KEGG   DRUG: Irinotecan hydrochloride
Entry
D01061                      Drug                                   
Name
Irinotecan hydrochloride (USP);
Irinotecan hydrochloride hydrate (JP18);
Irinotecan hydrochloride trihydrate;
CPT 11;
CPT-11;
Campto (TN);
Camptosar (TN);
Onivyde (TN)
Product
  Generic
Formula
C33H38N4O6. 3H2O. HCl
Exact mass
676.2875
Mol weight
677.1848
Structure
Simcomp
Class
Antineoplastic
 DG01529  Topoisomerase inhibitor
  DG01526  Topoisomerase I inhibitor
Metabolizing enzyme substrate
 DG01633  CYP3A/CYP3A4 substrate
  DG02913  CYP3A4 substrate
 DG02970  CES substrate
 DG02924  UGT substrate
  DG03183  UGT1A1 substrate
Remark
Therapeutic category: 4240
ATC code: L01CE02
Chemical structure group: DG00726
Product (DG00726): D01061<JP/US>
Efficacy
Antineoplastic, Topoisomerase I inhibitor
  Disease
Adenocarcinoma of the pancreas [DS:H00019]
Carcinoma of the colon or rectum [DS:H00020]
Comment
Camptothecin [CPD:C01897] derivative
Irinotecan forms cleavable complex with DNA and inhibit DNA synthesis.
Active form of prodrug: SN-38 [CPD:C11173]
Target
TOP1 [HSA:7150] [KO:K03163]
Metabolism
Enzyme: CES [HSA:1066 221223 23491 8824]; CYP3A4 [HSA:1576], UGT1A1 [HSA:54658]
Interaction
Structure map
map07042  Antineoplastics - agents from natural products
Other map
map04976  Bile secretion
Brite
Anatomical Therapeutic Chemical (ATC) classification [BR:br08303]
 L ANTINEOPLASTIC AND IMMUNOMODULATING AGENTS
  L01 ANTINEOPLASTIC AGENTS
   L01C PLANT ALKALOIDS AND OTHER NATURAL PRODUCTS
    L01CE Topoisomerase 1 (TOP1) inhibitors
     L01CE02 Irinotecan
      D01061  Irinotecan hydrochloride (USP) <JP/US>
Therapeutic category of drugs in Japan [BR:br08301]
 4  Agents affecting cellular function
  42  Antineoplastics
   424  Plant extract preparations
    4240  Plant extract preparations
     D01061  Irinotecan hydrochloride (USP); Irinotecan hydrochloride hydrate (JP18)
Drug groups [BR:br08330]
 Antineoplastic
  DG01529  Topoisomerase inhibitor
   DG01526  Topoisomerase I inhibitor
    DG00726  Irinotecan
     D01061  Irinotecan hydrochloride
 Metabolizing enzyme substrate
  DG01633  CYP3A/CYP3A4 substrate
   DG02913  CYP3A4 substrate
    DG00726  Irinotecan
     D01061  Irinotecan hydrochloride
  DG02970  CES substrate
   DG00726  Irinotecan
    D01061  Irinotecan hydrochloride
  DG02924  UGT substrate
   DG03183  UGT1A1 substrate
    DG00726  Irinotecan
     D01061  Irinotecan hydrochloride
Target-based classification of drugs [BR:br08310]
 Enzymes
  Isomerases (EC5)
   DNA topoisomerase
    TOP1
     D01061  Irinotecan hydrochloride (USP) <JP/US>
Drugs listed in the Japanese Pharmacopoeia [BR:br08311]
 Chemicals
  D01061  Irinotecan hydrochloride
  D01061  Irinotecan hydrochloride injection
New drug approvals in Europe [br08329.html]
 European public assessment reports (EPAR) authorised medicine
  D01061
Drug metabolizing enzymes and transporters [br08309.html]
 Drug metabolizing enzymes
  D01061
Pharmacogenomic biomarkers [br08341.html]
 Polymorphisms and mutations affecting drug response
  D01061
Drug groups [BR:br08330]
 Antineoplastic
  DG01529  Topoisomerase inhibitor
   DG01526  Topoisomerase I inhibitor
    DG00726  Irinotecan
 Metabolizing enzyme substrate
  DG01633  CYP3A/CYP3A4 substrate
   DG02913  CYP3A4 substrate
    DG00726  Irinotecan
  DG02970  CES substrate
   DG00726  Irinotecan
  DG02924  UGT substrate
   DG03183  UGT1A1 substrate
    DG00726  Irinotecan
Prodrugs [br08324.html]
 DG00726
Other DBs
CAS: 136572-09-3
PubChem: 7848124
ChEBI: 90881
LigandBox: D01061
LinkDB
KCF data

ATOM        47
            1   X   Cl    6.3178  -11.7757
            2   O0  O    10.5410  -11.7757
            3   C8y C    12.1100   -7.2100
            4   C8x C    12.1100   -8.6100
            5   C8x C    13.3224   -9.3100
            6   C8y C    14.5349   -8.6100
            7   C8y C    14.5349   -7.2100
            8   C8x C    13.3224   -6.5100
            9   N5x N    15.7473   -9.3100
            10  C8y C    16.9597   -8.6100
            11  C8y C    16.9597   -7.2100
            12  C8y C    15.7473   -6.5100
            13  O7a O    10.8976   -6.5100
            14  C7a C     9.6851   -7.2100
            15  O6a O     9.6851   -8.6100
            16  N1y N     8.4540   -6.4990
            17  C1x C     8.4543   -5.1101
            18  C1x C     7.2420   -4.4098
            19  C1y C     6.0294   -5.1095
            20  C1x C     6.0291   -6.4984
            21  C1x C     7.2414   -7.1987
            22  N1y N     4.8103   -4.4053
            23  C1x C     4.8107   -3.0101
            24  C1x C     3.5985   -2.3098
            25  C1x C     2.3859   -3.0094
            26  C1x C     2.3854   -4.4045
            27  C1x C     3.5977   -5.1049
            28  C8y C    18.2912   -9.0426
            29  N4y N    19.1141   -7.9100
            30  C1x C    18.2912   -6.7774
            31  C8y C    20.5100   -7.9100
            32  C8y C    21.2100   -9.1224
            33  C8y C    20.5196  -10.3179
            34  C8x C    19.1103  -10.3180
            35  C1z C    21.2195  -11.5304
            36  C7x C    22.6195  -11.5306
            37  O7x O    23.3099  -10.3351
            38  C1x C    22.6100   -9.1226
            39  O5x O    21.2100   -6.6976
            40  O6a O    23.3254  -12.7534
            41  C1b C    15.7473   -5.1100
            42  C1a C    14.5369   -4.4112
            43  C1b C    19.8195  -11.5304
            44  O1a O    21.2195  -12.9500
            45  C1a C    19.1121  -12.7636
            46  O0  O    10.5410  -11.7757
            47  O0  O    10.5410  -11.7757
BOND        49
            1     3   4 2
            2     4   5 1
            3     5   6 2
            4     6   7 1
            5     7   8 2
            6     3   8 1
            7     6   9 1
            8     9  10 2
            9    10  11 1
            10   11  12 2
            11    7  12 1
            12    3  13 1
            13   13  14 1
            14   14  15 2
            15   14  16 1
            16   16  17 1
            17   17  18 1
            18   18  19 1
            19   19  20 1
            20   20  21 1
            21   16  21 1
            22   19  22 1
            23   22  23 1
            24   23  24 1
            25   24  25 1
            26   25  26 1
            27   26  27 1
            28   22  27 1
            29   10  28 1
            30   28  29 1
            31   29  30 1
            32   11  30 1
            33   29  31 1
            34   31  32 1
            35   32  33 2
            36   33  34 1
            37   33  35 1
            38   35  36 1
            39   36  37 1
            40   37  38 1
            41   32  38 1
            42   34  28 2
            43   31  39 2
            44   36  40 2
            45   12  41 1
            46   41  42 1
            47   35  43 1 #Down
            48   35  44 1 #Up
            49   43  45 1
BRACKET     1     8.6800  -12.7400    8.6800  -10.6400
            1    11.0600  -10.6400   11.0600  -12.7400
            1  3
 ORIGINAL  1    2
 REPEAT    1   46  47

» Japanese version   » Back

KEGG   DRUG: Irinotecan
Entry
D08086                      Drug                                   
Name
Irinotecan (INN);
Biotecan (TN)
Formula
C33H38N4O6
Exact mass
586.2791
Mol weight
586.678
Structure
Simcomp
Class
Antineoplastic
 DG01529  Topoisomerase inhibitor
  DG01526  Topoisomerase I inhibitor
Metabolizing enzyme substrate
 DG01633  CYP3A/CYP3A4 substrate
  DG02913  CYP3A4 substrate
 DG02970  CES substrate
 DG02924  UGT substrate
  DG03183  UGT1A1 substrate
Remark
Same as: C16641
ATC code: L01CE02
Chemical structure group: DG00726
Product (DG00726): D01061<JP/US>
Efficacy
Antineoplastic, Topoisomerase I inhibitor
Comment
Camptothecin [CPD:C01897] derivative
Active form of prodrug: SN-38 [CPD:C11173]
Target
TOP1 [HSA:7150] [KO:K03163]
Metabolism
Enzyme: CES [HSA:1066 221223 23491 8824]; CYP3A4 [HSA:1576], UGT1A1 [HSA:54658]
Interaction
Structure map
map07042  Antineoplastics - agents from natural products
Other map
map00983  Drug metabolism - other enzymes
map04976  Bile secretion
Brite
Anatomical Therapeutic Chemical (ATC) classification [BR:br08303]
 L ANTINEOPLASTIC AND IMMUNOMODULATING AGENTS
  L01 ANTINEOPLASTIC AGENTS
   L01C PLANT ALKALOIDS AND OTHER NATURAL PRODUCTS
    L01CE Topoisomerase 1 (TOP1) inhibitors
     L01CE02 Irinotecan
      D08086  Irinotecan (INN)
Drug groups [BR:br08330]
 Antineoplastic
  DG01529  Topoisomerase inhibitor
   DG01526  Topoisomerase I inhibitor
    DG00726  Irinotecan
     D08086  Irinotecan
 Metabolizing enzyme substrate
  DG01633  CYP3A/CYP3A4 substrate
   DG02913  CYP3A4 substrate
    DG00726  Irinotecan
     D08086  Irinotecan
  DG02970  CES substrate
   DG00726  Irinotecan
    D08086  Irinotecan
  DG02924  UGT substrate
   DG03183  UGT1A1 substrate
    DG00726  Irinotecan
     D08086  Irinotecan
Target-based classification of drugs [BR:br08310]
 Enzymes
  Isomerases (EC5)
   DNA topoisomerase
    TOP1
     D08086  Irinotecan (INN)
Drug metabolizing enzymes and transporters [br08309.html]
 Drug metabolizing enzymes
  D08086
Prodrugs [br08324.html]
 D08086
Drug groups [BR:br08330]
 Antineoplastic
  DG01529  Topoisomerase inhibitor
   DG01526  Topoisomerase I inhibitor
    DG00726  Irinotecan
 Metabolizing enzyme substrate
  DG01633  CYP3A/CYP3A4 substrate
   DG02913  CYP3A4 substrate
    DG00726  Irinotecan
  DG02970  CES substrate
   DG00726  Irinotecan
  DG02924  UGT substrate
   DG03183  UGT1A1 substrate
    DG00726  Irinotecan
Prodrugs [br08324.html]
 DG00726
Other DBs
CAS: 97682-44-5
PubChem: 96024776
ChEBI: 80630
PDB-CCD: CP0[PDBj]
LigandBox: D08086
NIKKAJI: J261.801J
LinkDB
KCF data

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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