METHADONE HYDRIODIDE

Details

Stereochemistry	RACEMIC
Molecular Formula	C21H27NO.HI
Molecular Weight	437.3576
Optical Activity	( + / - )
Defined Stereocenters	0 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

SMILES

I.CCC(=O)C(CC(C)N(C)C)(C1=CC=CC=C1)C2=CC=CC=C2

InChI

InChIKey=BUQLQYUUFYFANQ-UHFFFAOYSA-N

InChI=1S/C21H27NO.HI/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

HIDE SMILES / InChI

Molecular Formula	HI
Molecular Weight	127.91241
Charge	0
Count	MOL RATIO 1 MOL RATIO (average)

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Molecular Formula	C21H27NO
Molecular Weight	309.4452
Charge	0
Count	MOL RATIO 1 MOL RATIO (average)

Stereochemistry	RACEMIC
Additional Stereochemistry	No
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

Primary Target	Pharmacology	Condition	Potency
Mu opioid receptor 231	Agonist 2,752		3.51 nM [Ki]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Pain 619	Palliative		Approved 8,583	DOLOPHINE HYDROCHLORIDE
Detoxification & maintenance treatment of opioid addiction 4	Palliative		Approved 8,583	DOLOPHINE HYDROCHLORIDE

C_max

Value	Dose	Analyte	Population
494 ng/mL	76 mg 1 times / day steady-state, oral	METHADONE plasma	Homo sapiens
40.2 ng/mL	10 mg single, oral	METHADONE plasma	Homo sapiens
548 ng/mL	0.89 mg/kg 1 times / day steady-state, oral	METHADONE plasma	Homo sapiens
54 ng/mL	0.89 mg/kg 1 times / day steady-state, oral	2-ETHYLIDENE-1,5-DIMETHYL-3,3-DIPHENYLPYRROLIDINE plasma	Homo sapiens

AUC

Value	Dose	Analyte	Population
8.27 μg × h/mL	76 mg 1 times / day steady-state, oral	METHADONE plasma	Homo sapiens
1073 ng × h/mL	10 mg single, oral	METHADONE plasma	Homo sapiens
8.54 mg × h/L	0.89 mg/kg 1 times / day steady-state, oral	METHADONE plasma	Homo sapiens
0.61 mg × h/L	0.89 mg/kg 1 times / day steady-state, oral	2-ETHYLIDENE-1,5-DIMETHYL-3,3-DIPHENYLPYRROLIDINE plasma	Homo sapiens

T_1/2

Value	Dose	Analyte	Population
39 h	76 mg 1 times / day steady-state, oral	METHADONE plasma	Homo sapiens
39.3 h	10 mg single, oral	METHADONE plasma	Homo sapiens
31.2 h	0.89 mg/kg 1 times / day steady-state, oral	METHADONE plasma	Homo sapiens

Doses

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Dose	Population	Adverse events
10 mg 3 times / day multiple, intravenous Recommended	pregnant, adult	Other AEs: Withdrawal syndrome neonatal...
10 mg 3 times / day multiple, intravenous Recommended	unhealthy, adult	Other AEs: Respiratory depression, Addiction...
20 mg single, oral Recommended	unhealthy, adult	Other AEs: Respiratory depression, QT interval prolonged...

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AEs

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AE	Significance	Dose	Population
Withdrawal syndrome neonatal		10 mg 3 times / day multiple, intravenous Recommended	pregnant, adult
Addiction		10 mg 3 times / day multiple, intravenous Recommended	unhealthy, adult
QT interval prolonged	grade 5	10 mg 3 times / day multiple, intravenous Recommended	unhealthy, adult
Respiratory depression	grade 5	10 mg 3 times / day multiple, intravenous Recommended	unhealthy, adult
QT interval prolonged		20 mg single, oral Recommended	unhealthy, adult

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Overview

CYP3A4	CYP2C9	CYP2D6	hERG
substrate 1,946 inhibitor 2,252	substrate 1,193	substrate 1,388 inhibitor 2,507	inhibitor 2,217

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP2E1 1,060 CYP1A 70 CYP2B 16 CYP2C 20 UGT2B7 197 UGT2B4 23	CYP2B6 776 CYP2C19 1,119 P-gp 2,052 OATP1A2 67 OATP1B1 503 OATP1B3 435 OATP2B1 122 OCT1 393 OCT2 434 OCT3 92 BCRP 697

Drug as perpetrator

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Target	Modality	Activity
UGT2B4 23	inhibitor 4,027	major [Inhibition 0.6 uM]
CYP1A 122	inhibitor 4,027	no
CYP2B 41	inhibitor 4,027	no
CYP2C 37	inhibitor 4,027	no
CYP2E1 1,146	inhibitor 4,027	no

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Drug as victim

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Target	Modality	Activity
BCRP 697	substrate 4,014	no
OATP1A2 67	substrate 4,014	no
OATP1B1 503	substrate 4,014	no
OATP1B3 435	substrate 4,014	no
OATP2B1 122	substrate 4,014	no

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Tox targets

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Target	Modality	Activity	Metabolite	Clinical evidence
hERG 2,263	inhibitor 2,237

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Sourcing

Sourcing

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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

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PubMed

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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
Desipramine in opioid-dependent cocaine abusers maintained on buprenorphine vs methadone.	1999 Sep	12884887
Intravenous clonidine use in a neonate experiencing opioid-induced myoclonus.	2001 Aug	11506132

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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.

Substance Class	Chemical
Record UNII	MS4P249SDR
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

3-HEPTANONE, 6-(DIMETHYLAMINO)-4,4-DIPHENYL-, HYDRIODIDE

Preferred Name

English

METHADONE HYDRIODIDE

Common Name

English

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Code System

Code

Type

Description

FDA UNII

MS4P249SDR

PRIMARY

PUBCHEM

171389978

PRIMARY

CAS

16896-75-6

PRIMARY

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					UC6VBE7V1Z

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SMILES

InChI

CNS Activity

Originator

Approval Year

Targets

Conditions

Cmax

AUC

T1/2

Doses

AEs

Overview

OverviewOther

Drug as perpetrator​

Drug as victim

Tox targets

Sourcing

PubMed

Patents

Sample Use Guides

C_max

T_1/2

Drug as perpetrator