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
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
3913
Curator's Comment: https://www.ncbi.nlm.nih.gov/pubmed/5084666

Originator

Approval Year

1947
99
Targets

Targets

Primary TargetPharmacologyConditionPotency
Agonist
2678
 3.51 nM [Ki]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Palliative
Approved
8429
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
8429
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
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/8641323/
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
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/15151520/
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
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
54 ng/mL
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/8641323/
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
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/8641323/
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
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/15151520/
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
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
0.61 mg × h/L
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/8641323/
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
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/8641323/
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
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/15151520/
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
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
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:
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 (starting)
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 (starting)
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 (starting)
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 (starting)
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 (starting)
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 (starting)
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 (starting)
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 (starting)
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 (starting)
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
1737

inhibitor
1587
substrate
1037
substrate
1217

inhibitor
1852
inhibitor
1612

OverviewOther

Other InhibitorOther SubstrateOther Inducer
CYP2E1
882

CYP1A
72

CYP2B
15

CYP2C
19

UGT2B7
146

UGT2B4
19
CYP2B6
664

CYP2C19
991

P-gp
1537

OATP1A2
62

OATP1B1
406

OATP1B3
350

OATP2B1
104

OCT1
327

OCT2
355

OCT3
80

BCRP
561
Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
UGT2B4
19
 major [Inhibition 0.6 uM]
CYP1A
121
 no
CYP2B
40
 no
CYP2C
34
 no
CYP2E1
970
 no
UGT2B7
157
 unlikely
CYP3A4
1925
 yes [Ki 100 uM]
CYP2D6
1891
 yes [Ki 2.5 uM]
Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
BCRP
561
 no
OATP1A2
62
 no
OATP1B1
406
 no
OATP1B3
350
 no
OATP2B1
104
 no
OCT1
327
 no
OCT2
355
 no
OCT3
80
 no
P-gp
1537
 yes
CYP2B6
664
 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
991
 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
1037
 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
1217
 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
1737
 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
1647
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
Transient hypertension. Associated with methadone intoxication.
1976 Nov
Rhabdomyolysis and acute renal failure following methadone abuse.
1992
Cocaine-associated panic attacks in methadone-maintained patients.
1992
Modulating effect of alcohol use on cocaine use.
2000 Jan-Feb
Thrice-weekly versus daily buprenorphine maintenance.
2000 Jun 15
[Methadone withdrawal syndrome induced by nevirapine].
2000 Mar 18
Pain responses in methadone-maintained opioid abusers.
2000 Oct
Effect of perinatal buprenorphine exposure on development in the rat.
2001 Aug
Enteral methadone to expedite fentanyl discontinuation and prevent opioid abstinence syndrome in the PICU.
2001 Dec
Methadone is safe for treating hospitalized patients with severe pain.
2001 Dec
Reversible spastic paraparesis induced by high-dose intravenous methadone.
2001 Feb
Pain intolerance in opioid-maintained former opiate addicts: effect of long-acting maintenance agent.
2001 Jul 1
[Olanzapine efficacy in the treatment of cocaine abuse in methadone maintenance patients. Interaction with plasma levels].
2001 Jul-Aug
Sleep-disordered breathing in stable methadone programme patients: a pilot study.
2001 Mar
Effects of urine testing frequency on outcome in a methadone take-home contingency program.
2001 Mar 1
Continuous epidural infusion of racemic methadone results in effective postoperative analgesia and low plasma concentrations.
2002 Jan
Neuropsychological correlates of opioid dependence and withdrawal.
2003 Apr
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
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
Directly observed therapy for the management of HIV-infected patients in a methadone program.
2004 Jun 1
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
Intravenous ketamine infusion as an adjuvant to morphine in a 2-year-old with severe cancer pain from metastatic neuroblastoma.
2004 Oct
Methadone-related Torsades de Pointes in a sickle cell patient treated for chronic pain.
2005 Apr
[Methadone-induced heart arrhythmia].
2005 Aug 11
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
Patents

Patents

JP2000212069A
12
JP2002527384A
12
JP2007507532A
34
JP2007525670A
148
JP2011528275A
455
JPH02247157A
3

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 Fri Dec 15 15:04:46 GMT 2023
Edited
by admin
on Fri Dec 15 15:04:46 GMT 2023
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
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
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-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
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
SMS_ID
100000091046
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
28017
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
MERCK INDEX
m7286
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 Merck Index
NCI_THESAURUS
C62044
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
HSDB
3119
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
EVMPD
SUB08833MIG
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
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
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
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
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PUBCHEM
4095
Created by admin on Fri Dec 15 15:04:46 GMT 2023 , Edited by admin on Fri Dec 15 15:04:46 GMT 2023
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ChEMBL
CHEMBL651
Created by admin on Fri Dec 15 15:04:46 GMT 2023 , Edited by admin on Fri Dec 15 15:04:46 GMT 2023
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MESH
D008691
Created by admin on Fri Dec 15 15:04:46 GMT 2023 , Edited by admin on Fri Dec 15 15:04:46 GMT 2023
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INN
788
Created by admin on Fri Dec 15 15:04:46 GMT 2023 , Edited by admin on Fri Dec 15 15:04:46 GMT 2023
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DAILYMED
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
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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
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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
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IUPHAR
5458
Created by admin on Fri Dec 15 15:04:46 GMT 2023 , Edited by admin on Fri Dec 15 15:04:46 GMT 2023
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DRUG CENTRAL
1728
Created by admin on Fri Dec 15 15:04:46 GMT 2023 , Edited by admin on Fri Dec 15 15:04:46 GMT 2023
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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
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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
Related Record Type Details
Structure of METHADONE HYDROBROMIDE
SALT/SOLVATE -> PARENT
CYTOCHROME P450 2D6
METABOLIC ENZYME -> SUBSTRATE
CYTOCHROME P450 2C8
METABOLIC ENZYME -> SUBSTRATE
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->ANTAGONIST
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 μ-opioid receptor selectivity
Structure of METHADONE HYDROBROMIDE
SALT/SOLVATE -> PARENT
APPROXIMATE PURE ANHYDROUS DRUG CONTENT (IN PERCENT)
MULTIDRUG RESISTANCE PROTEIN 1
TRANSPORTER -> SUBSTRATE
Structure of METHADONE HYDROCHLORIDE
SALT/SOLVATE -> PARENT
APPROXIMATE PURE ANHYDROUS DRUG CONTENT (IN PERCENT)
MU-TYPE OPIOID RECEPTOR
TARGET -> INHIBITOR
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
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