KEGG   DRUG: D08479Help
Entry
D08479                      Drug                                   

Name
Rifampicin sodium;
Rifadine (TN)
Formula
C43H58N4O12. Na
Exact mass
845.3949
Mol weight
845.93
Structure
Mol fileKCF fileDB searchJmolKegDraw
Activity
Antitubercular;
Antibiotic [DS:H00342]
Remark
ATC code: 
Drug group: 
Comment
Semisynthetic analogue of Rifamycin [DR:D02549]
Target
23S rRNA of 50S ribosomal subunit, protein synthesis inhibitor [KO:K01980];
DNA-dependent RNA polymerase inhibitor, RNA synthesis inhibitor
  Pathway
ko03010  Ribosome  
 
Metabolism
Enzyme: CYP3A4 [HSA:1576]
Transporter: SLCO1B1 [HSA:10599]
Interaction
CYP induction: CYP3A [HSA:1576 1577 1551], CYP2C19 [HSA:1557], CYP2B6 [HSA:1555], CYP2C8 [HSA:1558], CYP2C9 [HSA:1559], CYP2D6 [HSA:1565]
Transporter induction: SLCO1B1 [HSA:10599], SLCO1B3 [HSA:28234], SLCO1A2 [HSA:6579], SLCO2B1 [HSA:11309], ABCB11 [HSA:8647]
Transporter inhibition: ABCC2 [HSA:1244]
Drug interaction
Structure map
Rifamycins
Brite
Anatomical Therapeutic Chemical (ATC) classification [BR:br08303]
 J ANTIINFECTIVES FOR SYSTEMIC USE
  J04 ANTIMYCOBACTERIALS
   J04A DRUGS FOR TREATMENT OF TUBERCULOSIS
    J04AB Antibiotics
     J04AB02 Rifampicin
      D08479  Rifampicin sodium
Antiinfectives [BR:br08307]
 Antibacterials
  Nucleic acid synthesis inhibitor
   RNA polymerase inhibitor
    Rifampicin
     D08479  Rifampicin sodium
Cytochrome P450 interactions [BR:br08309]
 Substrates
  CYP3A4
   Rifampicin
    D08479  Rifampicin sodium
 Inducers
  CYP2B6
   Rifampicin
    D08479  Rifampicin sodium
  CYP2C8
   Rifampicin
    D08479  Rifampicin sodium
  CYP2C9
   Rifampicin
    D08479  Rifampicin sodium
  CYP2C19
   Rifampicin
    D08479  Rifampicin sodium
  CYP2D6
   Rifampicin
    D08479  Rifampicin sodium
  CYP3A4
   Rifampicin
    D08479  Rifampicin sodium
BRITE hierarchy
Other DBs
CAS: 
38776-75-9
PubChem: 
LigandBox: 
KCF data Show

ATOM        60
            1   C1c C    20.5100  -14.4200
            2   C1c C    20.5100  -15.8200
            3   O1a O    22.8900  -15.7500
            4   C1c C    22.8900  -14.4200
            5   C1c C    21.6300  -13.7900
            6   C2b C    25.2000  -14.4200
            7   C1c C    24.0100  -13.7900
            8   C5a C    26.3900  -16.5200
            9   C2c C    27.5100  -15.8200
            10  C2b C    27.5100  -14.4200
            11  C2b C    26.3900  -13.7900
            12  C1a C    24.0100  -12.3900
            13  C1a C    21.6300  -12.3900
            14  O1a O    19.3900  -13.7900
            15  C1a C    28.7000  -16.5200
            16  O5a O    25.2700  -15.8200
            17  N1b N    26.3900  -18.1300
            18  C1c C    19.3900  -16.5200
            19  O7a O    18.2000  -15.8200
            20  C1c C    19.3900  -18.1300
            21  C8y C    25.2700  -18.8300
            22  C8y C    25.2700  -20.1600
            23  C8y C    24.0100  -18.1300
            24  C8y C    22.8900  -18.8300
            25  C8y C    22.8900  -20.1600
            26  C8y C    24.0100  -20.8600
            27  C8y C    21.7000  -18.1300
            28  C8y C    20.5100  -18.8300
            29  C8y C    20.5100  -20.1600
            30  C8y C    21.7000  -20.8600
            31  O1a O    24.0100  -16.8000
            32  O1a O    21.7000  -16.8000
            33  C1a C    19.3900  -14.7700
            34  C7a C    17.0100  -15.1900
            35  C1a C    15.8900  -15.8200
            36  O6a O    17.0100  -13.7900
            37  C1c C    18.2000  -18.8300
            38  O2a O    17.0800  -18.1300
            39  C2b C    18.2000  -20.1600
            40  C1a C    18.2000  -17.2200
            41  C1a C    15.8900  -18.8300
            42  C2b C    17.0800  -20.8600
            43  O2a O    17.0800  -22.1900
            44  O2x O    19.3900  -20.8600
            45  C1z C    19.3900  -22.1900
            46  C5x C    21.7000  -22.1900
            47  C1a C    19.3900  -23.5200
            48  C1a C    20.5100  -17.5000
            49  O1a O    24.0100  -22.1900
            50  O5x O    22.8200  -22.8900
            51  C2b C    26.3900  -20.8600
            52  N2b N    27.5800  -20.1600
            53  N1y N    28.7700  -20.8600
            54  C1x C    28.7700  -22.2600
            55  C1x C    29.9600  -22.9600
            56  N1y N    31.2200  -22.2600
            57  C1x C    31.2200  -20.8600
            58  C1x C    30.0300  -20.1600
            59  C1a C    32.4100  -22.9600
            60  Z   Na   33.9500  -17.8500
BOND        63
            1     1   2 1
            2     4   3 1 #Down
            3     4   5 1
            4     1   5 1
            5     6   7 1
            6     4   7 1
            7     8   9 1
            8     9  10 2
            9    10  11 1
            10    6  11 2
            11    7  12 1 #Up
            12    5  13 1 #Down
            13    1  14 1 #Down
            14    9  15 1
            15    8  16 2
            16    8  17 1
            17    2  18 1
            18   18  19 1 #Up
            19   18  20 1
            20   17  21 1
            21   21  22 1
            22   21  23 2
            23   23  24 1
            24   24  25 1
            25   25  26 1
            26   24  27 2
            27   27  28 1
            28   28  29 2
            29   29  30 1
            30   25  30 2
            31   23  31 1
            32   27  32 1
            33    2  33 1 #Up
            34   19  34 1
            35   34  35 1
            36   34  36 2
            37   26  22 2
            38   20  37 1
            39   37  38 1 #Down
            40   37  39 1
            41   20  40 1 #Down
            42   38  41 1
            43   39  42 2
            44   42  43 1
            45   29  44 1
            46   44  45 1
            47   43  45 1
            48   30  46 1
            49   45  46 1
            50   45  47 1 #Down
            51   28  48 1
            52   26  49 1
            53   50  46 2
            54   22  51 1
            55   51  52 2
            56   52  53 1
            57   53  54 1
            58   54  55 1
            59   55  56 1
            60   56  57 1
            61   57  58 1
            62   53  58 1
            63   56  59 1

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