGO from human mu opioid receptor expressed in HEK293 cell... 34011153
Aldehyde oxidase 1 Ki = 30.0 nM 7.52 Inhibition of rat aldehyde oxidase 20853847
Kappa-type opioid receptor IC50 = 512.0 nM 6.29 Binding affinity against opioid receptor kappa 1 using [3H]- U-69,593 radioligan... 11585443
Delta-type opioid receptor IC50 = 1090.0 nM 5.96 Binding affinity against delta-opiate receptor (human) using [3H]-DPDPE radiolig... 11585443
D(3) dopamine receptor Ki = 2110.0 nM 5.68 Displacement of [3H]-N-methylspiperone from human dopamine D3 receptor expressed... 34011153
ATP-dependent translocase ABCB1 IC50 = 7500.0 nM 5.12 TP_TRANSPORTER: inhibition of Rhodamine 123 transepithelial transport (basal to ... 11408360
Voltage-gated inwardly rectifying potassium channel KCNH2 IC50 = 9772.37 nM 5.01 Inhibitory concentration against potassium channel HERG 15911273
Cytochrome P450 2B6 Ki = 10000.0 nM 5.0 Inactivation of C-terminal His4-tagged human CYP2B6 lacking 21 N-terminal residu... 22685215
Unchecked IC50 = 23000.0 nM 4.64 Inhibition of AZT (0.02 mM) glucuronidation by human UGT enzymes from liver micr... 15781124
D(4) dopamine receptor Ki = 26200.0 nM 4.58 Displacement of [3H]-N-methylspiperone from human dopamine D4 receptor expressed... 34011153
Voltage-gated L-type calcium channel IC50 = 37400.0 nM 4.43 Inhibition of Cav1.2 current measured using QPatch automatic path clamp system i... 23812503
Mas-related G-protein coupled receptor member X2 EC50 = 43651.58 nM 4.36 Agonist activity at MRGPRX2 (unknown origin) expressed in HTLA cells assessed as... 28288109

Literature References

PubMed DOI Target Context # Activities
23298862 10.1124/dmd.112.050625 ADMET 24
22685215 10.1124/dmd.112.045971 Cytochrome P450 2B6 15
22194678 10.1371/journal.pcbi.1002310 Hepatotoxicity 14
16621936 10.1124/dmd.105.006619 ADMET 8
20070106 10.1021/jm901371v Homo sapiens 8
- 10.6019/CHEMBL4651402 SARS-CoV-2 4
18426954 10.1124/dmd.108.020479 ADMET 4
28288109 10.1038/nchembio.2334 Mas-related G-protein coupled receptor member X2 4
660594 10.1021/jm00203a014 Rattus norvegicus 4
20014752 10.1021/tx900326k Hepatotoxicity 3
26948801 10.1016/j.drudis.2016.02.015 Homo sapiens 2
11408360 - ATP-dependent translocase ABCB1 2
23139379 10.1124/dmd.112.049312 Rattus norvegicus 2
19445515 10.1021/jm900403j Homo sapiens 2
966252 10.1021/jm00230a015 Mus musculus 2
7097722 10.1021/jm00348a016 Mu-type opioid receptor 2
10891117 10.1021/jm0000564 No relevant target 2
23139379 10.1124/dmd.112.049312 ADMET 2
14971904 10.1021/jm030408h ADMET 2
22328583 10.1124/dmd.111.043505 Cytochrome P450 2J2 2

Data from ChEMBL 36 via Core Engine