KEGG   DRUG: IrinotecanHelp
Entry
D08086                      Drug                                   

Name
Irinotecan (INN);
Biotecan (TN)
Formula
C33H38N4O6
Exact mass
586.2791
Mol weight
586.678
Structure
Mol fileKCF fileDB searchJmolKegDraw
Class
Other
 DG01529  Topoisomerase inhibitor
  DG01526  Topoisomerase I inhibitor
Cyp substrate
 DG01633  CYP3A substrate
Transporter substrate
 DG01665  P-glycoprotein substrate
 DG01913  BCRP substrate
Remark
Same as: 
ATC code: 
Chemical group: 
Activity
Antineoplastic, Topoisomerase I inhibitor
Comment
Camptothecin [CPD:C01897] derivative
Target
TOP1 [HSA:7150] [KO:K03163]
Metabolism
Enzyme: CYP3A4 [HSA:1576], CYP3A5 [HSA:1577], CYP3A7 [HSA:1551]
Transporter: ABCB1 [HSA:5243], ABCG2 [HSA:9429]
Interaction
Genomic biomarker: UGT1A1 [HSA:54658]
Drug interaction
Structure map
Antineoplastics - agents from natural products
Other map
Drug metabolism - other enzymes
Bile secretion
Brite
Anatomical Therapeutic Chemical (ATC) classification [BR:br08303]
 L ANTINEOPLASTIC AND IMMUNOMODULATING AGENTS
  L01 ANTINEOPLASTIC AGENTS
   L01X OTHER ANTINEOPLASTIC AGENTS
    L01XX Other antineoplastic agents
     L01XX19 Irinotecan
      D08086  Irinotecan (INN)
Target-based classification of drugs [BR:br08310]
 Enzymes
  Isomerases
   topoisomerase I
    Irinotecan
     D08086  Irinotecan (INN)
Cytochrome P450 interactions [BR:br08309]
 CYP substrates
  CYP3A4
   Irinotecan
    D08086  Irinotecan (INN)
  CYP3A5
   Irinotecan
    D08086  Irinotecan (INN)
  CYP3A7
   Irinotecan
    D08086  Irinotecan (INN)
 Transporter substrates
  ABCB1
   Irinotecan
    D08086  Irinotecan (INN)
  ABCG2
   Irinotecan
    D08086  Irinotecan (INN)
Phytochemicals used as drugs [BR:br08306]
 Alkaloids
  Alkaloids derived from tryptophan and anthranillic acid
   Quinoline alkaloids
    D08086  Irinotecan (INN)
BRITE hierarchy
Other DBs
CAS: 
97682-44-5
PubChem: 
PDB-CCD: 
LigandBox: 
NIKKAJI: 
KCF data Show

ATOM        43
            1   C8y C    23.4500  -17.5000
            2   C8x C    23.4500  -18.9000
            3   C8x C    24.6400  -19.6000
            4   C8y C    25.8300  -18.9000
            5   C8y C    25.8300  -17.5000
            6   C8x C    24.6400  -16.8000
            7   N5x N    27.0900  -19.6000
            8   C8y C    28.2800  -18.9000
            9   C8y C    28.2800  -17.5000
            10  C8y C    27.0900  -16.8000
            11  O7a O    22.1900  -16.8000
            12  C7a C    21.0000  -17.5000
            13  O6a O    21.0000  -18.9000
            14  N1y N    19.8100  -16.8000
            15  C1x C    19.8100  -15.4700
            16  C1x C    18.5500  -14.7700
            17  C1y C    17.3600  -15.4700
            18  C1x C    17.3600  -16.8000
            19  C1x C    18.5500  -17.5000
            20  N1y N    16.1700  -14.7700
            21  C1x C    16.1700  -13.3700
            22  C1x C    14.9100  -12.6700
            23  C1x C    13.7200  -13.3700
            24  C1x C    13.7200  -14.7700
            25  C1x C    14.9100  -15.4700
            26  C8y C    29.6100  -19.3200
            27  N4y N    30.4500  -18.2000
            28  C1x C    29.6100  -17.0800
            29  C8y C    31.7800  -18.2000
            30  C8y C    32.4800  -19.3900
            31  C8y C    31.8500  -20.5800
            32  C8x C    30.3800  -20.5800
            33  C1z C    32.5500  -21.7700
            34  C7x C    33.8800  -21.7700
            35  O7x O    34.5100  -20.5800
            36  C1x C    33.8100  -19.3900
            37  O5x O    32.4800  -16.9400
            38  O6a O    34.5800  -23.0300
            39  C1b C    27.0900  -15.4700
            40  C1a C    25.8300  -14.7700
            41  C1b C    31.1500  -21.7700
            42  O1a O    32.5500  -23.2400
            43  C1a C    30.4500  -23.0300
BOND        49
            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 2
            9     8   9 1
            10    9  10 2
            11    5  10 1
            12    1  11 1
            13   11  12 1
            14   12  13 2
            15   12  14 1
            16   14  15 1
            17   15  16 1
            18   16  17 1
            19   17  18 1
            20   18  19 1
            21   14  19 1
            22   17  20 1
            23   20  21 1
            24   21  22 1
            25   22  23 1
            26   23  24 1
            27   24  25 1
            28   20  25 1
            29    8  26 1
            30   26  27 1
            31   27  28 1
            32    9  28 1
            33   27  29 1
            34   29  30 1
            35   30  31 2
            36   31  32 1
            37   31  33 1
            38   33  34 1
            39   34  35 1
            40   35  36 1
            41   30  36 1
            42   32  26 2
            43   29  37 2
            44   34  38 2
            45   10  39 1
            46   39  40 1
            47   33  41 1 #Down
            48   33  42 1 #Up
            49   41  43 1

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