KEGG   DRUG: D00184Help
Entry
D00184                      Drug                                   

Name
Ciclosporin (JP16);
Cyclosporine (USP);
Gengraf (TN);
Neoral (TN);
Restasis (TN);
Sandimmune (TN)
Product
  Generic
Formula
C62H111N11O12
Exact mass
1201.8414
Mol weight
1202.6112
Structure
Mol fileKCF fileDB searchJmolKegDraw
Sequence
0 D-Ala  1 Leu  2 Leu  3 Val  4 Thr  5 Abu  6 Sar  7 Leu  8 Val
9 Leu  10 Ala  (Cyclization: 0-10)
  Type
NRP
Source
Cylindrocarpon lucidum [TAX:301100], Tolypocladium inflatum [TAX:29910]
Activity
Immunosuppressant [DS:H00083 H00084]
Remark
Same as: 
Therapeutic category: 
ATC code: 
Comment
Complex Ciclosporin and cyclophilin [BR:ko03110] inhibit calcineurin.
Target
calcineurin inhibitor [HSA:5530 5532 5533 5534 5535 11261 63928] [KO:K04348 K06268 K17610 K17611]
  Pathway
hsa04660  T cell receptor signaling pathway  
 
Metabolism
Enzyme: CYP3A4 [HSA:1576], CYP3A5 [HSA:1577], CYP3A7 [HSA:1551]
Transporter: ABCB1 [HSA:5243]
Interaction
CYP inhibition: CYP3A4 [HSA:1576]
Transporter inhibition: SLCO1B1 [HSA:10599], SLCO1B3 [HSA:28234], SLCO2B1 [HSA:11309], ABCB1 [HSA:5243], ABCB11 [HSA:8647], ABCC2 [HSA:1244], ABCB4 [HSA:5244], ABCG2 [HSA:9429]
Drug interaction
Structure map
Immunosuppressive agents
Other map
Bile secretion
Brite
Anatomical Therapeutic Chemical (ATC) classification [BR:br08303]
 L ANTINEOPLASTIC AND IMMUNOMODULATING AGENTS
  L04 IMMUNOSUPPRESSANTS
   L04A IMMUNOSUPPRESSANTS
    L04AD Calcineurin inhibitors
     L04AD01 Ciclosporin
      D00184  Ciclosporin (JP16); Cyclosporine (USP)
 S SENSORY ORGANS
  S01 OPHTHALMOLOGICALS
   S01X OTHER OPHTHALMOLOGICALS
    S01XA Other ophthalmologicals
     S01XA18 Ciclosporin
      D00184  Ciclosporin (JP16); Cyclosporine (USP)
USP drug classification [BR:br08302]
 Immunological Agents
  Immune Suppressants
   Cyclosporine
    D00184  Ciclosporin (JP16); Cyclosporine (USP)
 Ophthalmic Agents
  Ophthalmic Agents, Other
   Cyclosporine
    D00184  Ciclosporin (JP16); Cyclosporine (USP)
Therapeutic category of drugs in Japan [BR:br08301]
 1  Agents affecting nervous system and sensory organs
  13  Agents affecting sensory organs
   131  Ophthalmic agents
    1319  Others
     D00184  Ciclosporin (JP16); Cyclosporine (USP)
 3  Agents affecting metabolism
  39  Other agents affecting metabolism
   399  Miscellaneous
    3999  Others
     D00184  Ciclosporin (JP16); Cyclosporine (USP)
Target-based classification of drugs [BR:br08310]
 Enzymes
  Hydrolases
   calcineurin
    Ciclosporin
     D00184  Cyclosporine (USP)
Cytochrome P450 interactions [BR:br08309]
 Substrates
  CYP3A4
   Ciclosporin
    D00184  Ciclosporin (JP16); Cyclosporine (USP)
  CYP3A5
   Ciclosporin
    D00184  Ciclosporin (JP16); Cyclosporine (USP)
  CYP3A7
   Ciclosporin
    D00184  Ciclosporin (JP16); Cyclosporine (USP)
 Inhbitors
  CYP3A4
   Ciclosporin
    D00184  Ciclosporin (JP16); Cyclosporine (USP)
  CYP3A
   Ciclosporin
    D00184  Ciclosporin (JP16); Cyclosporine (USP)
Drugs listed in the Japanese Pharmacopoeia [BR:br08311]
 Chemicals
  D00184  Ciclosporin
BRITE hierarchy
Other DBs
CAS: 
59865-13-3
PubChem: 
DrugBank: 
LigandBox: 
NIKKAJI: 
KCF data Show

ATOM        85
            1   C1c C    28.1636  -12.7243
            2   N1c N    27.0718  -13.3558
            3   C5a C    29.2552  -13.3558
            4   C1c C    28.1636  -11.4670
            5   C5a C    25.9801  -12.7243
            6   C1a C    27.0718  -14.6131
            7   N1b N    30.3469  -12.7243
            8   O5a O    29.2552  -14.6131
            9   C1c C    29.2552  -10.8353
            10  O1a O    27.0718  -10.8353
            11  C1c C    24.8884  -13.3558
            12  O5a O    25.9801  -11.4670
            13  C1c C    31.4386  -13.3558
            14  C1a C    30.3469  -11.4670
            15  N1c N    23.7969  -12.7243
            16  C1c C    24.9524  -15.0494
            17  C5a C    32.5303  -12.7243
            18  C1b C    31.4386  -14.6131
            19  C5a C    22.7052  -13.3558
            20  C1a C    23.7969  -11.4670
            21  C1a C    23.8607  -15.6811
            22  C1a C    26.0440  -15.6811
            23  N1c N    33.6219  -13.3558
            24  O5a O    32.5303  -11.4670
            25  C1c C    21.6136  -12.7243
            26  O5a O    22.7052  -14.6131
            27  C1b C    33.6219  -14.6131
            28  C1a C    34.7137  -12.7243
            29  N1c N    20.5219  -13.3558
            30  C1b C    21.6136  -11.4670
            31  C5a C    34.7137  -15.2449
            32  C5a C    20.5219  -16.7532
            33  C1a C    19.2584  -13.3558
            34  C1c C    20.5219  -10.8353
            35  N1c N    34.7075  -16.8653
            36  O5a O    35.8054  -14.6131
            37  C1c C    19.4302  -18.5750
            38  C1a C    20.5219   -9.5720
            39  C1a C    19.4302  -11.4670
            40  C1c C    34.7137  -19.8322
            41  C1a C    35.9525  -16.8677
            42  N1c N    19.4302  -19.8322
            43  C1b C    18.3385  -17.9432
            44  C5a C    33.6219  -20.4640
            45  C1b C    35.8054  -20.4640
            46  C5a C    20.5219  -20.4640
            47  C1a C    18.3385  -20.4640
            48  C1c C    17.2468  -18.5750
            49  N1b N    32.5303  -19.8322
            50  O5a O    33.6219  -21.7213
            51  C1c C    36.8971  -19.8322
            52  C1c C    21.6136  -19.8322
            53  O5a O    20.5219  -21.7213
            54  C1a C    16.1552  -17.9432
            55  C1c C    31.4386  -20.4640
            56  C1a C    37.9888  -20.4640
            57  C1a C    36.8971  -18.5750
            58  N1b N    22.7052  -20.4640
            59  C1a C    21.6136  -18.6450
            60  C5a C    30.3469  -19.8322
            61  C1c C    31.4631  -22.1013
            62  C5a C    23.7969  -19.8322
            63  N1c N    29.2552  -20.4640
            64  O5a O    30.3469  -18.5750
            65  C1a C    30.2978  -23.0643
            66  C1a C    32.5731  -22.9662
            67  C1c C    24.8884  -20.4640
            68  O5a O    23.7969  -18.5750
            69  C1c C    28.1636  -19.8322
            70  C1a C    29.2552  -21.7213
            71  N1b N    25.9801  -19.8322
            72  C1a C    24.8884  -21.7213
            73  C5a C    27.0718  -20.4640
            74  C1b C    28.1636  -17.4739
            75  O5a O    27.0718  -21.7213
            76  C1c C    29.2552  -16.8421
            77  C1a C    29.2492  -15.5788
            78  C1a C    30.3469  -17.4678
            79  C1a C    32.6521  -15.3129
            80  C1a C    17.2463  -19.9498
            81  O5a O    21.7154  -17.4420
            82  C1b C    29.2552   -9.4500
            83  C2b C    30.4713   -8.7480
            84  C2b C    31.6685   -9.4394
            85  C1a C    32.8550   -8.7544
BOND        85
            1     1   2 1
            2     1   3 1
            3     1   4 1
            4     2   5 1
            5     2   6 1
            6     3   7 1
            7     3   8 2
            8     4   9 1
            9     4  10 1
            10    5  11 1
            11    5  12 2
            12    7  13 1
            13    9  14 1
            14   11  15 1
            15   11  16 1
            16   13  17 1
            17   13  18 1
            18   15  19 1
            19   15  20 1
            20   16  21 1
            21   16  22 1
            22   17  23 1
            23   17  24 2
            24   19  25 1
            25   19  26 2
            26   23  27 1
            27   23  28 1
            28   25  29 1
            29   25  30 1
            30   27  31 1
            31   29  32 1
            32   29  33 1
            33   30  34 1
            34   31  35 1
            35   31  36 2
            36   34  38 1
            37   34  39 1
            38   35  40 1
            39   35  41 1
            40   37  42 1
            41   37  43 1
            42   40  44 1
            43   40  45 1
            44   42  46 1
            45   42  47 1
            46   43  48 1
            47   44  49 1
            48   44  50 2
            49   45  51 1
            50   46  52 1
            51   46  53 2
            52   48  54 1
            53   49  55 1
            54   51  56 1
            55   51  57 1
            56   52  58 1
            57   52  59 1
            58   55  60 1
            59   55  61 1
            60   58  62 1
            61   60  63 1
            62   60  64 2
            63   61  65 1
            64   61  66 1
            65   62  67 1
            66   62  68 2
            67   63  69 1
            68   63  70 1
            69   67  71 1
            70   67  72 1
            71   69  73 1
            72   69  74 1
            73   73  75 2
            74   74  76 1
            75   76  77 1
            76   76  78 1
            77   71  73 1
            78   18  79 1
            79   48  80 1
            80   32  81 2
            81   37  32 1
            82    9  82 1
            83   82  83 1
            84   83  84 2
            85   84  85 1

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