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
IRINOTECAN HYDROCHLOIDE (BluePoint Laboratories), IRINOTECAN HYDROCHLOIDE (Gland Pharma Limited), IRINOTECAN HYDROCHLOIDE (Xiromed LLC), IRINOTECAN HYDROCHLORIDE (Actavis Pharma), IRINOTECAN HYDROCHLORIDE (Actavis Pharma), IRINOTECAN HYDROCHLORIDE (Apotex Corp.), IRINOTECAN HYDROCHLORIDE (Areva Pharmaceuticals), IRINOTECAN HYDROCHLORIDE (Areva Pharmaceuticals), IRINOTECAN HYDROCHLORIDE (Armas Pharmaceuticals), IRINOTECAN HYDROCHLORIDE (Armas Pharmaceuticals), IRINOTECAN HYDROCHLORIDE (Armas Pharmaceuticals), IRINOTECAN HYDROCHLORIDE (AuroMedics Pharma LLC), IRINOTECAN HYDROCHLORIDE (Fresenius Kabi USA), IRINOTECAN HYDROCHLORIDE (Hikma Pharmaceuticals USA), IRINOTECAN HYDROCHLORIDE (Hikma Pharmaceuticals USA), IRINOTECAN HYDROCHLORIDE (Hospira), IRINOTECAN HYDROCHLORIDE (Ingenus Pharmaceuticals), IRINOTECAN HYDROCHLORIDE (Northstar Rx LLC), IRINOTECAN HYDROCHLORIDE (Qilu Pharmaceutical), IRINOTECAN HYDROCHLORIDE (Sagent Pharmaceuticals)
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
ChEMBL: CHEMBL3989514
DrugBank: DB00762
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

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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
ChEMBL: CHEMBL481
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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