KEGG   DRUG: Tacrolimus
Entry
D00107                      Drug                                   
Name
Tacrolimus (USP/INN);
Tacrolimus hydrate (JP18);
Prograf (TN);
Protopic (TN)
Product
ASTAGRAF XL (Astellas Pharma US), ENVARSUS (Veloxis Pharmaceuticals), PROGRAF (Astellas Pharma US), PROTOPIC (LEO Pharma), TACROLIMUS (Padagis Israel Pharmaceuticals)
  Generic
TACROLIMUS (A-S Medication Solutions), TACROLIMUS (Accord Healthcare), TACROLIMUS (Accord Healthcare), TACROLIMUS (Ajenat Pharmaceuticals LLC), TACROLIMUS (American Health Packaging), TACROLIMUS (Aphena Pharma Solutions - Tennessee), TACROLIMUS (Ascend Laboratories), TACROLIMUS (BPI LABS LLC), TACROLIMUS (Belcher Pharmaceuticals), TACROLIMUS (Biocon Pharma), TACROLIMUS (BionPharma Inc.,), TACROLIMUS (Bryant Ranch Prepack), TACROLIMUS (Bryant Ranch Prepack), TACROLIMUS (Bryant Ranch Prepack), TACROLIMUS (Bryant Ranch Prepack), TACROLIMUS (Bryant Ranch Prepack), TACROLIMUS (Bryant Ranch Prepack), TACROLIMUS (CONCORD BIOTECH LIMITED), TACROLIMUS (Cardinal Health 107), TACROLIMUS (Cardinal Health 107), TACROLIMUS (Chengdu Suncadia Medicine), TACROLIMUS (Direct_Rx), TACROLIMUS (Dr. Reddy's Laboratories Limited), TACROLIMUS (E. Fougera & Co. a division of Fougera Pharmaceuticals), TACROLIMUS (Encube Ethicals Private Limited), TACROLIMUS (Glenmark Pharmaceuticals), TACROLIMUS (Glenmark Pharmaceuticals), TACROLIMUS (Golden State Medical Supply), TACROLIMUS (Major Pharmaceuticals), TACROLIMUS (Major Pharmaceuticals), TACROLIMUS (Mayne Pharma), TACROLIMUS (Mylan Institutional), TACROLIMUS (Mylan Pharmaceuticals), TACROLIMUS (NORTHSTAR RX LLC), TACROLIMUS (Panacea Biotec Limited), TACROLIMUS (Proficient Rx LP), TACROLIMUS (Quallent Pharmaceuticals Health LLC), TACROLIMUS (REMEDYREPACK), TACROLIMUS (Sandoz), TACROLIMUS (Strides Pharma Science Limited)
Formula
C44H69NO12. H2O
Exact mass
821.4925
Mol weight
822.03
Structure
Simcomp
Source
Streptomyces tsukubaensis [TAX:83656]
Class
Immunological agent
 DG03129  Calcineurin inhibitor
Anti-inflammatory
 DG01985  Disease modifying anti-rheumatic drug (DMARD)
Dermatological agent
 DG03243  Atopic dermatitis agent
Metabolizing enzyme substrate
 DG01633  CYP3A/CYP3A4 substrate
  DG02913  CYP3A4 substrate
Remark
Therapeutic category: 1319 2699 3999
ATC code: D11AH01 L04AD02
Chemical structure group: DG00439
Product (DG00439): D00107<JP/US>
Efficacy
Antiallergic, Immunosuppressant, Calcineurin inhibitor
  Disease
Organ rejection in kidney transplant [DS:H00083]
Organ rejection in liver transplant [DS:H00083]
Organ rejection in heart transplant [DS:H00083]
Atopic dermatitis [DS:H01358]
Comment
Tacrolimus and FK506-binding protein [HSA:2280 2281] complex inhibits 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: CYP3A4 [HSA:1576]
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
      D00107  Tacrolimus (USP/INN) <JP/US>
 L ANTINEOPLASTIC AND IMMUNOMODULATING AGENTS
  L04 IMMUNOSUPPRESSANTS
   L04A IMMUNOSUPPRESSANTS
    L04AD Calcineurin inhibitors
     L04AD02 Tacrolimus
      D00107  Tacrolimus (USP/INN) <JP/US>
USP drug classification [BR:br08302]
 Dermatological Agents
  Dermatitis and Pruitus Agents
   Dermatitis and Pruitus Agents, Other
    Tacrolimus
     D00107  Tacrolimus (USP/INN)
 Immunological Agents
  Immunosuppressants
   Calcineurin Inhibitors
    Tacrolimus
     D00107  Tacrolimus (USP/INN)
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
     D00107  Tacrolimus (USP/INN); Tacrolimus hydrate (JP18)
 2  Agents affecting individual organs
  26  Epidermides
   269  Miscellaneous
    2699  Others
     D00107  Tacrolimus (USP/INN); Tacrolimus hydrate (JP18)
 3  Agents affecting metabolism
  39  Other agents affecting metabolism
   399  Miscellaneous
    3999  Others
     D00107  Tacrolimus (USP/INN); Tacrolimus hydrate (JP18)
Drug groups [BR:br08330]
 Immunological agent
  DG03129  Calcineurin inhibitor
   DG00439  Tacrolimus
    D00107  Tacrolimus
 Anti-inflammatory
  DG01985  Disease modifying anti-rheumatic drug (DMARD)
   DG00439  Tacrolimus
    D00107  Tacrolimus
 Dermatological agent
  DG03243  Atopic dermatitis agent
   D00107  Tacrolimus
 Metabolizing enzyme substrate
  DG01633  CYP3A/CYP3A4 substrate
   DG02913  CYP3A4 substrate
    DG00439  Tacrolimus
     D00107  Tacrolimus
Drug classes [BR:br08332]
 Immunological agent
  DG03129  Calcineurin inhibitor
   D00107  Tacrolimus
 Antirheumatic agent
  DG01985  Disease modifying anti-rheumatic drug (DMARD)
   D00107  Tacrolimus
 Dermatological agent
  DG03243  Atopic dermatitis agent
   D00107  Tacrolimus
Target-based classification of drugs [BR:br08310]
 Enzymes
  Hydrolases (EC3)
   Phosphatases
    PPP3C/PPP3R/CHP
     D00107  Tacrolimus (USP/INN) <JP/US>
Drugs listed in the Japanese Pharmacopoeia [BR:br08311]
 Chemicals
  D00107  Tacrolimus hydrate
  D00107  Tacrolimus capsules
New drug approvals in Europe [br08329.html]
 European public assessment reports (EPAR) authorised medicine
  D00107
Drug metabolizing enzymes and transporters [br08309.html]
 Drug metabolizing enzymes
  D00107
Drug groups [BR:br08330]
 Immunological agent
  DG03129  Calcineurin inhibitor
   DG00439  Tacrolimus
 Anti-inflammatory
  DG01985  Disease modifying anti-rheumatic drug (DMARD)
   DG00439  Tacrolimus
 Metabolizing enzyme substrate
  DG01633  CYP3A/CYP3A4 substrate
   DG02913  CYP3A4 substrate
    DG00439  Tacrolimus
Other DBs
CAS: 109581-93-3
PubChem: 7847175
ChEBI: 61057
LigandBox: D00107
NIKKAJI: J1.629.005J
LinkDB
KCF data

ATOM        58
            1   O0  O    31.6167  -21.2567
            2   C2c C    22.3300  -12.4600
            3   C2b C    22.3300  -11.0600
            4   C1y C    21.1400  -10.2900
            5   C1x C    21.1400   -8.8900
            6   C1x C    19.8800   -8.1900
            7   C1y C    18.6900   -8.8900
            8   C1y C    18.6900  -10.2900
            9   C1x C    19.8800  -11.0600
            10  O2a O    17.5000  -11.0600
            11  O1a O    17.5000   -8.1900
            12  C1a C    16.3100  -10.2900
            13  C1c C    23.5900  -13.1600
            14  C1a C    21.1400  -13.1600
            15  C1c C    24.7800  -12.4600
            16  C1c C    25.9700  -13.1600
            17  C1b C    25.9700  -14.5600
            18  C5a C    27.3000  -15.1200
            19  C1c C    27.9300  -16.4500
            20  C2b C    27.2300  -17.7100
            21  C2c C    25.9700  -18.4100
            22  C1a C    24.7800  -17.7100
            23  C1b C    25.9700  -19.8100
            24  C1c C    24.7800  -20.5100
            25  C1a C    23.5900  -19.8100
            26  C1b C    25.4800  -21.7000
            27  C1c C    24.5000  -22.8200
            28  C1y C    23.1700  -22.4000
            29  C1y C    22.1200  -23.4500
            30  C1x C    20.7900  -23.1000
            31  C1y C    20.4400  -21.7000
            32  C1z C    21.4200  -20.7200
            33  O2x O    22.8200  -21.0700
            34  O2a O    22.5400  -24.7800
            35  O2a O    24.8500  -24.1500
            36  C1a C    26.1800  -24.5700
            37  C1a C    21.4900  -25.7600
            38  O1a O    22.6800  -20.0900
            39  C5a C    20.7200  -19.5300
            40  C5a C    21.4200  -18.2700
            41  N1y N    20.7200  -17.0800
            42  C1x C    19.3200  -17.0800
            43  C1y C    21.4200  -15.8900
            44  C1x C    20.7200  -14.6300
            45  C1x C    19.3200  -14.6300
            46  C1x C    18.6200  -15.8200
            47  O5a O    22.8900  -18.2700
            48  O5a O    19.3200  -19.5300
            49  C1a C    19.0400  -21.3500
            50  C7a C    22.8900  -15.8900
            51  O6a O    23.5900  -17.0800
            52  O7a O    23.5900  -14.6300
            53  C1a C    24.7800  -11.0600
            54  O1a O    27.1600  -12.4600
            55  O5a O    28.3500  -14.3500
            56  C1b C    29.3300  -16.4500
            57  C2b C    30.1000  -15.3300
            58  C2a C    31.4300  -15.2600
BOND        60
            1     2   3 2
            2     4   3 1 #Up
            3     4   5 1
            4     5   6 1
            5     6   7 1
            6     7   8 1
            7     8   9 1
            8     4   9 1
            9     8  10 1 #Up
            10    7  11 1 #Down
            11   10  12 1
            12    2  13 1
            13    2  14 1
            14   13  15 1
            15   15  16 1
            16   16  17 1
            17   17  18 1
            18   18  19 1
            19   19  20 1
            20   20  21 2
            21   21  22 1
            22   21  23 1
            23   23  24 1
            24   24  25 1 #Up
            25   24  26 1
            26   26  27 1
            27   27  28 1
            28   28  29 1
            29   29  30 1
            30   30  31 1
            31   31  32 1
            32   32  33 1
            33   33  28 1
            34   29  34 1 #Up
            35   27  35 1 #Down
            36   35  36 1
            37   34  37 1
            38   32  38 1 #Up
            39   32  39 1
            40   39  40 1
            41   42  41 1
            42   41  43 1
            43   43  44 1
            44   44  45 1
            45   45  46 1
            46   42  46 1
            47   40  41 1
            48   40  47 2
            49   39  48 2
            50   31  49 1 #Up
            51   43  50 1
            52   50  51 2
            53   50  52 1
            54   13  52 1 #Down
            55   15  53 1 #Down
            56   16  54 1 #Up
            57   18  55 2
            58   19  56 1 #Down
            59   56  57 1
            60   57  58 2

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