U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

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

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

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

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
3.51 nM [Ki]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Palliative
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
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
548 ng/mL
60 mg 1 times / day steady-state, oral
dose: 60 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
METHADONE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FED
494 ng/mL
70 mg 1 times / day steady-state, oral
dose: 70 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
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
54 ng/mL
60 mg 1 times / day steady-state, oral
dose: 60 mg
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
8.54 mg × h/L
60 mg 1 times / day steady-state, oral
dose: 60 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
METHADONE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FED
8.27 μg × h/mL
70 mg 1 times / day steady-state, oral
dose: 70 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
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
0.61 mg × h/L
60 mg 1 times / day steady-state, oral
dose: 60 mg
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
31.2 h
60 mg 1 times / day steady-state, oral
dose: 60 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
METHADONE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FED
39 h
70 mg 1 times / day steady-state, oral
dose: 70 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
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
Doses

Doses

DosePopulationAdverse events​
10 mg 3 times / day multiple, intravenous (starting)
Recommended
Dose: 10 mg, 3 times / day
Route: intravenous
Route: multiple
Dose: 10 mg, 3 times / day
Sources:
pregnant, adult
Health Status: pregnant
Age Group: adult
Sex: F
Sources:
Other AEs: Withdrawal syndrome neonatal...
10 mg 3 times / day multiple, intravenous (starting)
Recommended
Dose: 10 mg, 3 times / day
Route: intravenous
Route: multiple
Dose: 10 mg, 3 times / day
Sources:
unhealthy, adult
Other AEs: Respiratory depression, Addiction...
Other AEs:
Respiratory depression (grade 5)
Addiction
QT interval prolonged (grade 5)
Sources:
20 mg single, oral (starting)
Recommended
Dose: 20 mg
Route: oral
Route: single
Dose: 20 mg
Sources:
unhealthy, adult
Other AEs: Respiratory depression, QT interval prolonged...
Other AEs:
Respiratory depression (grade 5)
QT interval prolonged
Arrhythmia (serious)
Sources:
AEs

AEs

AESignificanceDosePopulation
Withdrawal syndrome neonatal
10 mg 3 times / day multiple, intravenous (starting)
Recommended
Dose: 10 mg, 3 times / day
Route: intravenous
Route: multiple
Dose: 10 mg, 3 times / day
Sources:
pregnant, adult
Health Status: pregnant
Age Group: adult
Sex: F
Sources:
Addiction
10 mg 3 times / day multiple, intravenous (starting)
Recommended
Dose: 10 mg, 3 times / day
Route: intravenous
Route: multiple
Dose: 10 mg, 3 times / day
Sources:
unhealthy, adult
QT interval prolonged grade 5
10 mg 3 times / day multiple, intravenous (starting)
Recommended
Dose: 10 mg, 3 times / day
Route: intravenous
Route: multiple
Dose: 10 mg, 3 times / day
Sources:
unhealthy, adult
Respiratory depression grade 5
10 mg 3 times / day multiple, intravenous (starting)
Recommended
Dose: 10 mg, 3 times / day
Route: intravenous
Route: multiple
Dose: 10 mg, 3 times / day
Sources:
unhealthy, adult
QT interval prolonged
20 mg single, oral (starting)
Recommended
Dose: 20 mg
Route: oral
Route: single
Dose: 20 mg
Sources:
unhealthy, adult
Respiratory depression grade 5
20 mg single, oral (starting)
Recommended
Dose: 20 mg
Route: oral
Route: single
Dose: 20 mg
Sources:
unhealthy, adult
Arrhythmia serious
20 mg single, oral (starting)
Recommended
Dose: 20 mg
Route: oral
Route: single
Dose: 20 mg
Sources:
unhealthy, adult
OverviewDrug as perpetrator​Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
no
no
no
no
no
no
no
no
yes
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
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
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
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
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
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
Efficacy of an enteral 10-day methadone wean to prevent opioid withdrawal in fentanyl-tolerant pediatric intensive care unit patients.
2001 Oct
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
Dose-related effects of methadone on QT prolongation in a series of patients with torsade de pointes.
2003 Jun
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
Methadone maintenance and male sexual dysfunction.
2005
Cocaine-related torsade de pointes in a methadone maintenance patient.
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
Measurement of QTc in patients receiving chronic methadone therapy.
2005 Apr
Methadone-related Torsades de Pointes in a sickle cell patient treated for chronic pain.
2005 Apr
Methadone versus buprenorphine with contingency management or performance feedback for cocaine and opioid dependence.
2005 Feb
Methadone-induced bradycardia.
2005 Jul
Neuropsychological functioning in methadone maintenance patients versus abstinent heroin abusers.
2005 Jun 1
Dextromethorphan-induced delirium and possible methadone interaction.
2005 Mar
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
Methadone treatment of chronic non-malignant pain and opioid dependence--a long-term follow-up.
2006 Apr
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
Patents

Sample Use Guides

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 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.
Name Type Language
METHADONE
HSDB   INN   MI   VANDF   WHO-DD  
INN  
Official 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
IDS-NM-002
Code 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 Fri Dec 15 15:04:46 GMT 2023 , Edited by admin on Fri Dec 15 15:04:46 GMT 2023
NCI_THESAURUS C1506
Created by admin on Fri Dec 15 15:04:46 GMT 2023 , Edited by admin on Fri Dec 15 15:04:46 GMT 2023
NDF-RT N0000175684
Created by admin on Fri Dec 15 15:04:46 GMT 2023 , Edited by admin on Fri Dec 15 15:04:46 GMT 2023
WHO-ATC N02AC52
Created by admin on Fri Dec 15 15:04:46 GMT 2023 , Edited by admin on Fri Dec 15 15:04:46 GMT 2023
NCI_THESAURUS C67413
Created by admin on Fri Dec 15 15:04:46 GMT 2023 , Edited by admin on Fri Dec 15 15:04:46 GMT 2023
DEA NO. 9250
Created by admin on Fri Dec 15 15:04:46 GMT 2023 , Edited by admin on Fri Dec 15 15:04:46 GMT 2023
LIVERTOX NBK548084
Created by admin on Fri Dec 15 15:04:46 GMT 2023 , Edited by admin on Fri Dec 15 15:04:46 GMT 2023
WHO-VATC QN07BC02
Created by admin on Fri Dec 15 15:04:46 GMT 2023 , Edited by admin on Fri Dec 15 15:04:46 GMT 2023
CFR 21 CFR 862.3620
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WHO-ESSENTIAL MEDICINES LIST 24.5
Created by admin on Fri Dec 15 15:04:46 GMT 2023 , Edited by admin on Fri Dec 15 15:04:46 GMT 2023
WHO-VATC QN02AC52
Created by admin on Fri Dec 15 15:04:46 GMT 2023 , Edited by admin on Fri Dec 15 15:04:46 GMT 2023
NDF-RT N0000175690
Created by admin on Fri Dec 15 15:04:46 GMT 2023 , Edited by admin on Fri Dec 15 15:04:46 GMT 2023
Code System Code Type Description
ECHA (EC/EINECS)
200-996-9
Created by admin on Fri Dec 15 15:04:46 GMT 2023 , Edited by admin on Fri Dec 15 15:04:46 GMT 2023
PRIMARY
RXCUI
6813
Created by admin on Fri Dec 15 15:04:46 GMT 2023 , Edited by admin on Fri Dec 15 15:04:46 GMT 2023
PRIMARY RxNorm
EPA CompTox
DTXSID7023273
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PRIMARY
SMS_ID
100000091046
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PRIMARY
CHEBI
28017
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PRIMARY
MERCK INDEX
m7286
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PRIMARY Merck Index
NCI_THESAURUS
C62044
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PRIMARY
HSDB
3119
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PRIMARY
EVMPD
SUB08833MIG
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PRIMARY
DRUG BANK
DB00333
Created by admin on Fri Dec 15 15:04:46 GMT 2023 , Edited by admin on Fri Dec 15 15:04:46 GMT 2023
PRIMARY
CHEBI
167309
Created by admin on Fri Dec 15 15:04:46 GMT 2023 , Edited by admin on Fri Dec 15 15:04:46 GMT 2023
PRIMARY
CHEBI
6807
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PRIMARY
CAS
76-99-3
Created by admin on Fri Dec 15 15:04:46 GMT 2023 , Edited by admin on Fri Dec 15 15:04:46 GMT 2023
PRIMARY
PUBCHEM
4095
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PRIMARY
ChEMBL
CHEMBL651
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PRIMARY
MESH
D008691
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PRIMARY
INN
788
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PRIMARY
DAILYMED
UC6VBE7V1Z
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PRIMARY
FDA UNII
UC6VBE7V1Z
Created by admin on Fri Dec 15 15:04:46 GMT 2023 , Edited by admin on Fri Dec 15 15:04:46 GMT 2023
PRIMARY
LACTMED
Methadone
Created by admin on Fri Dec 15 15:04:46 GMT 2023 , Edited by admin on Fri Dec 15 15:04:46 GMT 2023
PRIMARY
IUPHAR
5458
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PRIMARY
DRUG CENTRAL
1728
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PRIMARY
CHEBI
50140
Created by admin on Fri Dec 15 15:04:46 GMT 2023 , Edited by admin on Fri Dec 15 15:04:46 GMT 2023
PRIMARY
WIKIPEDIA
METHADONE
Created by admin on Fri Dec 15 15:04:46 GMT 2023 , Edited by admin on Fri Dec 15 15:04:46 GMT 2023
PRIMARY
CAS
297-88-1
Created by admin on Fri Dec 15 15:04:46 GMT 2023 , Edited by admin on Fri Dec 15 15:04:46 GMT 2023
SUPERSEDED