KEGG   DRUG: Rifaximin
Entry
D02554                      Drug                                   
Name
Rifaximin (JAN/USAN/INN);
Xifaxan (TN)
Product
Formula
C43H51N3O11
Exact mass
785.3524
Mol weight
785.8785
Structure
Simcomp
Class
Antibacterial
 DG01966  Antitubercular
  DG01598  Rifamycin antibiotic
Metabolizing enzyme substrate
 DG01633  CYP3A/CYP3A4 substrate
  DG02913  CYP3A4 substrate
Metabolizing enzyme inducer
 DG02853  CYP3A/CYP3A4 inducer
  DG01635  CYP3A4 inducer
Transporter substrate
 DG01665  ABCB1 substrate
 DG02857  SLCO1A2 substrate
 DG02856  SLCO1B1 substrate
 DG02932  SLCO1B3 substrate
Transporter inhibitor
 DG01622  ABCB1 inhibitor
 DG03008  SLCO1A2 inhibitor
 DG02865  SLCO1B1 inhibitor
 DG02907  SLCO1B3 inhibitor
Remark
Therapeutic category: 6199
ATC code: A07AA11 D06AX11
Product: D02554<JP/US>
Efficacy
Antibacterial, Antihyperammonemic
  Disease
Hepatic encephalopathy [DS:H01506]
Comment
Rifamycin derivative
Target
DNA-directed RNA polymerase subunit beta [KO:K03043]
  Pathway
ko03020  RNA polymerase
Metabolism
Enzyme: CYP3A4 [HSA:1576]
Transporter: ABCB1 [HSA:5243], SLCO1A2 [HSA:6579], SLCO1B1 [HSA:10599], SLCO1B3 [HSA:28234]
Interaction
CYP induction: CYP3A4 [HSA:1576]
Transporter inhibition: ABCB1 [HSA:5243], SLCO1A2 [HSA:6579], SLCO1B1 [HSA:10599], SLCO1B3 [HSA:28234]
Structure map
map07023  Rifamycins
Brite
Anatomical Therapeutic Chemical (ATC) classification [BR:br08303]
 A ALIMENTARY TRACT AND METABOLISM
  A07 ANTIDIARRHEALS, INTESTINAL ANTIINFLAMMATORY/ANTIINFECTIVE AGENTS
   A07A INTESTINAL ANTIINFECTIVES
    A07AA Antibiotics
     A07AA11 Rifaximin
      D02554  Rifaximin (JAN/USAN/INN) <JP/US>
 D DERMATOLOGICALS
  D06 ANTIBIOTICS AND CHEMOTHERAPEUTICS FOR DERMATOLOGICAL USE
   D06A ANTIBIOTICS FOR TOPICAL USE
    D06AX Other antibiotics for topical use
     D06AX11 Rifaximin
      D02554  Rifaximin (JAN/USAN/INN) <JP/US>
USP drug classification [BR:br08302]
 Antibacterials
  Antibacterials, Other
   Rifaximin
    D02554  Rifaximin (JAN/USAN/INN)
 Gastrointestinal Agents
  Anti-Diarrheal Agents
   Rifaximin
    D02554  Rifaximin (JAN/USAN/INN)
  Gastrointestinal Agents, Other
   Rifaximin
    D02554  Rifaximin (JAN/USAN/INN)
Therapeutic category of drugs in Japan [BR:br08301]
 6  Agents against pathologic organisms and parasites
  61  Antibiotics
   619  Miscellaneous
    6199  Miscellaneous
     D02554  Rifaximin (JAN/USAN/INN)
Drug groups [BR:br08330]
 Antibacterial
  DG01966  Antitubercular
   DG01598  Rifamycin antibiotic
    D02554  Rifaximin
 Metabolizing enzyme substrate
  DG01633  CYP3A/CYP3A4 substrate
   DG02913  CYP3A4 substrate
    D02554  Rifaximin
 Metabolizing enzyme inducer
  DG02853  CYP3A/CYP3A4 inducer
   DG01635  CYP3A4 inducer
    D02554  Rifaximin
 Transporter substrate
  DG01665  ABCB1 substrate
   D02554  Rifaximin
  DG02857  SLCO1A2 substrate
   D02554  Rifaximin
  DG02856  SLCO1B1 substrate
   D02554  Rifaximin
  DG02932  SLCO1B3 substrate
   D02554  Rifaximin
 Transporter inhibitor
  DG01622  ABCB1 inhibitor
   D02554  Rifaximin
  DG03008  SLCO1A2 inhibitor
   D02554  Rifaximin
  DG02865  SLCO1B1 inhibitor
   D02554  Rifaximin
  DG02907  SLCO1B3 inhibitor
   D02554  Rifaximin
Antimicrobials [BR:br08307]
 Antibacterials
  Nucleic acid synthesis inhibitor
   Rifamycin
    D02554  Rifaximin (JAN/USAN/INN) <JP/US>
New drug approvals in the USA [br08319.html]
 New molecular entities and new therapeutic biological products
  D02554
New drug approvals in Japan [br08318.html]
 Drugs with new active ingredients
  D02554
New drug approvals in the USA, Europe and Japan [br08328.html]
 Approval dates by FDA, EMA and PMDA
  D02554
Drug metabolizing enzymes and transporters [br08309.html]
 Drug metabolizing enzymes
  D02554
 Drug transporters
  D02554
Other DBs
CAS: 80621-81-4
PubChem: 17396725
ChEBI: 75246
PDB-CCD: RXM[PDBj]
LigandBox: D02554
NIKKAJI: J171.233K
LinkDB
KCF data

ATOM        57
            1   C1c C    32.1192  -10.8276
            2   C1c C    32.1192  -12.2327
            3   O1a O    34.4611  -12.1658
            4   C1c C    34.4611  -10.8276
            5   C1c C    33.2567  -10.1584
            6   C2b C    36.7362  -10.8276
            7   C1c C    35.5987  -10.1584
            8   C5a C    37.9406  -12.9019
            9   C2c C    39.0781  -12.2327
            10  C2b C    39.0781  -10.8276
            11  C2b C    37.9406  -10.1584
            12  C1a C    35.5987   -8.8202
            13  C1a C    33.2567   -8.8202
            14  O1a O    30.9817  -10.1584
            15  C1a C    40.2157  -12.9019
            16  O5a O    36.8031  -12.2327
            17  N1b N    37.9406  -14.5078
            18  C1c C    30.9817  -12.9019
            19  O7a O    29.8441  -12.2327
            20  C1c C    30.9817  -14.5078
            21  C8y C    36.8031  -15.1769
            22  C8y C    36.8031  -16.5152
            23  C8y C    35.5987  -14.5078
            24  C8y C    34.4611  -15.1769
            25  C8y C    34.4611  -16.5152
            26  C8y C    35.5987  -17.1843
            27  C8y C    33.3236  -14.5078
            28  C8y C    32.1192  -15.1769
            29  C8y C    32.1192  -16.5152
            30  C8y C    33.3236  -17.1843
            31  O1a O    35.5987  -13.1695
            32  O1a O    33.3236  -13.1695
            33  C1a C    30.9817  -11.1621
            34  C7a C    28.6397  -11.5636
            35  C1a C    27.5022  -12.2327
            36  O6a O    28.6397  -10.2253
            37  C1c C    29.8441  -15.1769
            38  O2a O    28.7066  -14.5078
            39  C2b C    29.8441  -16.5152
            40  C1a C    29.8441  -13.5710
            41  C1a C    27.5691  -15.1769
            42  C2b C    28.7066  -17.1843
            43  O2a O    28.7066  -18.5226
            44  O2x O    30.9817  -17.1843
            45  C1z C    30.9817  -18.5226
            46  C5x C    33.3236  -18.5226
            47  C1a C    30.9817  -19.8608
            48  C1a C    32.1192  -13.8387
            49  N5x N    35.5987  -18.5226
            50  C8y C    37.9406  -18.5226
            51  N4y N    37.9406  -17.1843
            52  O5x O    34.3942  -19.1917
            53  C8x C    39.1530  -19.2226
            54  C8y C    40.3655  -18.5226
            55  C8x C    40.3655  -17.1843
            56  C8x C    39.1530  -16.4843
            57  C1a C    41.6083  -19.2398
BOND        62
            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  51 1
            54   22  51 1
            55   52  46 2
            56   49  50 2
            57   50  53 1
            58   53  54 2
            59   54  55 1
            60   55  56 2
            61   51  56 1
            62   54  57 1

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