KEGG   DRUG: TacrolimusHelp
Entry
D08556                      Drug                                   

Name
Tacrolimus (INN);
Prograf (TN)
Product
Formula
C44H69NO12
Exact mass
803.482
Mol weight
804.0182
Structure
Mol fileKCF fileDB search
Simcomp SIMCOMP
Sequence
0 Ska  1 Mtk  2 Mtk  3 Man  4 Pyd  5 Mte  6 Mte  7 Mak  8 Mae
9 Mtn  10 Man  11 Pip
  Type
PKNRP
Source
Streptomyces tsukubaensis [TAX:83656]
Class
Anti-inflammatory
 DG01985  Disease modifying anti-rheumatic drugs (DMARDs)
Enzyme substrate
 DG01633  CYP3A substrate
Remark
Same as: C01375
ATC code: D11AH01 L04AD02
Chemical structure group: DG00439
Product (DG00439): D08556<US> D00107<JP/US>
Efficacy
Antiallergic, Immunosuppressant, Calcineurin inhibitor
Comment
Tacrolimus and FK506 binding protein (FKBP12/12.6) [HSA:2280 2281] [KO:K09568] inhibit calcineurin.
Target
PPP3C/PPP3R/CHP [HSA:5530 5532 5533 5534 5535 11261 63928] [KO:K04348 K06268 K17610 K17611]
  Pathway
hsa04010  MAPK signaling pathway
hsa04218  Cellular senescence
hsa04380  Osteoclast differentiation
hsa04650  Natural killer cell mediated cytotoxicity
hsa04658  Th1 and Th2 cell differentiation
hsa04659  Th17 cell differentiation
hsa04660  T cell receptor signaling pathway
Metabolism
Enzyme: CYP3A [HSA:1576 1577 1551]
Interaction
Drug interaction
Structure map
map07046  Immunosuppressive agents
map07050  Antirheumatics - DMARDs and biological agents
Brite
Anatomical Therapeutic Chemical (ATC) classification [BR:br08303]
 D DERMATOLOGICALS
  D11 OTHER DERMATOLOGICAL PREPARATIONS
   D11A OTHER DERMATOLOGICAL PREPARATIONS
    D11AH Agents for dermatitis, excluding corticosteroids
     D11AH01 Tacrolimus
      D08556  Tacrolimus (INN) <US>
 L ANTINEOPLASTIC AND IMMUNOMODULATING AGENTS
  L04 IMMUNOSUPPRESSANTS
   L04A IMMUNOSUPPRESSANTS
    L04AD Calcineurin inhibitors
     L04AD02 Tacrolimus
      D08556  Tacrolimus (INN) <US>
USP drug classification [BR:br08302]
 Dermatological Agents
  Tacrolimus
   D08556  Tacrolimus (INN)
 Immunological Agents
  Immune Suppressants
   Tacrolimus
    D08556  Tacrolimus (INN)
Target-based classification of drugs [BR:br08310]
 Enzymes
  Hydrolases (EC3)
   Serine/threonine phosphatase
    PPP3C/PPP3R/CHP
     D08556  Tacrolimus (INN) <US>
BRITE hierarchy
Other DBs
CAS: 104987-11-3
PubChem: 96025241
ChEBI: 61049
ChEMBL: CHEMBL269732
DrugBank: DB00864
PDB-CCD: FK5[PDBj]
LigandBox: D08556
NIKKAJI: J313.679E
LinkDB All DBs
KCF data Show

ATOM        57
            1   C2c C    22.4000  -12.4600
            2   C2b C    22.4000  -11.0600
            3   C1y C    21.2100  -10.2900
            4   C1x C    21.2100   -8.8900
            5   C1x C    19.9500   -8.1900
            6   C1y C    18.7600   -8.8900
            7   C1y C    18.7600  -10.2900
            8   C1x C    19.9500  -11.0600
            9   O2a O    17.5700  -11.0600
            10  O1a O    17.5700   -8.1900
            11  C1a C    16.3800  -10.2900
            12  C1c C    23.5900  -13.1600
            13  C1a C    21.2100  -13.1600
            14  C1c C    24.7800  -12.4600
            15  C1c C    25.9700  -13.1600
            16  C1b C    25.9700  -14.5600
            17  C5a C    27.3000  -15.1200
            18  C1c C    27.9300  -16.4500
            19  C2b C    27.2300  -17.7100
            20  C2c C    25.9700  -18.4100
            21  C1a C    24.7800  -17.7100
            22  C1b C    25.9700  -19.8100
            23  C1c C    24.7800  -20.5100
            24  C1a C    23.5900  -19.8100
            25  C1b C    25.4800  -21.7000
            26  C1c C    24.5000  -22.7500
            27  C1y C    23.1700  -22.4000
            28  C1y C    22.1900  -23.3800
            29  C1x C    20.8600  -23.0300
            30  C1y C    20.5100  -21.7000
            31  C1z C    21.4900  -20.7200
            32  O2x O    22.8200  -21.0700
            33  O2a O    22.5400  -24.7100
            34  O2a O    24.8500  -24.0800
            35  C1a C    26.1800  -24.5000
            36  C1a C    21.5600  -25.6900
            37  O1a O    22.6800  -20.0900
            38  C5a C    20.7900  -19.5300
            39  C5a C    21.4900  -18.2700
            40  N1y N    20.7900  -17.0800
            41  C1x C    19.3900  -17.0800
            42  C1y C    21.4900  -15.8900
            43  C1x C    20.7900  -14.6300
            44  C1x C    19.3900  -14.6300
            45  C1x C    18.6900  -15.8200
            46  O5a O    22.8900  -18.2700
            47  O5a O    19.3900  -19.5300
            48  C1a C    19.1100  -21.3500
            49  C7a C    22.8900  -15.8900
            50  O6a O    23.5900  -17.0800
            51  O7a O    23.5900  -14.6300
            52  C1a C    24.7800  -11.0600
            53  O1a O    27.1600  -12.4600
            54  O5a O    28.3500  -14.3500
            55  C1b C    29.3300  -16.4500
            56  C2b C    30.1000  -15.3300
            57  C2a C    31.4300  -15.2600
BOND        60
            1     1   2 2
            2     3   2 1 #Up
            3     3   4 1
            4     4   5 1
            5     5   6 1
            6     6   7 1
            7     7   8 1
            8     3   8 1
            9     7   9 1 #Up
            10    6  10 1 #Down
            11    9  11 1
            12    1  12 1
            13    1  13 1
            14   12  14 1
            15   14  15 1
            16   15  16 1
            17   16  17 1
            18   17  18 1
            19   18  19 1
            20   19  20 2
            21   20  21 1
            22   20  22 1
            23   22  23 1
            24   23  24 1 #Up
            25   23  25 1
            26   25  26 1
            27   26  27 1
            28   27  28 1
            29   28  29 1
            30   29  30 1
            31   30  31 1
            32   31  32 1
            33   32  27 1
            34   28  33 1 #Up
            35   26  34 1 #Down
            36   34  35 1
            37   33  36 1
            38   31  37 1 #Up
            39   31  38 1
            40   38  39 1
            41   41  40 1
            42   40  42 1
            43   42  43 1
            44   43  44 1
            45   44  45 1
            46   41  45 1
            47   39  40 1
            48   39  46 2
            49   38  47 2
            50   30  48 1 #Up
            51   42  49 1
            52   49  50 2
            53   49  51 1
            54   12  51 1 #Down
            55   14  52 1 #Down
            56   15  53 1 #Up
            57   17  54 2
            58   18  55 1 #Down
            59   55  56 1
            60   56  57 2

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