KEGG   DRUG: Imipramine hydrochloride
Entry
D00815                      Drug                                   
Name
Imipramine hydrochloride (JP18/USP);
Tofranil (TN)
Product
  Generic
Formula
C19H24N2. HCl
Exact mass
316.1706
Mol weight
316.8682
Structure
Simcomp
Class
Neuropsychiatric agent
 DG01730  Non-selective monoamine reuptake inhibitor
 DG01728  Tricyclic antidepressant
Metabolizing enzyme substrate
 DG01892  CYP1A2 substrate
 DG01639  CYP2C19 substrate
 DG01644  CYP2D6 substrate
 DG01633  CYP3A/CYP3A4 substrate
  DG02913  CYP3A4 substrate
Remark
Same as: C07982
Therapeutic category: 1174
ATC code: N06AA02
Chemical structure group: DG00928
Product (DG00928): D00815<JP/US> D08071<US>
Efficacy
Antidepressant, Serotonin-noradrenaline reuptake inhibitor (SNRI)
  Disease
Depression [DS:H01646]
Comment
Active form of prodrug: Desipramine [DR:D07791]
Target
SLC6A4 (HTT) [HSA:6532] [KO:K05037]
SLC6A2 (NAT1) [HSA:6530] [KO:K05035]
  Pathway
hsa04721  Synaptic vesicle cycle
hsa04726  Serotonergic synapse
Metabolism
Enzyme: CYP2D6 [HSA:1565]; CYP1A2 [HSA:1544], CYP3A4 [HSA:1576], CYP2C19 [HSA:1557]
Interaction
Structure map
map07027  Antidepressants
map07213  Dopamine receptor agonists/antagonists
map07234  Neurotransmitter transporter inhibitors
Brite
Anatomical Therapeutic Chemical (ATC) classification [BR:br08303]
 N NERVOUS SYSTEM
  N06 PSYCHOANALEPTICS
   N06A ANTIDEPRESSANTS
    N06AA Non-selective monoamine reuptake inhibitors
     N06AA02 Imipramine
      D00815  Imipramine hydrochloride (JP18/USP) <JP/US>
USP drug classification [BR:br08302]
 Antidepressants
  Tricyclics
   Imipramine
    D00815  Imipramine hydrochloride (JP18/USP)
Therapeutic category of drugs in Japan [BR:br08301]
 1  Agents affecting nervous system and sensory organs
  11  Agents affecting central nervous system
   117  Psychotropics
    1174  Imipramines
     D00815  Imipramine hydrochloride (JP18/USP)
Drug groups [BR:br08330]
 Neuropsychiatric agent
  DG01730  Non-selective monoamine reuptake inhibitor
   DG00928  Imipramine
    D00815  Imipramine hydrochloride
  DG01728  Tricyclic antidepressant
   DG00928  Imipramine
    D00815  Imipramine hydrochloride
 Metabolizing enzyme substrate
  DG01892  CYP1A2 substrate
   DG00928  Imipramine
    D00815  Imipramine hydrochloride
  DG01639  CYP2C19 substrate
   DG00928  Imipramine
    D00815  Imipramine hydrochloride
  DG01644  CYP2D6 substrate
   DG00928  Imipramine
    D00815  Imipramine hydrochloride
  DG01633  CYP3A/CYP3A4 substrate
   DG02913  CYP3A4 substrate
    DG00928  Imipramine
     D00815  Imipramine hydrochloride
Drug classes [BR:br08332]
 Neuropsychiatric agent
  DG01730  Non-selective monoamine reuptake inhibitor
   D00815  Imipramine hydrochloride
Target-based classification of drugs [BR:br08310]
 Transporters
  Solute carrier family
   SLC6
    SLC6A2 (NAT1)
     D00815  Imipramine hydrochloride (JP18/USP) <JP/US>
    SLC6A4 (HTT)
     D00815  Imipramine hydrochloride (JP18/USP) <JP/US>
Drugs listed in the Japanese Pharmacopoeia [BR:br08311]
 Chemicals
  D00815  Imipramine hydrochloride
  D00815  Imipramine hydrochloride tablets
Drug metabolizing enzymes and transporters [br08309.html]
 Drug metabolizing enzymes
  D00815
Pharmacogenomic biomarkers [br08341.html]
 Polymorphisms and mutations affecting drug response
  D00815
Drug groups [BR:br08330]
 Neuropsychiatric agent
  DG01730  Non-selective monoamine reuptake inhibitor
   DG00928  Imipramine
  DG01728  Tricyclic antidepressant
   DG00928  Imipramine
 Metabolizing enzyme substrate
  DG01892  CYP1A2 substrate
   DG00928  Imipramine
  DG01639  CYP2C19 substrate
   DG00928  Imipramine
  DG01644  CYP2D6 substrate
   DG00928  Imipramine
  DG01633  CYP3A/CYP3A4 substrate
   DG02913  CYP3A4 substrate
    DG00928  Imipramine
Prodrugs [br08324.html]
 DG00928
Other DBs
CAS: 113-52-0
PubChem: 7847880
ChEBI: 5882
LigandBox: D00815
NIKKAJI: J243.988C
LinkDB
KCF data

ATOM        22
            1   C1x C    12.8734  -13.8694
            2   C8y C    12.0313  -12.7598
            3   C8y C    12.3665  -11.4030
            4   N1y N    13.6275  -10.8249
            5   C1x C    14.2792  -13.8946
            6   C8y C    14.8811  -11.4472
            7   C8y C    15.1676  -12.8159
            8   C8x C    11.3594  -10.4346
            9   C8x C    10.0174  -10.8227
            10  C8x C     9.6822  -12.1795
            11  C8x C    10.6893  -13.1476
            12  C8x C    16.4988  -13.2530
            13  C8x C    17.5430  -12.3186
            14  C8x C    17.2566  -10.9499
            15  C8x C    15.9252  -10.5128
            16  C1b C    13.6492   -9.4500
            17  C1b C    14.8732   -8.7689
            18  C1b C    16.0416   -9.4684
            19  N1c N    17.2637   -8.7883
            20  C1a C    18.4984   -9.5269
            21  C1a C    17.2857   -7.4200
            22  X   Cl   20.1600  -11.7600
BOND        23
            1     3   4 1
            2     1   5 1
            3     4   6 1
            4     2   3 1
            5     5   7 1
            6     1   2 1
            7     6   7 1
            8     3   8 2
            9     8   9 1
            10    9  10 2
            11   10  11 1
            12    2  11 2
            13    7  12 2
            14   12  13 1
            15   13  14 2
            16   14  15 1
            17    6  15 2
            18    4  16 1
            19   16  17 1
            20   17  18 1
            21   18  19 1
            22   19  20 1
            23   19  21 1

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KEGG   DRUG: Imipramine
Entry
D08070                      Drug                                   
Name
Imipramine (INN);
Tofranil (TN)
Formula
C19H24N2
Exact mass
280.1939
Mol weight
280.4073
Structure
Simcomp
Class
Neuropsychiatric agent
 DG01730  Non-selective monoamine reuptake inhibitor
 DG01728  Tricyclic antidepressant
Metabolizing enzyme substrate
 DG01892  CYP1A2 substrate
 DG01639  CYP2C19 substrate
 DG01644  CYP2D6 substrate
 DG01633  CYP3A/CYP3A4 substrate
  DG02913  CYP3A4 substrate
Remark
Same as: C07049
ATC code: N06AA02
Chemical structure group: DG00928
Product (DG00928): D00815<JP/US> D08071<US>
Efficacy
Antidepressant, Serotonin-noradrenaline reuptake inhibitor (SNRI)
Comment
Active form of prodrug: Desipramine [DR:D07791]
Target
SLC6A4 (HTT) [HSA:6532] [KO:K05037]
SLC6A2 (NAT1) [HSA:6530] [KO:K05035]
  Pathway
hsa04721  Synaptic vesicle cycle
hsa04726  Serotonergic synapse
Metabolism
Enzyme: CYP2D6 [HSA:1565]; CYP1A2 [HSA:1544], CYP3A4 [HSA:1576], CYP2C19 [HSA:1557]
Interaction
Structure map
map07027  Antidepressants
map07234  Neurotransmitter transporter inhibitors
Brite
Anatomical Therapeutic Chemical (ATC) classification [BR:br08303]
 N NERVOUS SYSTEM
  N06 PSYCHOANALEPTICS
   N06A ANTIDEPRESSANTS
    N06AA Non-selective monoamine reuptake inhibitors
     N06AA02 Imipramine
      D08070  Imipramine (INN)
Drug groups [BR:br08330]
 Neuropsychiatric agent
  DG01730  Non-selective monoamine reuptake inhibitor
   DG00928  Imipramine
    D08070  Imipramine
  DG01728  Tricyclic antidepressant
   DG00928  Imipramine
    D08070  Imipramine
 Metabolizing enzyme substrate
  DG01892  CYP1A2 substrate
   DG00928  Imipramine
    D08070  Imipramine
  DG01639  CYP2C19 substrate
   DG00928  Imipramine
    D08070  Imipramine
  DG01644  CYP2D6 substrate
   DG00928  Imipramine
    D08070  Imipramine
  DG01633  CYP3A/CYP3A4 substrate
   DG02913  CYP3A4 substrate
    DG00928  Imipramine
     D08070  Imipramine
Target-based classification of drugs [BR:br08310]
 Transporters
  Solute carrier family
   SLC6
    SLC6A2 (NAT1)
     D08070  Imipramine (INN)
    SLC6A4 (HTT)
     D08070  Imipramine (INN)
Drug metabolizing enzymes and transporters [br08309.html]
 Drug metabolizing enzymes
  D08070
Prodrugs [br08324.html]
 D08070
Drug groups [BR:br08330]
 Neuropsychiatric agent
  DG01730  Non-selective monoamine reuptake inhibitor
   DG00928  Imipramine
  DG01728  Tricyclic antidepressant
   DG00928  Imipramine
 Metabolizing enzyme substrate
  DG01892  CYP1A2 substrate
   DG00928  Imipramine
  DG01639  CYP2C19 substrate
   DG00928  Imipramine
  DG01644  CYP2D6 substrate
   DG00928  Imipramine
  DG01633  CYP3A/CYP3A4 substrate
   DG02913  CYP3A4 substrate
    DG00928  Imipramine
Prodrugs [br08324.html]
 DG00928
Other DBs
CAS: 50-49-7
PubChem: 96024761
ChEBI: 47499
PDB-CCD: IXX[PDBj]
LigandBox: D08070
NIKKAJI: J8.587A
LinkDB
KCF data

ATOM        21
            1   C1x C    22.9600  -21.1400
            2   C8y C    22.1200  -20.0200
            3   C8y C    22.4700  -18.6900
            4   N1y N    23.7300  -18.1300
            5   C1x C    24.3600  -21.1400
            6   C8y C    24.9900  -18.7600
            7   C8y C    25.2700  -20.0900
            8   C8x C    21.4200  -17.7100
            9   C8x C    20.0900  -18.1300
            10  C8x C    19.7400  -19.4600
            11  C8x C    20.7900  -20.4400
            12  C8x C    26.6000  -20.5100
            13  C8x C    27.6500  -19.6000
            14  C8x C    27.3700  -18.2000
            15  C8x C    26.0400  -17.7800
            16  C1b C    23.7300  -16.7300
            17  C1b C    24.9200  -16.0300
            18  C1b C    26.1100  -16.7300
            19  N1c N    27.3700  -16.1000
            20  C1a C    28.5600  -16.8000
            21  C1a C    27.3700  -14.7000
BOND        23
            1     3   4 1
            2     1   5 1
            3     4   6 1
            4     2   3 1
            5     5   7 1
            6     1   2 1
            7     6   7 1
            8     3   8 2
            9     8   9 1
            10    9  10 2
            11   10  11 1
            12    2  11 2
            13    7  12 2
            14   12  13 1
            15   13  14 2
            16   14  15 1
            17    6  15 2
            18    4  16 1
            19   16  17 1
            20   17  18 1
            21   18  19 1
            22   19  20 1
            23   19  21 1

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