KEGG   DRUG: Rifampicin sodium
Entry
D08479                      Drug                                   
Name
Rifampicin sodium;
Rifadine (TN)
Formula
C43H58N4O12. Na
Exact mass
845.3949
Mol weight
845.93
Structure
Simcomp
Class
Antibacterial
 DG01966  Antitubercular
  DG01598  Rifamycin antibiotic
Metabolizing enzyme inducer
 DG02853  CYP3A/CYP3A4 inducer
  DG01635  CYP3A4 inducer
 DG03195  UGT inducer
Transporter inhibitor
 DG02865  SLCO1B1 inhibitor
 DG02907  SLCO1B3 inhibitor
Transporter inducer
 DG01893  ABCB1 inducer
Remark
ATC code: J04AB02
Chemical structure group: DG00639
Product (DG00639): D00211<JP/US>
Efficacy
Antibacterial (tuberculostatic), RNA polymerase inhibitor
Comment
Semisynthetic analog of Rifamycin [DR:D02549]
Target
DNA-directed RNA polymerase subunit beta [KO:K03043 K03046]
  Pathway
ko03020  RNA polymerase
Interaction
CYP induction: CYP3A4 [HSA:1576]
Transporter induction: ABCB1 [HSA:5243]
Enzyme induction: UGT [KO:K00699]
Transporter inhibition: SLCO1B1 [HSA:10599], SLCO1B3 [HSA:28234]
Structure map
map07023  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
Drug groups [BR:br08330]
 Antibacterial
  DG01966  Antitubercular
   DG01598  Rifamycin antibiotic
    DG00639  Rifampicin
     D08479  Rifampicin sodium
 Metabolizing enzyme inducer
  DG02853  CYP3A/CYP3A4 inducer
   DG01635  CYP3A4 inducer
    DG00639  Rifampicin
     D08479  Rifampicin sodium
  DG03195  UGT inducer
   DG00639  Rifampicin
    D08479  Rifampicin sodium
 Transporter inhibitor
  DG02865  SLCO1B1 inhibitor
   DG00639  Rifampicin
    D08479  Rifampicin sodium
  DG02907  SLCO1B3 inhibitor
   DG00639  Rifampicin
    D08479  Rifampicin sodium
 Transporter inducer
  DG01893  ABCB1 inducer
   DG00639  Rifampicin
    D08479  Rifampicin sodium
Antimicrobials [BR:br08307]
 Antibacterials
  Nucleic acid synthesis inhibitor
   Rifamycin
    D08479  Rifampicin sodium
Drug metabolizing enzymes and transporters [br08309.html]
 Drug metabolizing enzymes
  D08479
 Drug transporters
  D08479
Drug groups [BR:br08330]
 Antibacterial
  DG01966  Antitubercular
   DG01598  Rifamycin antibiotic
    DG00639  Rifampicin
 Metabolizing enzyme inducer
  DG02853  CYP3A/CYP3A4 inducer
   DG01635  CYP3A4 inducer
    DG00639  Rifampicin
  DG03195  UGT inducer
   DG00639  Rifampicin
 Transporter inhibitor
  DG02865  SLCO1B1 inhibitor
   DG00639  Rifampicin
  DG02907  SLCO1B3 inhibitor
   DG00639  Rifampicin
 Transporter inducer
  DG01893  ABCB1 inducer
   DG00639  Rifampicin
Antimicrobials abbreviations [BR:br08327]
 Antibacterials
  Nucleic acid synthesis inhibitor
   Rifamycin
    DG00639  Rifampicin
Other DBs
CAS: 38776-75-9
PubChem: 96025165
LigandBox: D08479
LinkDB
KCF data

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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