KEGG   DRUG: Chlorpromazine
Entry
D00270                      Drug                                   
Name
Chlorpromazine (USP/INN);
Thorazine (TN)
Formula
C17H19ClN2S
Exact mass
318.0957
Mol weight
318.86
Structure
Simcomp
Class
Cardiovascular agent
 DG01466  Adrenergic receptor antagonist
  DG01465  alpha-Adrenergic receptor antagonist
   DG01460  alpha2-Adrenergic receptor antagonist
Neuropsychiatric agent
 DG01478  Dopamine antagonist
  DG01474  Dopamine D2-receptor antagonist
 DG01491  Muscarinic cholinergic receptor antagonist
 DG03200  Antipsychotic agent
  DG01905  Phenothiazine antipsychotics
Anti-allergic agent
 DG01557  Histamine receptor antagonist
  DG01482  Histamine receptor H1 antagonist
Metabolizing enzyme substrate
 DG01644  CYP2D6 substrate
Metabolizing enzyme inhibitor
 DG01645  CYP2D6 inhibitor
Remark
Same as: C06906
ATC code: N05AA01
Chemical structure group: DG00867
Product (DG00867): D00789<JP/US> D04034<JP>
Efficacy
Antipsychotic, Anti-emetic
Comment
Phenothiazine derivative
Target
HTR2 [HSA:3356 3357 3358] [KO:K04157]
HRH1 [HSA:3269] [KO:K04149]
ADRA2 [HSA:150 151 152] [KO:K04138 K04139 K04140]
DRD2 [HSA:1813] [KO:K04145]
CHRM [HSA:1128 1129 1131 1132 1133] [KO:K04129 K04130 K04131 K04132 K04133]
  Pathway
hsa04080  Neuroactive ligand-receptor interaction
hsa04725  Cholinergic synapse
hsa04726  Serotonergic synapse
hsa04728  Dopaminergic synapse
Metabolism
Enzyme: CYP2D6 [HSA:1565]
Interaction
CYP inhibition: CYP2D6 [HSA:1565]
Structure map
map07028  Antipsychotics
map07029  Antipsychotics - phenothiazines
map07048  Antimigraines
map07212  Histamine H1 receptor antagonists
map07213  Dopamine receptor agonists/antagonists
Brite
Anatomical Therapeutic Chemical (ATC) classification [BR:br08303]
 N NERVOUS SYSTEM
  N05 PSYCHOLEPTICS
   N05A ANTIPSYCHOTICS
    N05AA Phenothiazines with aliphatic side-chain
     N05AA01 Chlorpromazine
      D00270  Chlorpromazine (USP/INN)
Drug groups [BR:br08330]
 Cardiovascular agent
  DG01466  Adrenergic receptor antagonist
   DG01465  alpha-Adrenergic receptor antagonist
    DG01460  alpha2-Adrenergic receptor antagonist
     DG00867  Chlorpromazine
      D00270  Chlorpromazine
 Neuropsychiatric agent
  DG01478  Dopamine antagonist
   DG01474  Dopamine D2-receptor antagonist
    DG00867  Chlorpromazine
     D00270  Chlorpromazine
  DG01491  Muscarinic cholinergic receptor antagonist
   DG00867  Chlorpromazine
    D00270  Chlorpromazine
  DG03200  Antipsychotic agent
   DG01905  Phenothiazine antipsychotics
    DG00867  Chlorpromazine
     D00270  Chlorpromazine
 Anti-allergic agent
  DG01557  Histamine receptor antagonist
   DG01482  Histamine receptor H1 antagonist
    DG00867  Chlorpromazine
     D00270  Chlorpromazine
 Metabolizing enzyme substrate
  DG01644  CYP2D6 substrate
   DG00867  Chlorpromazine
    D00270  Chlorpromazine
 Metabolizing enzyme inhibitor
  DG01645  CYP2D6 inhibitor
   DG00867  Chlorpromazine
    D00270  Chlorpromazine
Target-based classification of drugs [BR:br08310]
 G Protein-coupled receptors
  Rhodopsin family
   Acetylcholine (muscarinic)
    CHRM
     D00270  Chlorpromazine (USP/INN)
   Adrenaline
    ADRA2
     D00270  Chlorpromazine (USP/INN)
   Dopamine
    DRD2
     D00270  Chlorpromazine (USP/INN)
   Histamine
    HRH1
     D00270  Chlorpromazine (USP/INN)
   Serotonin
    HTR2
     D00270  Chlorpromazine (USP/INN)
Drug metabolizing enzymes and transporters [br08309.html]
 Drug metabolizing enzymes
  D00270
Drug groups [BR:br08330]
 Cardiovascular agent
  DG01466  Adrenergic receptor antagonist
   DG01465  alpha-Adrenergic receptor antagonist
    DG01460  alpha2-Adrenergic receptor antagonist
     DG00867  Chlorpromazine
 Neuropsychiatric agent
  DG01478  Dopamine antagonist
   DG01474  Dopamine D2-receptor antagonist
    DG00867  Chlorpromazine
  DG01491  Muscarinic cholinergic receptor antagonist
   DG00867  Chlorpromazine
  DG03200  Antipsychotic agent
   DG01905  Phenothiazine antipsychotics
    DG00867  Chlorpromazine
 Anti-allergic agent
  DG01557  Histamine receptor antagonist
   DG01482  Histamine receptor H1 antagonist
    DG00867  Chlorpromazine
 Metabolizing enzyme substrate
  DG01644  CYP2D6 substrate
   DG00867  Chlorpromazine
 Metabolizing enzyme inhibitor
  DG01645  CYP2D6 inhibitor
   DG00867  Chlorpromazine
Other DBs
CAS: 50-53-3
PubChem: 7847336
ChEBI: 3647
PDB-CCD: Z80[PDBj]
LigandBox: D00270
NIKKAJI: J2.794D
LinkDB
KCF data

ATOM        21
            1   C8x C     3.4300  -16.7300
            2   C8x C     3.4300  -18.1300
            3   C8x C     4.6424  -18.8300
            4   C8y C     5.8549  -18.1300
            5   C8y C     5.8549  -16.7300
            6   C8x C     4.6424  -16.0300
            7   S2x S     7.0673  -18.8300
            8   C8y C     8.2797  -18.1300
            9   C8y C     8.2797  -16.7300
            10  N4y N     7.0673  -16.0300
            11  C8x C     9.4922  -18.8300
            12  C8x C    10.7046  -18.1300
            13  C8y C    10.7046  -16.7300
            14  C8x C     9.4922  -16.0300
            15  C1b C     7.0673  -14.6300
            16  C1b C     8.2818  -13.9288
            17  C1b C     9.4783  -14.6198
            18  N1c N    10.6651  -13.9346
            19  C1a C    11.8566  -14.6228
            20  C1a C    10.6653  -12.5302
            21  X   Cl   11.9211  -16.0277
BOND        23
            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     4   7 1
            8     7   8 1
            9     8   9 1
            10    9  10 1
            11    5  10 1
            12    8  11 2
            13   11  12 1
            14   12  13 2
            15   13  14 1
            16    9  14 2
            17   10  15 1
            18   15  16 1
            19   16  17 1
            20   17  18 1
            21   18  19 1
            22   18  20 1
            23   13  21 1

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