METHADONE

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

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

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	( + / - )

Approval Year

Substance Class	Chemical Created by `admin` on `Fri Dec 15 15:04:46 UTC 2023` Edited by `admin` on `Fri Dec 15 15:04:46 UTC 2023`
Record UNII	UC6VBE7V1Z
Record Status	`Validated (UNII)`
Record Version

Download

Name

Type

Language

METHADONE

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 UTC 2023 , Edited by admin on Fri Dec 15 15:04:46 UTC 2023

NCI_THESAURUS

C1506

Created by admin on Fri Dec 15 15:04:46 UTC 2023 , Edited by admin on Fri Dec 15 15:04:46 UTC 2023

NDF-RT

N0000175684

Created by admin on Fri Dec 15 15:04:46 UTC 2023 , Edited by admin on Fri Dec 15 15:04:46 UTC 2023

WHO-ATC

N02AC52

Created by admin on Fri Dec 15 15:04:46 UTC 2023 , Edited by admin on Fri Dec 15 15:04:46 UTC 2023

NCI_THESAURUS

C67413

Created by admin on Fri Dec 15 15:04:46 UTC 2023 , Edited by admin on Fri Dec 15 15:04:46 UTC 2023

DEA NO.

9250

Created by admin on Fri Dec 15 15:04:46 UTC 2023 , Edited by admin on Fri Dec 15 15:04:46 UTC 2023

LIVERTOX

NBK548084

Created by admin on Fri Dec 15 15:04:46 UTC 2023 , Edited by admin on Fri Dec 15 15:04:46 UTC 2023

WHO-VATC

QN07BC02

Created by admin on Fri Dec 15 15:04:46 UTC 2023 , Edited by admin on Fri Dec 15 15:04:46 UTC 2023

CFR

21 CFR 862.3620

Created by admin on Fri Dec 15 15:04:46 UTC 2023 , Edited by admin on Fri Dec 15 15:04:46 UTC 2023

WHO-ESSENTIAL MEDICINES LIST

24.5

Created by admin on Fri Dec 15 15:04:46 UTC 2023 , Edited by admin on Fri Dec 15 15:04:46 UTC 2023

WHO-VATC

QN02AC52

Created by admin on Fri Dec 15 15:04:46 UTC 2023 , Edited by admin on Fri Dec 15 15:04:46 UTC 2023

NDF-RT

N0000175690

Created by admin on Fri Dec 15 15:04:46 UTC 2023 , Edited by admin on Fri Dec 15 15:04:46 UTC 2023

Code System Code Type Description

ECHA (EC/EINECS)

200-996-9

Created by admin on Fri Dec 15 15:04:46 UTC 2023 , Edited by admin on Fri Dec 15 15:04:46 UTC 2023

PRIMARY

RXCUI

6813

Created by admin on Fri Dec 15 15:04:46 UTC 2023 , Edited by admin on Fri Dec 15 15:04:46 UTC 2023

PRIMARY

RxNorm

EPA CompTox

DTXSID7023273

Created by admin on Fri Dec 15 15:04:46 UTC 2023 , Edited by admin on Fri Dec 15 15:04:46 UTC 2023

PRIMARY

SMS_ID

100000091046

Created by admin on Fri Dec 15 15:04:46 UTC 2023 , Edited by admin on Fri Dec 15 15:04:46 UTC 2023

PRIMARY

CHEBI

28017

Created by admin on Fri Dec 15 15:04:46 UTC 2023 , Edited by admin on Fri Dec 15 15:04:46 UTC 2023

PRIMARY

MERCK INDEX

m7286

Created by admin on Fri Dec 15 15:04:46 UTC 2023 , Edited by admin on Fri Dec 15 15:04:46 UTC 2023

PRIMARY

Merck Index

NCI_THESAURUS

C62044

Created by admin on Fri Dec 15 15:04:46 UTC 2023 , Edited by admin on Fri Dec 15 15:04:46 UTC 2023

PRIMARY

HSDB

3119

Created by admin on Fri Dec 15 15:04:46 UTC 2023 , Edited by admin on Fri Dec 15 15:04:46 UTC 2023

PRIMARY

EVMPD

SUB08833MIG

Created by admin on Fri Dec 15 15:04:46 UTC 2023 , Edited by admin on Fri Dec 15 15:04:46 UTC 2023

PRIMARY

DRUG BANK

DB00333

Created by admin on Fri Dec 15 15:04:46 UTC 2023 , Edited by admin on Fri Dec 15 15:04:46 UTC 2023

PRIMARY

CHEBI

167309

Created by admin on Fri Dec 15 15:04:46 UTC 2023 , Edited by admin on Fri Dec 15 15:04:46 UTC 2023

PRIMARY

CHEBI

6807

Created by admin on Fri Dec 15 15:04:46 UTC 2023 , Edited by admin on Fri Dec 15 15:04:46 UTC 2023

PRIMARY

CAS

76-99-3

Created by admin on Fri Dec 15 15:04:46 UTC 2023 , Edited by admin on Fri Dec 15 15:04:46 UTC 2023

PRIMARY

PUBCHEM

4095

Created by admin on Fri Dec 15 15:04:46 UTC 2023 , Edited by admin on Fri Dec 15 15:04:46 UTC 2023

PRIMARY

ChEMBL

CHEMBL651

Created by admin on Fri Dec 15 15:04:46 UTC 2023 , Edited by admin on Fri Dec 15 15:04:46 UTC 2023

PRIMARY

MESH

D008691

Created by admin on Fri Dec 15 15:04:46 UTC 2023 , Edited by admin on Fri Dec 15 15:04:46 UTC 2023

PRIMARY

INN

788

Created by admin on Fri Dec 15 15:04:46 UTC 2023 , Edited by admin on Fri Dec 15 15:04:46 UTC 2023

PRIMARY

DAILYMED

UC6VBE7V1Z

Created by admin on Fri Dec 15 15:04:46 UTC 2023 , Edited by admin on Fri Dec 15 15:04:46 UTC 2023

PRIMARY

FDA UNII

UC6VBE7V1Z

Created by admin on Fri Dec 15 15:04:46 UTC 2023 , Edited by admin on Fri Dec 15 15:04:46 UTC 2023

PRIMARY

LACTMED

Methadone

Created by admin on Fri Dec 15 15:04:46 UTC 2023 , Edited by admin on Fri Dec 15 15:04:46 UTC 2023

PRIMARY

IUPHAR

5458

Created by admin on Fri Dec 15 15:04:46 UTC 2023 , Edited by admin on Fri Dec 15 15:04:46 UTC 2023

PRIMARY

DRUG CENTRAL

1728

Created by admin on Fri Dec 15 15:04:46 UTC 2023 , Edited by admin on Fri Dec 15 15:04:46 UTC 2023

PRIMARY

CHEBI

50140

Created by admin on Fri Dec 15 15:04:46 UTC 2023 , Edited by admin on Fri Dec 15 15:04:46 UTC 2023

PRIMARY

WIKIPEDIA

METHADONE

Created by admin on Fri Dec 15 15:04:46 UTC 2023 , Edited by admin on Fri Dec 15 15:04:46 UTC 2023

PRIMARY

CAS

297-88-1

Created by admin on Fri Dec 15 15:04:46 UTC 2023 , Edited by admin on Fri Dec 15 15:04:46 UTC 2023

SUPERSEDED

Related Record Type Details


					8CJ41S2M6U

METHADONE HYDROBROMIDE

SALT/SOLVATE -> PARENT


					8E4LAA4357

CYTOCHROME P450 2D6

METABOLIC ENZYME -> SUBSTRATE


					L0423Z5LDW

CYTOCHROME P450 2C8

METABOLIC ENZYME -> SUBSTRATE


					081I12ZA58

CYTOCHROME P450 2C19

METABOLIC ENZYME -> SUBSTRATE

Comments:

CYP2C19 preferentially metabolized (R)-methadone,


					0UY97CSG1T

CYTOCHROME P450 2B6

METABOLIC ENZYME -> SUBSTRATE

Comments:

CYP2B6 preferentially metabolized (S)-methadone,


					8CJ41S2M6U

METHADONE HYDROBROMIDE

PARENT -> SALT/SOLVATE


					1PE72K8X46

MU-TYPE OPIOID RECEPTOR

TARGET->ANTAGONIST


					6D53G0FD0Z

PLASMA PROTEIN FRACTION (HUMAN)

BINDER->LIGAND

Interaction Type:

BINDING

Amount:


					PUO0521HZV

CYTOCHROME P450 3A4

METABOLIC ENZYME -> SUBSTRATE

Comments:

CYP3A4 showed no preference between the two enantiomers


					6Y75Z4E8NS

ACTIVE ENANTIOMER->RACEMATE

Comments:

approximately 50x the potency of the S-(+)-enantiomer as well as greater μ-opioid receptor selectivity


					8CJ41S2M6U

METHADONE HYDROBROMIDE

SALT/SOLVATE -> PARENT

Comments:

APPROXIMATE PURE ANHYDROUS DRUG CONTENT (IN PERCENT)

Amount:


					22ES734693

MULTIDRUG RESISTANCE PROTEIN 1

TRANSPORTER -> SUBSTRATE

229809935B

METHADONE HYDROCHLORIDE

SALT/SOLVATE -> PARENT

Comments:

APPROXIMATE PURE ANHYDROUS DRUG CONTENT (IN PERCENT)

Amount:


					1PE72K8X46

MU-TYPE OPIOID RECEPTOR

TARGET -> INHIBITOR

Amount:

Related Record Type Details


					Z3LC48U94I

2-ETHYLIDENE-1,5-DIMETHYL-3,3-DIPHENYLPYRROLIDINE

METABOLITE INACTIVE -> PARENT

Comments:

The hierarchy of EDDPgeneration was CYP2B6 > CYP2C19zCYP3A4

Interaction Type:

MAJOR


					NNB4I01PA7

PARENT -> METABOLITE

Interaction Type:

MINOR


					42N6J1Z84U

METABOLITE -> PARENT

Interaction Type:

MINOR


					WQH8WZB3CW

2-ETHYL-5-METHYL-3,3-DIPHENYLPYRROLIDINE

METABOLITE -> PARENT

Comments:

5-10% of the dose but there is a large individual variation due to pH, urine volume, dose and metabolic rate

Interaction Type:

MINOR


					LTG1R1T3K3

DESMETHYLMETHADONE

METABOLITE ACTIVE -> PARENT


					9WQ3JEE33F

METABOLITE ACTIVE -> PARENT


					7Y6CD3S4VU

METABOLITE ACTIVE -> PARENT

Related Record Type Details


					UC6VBE7V1Z

METHADONE

ACTIVE MOIETY

Name	Property Type	Amount	Referenced Substance	Defining	Parameters	References
Biological Half-life	PHARMACOKINETIC				Elimination PHARMACOKINETIC