Sirolimus


Entry
D00753                      Drug                                   
Name
Sirolimus (JAN/USAN/INN);
Rapamune (TN);
Rapamycin (TN)
Product
FYARRO (Aadi Bioscience), HYFTOR (Nobelpharma America), RAPAMUNE (Wyeth Pharmaceuticals LLC)
  Generic
SIROLIMUS (American Health Packaging), SIROLIMUS (Amneal Pharmaceuticals NY LLC), SIROLIMUS (Apotex Corp), SIROLIMUS (Ascend Laboratories), SIROLIMUS (AvPAK), SIROLIMUS (Cadila Healthcare Limited), SIROLIMUS (Dr. Reddy's Laboratories Limited), SIROLIMUS (Glenmark Pharmaceuticals), SIROLIMUS (Greenstone LLC), SIROLIMUS (Greenstone LLC), SIROLIMUS (Major Pharmaceuticals), SIROLIMUS (Major Pharmaceuticals), SIROLIMUS (NORTHSTAR RX LLC), SIROLIMUS (Torrent pharmaceuticals limited), SIROLIMUS (VistaPharm), SIROLIMUS (Zydus Pharmaceuticals (USA))
Formula
C51H79NO13
Exact mass
913.5551
Mol weight
914.1719
Structure
Simcomp
Sequence
0 Ska  1 Mtk  2 Man  3 Mtd  4 Mtk  5 Man  6 Mte  7 Mtd  8 Mad
9 Mad  10 Mtk  11 Mak  12 Mae  13 Mtn  14 Man  15 Pip
  Type
PK
Source
Streptomyces hygroscopicus [TAX:1912]
Class
Antineoplastic
 DG01597  mTOR inhibitor
Metabolizing enzyme substrate
 DG01633  CYP3A/CYP3A4 substrate
  DG02913  CYP3A4 substrate
Metabolizing enzyme inhibitor
 DG02852  CYP3A/CYP3A4 inhibitor
  DG01522  CYP3A4 inhibitor
Transporter substrate
 DG01665  ABCB1 substrate
Remark
Same as: C07909
Therapeutic category: 4291
ATC code: L04AA10 S01XA23
Product: D00753<JP/US>
Efficacy
Antineoplastic, Immunosuppressant, mTOR inhibitor
  Disease
Organ rejection in renal transplantation [DS:H00083]
Lymphangioleiomyomatosis [DS:H00896]
Target
MTOR [HSA:2475] [KO:K07203]
  Pathway
hsa04150  mTOR signaling pathway
hsa05200  Pathways in cancer
Metabolism
Enzyme: CYP3A4 [HSA:1576]
Transporter: ABCB1 [HSA:5243]
Interaction
CYP inhibition: CYP3A4 [HSA:1576]
Structure map
map07042  Antineoplastics - agents from natural products
map07046  Immunosuppressive agents
Other map
map04139  Mitophagy - yeast
Brite
Anatomical Therapeutic Chemical (ATC) classification [BR:br08303]
 L ANTINEOPLASTIC AND IMMUNOMODULATING AGENTS
  L04 IMMUNOSUPPRESSANTS
   L04A IMMUNOSUPPRESSANTS
    L04AA Selective immunosuppressants
     L04AA10 Sirolimus
      D00753  Sirolimus (JAN/USAN/INN) <JP/US>
 S SENSORY ORGANS
  S01 OPHTHALMOLOGICALS
   S01X OTHER OPHTHALMOLOGICALS
    S01XA Other ophthalmologicals
     S01XA23 Sirolimus
      D00753  Sirolimus (JAN/USAN/INN) <JP/US>
USP drug classification [BR:br08302]
 Immunological Agents
  Immunosuppressants
   mTOR Inhibitors
    Sirolimus
     D00753  Sirolimus (JAN/USAN/INN)
Therapeutic category of drugs in Japan [BR:br08301]
 4  Agents affecting cellular function
  42  Antineoplastics
   429  Miscellaneous
    4291  Other Antitumors
     D00753  Sirolimus (JAN/USAN/INN)
Drug groups [BR:br08330]
 Antineoplastic
  DG01597  mTOR inhibitor
   D00753  Sirolimus
 Metabolizing enzyme substrate
  DG01633  CYP3A/CYP3A4 substrate
   DG02913  CYP3A4 substrate
    D00753  Sirolimus
 Metabolizing enzyme inhibitor
  DG02852  CYP3A/CYP3A4 inhibitor
   DG01522  CYP3A4 inhibitor
    D00753  Sirolimus
 Transporter substrate
  DG01665  ABCB1 substrate
   D00753  Sirolimus
Drug classes [BR:br08332]
 Antineoplastic
  DG01597  mTOR inhibitor
   D00753  Sirolimus
Target-based classification of drugs [BR:br08310]
 Protein kinases
  Serine/threonine kinases
   Other
    MTOR
     D00753  Sirolimus (JAN/USAN/INN) <JP/US>
New drug approvals in the USA [br08319.html]
 New molecular entities and new therapeutic biological products
  D00753
New drug approvals in Europe [br08329.html]
 European public assessment reports (EPAR) authorised medicine
  D00753
New drug approvals in Japan [br08318.html]
 Drugs with new active ingredients
  D00753
New drug approvals in the USA, Europe and Japan [br08328.html]
 Approval dates by FDA, EMA and PMDA
  D00753
Drug metabolizing enzymes and transporters [br08309.html]
 Drug metabolizing enzymes
  D00753
 Drug transporters
  D00753
Other DBs
CAS: 53123-88-9
PubChem: 7847818
ChEBI: 9168
PDB-CCD: RAP[PDBj]
LigandBox: D00753
NIKKAJI: J137.896A
KCF data

ATOM        65
            1   N1y N    29.3831  -21.8402
            2   C1y C    30.5814  -21.1478
            3   C5a C    29.3715  -23.2362
            4   C1x C    28.1732  -21.1478
            5   C7a C    31.7856  -21.8459
            6   C1x C    30.5814  -19.7517
            7   C5a C    28.1556  -23.9343
            8   O5a O    30.5697  -23.9518
            9   C1x C    28.1732  -19.7517
            10  O7a O    32.9957  -21.1595
            11  O6a O    31.7915  -22.9628
            12  C1x C    29.3831  -19.0420
            13  C1z C    28.1440  -25.3304
            14  O5a O    26.9399  -23.2304
            15  C1c C    34.2056  -21.8518
            16  O2x O    29.3541  -26.0284
            17  C1y C    26.7188  -26.0227
            18  O1a O    28.1383  -26.7325
            19  C1c C    35.4157  -21.1654
            20  C1b C    34.2056  -23.2478
            21  C1y C    29.3425  -27.4363
            22  C1x C    26.7770  -27.4130
            23  C1a C    25.4973  -25.3187
            24  C1b C    36.6255  -21.8633
            25  C1a C    35.4098  -19.7633
            26  C5a C    35.4157  -23.9401
            27  C1b C    30.5350  -28.1401
            28  C1x C    28.1207  -28.1285
            29  C1y C    37.8298  -21.1595
            30  C1c C    35.4157  -25.3304
            31  O5a O    36.6255  -23.2304
            32  C1c C    30.5291  -29.5305
            33  C1x C    39.0396  -21.8518
            34  C1x C    37.8181  -19.7576
            35  C2b C    36.6255  -26.0227
            36  C1a C    34.1998  -26.0227
            37  C2c C    31.7333  -30.2343
            38  O2a O    29.3133  -30.2170
            39  C1y C    40.2497  -21.1537
            40  C1x C    39.0280  -19.0536
            41  C2c C    36.6255  -27.4130
            42  C2b C    31.7216  -31.6248
            43  C1a C    32.9375  -29.5305
            44  C1a C    29.3075  -31.6189
            45  C1y C    40.2438  -19.7517
            46  O2a O    41.4539  -21.8459
            47  C1c C    37.8298  -28.1110
            48  C1a C    35.4098  -28.1110
            49  C2b C    32.9258  -32.3343
            50  O1a O    41.4539  -19.0420
            51  C1a C    42.6638  -21.1421
            52  C1c C    37.8298  -29.5013
            53  O1a O    39.0339  -27.4013
            54  C2b C    32.9200  -33.7247
            55  C5a C    39.0339  -30.1878
            56  O2a O    36.6139  -30.1878
            57  C2b C    34.1183  -34.4286
            58  C1c C    39.0339  -31.5839
            59  O5a O    40.2438  -29.4897
            60  C1a C    36.6082  -31.5899
            61  C2b C    35.3282  -33.7247
            62  C1b C    37.8298  -32.2819
            63  C1a C    40.2438  -32.2819
            64  C1c C    36.7303  -33.7247
            65  C1a C    37.0850  -35.0743
BOND        68
            1     1   2 1
            2     1   3 1
            3     1   4 1
            4     2   5 1 #Up
            5     2   6 1
            6     3   7 1
            7     3   8 2
            8     4   9 1
            9     5  10 1
            10    5  11 2
            11    6  12 1
            12    7  13 1
            13    7  14 2
            14   10  15 1
            15   13  16 1 #Down
            16   13  17 1
            17   13  18 1 #Up
            18   15  19 1
            19   15  20 1
            20   21  16 1 #Down
            21   17  22 1
            22   17  23 1 #Up
            23   19  24 1
            24   19  25 1 #Down
            25   20  26 1
            26   21  27 1
            27   21  28 1
            28   24  29 1
            29   26  30 1
            30   26  31 2
            31   27  32 1
            32   29  33 1
            33   29  34 1
            34   30  35 1
            35   30  36 1 #Up
            36   32  37 1
            37   32  38 1 #Up
            38   33  39 1
            39   34  40 1
            40   35  41 2
            41   37  42 2
            42   37  43 1
            43   38  44 1
            44   39  45 1
            45   39  46 1 #Down
            46   41  47 1
            47   41  48 1
            48   42  49 1
            49   45  50 1 #Up
            50   46  51 1
            51   47  52 1
            52   47  53 1 #Up
            53   49  54 2
            54   52  55 1
            55   52  56 1 #Down
            56   54  57 1
            57   55  58 1
            58   55  59 2
            59   56  60 1
            60   57  61 2
            61   58  62 1
            62   58  63 1 #Down
            63   61  64 1
            64   64  65 1 #Down
            65    9  12 1
            66   22  28 1
            67   40  45 1
            68   62  64 1