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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
Defined Stereocenters 0 / 1
E/Z Centers 0
Optical Activity ( + / - )

Description

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

Targets

Primary TargetPharmacologyConditionPotency
3.51 nM [Ki]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Palliative
DOLOPHINE HYDROCHLORIDE
PubMed

PubMed

TitleDatePubMed
Reversible spastic paraparesis induced by high-dose intravenous methadone.
2001 Feb
Tiagabine increases cocaine-free urines in cocaine-dependent methadone-treated patients: results of a randomized pilot study.
2003 Nov
QT prolongation and Torsades de Pointes in patients infected with human immunodeficiency virus and treated with methadone.
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
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
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-induced heart arrhythmia].
2005 Aug 11
Factors associated with methadone maintenance therapy use among a cohort of polysubstance using injection drug users in Vancouver.
2005 Dec 12
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
[Methadone and sleep apnea syndrome].
2005 Mar
Caution with nalbuphine in patients on long-term opioids.
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

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: Oral; Intravenous; Subcutaneously; Intramuscular
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 Tue Oct 22 00:41:23 UTC 2019
Edited
by admin
on Tue Oct 22 00:41:23 UTC 2019
Record UNII
UC6VBE7V1Z
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
METHADONE
HSDB   INN   MI   VANDF   WHO-DD  
INN  
Official Name English
METHADONE [MI]
Common Name English
METHADONE [WHO-DD]
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
Classification Tree Code System Code
WHO-ATC N07BC02
Created by admin on Tue Oct 22 00:41:23 UTC 2019 , Edited by admin on Tue Oct 22 00:41:23 UTC 2019
NCI_THESAURUS C1506
Created by admin on Tue Oct 22 00:41:23 UTC 2019 , Edited by admin on Tue Oct 22 00:41:23 UTC 2019
NDF-RT N0000175684
Created by admin on Tue Oct 22 00:41:23 UTC 2019 , Edited by admin on Tue Oct 22 00:41:23 UTC 2019
WHO-ATC N02AC52
Created by admin on Tue Oct 22 00:41:23 UTC 2019 , Edited by admin on Tue Oct 22 00:41:23 UTC 2019
NCI_THESAURUS C67413
Created by admin on Tue Oct 22 00:41:23 UTC 2019 , Edited by admin on Tue Oct 22 00:41:23 UTC 2019
DEA NO. 9250
Created by admin on Tue Oct 22 00:41:23 UTC 2019 , Edited by admin on Tue Oct 22 00:41:23 UTC 2019
LIVERTOX 611
Created by admin on Tue Oct 22 00:41:23 UTC 2019 , Edited by admin on Tue Oct 22 00:41:23 UTC 2019
WHO-VATC QN07BC02
Created by admin on Tue Oct 22 00:41:23 UTC 2019 , Edited by admin on Tue Oct 22 00:41:23 UTC 2019
CFR 21 CFR 862.3620
Created by admin on Tue Oct 22 00:41:23 UTC 2019 , Edited by admin on Tue Oct 22 00:41:23 UTC 2019
WHO-ESSENTIAL MEDICINES LIST 24.5
Created by admin on Tue Oct 22 00:41:23 UTC 2019 , Edited by admin on Tue Oct 22 00:41:23 UTC 2019
WHO-VATC QN02AC52
Created by admin on Tue Oct 22 00:41:23 UTC 2019 , Edited by admin on Tue Oct 22 00:41:23 UTC 2019
NDF-RT N0000175690
Created by admin on Tue Oct 22 00:41:23 UTC 2019 , Edited by admin on Tue Oct 22 00:41:23 UTC 2019
Code System Code Type Description
ECHA (EC/EINECS)
200-996-9
Created by admin on Tue Oct 22 00:41:23 UTC 2019 , Edited by admin on Tue Oct 22 00:41:23 UTC 2019
PRIMARY
RXCUI
6813
Created by admin on Tue Oct 22 00:41:23 UTC 2019 , Edited by admin on Tue Oct 22 00:41:23 UTC 2019
PRIMARY RxNorm
EPA CompTox
76-99-3
Created by admin on Tue Oct 22 00:41:23 UTC 2019 , Edited by admin on Tue Oct 22 00:41:23 UTC 2019
PRIMARY
MERCK INDEX
M7286
Created by admin on Tue Oct 22 00:41:23 UTC 2019 , Edited by admin on Tue Oct 22 00:41:23 UTC 2019
PRIMARY Merck Index
NCI_THESAURUS
C62044
Created by admin on Tue Oct 22 00:41:23 UTC 2019 , Edited by admin on Tue Oct 22 00:41:23 UTC 2019
PRIMARY
HSDB
76-99-3
Created by admin on Tue Oct 22 00:41:23 UTC 2019 , Edited by admin on Tue Oct 22 00:41:23 UTC 2019
PRIMARY
EVMPD
SUB08833MIG
Created by admin on Tue Oct 22 00:41:23 UTC 2019 , Edited by admin on Tue Oct 22 00:41:23 UTC 2019
PRIMARY
DRUG BANK
DB00333
Created by admin on Tue Oct 22 00:41:23 UTC 2019 , Edited by admin on Tue Oct 22 00:41:23 UTC 2019
PRIMARY
CAS
76-99-3
Created by admin on Tue Oct 22 00:41:23 UTC 2019 , Edited by admin on Tue Oct 22 00:41:23 UTC 2019
PRIMARY
PUBCHEM
4095
Created by admin on Tue Oct 22 00:41:23 UTC 2019 , Edited by admin on Tue Oct 22 00:41:23 UTC 2019
PRIMARY
ChEMBL
CHEMBL651
Created by admin on Tue Oct 22 00:41:23 UTC 2019 , Edited by admin on Tue Oct 22 00:41:23 UTC 2019
PRIMARY
MESH
D008691
Created by admin on Tue Oct 22 00:41:23 UTC 2019 , Edited by admin on Tue Oct 22 00:41:23 UTC 2019
PRIMARY
INN
788
Created by admin on Tue Oct 22 00:41:23 UTC 2019 , Edited by admin on Tue Oct 22 00:41:23 UTC 2019
PRIMARY
IUPHAR
5458
Created by admin on Tue Oct 22 00:41:23 UTC 2019 , Edited by admin on Tue Oct 22 00:41:23 UTC 2019
PRIMARY
LactMed
76-99-3
Created by admin on Tue Oct 22 00:41:23 UTC 2019 , Edited by admin on Tue Oct 22 00:41:23 UTC 2019
PRIMARY
WIKIPEDIA
METHADONE
Created by admin on Tue Oct 22 00:41:23 UTC 2019 , Edited by admin on Tue Oct 22 00:41:23 UTC 2019
PRIMARY
CAS
297-88-1
Created by admin on Tue Oct 22 00:41:23 UTC 2019 , Edited by admin on Tue Oct 22 00:41:23 UTC 2019
SUPERSEDED
Related Record Type Details
SALT/SOLVATE -> PARENT
TRANSPORTER -> SUBSTRATE
METABOLIC ENZYME -> SUBSTRATE
CYP2C19 preferentially metabolized (R)-methadone,
METABOLIC ENZYME -> SUBSTRATE
CYP2B6 preferentially metabolized (S)-methadone,
PARENT -> SALT/SOLVATE
BINDER->LIGAND
BINDING
METABOLIC ENZYME -> SUBSTRATE
CYP3A4 showed no preference between the two enantiomers
ACTIVE ENANTIOMER->RACEMATE
approximately 50x the potency of the S-(+)-enantiomer as well as greater ?-opioid receptor selectivity
SALT/SOLVATE -> PARENT
APPROXIMATE PURE ANHYDROUS DRUG CONTENT (IN PERCENT)
SALT/SOLVATE -> PARENT
APPROXIMATE PURE ANHYDROUS DRUG CONTENT (IN PERCENT)
Related Record Type Details
METABOLITE INACTIVE -> PARENT
The hierarchy of EDDPgeneration was CYP2B6 > CYP2C19zCYP3A4
MAJOR
PARENT -> METABOLITE
MINOR
METABOLITE -> PARENT
MINOR
METABOLITE ACTIVE -> PARENT
Related Record Type Details
ACTIVE MOIETY
Name Property Type Amount Referenced Substance Defining Parameters References
Biological Half-life PHARMACOKINETIC Elimination
PHARMACOKINETIC