Details
Stereochemistry | RACEMIC |
Molecular Formula | C21H27NO.ClH |
Molecular Weight | 345.906 |
Optical Activity | ( + / - ) |
Defined Stereocenters | 0 / 1 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
Cl.CCC(=O)C(CC(C)N(C)C)(C1=CC=CC=C1)C2=CC=CC=C2
InChI
InChIKey=FJQXCDYVZAHXNS-UHFFFAOYSA-N
InChI=1S/C21H27NO.ClH/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;1H
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 | ( + / - ) |
Molecular Formula | ClH |
Molecular Weight | 36.461 |
Charge | 0 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
DescriptionCurator'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
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.
Originator
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL233 |
3.51 nM [Ki] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Palliative | DOLOPHINE HYDROCHLORIDE Approved UseFor 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 Date1947 |
|||
Palliative | DOLOPHINE HYDROCHLORIDE Approved UseFor 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 Date1947 |
Cmax
Value | Dose | Co-administered | 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 | Co-administered | 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 |
T1/2
Value | Dose | Co-administered | 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: |
pregnant, adult Health Status: pregnant Age Group: adult Sex: F Sources: |
Other AEs: Withdrawal syndrome neonatal... Other AEs: Withdrawal syndrome neonatal Sources: |
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: |
unhealthy, adult Health Status: unhealthy Age Group: adult Sources: |
Other AEs: Respiratory depression, Addiction... Other AEs: Respiratory depression (grade 5) Sources: Addiction QT interval prolonged (grade 5) |
20 mg single, oral Recommended Dose: 20 mg Route: oral Route: single Dose: 20 mg Sources: |
unhealthy, adult Health Status: unhealthy Age Group: adult Sources: |
Other AEs: Respiratory depression, QT interval prolonged... Other AEs: Respiratory depression (grade 5) Sources: QT interval prolonged Arrhythmia (serious) |
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: |
pregnant, adult Health Status: pregnant Age Group: adult Sex: F Sources: |
|
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: |
unhealthy, adult Health Status: unhealthy Age Group: adult Sources: |
|
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: |
unhealthy, adult Health Status: unhealthy Age Group: adult Sources: |
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: |
unhealthy, adult Health Status: unhealthy Age Group: adult Sources: |
QT interval prolonged | 20 mg single, oral Recommended Dose: 20 mg Route: oral Route: single Dose: 20 mg Sources: |
unhealthy, adult Health Status: unhealthy Age Group: adult Sources: |
|
Respiratory depression | grade 5 | 20 mg single, oral Recommended Dose: 20 mg Route: oral Route: single Dose: 20 mg Sources: |
unhealthy, adult Health Status: unhealthy Age Group: adult Sources: |
Arrhythmia | serious | 20 mg single, oral Recommended Dose: 20 mg Route: oral Route: single Dose: 20 mg Sources: |
unhealthy, adult Health Status: unhealthy Age Group: adult Sources: |
Overview
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
---|---|---|---|
OverviewOther
Other Inhibitor | Other Substrate | Other Inducer |
---|---|---|
Drug as perpetrator
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Sources: https://pubmed.ncbi.nlm.nih.gov/20484152/ Page: 8.0 |
major [Inhibition 0.6 uM] | |||
no | ||||
no | ||||
no | ||||
no | ||||
Sources: https://pubmed.ncbi.nlm.nih.gov/20484152/ Page: 8.0 |
unlikely | |||
yes [Ki 100 uM] | ||||
yes [Ki 2.5 uM] |
Drug as victim
Target | Modality | Activity | Metabolite | Clinical 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
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
PubMed
Title | Date | PubMed |
---|---|---|
Rhabdomyolysis and acute renal failure following methadone abuse. | 1992 |
|
Methadone dose increase and abstinence reinforcement for treatment of continued heroin use during methadone maintenance. | 2000 Apr |
|
Methadone, ciprofloxacin, and adverse drug reactions. | 2000 Dec 16 |
|
Disulfiram treatment for cocaine dependence in methadone-maintained opioid addicts. | 2000 Feb |
|
Thrice-weekly versus daily buprenorphine maintenance. | 2000 Jun 15 |
|
[Methadone withdrawal syndrome induced by nevirapine]. | 2000 Mar 18 |
|
Methadone maintenance treatment (MMT): a review of historical and clinical issues. | 2000 Oct-Nov |
|
Intravenous clonidine use in a neonate experiencing opioid-induced myoclonus. | 2001 Aug |
|
Effect of perinatal buprenorphine exposure on development in the rat. | 2001 Aug |
|
Methadone maintenance patients are cross-tolerant to the antinociceptive effects of morphine. | 2001 Aug |
|
Reversible spastic paraparesis induced by high-dose intravenous methadone. | 2001 Feb |
|
Family history influence on drug abuse severity and treatment outcome. | 2001 Feb 1 |
|
Methadone-induced myoclonus in advanced cancer. | 2001 Jan-Feb |
|
Pain intolerance in opioid-maintained former opiate addicts: effect of long-acting maintenance agent. | 2001 Jul 1 |
|
Reversible delirium during opiod switching from transdermal fentanyl to methadone. | 2001 Mar |
|
Sleep-disordered breathing in stable methadone programme patients: a pilot study. | 2001 Mar |
|
Efficacy of an enteral 10-day methadone wean to prevent opioid withdrawal in fentanyl-tolerant pediatric intensive care unit patients. | 2001 Oct |
|
Neuropsychological correlates of opioid dependence and withdrawal. | 2003 Apr |
|
Bile duct dilation with chronic methadone use in asymptomatic patients: ERCP findings in 6 patients. | 2003 Jul |
|
Dose-related effects of methadone on QT prolongation in a series of patients with torsade de pointes. | 2003 Jun |
|
Methadone treatment induces attenuation of cerebrovascular deficits associated with the prolonged abuse of cocaine and heroin. | 2003 Mar |
|
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 |
|
Safety of injectable opioid maintenance treatment for heroin dependence. | 2003 Oct 15 |
|
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 |
|
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 |
|
Intravenous ketamine infusion as an adjuvant to morphine in a 2-year-old with severe cancer pain from metastatic neuroblastoma. | 2004 Oct |
|
Effects of buprenorphine on cardiac repolarization in a patient with methadone-related torsade de pointes. | 2005 Apr |
|
Dextromethorphan-induced delirium and possible methadone interaction. | 2005 Mar |
|
Methadone-induced Torsade de pointes tachycardias. | 2005 May 14 |
|
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 |
|
Changes in HIV risk behaviors among patients receiving combined pharmacological and behavioral interventions for heroin and cocaine dependence. | 2006 May |
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 Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/11561100
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
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admin
on
Edited
Mon Mar 31 17:50:41 GMT 2025
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on
Mon Mar 31 17:50:41 GMT 2025
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Record UNII |
229809935B
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Record Status |
Validated (UNII)
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Classification Tree | Code System | Code | ||
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NCI_THESAURUS |
C1506
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DEA NO. |
9250
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NCI_THESAURUS |
C67413
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CHEMBL651
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14184
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218337
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70181-39-4
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DBSALT000346
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70172-45-1
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DTXSID2020501
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100000091446
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1095-90-5
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214-140-7
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229809935B
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SUB03203MIG
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50140
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1398009
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125-56-4
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m7286
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C638
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PARENT -> SALT/SOLVATE | |||
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ENANTIOMER -> RACEMATE | |||
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ENANTIOMER -> RACEMATE | |||
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BASIS OF STRENGTH->SUBSTANCE |
ASSAY (TITRATION)
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BASIS OF STRENGTH->SUBSTANCE |
ASSAY (TITRATION)
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METABOLITE INACTIVE -> PARENT |
Cytochrome P450 enzymes, primarily CYP3A4, CYP2B6, and CYP2C19 and to a lesser extent CYP2C9 and CYP2D6, are responsible for conversion of methadone to EDDP and other inactive metabolites, which are excreted mainly in the urine.
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (GC)
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (GC)
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (GC)
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (GC)
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IMPURITY -> PARENT |
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ACTIVE MOIETY |