METHADONE

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 Search

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
Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2016/021624s006lbl.pdf
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

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Mu opioid receptor 231 Target ID: CHEMBL233 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2016/006134s040s041lbl.pdf	Agonist 2752		3.51 nM [Ki]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Pain 619 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2016/006134s040s041lbl.pdf	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
Detoxification & maintenance treatment of opioid addiction 4 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2016/006134s040s041lbl.pdf	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

C_max

Value	Dose	Analyte	Population
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

Value	Dose	Analyte	Population
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

T_1/2

Value	Dose	Analyte	Population
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

Dose	Population	Adverse 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

AE	Significance	Dose	Population
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

CYP3A4	CYP2C9	CYP2D6	hERG
substrate 1946 inhibitor 2252	substrate 1193	substrate 1388 inhibitor 2507	inhibitor 2217

OverviewOther

Other Inhibitor	Other Substrate	Other 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

Target	Modality	Activity
UGT2B4 23	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/20484152/ Page: 8.0	major [Inhibition 0.6 uM]
CYP1A 122	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/9020195/	no
CYP2B 41	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/9020195/	no
CYP2C 37	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/9020195/	no
CYP2E1 1146	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/9020195/	no
UGT2B7 210	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/20484152/ Page: 8.0	unlikely
CYP3A4 2633	inhibitor 4027 Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2014462/	yes [Ki 100 uM]
CYP2D6 2546	inhibitor 4027 Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC1381486/	yes [Ki 2.5 uM]

Drug as victim

Target	Modality	Activity	Clinical evidence
BCRP 697	substrate 4014 Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6339814/	no
OATP1A2 67	substrate 4014 Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6339814/	no
OATP1B1 503	substrate 4014 Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6339814/	no
OATP1B3 435	substrate 4014 Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6339814/	no
OATP2B1 122	substrate 4014 Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6339814/	no
OCT1 393	substrate 4014 Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6339814/	no
OCT2 434	substrate 4014 Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6339814/	no
OCT3 92	substrate 4014 Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6339814/	no
P-gp 2052	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/006134s049lbl.pdf#page=29; https://pubmed.ncbi.nlm.nih.gov/22035341/ Page: 29.0	yes
CYP2B6 776	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/006134s049lbl.pdf#page=29; https://pubmed.ncbi.nlm.nih.gov/22035341/ 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 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/006134s049lbl.pdf#page=29; https://pubmed.ncbi.nlm.nih.gov/22035341/ Page: 29.0
CYP2C19 1119	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/006134s049lbl.pdf#page=29; https://pubmed.ncbi.nlm.nih.gov/22035341/ 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 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/006134s049lbl.pdf#page=29; https://pubmed.ncbi.nlm.nih.gov/22035341/ Page: 29.0
CYP2C9 1193	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/006134s049lbl.pdf#page=29; https://pubmed.ncbi.nlm.nih.gov/22035341/ 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 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/006134s049lbl.pdf#page=29; https://pubmed.ncbi.nlm.nih.gov/22035341/ Page: 29.0
CYP2D6 1388	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/006134s049lbl.pdf#page=29; https://pubmed.ncbi.nlm.nih.gov/22035341/ 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 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/006134s049lbl.pdf#page=29; https://pubmed.ncbi.nlm.nih.gov/22035341/ Page: 29.0
CYP3A4 1946	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/006134s049lbl.pdf#page=29; https://pubmed.ncbi.nlm.nih.gov/22035341/ 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 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/006134s049lbl.pdf#page=29; https://pubmed.ncbi.nlm.nih.gov/22035341/ Page: 29.0

Tox targets

Target	Modality	Activity	Metabolite	Clinical evidence
hERG 2263	inhibitor 2237 Sources: https://pubmed.ncbi.nlm.nih.gov/17329992/

Sourcing

Vendor/Aggregator	ID	URL
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

Title	Date	PubMed
Neurological aspects of perinatal narcotic addiction and methadone treatment.	1975	1163365
Rhabdomyolysis and acute renal failure following methadone abuse.	1992	1436354
Cocaine-associated panic attacks in methadone-maintained patients.	1992	1314016
Intravenous clonidine use in a neonate experiencing opioid-induced myoclonus.	2001 Aug	11506132
A case of a methadone-induced movement disorder.	2001 Dec	11783819
Enteral methadone to expedite fentanyl discontinuation and prevent opioid abstinence syndrome in the PICU.	2001 Dec	11765307
Methadone is safe for treating hospitalized patients with severe pain.	2001 Dec	11744587
Reversible spastic paraparesis induced by high-dose intravenous methadone.	2001 Feb	14622789
From hit to lead. Combining two complementary methods for focused library design. Application to mu opiate ligands.	2001 Oct 11	11585443
Interindividual variability of the clinical pharmacokinetics of methadone: implications for the treatment of opioid dependence.	2002	12405865
Continuous epidural infusion of racemic methadone results in effective postoperative analgesia and low plasma concentrations.	2002 Jan	11782325
Cognitive impairment in methadone maintenance patients.	2002 Jun 1	12062778
Methadone induces CCR5 and promotes AIDS virus infection.	2002 May 22	12023039
Bradycardia associated with intravenous methadone administered for sedation in a patient with acute respiratory distress syndrome.	2002 Sep	12222559
Torsade de pointes associated with very-high-dose methadone.	2002 Sep 17	12230351
Utility of crossover designs in clinical trials: efficacy of desipramine vs. placebo in opioid-dependent cocaine abusers.	2002 Spring	12028741
Neuropsychological correlates of opioid dependence and withdrawal.	2003 Apr	12628632
Methadone treatment induces attenuation of cerebrovascular deficits associated with the prolonged abuse of cocaine and heroin.	2003 Mar	12629538
QTc interval prolongation associated with intravenous methadone.	2003 Oct	14527710
QT prolongation and Torsades de Pointes in patients infected with human immunodeficiency virus and treated with methadone.	2003 Oct 15	14556883
Safety of injectable opioid maintenance treatment for heroin dependence.	2003 Oct 15	14550686
[Development of transmural myocardial infarction in young persons with intact coronary arteries during methadone use for the treatment of heroine addiction].	2004	15477802
Relationship between prescribing and risk of opiate overdose among drug users in and out of maintenance treatment.	2004	14665804
Cost effectiveness of disulfiram: treating cocaine use in methadone-maintained patients.	2004 Apr	15063917
QT interval prolongation in patients on methadone with concomitant drugs.	2004 Aug	15232338
Methadone metabolism by human placenta.	2004 Aug 1	15242824
[Life-threatening, recurrent arrhythmia in patients on high-dose methadone treatment: torsade de pointes].	2004 Aug 30	15387312
Methadone-induced torsade de pointes in a patient with normal baseline QT interval.	2004 Jul-Aug	15471174
Directly observed therapy for the management of HIV-infected patients in a methadone program.	2004 Jun 1	15156430
The effect of quinidine, used as a probe for the involvement of P-glycoprotein, on the intestinal absorption and pharmacodynamics of methadone.	2004 May	15089813
Agonist-like or antagonist-like treatment for cocaine dependence with methadone for heroin dependence: two double-blind randomized clinical trials.	2004 May	15039761
Oral methadone for cancer pain: no indication of Q-T interval prolongation or torsades de pointes.	2004 Oct	15471646
Intravenous ketamine infusion as an adjuvant to morphine in a 2-year-old with severe cancer pain from metastatic neuroblastoma.	2004 Oct	15454842
[Preclinical management of accidental methadone intoxication of a 4-year-old girl. Antagonist or intubation?].	2004 Oct	15278196
[Long QT and torsade de pointes in a patient with acquired human immunodeficiency virus infection in multitherapy with drugs affecting cytochrome P450].	2004 Sep	15568612
Epidural clonidine, bupivacaine and methadone as the sole analgesic agent after thoracotomy for lung resection.	2004 Sep	15310347
Adipocyte-derived hormones in heroin addicts: the influence of methadone maintenance treatment.	2005	15717844
Methadone-related Torsades de Pointes in a sickle cell patient treated for chronic pain.	2005 Apr	15795907
[Methadone-induced heart arrhythmia].	2005 Aug 11	16100543
Dextromethorphan-induced delirium and possible methadone interaction.	2005 Mar	16089243
[Torsades de pointes during methadone treatment].	2005 Oct	16238992
Methadone doses of 100 mg or greater are more effective than lower doses at suppressing heroin self-administration in opioid-dependent volunteers.	2005 Oct	16185211
QT prolongation and syncope with methadone, doxepin, and a beta-blocker.	2005 Oct	16144878
Central sleep apnea in stable methadone maintenance treatment patients.	2005 Sep	16162728
Variables associated with perceived sleep disorders in methadone maintenance treatment (MMT) patients.	2006 Apr 28	16154297
Does naltrexone treatment lead to depression? Findings from a randomized controlled trial in subjects with opioid dependence.	2006 Jan	16496034
Bradycardia during methadone therapy in an infant.	2006 Jan	16395081
A randomized controlled trial of interim methadone maintenance.	2006 Jan	16389204
Frequency of high-risk use of QT-prolonging medications.	2006 Jun	16178046
Changes in HIV risk behaviors among patients receiving combined pharmacological and behavioral interventions for heroin and cocaine dependence.	2006 May	16085366

Patents

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.

Name

Type

Language

METHADONE

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