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This repository is under review for potential modification in compliance with Administration directives.

Details

Stereochemistry RACEMIC
Molecular Formula C21H27NO
Molecular Weight 309.4452
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of METHADONE

SMILES

CCC(=O)C(CC(C)N(C)C)(C1=CC=CC=C1)C2=CC=CC=C2

InChI

InChIKey=USSIQXCVUWKGNF-UHFFFAOYSA-N
InChI=1S/C21H27NO/c1-5-20(23)21(16-17(2)22(3)4,18-12-8-6-9-13-18)19-14-10-7-11-15-19/h6-15,17H,5,16H2,1-4H3

HIDE SMILES / InChI
Molecular Formula C21H27NO
Molecular Weight 309.4452
Charge 0
Count
Stereochemistry RACEMIC
Additional Stereochemistry No
Defined Stereocenters 0 / 1
E/Z Centers 0
Optical Activity ( + / - )

Description
Curator's Comment: description was created based on several sources, including: http://www.accessdata.fda.gov/drugsatfda_docs/label/2016/006134s040s041lbl.pdf | https://www.drugs.com/pro/diskets.html

Methadone, sold under the brand names Dolophine among others, is an synthetic opioid that is used as the hydrochloride to treat pain and as maintenance therapy or to help with detoxification in people with opioid dependence. Methadone hydrochloride is a mu-agonist; a synthetic opioid analgesic with multiple actions qualitatively similar to those of morphine. Some data also indicate that methadone acts as an antagonist at the NMDA-receptor. The contribution of NMDA receptor antagonism to methadone’s efficacy is unknown. Most common adverse reactions are: lightheadedness, dizziness, sedation, nausea, vomiting, and sweating. Avoid use mixed agonist/antagonist and partial agonist opioid analgesics with DOLOPHINE because they may reduce analgesic effect of DOLOPHINE or precipitate withdrawal symptoms.

CNS Activity

CNS Active
4002
Curator's Comment: https://www.ncbi.nlm.nih.gov/pubmed/5084666

Originator

Approval Year

1947
100
Targets

Targets

Primary TargetPharmacologyConditionPotency
Agonist
2752
 3.51 nM [Ki]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Palliative
Approved
8583
DOLOPHINE HYDROCHLORIDE

Approved Use

For the treatment of moderate to severe pain not responsive to non-narcotic analgesics. For detoxification treatment of opioid addiction (heroin or other morphine-like drugs). For maintenance treatment of opioid addiction (heroin or other morphine-like drugs), in conjunction with appropriate social and medical services. Note – Outpatient maintenance and outpatient detoxification treatment may be provided only by Opioid Treatment Programs (OTPs) certified by the Federal Substance Abuse and Mental Health Services Administration (SAMHSA) and registered by the Drug Enforcement Administration (DEA). This does not preclude the maintenance treatment of a patient with concurrent opioid addiction who is hospitalized for conditions other than opioid addiction and who requires temporary maintenance during the critical period of his/her stay, or of a patient whose enrollment has been verified in a program which has been certified for maintenance treatment with methadone.

Launch Date

1947
Palliative
Approved
8583
DOLOPHINE HYDROCHLORIDE

Approved Use

For the treatment of moderate to severe pain not responsive to non-narcotic analgesics. For detoxification treatment of opioid addiction (heroin or other morphine-like drugs). For maintenance treatment of opioid addiction (heroin or other morphine-like drugs), in conjunction with appropriate social and medical services. Note – Outpatient maintenance and outpatient detoxification treatment may be provided only by Opioid Treatment Programs (OTPs) certified by the Federal Substance Abuse and Mental Health Services Administration (SAMHSA) and registered by the Drug Enforcement Administration (DEA). This does not preclude the maintenance treatment of a patient with concurrent opioid addiction who is hospitalized for conditions other than opioid addiction and who requires temporary maintenance during the critical period of his/her stay, or of a patient whose enrollment has been verified in a program which has been certified for maintenance treatment with methadone.

Launch Date

1947
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
494 ng/mL
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/15151520/
76 mg 1 times / day steady-state, oral
dose: 76 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
METHADONE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
40.2 ng/mL
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/22621465/
10 mg single, oral
dose: 10 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
METHADONE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
548 ng/mL
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/8641323/
0.89 mg/kg 1 times / day steady-state, oral
dose: 0.89 mg/kg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
METHADONE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FED
54 ng/mL
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/8641323/
0.89 mg/kg 1 times / day steady-state, oral
dose: 0.89 mg/kg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
2-ETHYLIDENE-1,5-DIMETHYL-3,3-DIPHENYLPYRROLIDINE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FED
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
8.27 μg × h/mL
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/15151520/
76 mg 1 times / day steady-state, oral
dose: 76 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
METHADONE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
1073 ng × h/mL
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/22621465/
10 mg single, oral
dose: 10 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
METHADONE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
8.54 mg × h/L
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/8641323/
0.89 mg/kg 1 times / day steady-state, oral
dose: 0.89 mg/kg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
METHADONE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FED
0.61 mg × h/L
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/8641323/
0.89 mg/kg 1 times / day steady-state, oral
dose: 0.89 mg/kg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
2-ETHYLIDENE-1,5-DIMETHYL-3,3-DIPHENYLPYRROLIDINE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FED
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
39 h
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/15151520/
76 mg 1 times / day steady-state, oral
dose: 76 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
METHADONE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
39.3 h
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/22621465/
10 mg single, oral
dose: 10 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
METHADONE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
31.2 h
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/8641323/
0.89 mg/kg 1 times / day steady-state, oral
dose: 0.89 mg/kg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
METHADONE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FED
Doses

Doses

DosePopulationAdverse events​
10 mg 3 times / day multiple, intravenous
Recommended
Dose: 10 mg, 3 times / day
Route: intravenous
Route: multiple
Dose: 10 mg, 3 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/021624s010lbl.pdf
pregnant, adult
Health Status: pregnant
Age Group: adult
Sex: F
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/021624s010lbl.pdf
Other AEs: Withdrawal syndrome neonatal...
Other AEs:
Withdrawal syndrome neonatal
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/021624s010lbl.pdf
10 mg 3 times / day multiple, intravenous
Recommended
Dose: 10 mg, 3 times / day
Route: intravenous
Route: multiple
Dose: 10 mg, 3 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/021624s010lbl.pdf
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/021624s010lbl.pdf
Other AEs: Respiratory depression, Addiction...
Other AEs:
Respiratory depression (grade 5)
Addiction
QT interval prolonged (grade 5)
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/021624s010lbl.pdf
20 mg single, oral
Recommended
Dose: 20 mg
Route: oral
Route: single
Dose: 20 mg
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/017058s026lbl.pdf
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/017058s026lbl.pdf
Other AEs: Respiratory depression, QT interval prolonged...
Other AEs:
Respiratory depression (grade 5)
QT interval prolonged
Arrhythmia (serious)
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/017058s026lbl.pdf
AEs

AEs

AESignificanceDosePopulation
Withdrawal syndrome neonatal
10 mg 3 times / day multiple, intravenous
Recommended
Dose: 10 mg, 3 times / day
Route: intravenous
Route: multiple
Dose: 10 mg, 3 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/021624s010lbl.pdf
pregnant, adult
Health Status: pregnant
Age Group: adult
Sex: F
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/021624s010lbl.pdf
Addiction
10 mg 3 times / day multiple, intravenous
Recommended
Dose: 10 mg, 3 times / day
Route: intravenous
Route: multiple
Dose: 10 mg, 3 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/021624s010lbl.pdf
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/021624s010lbl.pdf
QT interval prolonged grade 5
10 mg 3 times / day multiple, intravenous
Recommended
Dose: 10 mg, 3 times / day
Route: intravenous
Route: multiple
Dose: 10 mg, 3 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/021624s010lbl.pdf
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/021624s010lbl.pdf
Respiratory depression grade 5
10 mg 3 times / day multiple, intravenous
Recommended
Dose: 10 mg, 3 times / day
Route: intravenous
Route: multiple
Dose: 10 mg, 3 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/021624s010lbl.pdf
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/021624s010lbl.pdf
QT interval prolonged
20 mg single, oral
Recommended
Dose: 20 mg
Route: oral
Route: single
Dose: 20 mg
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/017058s026lbl.pdf
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/017058s026lbl.pdf
Respiratory depression grade 5
20 mg single, oral
Recommended
Dose: 20 mg
Route: oral
Route: single
Dose: 20 mg
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/017058s026lbl.pdf
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/017058s026lbl.pdf
Arrhythmia serious
20 mg single, oral
Recommended
Dose: 20 mg
Route: oral
Route: single
Dose: 20 mg
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/017058s026lbl.pdf
unhealthy, adult
Health Status: unhealthy
Age Group: adult
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/017058s026lbl.pdf
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG
substrate
1946

inhibitor
2252
substrate
1193
substrate
1388

inhibitor
2507
inhibitor
2217

OverviewOther

Other InhibitorOther SubstrateOther Inducer
CYP2E1
1060

CYP1A
70

CYP2B
16

CYP2C
20

UGT2B7
197

UGT2B4
23
CYP2B6
776

CYP2C19
1119

P-gp
2052

OATP1A2
67

OATP1B1
503

OATP1B3
435

OATP2B1
122

OCT1
393

OCT2
434

OCT3
92

BCRP
697
Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
UGT2B4
23
 major [Inhibition 0.6 uM]
CYP1A
122
 no
CYP2B
41
 no
CYP2C
37
 no
CYP2E1
1146
 no
UGT2B7
210
 unlikely
CYP3A4
2633
 yes [Ki 100 uM]
CYP2D6
2546
 yes [Ki 2.5 uM]
Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
BCRP
697
 no
OATP1A2
67
 no
OATP1B1
503
 no
OATP1B3
435
 no
OATP2B1
122
 no
OCT1
393
 no
OCT2
434
 no
OCT3
92
 no
P-gp
2052
 yes
CYP2B6
776
 yes
yes (co-administration study)
Comment: CYP450 inducers: concomitant administration of rifampin resulted in a marked reduction in serum methadone levels and a concurrent appearance of withdrawal symptoms; phenytoin administration resulted in an approximately 50% reduction in methadone exposure and withdrawal symptoms occurred concurrently. CYP450 inhibitors: Repeat dose administration of oral voriconazole increased the peak plasma concentration (Cmax) and AUC of (R)-methadone by 31% and 47%, respectively, in subjects receiving a methadone maintenance dose. The Cmax and AUC of (S)-methadone increased by 65% and 103%, respectively
Page: 29.0
CYP2C19
1119
 yes
yes (co-administration study)
Comment: CYP450 inducers: concomitant administration of rifampin resulted in a marked reduction in serum methadone levels and a concurrent appearance of withdrawal symptoms; phenytoin administration resulted in an approximately 50% reduction in methadone exposure and withdrawal symptoms occurred concurrently. CYP450 inhibitors: Repeat dose administration of oral voriconazole increased the peak plasma concentration (Cmax) and AUC of (R)-methadone by 31% and 47%, respectively, in subjects receiving a methadone maintenance dose. The Cmax and AUC of (S)-methadone increased by 65% and 103%, respectively
Page: 29.0
CYP2C9
1193
 yes
yes (co-administration study)
Comment: CYP450 inducers: concomitant administration of rifampin resulted in a marked reduction in serum methadone levels and a concurrent appearance of withdrawal symptoms; phenytoin administration resulted in an approximately 50% reduction in methadone exposure and withdrawal symptoms occurred concurrently. CYP450 inhibitors: Repeat dose administration of oral voriconazole increased the peak plasma concentration (Cmax) and AUC of (R)-methadone by 31% and 47%, respectively, in subjects receiving a methadone maintenance dose. The Cmax and AUC of (S)-methadone increased by 65% and 103%, respectively
Page: 29.0
CYP2D6
1388
 yes
yes (co-administration study)
Comment: CYP450 inducers: concomitant administration of rifampin resulted in a marked reduction in serum methadone levels and a concurrent appearance of withdrawal symptoms; phenytoin administration resulted in an approximately 50% reduction in methadone exposure and withdrawal symptoms occurred concurrently. CYP450 inhibitors: Repeat dose administration of oral voriconazole increased the peak plasma concentration (Cmax) and AUC of (R)-methadone by 31% and 47%, respectively, in subjects receiving a methadone maintenance dose. The Cmax and AUC of (S)-methadone increased by 65% and 103%, respectively
Page: 29.0
CYP3A4
1946
 yes
yes (co-administration study)
Comment: CYP450 inducers: concomitant administration of rifampin resulted in a marked reduction in serum methadone levels and a concurrent appearance of withdrawal symptoms; phenytoin administration resulted in an approximately 50% reduction in methadone exposure and withdrawal symptoms occurred concurrently. CYP450 inhibitors: Repeat dose administration of oral voriconazole increased the peak plasma concentration (Cmax) and AUC of (R)-methadone by 31% and 47%, respectively, in subjects receiving a methadone maintenance dose. The Cmax and AUC of (S)-methadone increased by 65% and 103%, respectively
Page: 29.0
Tox targets

Tox targets

TargetModalityActivityMetaboliteClinical evidence
hERG
2263
Sourcing

Sourcing

Vendor/AggregatorIDURL
ChEBI
CHEBI:6807
https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:6807
eMolecules
979329
https://www.emolecules.com/cgi-bin/more?vid=979329
PubMed

PubMed

TitleDatePubMed
Rhabdomyolysis and acute renal failure following methadone abuse.
1992
Cocaine-associated panic attacks in methadone-maintained patients.
1992
Desipramine in opioid-dependent cocaine abusers maintained on buprenorphine vs methadone.
1999 Sep
Reversible spastic paraparesis induced by high-dose intravenous methadone.
2001 Feb
Bile duct dilation with chronic methadone use in asymptomatic patients: ERCP findings in 6 patients.
2003 Jul
The impact of methadone induction on cardiac conduction in opiate users.
2003 Jul 15
Tiagabine increases cocaine-free urines in cocaine-dependent methadone-treated patients: results of a randomized pilot study.
2003 Nov
QTc interval prolongation associated with intravenous methadone.
2003 Oct
QT prolongation and Torsades de Pointes in patients infected with human immunodeficiency virus and treated with methadone.
2003 Oct 15
Safety of injectable opioid maintenance treatment for heroin dependence.
2003 Oct 15
[Torsade de pointes: a severe and unknown adverse effect in a patient taking methadone].
2003 Oct 8
[Development of transmural myocardial infarction in young persons with intact coronary arteries during methadone use for the treatment of heroine addiction].
2004
Relationship between prescribing and risk of opiate overdose among drug users in and out of maintenance treatment.
2004
Cost effectiveness of disulfiram: treating cocaine use in methadone-maintained patients.
2004 Apr
QT interval prolongation in patients on methadone with concomitant drugs.
2004 Aug
Methadone metabolism by human placenta.
2004 Aug 1
[Life-threatening, recurrent arrhythmia in patients on high-dose methadone treatment: torsade de pointes].
2004 Aug 30
Obsessive-compulsive symptoms precipitated by methadone tapering.
2004 Dec
Methadone-induced torsade de pointes in a patient with normal baseline QT interval.
2004 Jul-Aug
Directly observed therapy for the management of HIV-infected patients in a methadone program.
2004 Jun 1
The effect of quinidine, used as a probe for the involvement of P-glycoprotein, on the intestinal absorption and pharmacodynamics of methadone.
2004 May
Agonist-like or antagonist-like treatment for cocaine dependence with methadone for heroin dependence: two double-blind randomized clinical trials.
2004 May
[Routine ECG in methadone-assisted rehabilitation is wrong prioritization].
2004 Nov 18
Oral methadone for cancer pain: no indication of Q-T interval prolongation or torsades de pointes.
2004 Oct
Intravenous ketamine infusion as an adjuvant to morphine in a 2-year-old with severe cancer pain from metastatic neuroblastoma.
2004 Oct
[Preclinical management of accidental methadone intoxication of a 4-year-old girl. Antagonist or intubation?].
2004 Oct
[Long QT and torsade de pointes in a patient with acquired human immunodeficiency virus infection in multitherapy with drugs affecting cytochrome P450].
2004 Sep
Epidural clonidine, bupivacaine and methadone as the sole analgesic agent after thoracotomy for lung resection.
2004 Sep
Cocaine-related torsade de pointes in a methadone maintenance patient.
2005
Adipocyte-derived hormones in heroin addicts: the influence of methadone maintenance treatment.
2005
QTc interval prolongation in patients on long-term methadone maintenance therapy.
2005
Effects of buprenorphine on cardiac repolarization in a patient with methadone-related torsade de pointes.
2005 Apr
Torsades de pointes with methadone.
2005 Apr
Methadone-related Torsades de Pointes in a sickle cell patient treated for chronic pain.
2005 Apr
[Methadone-induced heart arrhythmia].
2005 Aug 11
Methadone versus buprenorphine with contingency management or performance feedback for cocaine and opioid dependence.
2005 Feb
Dextromethorphan-induced delirium and possible methadone interaction.
2005 Mar
Methadone-induced Torsade de pointes tachycardias.
2005 May 14
QT prolongation and torsades de pointes among methadone users: reports to the FDA spontaneous reporting system.
2005 Nov
[Torsades de pointes during methadone treatment].
2005 Oct
Methadone doses of 100 mg or greater are more effective than lower doses at suppressing heroin self-administration in opioid-dependent volunteers.
2005 Oct
QT prolongation and syncope with methadone, doxepin, and a beta-blocker.
2005 Oct
Central sleep apnea in stable methadone maintenance treatment patients.
2005 Sep
Methadone treatment of chronic non-malignant pain and opioid dependence--a long-term follow-up.
2006 Apr
Variables associated with perceived sleep disorders in methadone maintenance treatment (MMT) patients.
2006 Apr 28
Does naltrexone treatment lead to depression? Findings from a randomized controlled trial in subjects with opioid dependence.
2006 Jan
Bradycardia during methadone therapy in an infant.
2006 Jan
A randomized controlled trial of interim methadone maintenance.
2006 Jan
Frequency of high-risk use of QT-prolonging medications.
2006 Jun
Changes in HIV risk behaviors among patients receiving combined pharmacological and behavioral interventions for heroin and cocaine dependence.
2006 May
Patents

Patents

JP2000212069A
13
JP2002527384A
13
JP2007507532A
35
JP2007525670A
150
JP2011528275A
456
JPH02247157A
4

Sample Use Guides

In Vivo Use Guide
Chronic pain: oral initial dose - 2.5 mg every 8 to 12 hours; Intravenous initial dose: 2.5 mg to 10 mg every 8 to 12 hours Opiate withdrawal: Initial dose - 20 to 30 mg orally; an additional 5 to 10 mg may be given orally after 2 to 4 hours if withdrawal symptoms have not been suppressed or if symptoms reappear. -Maximum initial dose: 30 mg -Maximum day 1 dose: 40 mg
Route of Administration: Other
In Vitro Use Guide
In the presence of 1 uM methadone, the maximum 86Rb+ efflux stimulated by nicotine (Emax) was markedly reduced, but the EC50 for nicotine was altered only slightly, if at all.
Substance Class Chemical
Created
by admin
on Mon Mar 31 17:45:41 GMT 2025
Edited
by admin
on Mon Mar 31 17:45:41 GMT 2025
Record UNII
UC6VBE7V1Z
Record Status Validated (UNII)
Record Version
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Name Type Language
METHADONE
HSDB   INN   MI   VANDF   WHO-DD  
INN  
Official Name English
IDS-NM-002
Preferred Name English
METHADONE [MI]
Common Name English
DIAMINON
Common Name English
PHYSEPTONE
Common Name English
6-(DIMETHYLAMINO)-4,4-DIPHENYL-3-HEPTANONE
Systematic Name English
EPTADONE
Common Name English
METHADONE [VANDF]
Common Name English
METHADONE [HSDB]
Common Name English
HEPTADONE
Common Name English
DOLOPHIN
Common Name English
DL-METHADONE
Common Name English
PHENADONE
Common Name English
METASEDIN
Common Name English
methadone [INN]
Common Name English
3-HEPTANONE, 6-(DIMETHYLAMINO)-4,4-DIPHENYL-
Systematic Name English
Methadone [WHO-DD]
Common Name English
Classification Tree Code System Code
WHO-ATC N07BC02
Created by admin on Mon Mar 31 17:45:41 GMT 2025 , Edited by admin on Mon Mar 31 17:45:41 GMT 2025
NCI_THESAURUS C1506
Created by admin on Mon Mar 31 17:45:41 GMT 2025 , Edited by admin on Mon Mar 31 17:45:41 GMT 2025
NDF-RT N0000175684
Created by admin on Mon Mar 31 17:45:41 GMT 2025 , Edited by admin on Mon Mar 31 17:45:41 GMT 2025
WHO-ATC N02AC52
Created by admin on Mon Mar 31 17:45:41 GMT 2025 , Edited by admin on Mon Mar 31 17:45:41 GMT 2025
NCI_THESAURUS C67413
Created by admin on Mon Mar 31 17:45:41 GMT 2025 , Edited by admin on Mon Mar 31 17:45:41 GMT 2025
DEA NO. 9250
Created by admin on Mon Mar 31 17:45:41 GMT 2025 , Edited by admin on Mon Mar 31 17:45:41 GMT 2025
LIVERTOX NBK548084
Created by admin on Mon Mar 31 17:45:41 GMT 2025 , Edited by admin on Mon Mar 31 17:45:41 GMT 2025
WHO-VATC QN07BC02
Created by admin on Mon Mar 31 17:45:41 GMT 2025 , Edited by admin on Mon Mar 31 17:45:41 GMT 2025
CFR 21 CFR 862.3620
Created by admin on Mon Mar 31 17:45:41 GMT 2025 , Edited by admin on Mon Mar 31 17:45:41 GMT 2025
WHO-ESSENTIAL MEDICINES LIST 24.5
Created by admin on Mon Mar 31 17:45:41 GMT 2025 , Edited by admin on Mon Mar 31 17:45:41 GMT 2025
WHO-VATC QN02AC52
Created by admin on Mon Mar 31 17:45:41 GMT 2025 , Edited by admin on Mon Mar 31 17:45:41 GMT 2025
NDF-RT N0000175690
Created by admin on Mon Mar 31 17:45:41 GMT 2025 , Edited by admin on Mon Mar 31 17:45:41 GMT 2025
Code System Code Type Description
ECHA (EC/EINECS)
200-996-9
Created by admin on Mon Mar 31 17:45:41 GMT 2025 , Edited by admin on Mon Mar 31 17:45:41 GMT 2025
PRIMARY
RXCUI
6813
Created by admin on Mon Mar 31 17:45:41 GMT 2025 , Edited by admin on Mon Mar 31 17:45:41 GMT 2025
PRIMARY RxNorm
EPA CompTox
DTXSID7023273
Created by admin on Mon Mar 31 17:45:41 GMT 2025 , Edited by admin on Mon Mar 31 17:45:41 GMT 2025
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SMS_ID
100000091046
Created by admin on Mon Mar 31 17:45:41 GMT 2025 , Edited by admin on Mon Mar 31 17:45:41 GMT 2025
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CHEBI
28017
Created by admin on Mon Mar 31 17:45:41 GMT 2025 , Edited by admin on Mon Mar 31 17:45:41 GMT 2025
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MERCK INDEX
m7286
Created by admin on Mon Mar 31 17:45:41 GMT 2025 , Edited by admin on Mon Mar 31 17:45:41 GMT 2025
PRIMARY Merck Index
NCI_THESAURUS
C62044
Created by admin on Mon Mar 31 17:45:41 GMT 2025 , Edited by admin on Mon Mar 31 17:45:41 GMT 2025
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HSDB
3119
Created by admin on Mon Mar 31 17:45:41 GMT 2025 , Edited by admin on Mon Mar 31 17:45:41 GMT 2025
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EVMPD
SUB08833MIG
Created by admin on Mon Mar 31 17:45:41 GMT 2025 , Edited by admin on Mon Mar 31 17:45:41 GMT 2025
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DRUG BANK
DB00333
Created by admin on Mon Mar 31 17:45:41 GMT 2025 , Edited by admin on Mon Mar 31 17:45:41 GMT 2025
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CHEBI
167309
Created by admin on Mon Mar 31 17:45:41 GMT 2025 , Edited by admin on Mon Mar 31 17:45:41 GMT 2025
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CHEBI
6807
Created by admin on Mon Mar 31 17:45:41 GMT 2025 , Edited by admin on Mon Mar 31 17:45:41 GMT 2025
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CAS
76-99-3
Created by admin on Mon Mar 31 17:45:41 GMT 2025 , Edited by admin on Mon Mar 31 17:45:41 GMT 2025
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PUBCHEM
4095
Created by admin on Mon Mar 31 17:45:41 GMT 2025 , Edited by admin on Mon Mar 31 17:45:41 GMT 2025
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ChEMBL
CHEMBL651
Created by admin on Mon Mar 31 17:45:41 GMT 2025 , Edited by admin on Mon Mar 31 17:45:41 GMT 2025
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MESH
D008691
Created by admin on Mon Mar 31 17:45:41 GMT 2025 , Edited by admin on Mon Mar 31 17:45:41 GMT 2025
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INN
788
Created by admin on Mon Mar 31 17:45:41 GMT 2025 , Edited by admin on Mon Mar 31 17:45:41 GMT 2025
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DAILYMED
UC6VBE7V1Z
Created by admin on Mon Mar 31 17:45:41 GMT 2025 , Edited by admin on Mon Mar 31 17:45:41 GMT 2025
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FDA UNII
UC6VBE7V1Z
Created by admin on Mon Mar 31 17:45:41 GMT 2025 , Edited by admin on Mon Mar 31 17:45:41 GMT 2025
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LACTMED
Methadone
Created by admin on Mon Mar 31 17:45:41 GMT 2025 , Edited by admin on Mon Mar 31 17:45:41 GMT 2025
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IUPHAR
5458
Created by admin on Mon Mar 31 17:45:41 GMT 2025 , Edited by admin on Mon Mar 31 17:45:41 GMT 2025
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DRUG CENTRAL
1728
Created by admin on Mon Mar 31 17:45:41 GMT 2025 , Edited by admin on Mon Mar 31 17:45:41 GMT 2025
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CHEBI
50140
Created by admin on Mon Mar 31 17:45:41 GMT 2025 , Edited by admin on Mon Mar 31 17:45:41 GMT 2025
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WIKIPEDIA
METHADONE
Created by admin on Mon Mar 31 17:45:41 GMT 2025 , Edited by admin on Mon Mar 31 17:45:41 GMT 2025
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CAS
297-88-1
Created by admin on Mon Mar 31 17:45:41 GMT 2025 , Edited by admin on Mon Mar 31 17:45:41 GMT 2025
SUPERSEDED
Related Record Type Details
Structure of METHADONE HYDROBROMIDE
SALT/SOLVATE -> PARENT
Structure of METHADONE HYDRIODIDE
SALT/SOLVATE -> PARENT
CYTOCHROME P450 2D6
METABOLIC ENZYME -> SUBSTRATE
CYTOCHROME P450 2C8
METABOLIC ENZYME -> SUBSTRATE
Involved in the metabolism of methadone, but its contribution to the metabolism of (R)-methadone was smaller than that of CYP3A4. For the metabolism of (S)-methadone, the roles of CYP2C8 and CYP3A4 appeared equal.
CYTOCHROME P450 2C19
METABOLIC ENZYME -> SUBSTRATE
CYP2C19 preferentially metabolized (R)-methadone,
CYTOCHROME P450 2B6
METABOLIC ENZYME -> SUBSTRATE
CYP2B6 preferentially metabolized (S)-methadone,
Structure of METHADONE HYDROBROMIDE
PARENT -> SALT/SOLVATE
MU-TYPE OPIOID RECEPTOR
TARGET -> AGONIST
PLASMA PROTEIN FRACTION (HUMAN)
BINDER->LIGAND
BINDING
CYTOCHROME P450 3A4
METABOLIC ENZYME -> SUBSTRATE
CYP3A4 showed no preference between the two enantiomers.
Structure of LEVOMETHADONE
ACTIVE ENANTIOMER->RACEMATE
approximately 50x the potency of the S-(+)-enantiomer as well as greater ?-opioid receptor selectivity
Structure of METHADONE HYDROBROMIDE
SALT/SOLVATE -> PARENT
APPROXIMATE PURE ANHYDROUS DRUG CONTENT (IN PERCENT)
MU-TYPE OPIOID RECEPTOR
TARGET -> AGONIST
Ki
Structure of METHADONE HYDROCHLORIDE
SALT/SOLVATE -> PARENT
APPROXIMATE PURE ANHYDROUS DRUG CONTENT (IN PERCENT)
MU-TYPE OPIOID RECEPTOR
TARGET -> AGONIST
Prolonged exposure methadone induces MOPr internalization comparable with that induced by DAMGO, whereas morphine produces much less MOPr heroin during relapse is due to receptor internalization. The blunting of the response to desensitization not receptor antagonism.
MULTIDRUG RESISTANCE PROTEIN 1
TRANSPORTER -> SUBSTRATE
Related Record Type Details
Structure of 2-ETHYLIDENE-1,5-DIMETHYL-3,3-DIPHENYLPYRROLIDINE
METABOLITE INACTIVE -> PARENT
The hierarchy of EDDPgeneration was CYP2B6 > CYP2C19zCYP3A4
MAJOR
Structure of DIMEPHEPTANOL
PARENT -> METABOLITE
MINOR
Structure of NORMETHADOL
METABOLITE -> PARENT
MINOR
Structure of 2-ETHYL-5-METHYL-3,3-DIPHENYLPYRROLIDINE
METABOLITE -> PARENT
5-10% of the dose but there is a large individual variation due to pH, urine volume, dose and metabolic rate
MINOR
Structure of DESMETHYLMETHADONE
METABOLITE ACTIVE -> PARENT
Structure of DINORMETHADONE
METABOLITE ACTIVE -> PARENT
Structure of DINORMETHADOL
METABOLITE ACTIVE -> PARENT
Related Record Type Details
Structure of METHADONE
ACTIVE MOIETY
Name Property Type Amount Referenced Substance Defining Parameters References
Biological Half-life PHARMACOKINETIC Elimination
PHARMACOKINETIC
NIH
NCATS
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ACCESSIBILITY
DISCLAIMER
HHS VULNERABILITY DISCLOSURE
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