KEGG   DRUG: Methadone
Entry
D08195                      Drug                                   
Name
Methadone (BAN)
Formula
C21H27NO
Exact mass
309.2093
Mol weight
309.4452
Structure
Simcomp
Class
Neuropsychiatric agent
 DG01498  NMDA receptor antagonist
 DG01564  Opioid receptor agonist
  DG01563  mu-Opioid receptor agonist
Analgesic
 DG01984  Opioid analgesics
Metabolizing enzyme substrate
 DG02919  CYP2B6 substrate
 DG02918  CYP2C8 substrate
 DG01642  CYP2C9 substrate
 DG01639  CYP2C19 substrate
 DG01644  CYP2D6 substrate
 DG01633  CYP3A/CYP3A4 substrate
  DG02913  CYP3A4 substrate
Metabolizing enzyme inducer
 DG02891  CYP2B6 inducer
 DG02853  CYP3A/CYP3A4 inducer
  DG01635  CYP3A4 inducer
Transporter substrate
 DG01665  ABCB1 substrate
Remark
Same as: C07163
ATC code: N07BC02
Chemical structure group: DG00999
Product (DG00999): D02102<JP/US>
Efficacy
Analgesic (narcotic), Opioid receptor agonist, NMDA receptor antagonist
Comment
Synthetic opioid
Phenylpiperidine derivative
Target
OPRM1 [HSA:4988] [KO:K04215]
GRIN (NMDAR) [HSA:2902 2903 2904 2905 2906] [KO:K05208 K05209 K05210 K05211 K05212]
  Pathway
hsa04080  Neuroactive ligand-receptor interaction
hsa04724  Glutamatergic synapse
hsa04728  Dopaminergic synapse
Metabolism
Enzyme: CYP3A4 [HSA:1576], CYP2B6 [HSA:1555]; CYP2C8 [HSA:1558], CYP2C9 [HSA:1559], CYP2C19 [HSA:1557], CYP2D6 [HSA:1565]
Transporter: ABCB1 [HSA:5243]
Interaction
CYP induction: CYP3A4 [HSA:1576], CYP2B6 [HSA:1555]
Structure map
map07039  Opioid analgesics
map07224  Opioid receptor agonists/antagonists
map07235  N-Methyl-D-aspartic acid (NMDA) receptor antagonists
Other map
map00982  Drug metabolism - cytochrome P450
Brite
Anatomical Therapeutic Chemical (ATC) classification [BR:br08303]
 N NERVOUS SYSTEM
  N07 OTHER NERVOUS SYSTEM DRUGS
   N07B DRUGS USED IN ADDICTIVE DISORDERS
    N07BC Drugs used in opioid dependence
     N07BC02 Methadone
      D08195  Methadone (BAN)
Drug groups [BR:br08330]
 Neuropsychiatric agent
  DG01498  NMDA receptor antagonist
   DG00999  Methadone
    D08195  Methadone
  DG01564  Opioid receptor agonist
   DG01563  mu-Opioid receptor agonist
    DG00999  Methadone
     D08195  Methadone
 Analgesic
  DG01984  Opioid analgesics
   DG00999  Methadone
    D08195  Methadone
 Metabolizing enzyme substrate
  DG02919  CYP2B6 substrate
   DG00999  Methadone
    D08195  Methadone
  DG02918  CYP2C8 substrate
   DG00999  Methadone
    D08195  Methadone
  DG01642  CYP2C9 substrate
   DG00999  Methadone
    D08195  Methadone
  DG01639  CYP2C19 substrate
   DG00999  Methadone
    D08195  Methadone
  DG01644  CYP2D6 substrate
   DG00999  Methadone
    D08195  Methadone
  DG01633  CYP3A/CYP3A4 substrate
   DG02913  CYP3A4 substrate
    DG00999  Methadone
     D08195  Methadone
 Metabolizing enzyme inducer
  DG02891  CYP2B6 inducer
   DG00999  Methadone
    D08195  Methadone
  DG02853  CYP3A/CYP3A4 inducer
   DG01635  CYP3A4 inducer
    DG00999  Methadone
     D08195  Methadone
 Transporter substrate
  DG01665  ABCB1 substrate
   DG00999  Methadone
    D08195  Methadone
Target-based classification of drugs [BR:br08310]
 G Protein-coupled receptors
  Rhodopsin family
   Opioid
    OPRM1
     D08195  Methadone (BAN)
 Ion channels
  Ligand-gated ion channels
   Glutamate (ionotropic), NMDA
    GRIN (NMDAR)
     D08195  Methadone (BAN)
Drug metabolizing enzymes and transporters [br08309.html]
 Drug metabolizing enzymes
  D08195
 Drug transporters
  D08195
Drug groups [BR:br08330]
 Neuropsychiatric agent
  DG01498  NMDA receptor antagonist
   DG00999  Methadone
  DG01564  Opioid receptor agonist
   DG01563  mu-Opioid receptor agonist
    DG00999  Methadone
 Analgesic
  DG01984  Opioid analgesics
   DG00999  Methadone
 Metabolizing enzyme substrate
  DG02919  CYP2B6 substrate
   DG00999  Methadone
  DG02918  CYP2C8 substrate
   DG00999  Methadone
  DG01642  CYP2C9 substrate
   DG00999  Methadone
  DG01639  CYP2C19 substrate
   DG00999  Methadone
  DG01644  CYP2D6 substrate
   DG00999  Methadone
  DG01633  CYP3A/CYP3A4 substrate
   DG02913  CYP3A4 substrate
    DG00999  Methadone
 Metabolizing enzyme inducer
  DG02891  CYP2B6 inducer
   DG00999  Methadone
  DG02853  CYP3A/CYP3A4 inducer
   DG01635  CYP3A4 inducer
    DG00999  Methadone
 Transporter substrate
  DG01665  ABCB1 substrate
   DG00999  Methadone
Other DBs
CAS: 76-99-3
PubChem: 96024885
ChEBI: 6807
LigandBox: D08195
NIKKAJI: J4.190D
LinkDB
KCF data

ATOM        23
            1   C8x C    21.0000  -19.2500
            2   C8x C    21.0000  -20.6500
            3   C8x C    22.1900  -21.3500
            4   C8x C    23.3800  -20.6500
            5   C8y C    23.3800  -19.2500
            6   C8x C    22.1900  -18.6200
            7   C8x C    25.6900  -20.6500
            8   C8y C    25.6900  -19.2500
            9   C1d C    24.5000  -18.6200
            10  C8x C    26.8800  -21.3500
            11  C8x C    28.0700  -20.6500
            12  C8x C    28.0700  -19.2500
            13  C8x C    26.8800  -18.6200
            14  C1b C    24.5000  -17.2200
            15  C1c C    25.6900  -16.5200
            16  C5a C    22.5400  -17.5000
            17  C1a C    26.8800  -17.2200
            18  N1c N    25.6900  -15.2600
            19  C1a C    26.8800  -14.5600
            20  C1a C    24.5000  -14.5600
            21  O5a O    22.5400  -16.1700
            22  C1b C    21.3500  -18.2000
            23  C1a C    20.2300  -17.5000
BOND        24
            1     1   2 2
            2     2   3 1
            3     3   4 2
            4     4   5 1
            5     5   6 2
            6     1   6 1
            7     7   8 1
            8     8   9 1
            9     5   9 1
            10    7  10 2
            11   10  11 1
            12   11  12 2
            13   12  13 1
            14    8  13 2
            15    9  14 1
            16   14  15 1
            17    9  16 1
            18   15  17 1
            19   15  18 1
            20   18  19 1
            21   18  20 1
            22   16  21 2
            23   16  22 1
            24   22  23 1

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