KEGG   DRUG: CyclosporineHelp
Entry
D00184                      Drug                                   

Name
Cyclosporine (USP);
Ciclosporin (JP17);
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]
Class
Cyp substrate
 DG01633  CYP3A4 substrate
Cyp inhibitor
 DG01522  CYP3A4 inhibitor
Transporter substrate
 DG01665  P-glycoprotein substrate
Remark
Same as: 
Therapeutic category: 
ATC code: 
Activity
Immunosuppressant
Comment
Complex Ciclosporin and cyclophilin [BR:ko03110] inhibit calcineurin.
Target
  Pathway
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  Cyclosporine (USP)
 S SENSORY ORGANS
  S01 OPHTHALMOLOGICALS
   S01X OTHER OPHTHALMOLOGICALS
    S01XA Other ophthalmologicals
     S01XA18 Ciclosporin
      D00184  Cyclosporine (USP)
USP drug classification [BR:br08302]
 Immunological Agents
  Immune Suppressants
   Cyclosporine
    D00184  Cyclosporine (USP)
 Ophthalmic Agents
  Ophthalmic Agents, Other
   Cyclosporine
    D00184  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  Cyclosporine (USP); Ciclosporin (JP17)
 3  Agents affecting metabolism
  39  Other agents affecting metabolism
   399  Miscellaneous
    3999  Others
     D00184  Cyclosporine (USP); Ciclosporin (JP17)
Target-based classification of drugs [BR:br08310]
 Enzymes
  Hydrolases
   calcineurin
    Ciclosporin
     D00184  Cyclosporine (USP)
Cytochrome P450 interactions [BR:br08309]
 CYP inhbitors
  CYP2C8
   Ciclosporin
    D00184  Cyclosporine (USP)
  CYP2C9
   Ciclosporin
    D00184  Cyclosporine (USP)
  CYP3A4
   Ciclosporin
    D00184  Cyclosporine (USP)
  CYP3A
   Ciclosporin
    D00184  Cyclosporine (USP)
 CYP substrates
  CYP3A4
   Ciclosporin
    D00184  Cyclosporine (USP)
  CYP3A5
   Ciclosporin
    D00184  Cyclosporine (USP)
  CYP3A7
   Ciclosporin
    D00184  Cyclosporine (USP)
  CYP3A
   Cyclosporine
    D00184  Cyclosporine (USP)
 Transporter inhibitors
  ABCB1
   Cyclosporine
    D00184  Cyclosporine (USP)
  ABCB4
   Ciclosporin
    D00184  Cyclosporine (USP)
  ABCB11
   Ciclosporin
    D00184  Cyclosporine (USP)
  ABCC2
   Ciclosporin
    D00184  Cyclosporine (USP)
  ABCG2
   Cyclosporine
    D00184  Cyclosporine (USP)
  SLCO1B1
   Cyclosporine
    D00184  Cyclosporine (USP)
  SLCO1B3
   Cyclosporine
    D00184  Cyclosporine (USP)
  SLCO2B1
   Ciclosporin
    D00184  Cyclosporine (USP)
 Transporter substrates
  ABCB1
   Ciclosporin
    D00184  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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