Sildenafil citrate


Entry
D02229                      Drug                                   
Name
Sildenafil citrate (JAN/USP);
Revatio (TN);
Viagra (TN)
Product
VIAGRA (A-S Medication Solutions), VIAGRA (Aphena Pharma Solutions - Tennessee), VIAGRA (Aphena Pharma Solutions - Tennessee), SILDENAFIL CITRATE (Greenstone LLC), VIAGRA (Pfizer Laboratories Div Pfizer), REVATIO (Pfizer Laboratories Div Pfizer)
  Generic
SILDENAFIL (A-S Medication Solutions), SILDENAFIL (A-S Medication Solutions), SILDENAFIL (A-S Medication Solutions), SILDENAFIL (A-S Medication Solutions), SILDENAFIL (A-S Medication Solutions), SILDENAFIL CITRATE (A-S Medication Solutions), SILDENAFIL (A-S Medication Solutions), SILDENAFIL CITRATE (A-S Medication Solutions), SILDENAFIL (A-S Medication Solutions), SILDENAFIL (A-S Medication Solutions), SILDENAFIL (A-S Medication Solutions), SILDENAFIL CITRATE (ATLANTIC BIOLOGICALS CORP.), SILDENAFIL (Actavis Pharma), SILDENAFIL CITRATE (Advagen Pharma), SILDENAFIL (Advagen Pharma), SILDENAFIL (Ajanta Pharma USA), SILDENAFIL CITRATE (Ajanta Pharma USA), SILDENAFIL (Ajanta Pharma USA), SILDENAFIL (American Health Packaging), SILDENAFIL (Amneal Pharmaceuticals LLC), SILDENAFIL (Amneal Pharmaceuticals NY LLC), SILDENAFIL (Amneal Pharmaceuticals NY LLC), SILDENAFIL (Aphena Pharma Solutions - Tennessee), SILDENAFIL (Aphena Pharma Solutions - Tennessee), SILDENAFIL (Aphena Pharma Solutions - Tennessee), SILDENAFIL (Asclemed USA), SILDENAFIL (Aurobindo Pharma Limited), SILDENAFIL (Aurobindo Pharma Limited), SILDENAFIL (AvKARE), SILDENAFIL (AvPAK), SILDENAFIL (BluePoint Laboratories), SILDENAFIL (BluePoint Laboratories), SILDENAFIL (Bryant Ranch Prepack), SILDENAFIL (Bryant Ranch Prepack), SILDENAFIL CITRATE (Bryant Ranch Prepack), SILDENAFIL (Bryant Ranch Prepack), SILDENAFIL (Bryant Ranch Prepack), SILDENAFIL (Bryant Ranch Prepack), SILDENAFIL (Bryant Ranch Prepack), SILDENAFIL (Bryant Ranch Prepack), SILDENAFIL (Bryant Ranch Prepack), SILDENAFIL (Bryant Ranch Prepack), SILDENAFIL (Bryant Ranch Prepack), SILDENAFIL (Bryant Ranch Prepack), SILDENAFIL (Bryant Ranch Prepack), SILDENAFIL (Camber Pharmaceuticals), SILDENAFIL (Camber Pharmaceuticals), SILDENAFIL (Camber Pharmaceuticals), SILDENAFIL (DIRECT RX), SILDENAFIL (DIRECT RX), SILDENAFIL CITRATE (Denton Pharma), SILDENAFIL (DirectRx), SILDENAFIL (Exelan Pharmaceuticals), SILDENAFIL (Greenstone LLC), SILDENAFIL (Lake Erie Medical DBA Quality Care Products LLC), SILDENAFIL (Lupin Pharmaceuticals), SILDENAFIL (Lupin Pharmaceuticals), SILDENAFIL (Macleods Pharmaceuticals Limited), SILDENAFIL (McKesson Corporation dba SKY Packaging), SILDENAFIL (Medsource Pharmaceuticals), SILDENAFIL (Mylan Pharmaceuticals), SILDENAFIL (NuCare Pharmaceuticals), SILDENAFIL (NuCare Pharmaceuticals), SILDENAFIL (NuCare Pharmaceuticals), SILDENAFIL (NuCare Pharmaceuticals), SILDENAFIL (NuCare Pharmaceuticals), SILDENAFIL (NuCare Pharmaceuticals), SILDENAFIL CITRATE (NuCare Pharmaceuticals), SILDENAFIL CITRATE (NuCare Pharmaceuticals), SILDENAFIL (NuCare Pharmaceuticals), SILDENAFIL (NuCare Pharmaceuticals), SILDENAFIL (NuCare Pharmaceuticals), SILDENAFIL (NuCare Pharmaceuticals), SILDENAFIL (NuCare Pharmaceuticals), SILDENAFIL (NuCare Pharmaceuticals), SILDENAFIL (NuCare Pharmaceuticals), SILDENAFIL (NuCare Pharmaceuticals), SILDENAFIL (NuCare Pharmaceuticals), SILDENAFIL (NuCare Pharmaceuticals), SILDENAFIL (PD-Rx Pharmaceuticals), SILDENAFIL (PD-Rx Pharmaceuticals), SILDENAFIL (PD-Rx Pharmaceuticals), SILDENAFIL CITRATE (PD-Rx Pharmaceuticals), SILDENAFIL CITRATE (PD-Rx Pharmaceuticals), SILDENAFIL (PD-Rx Pharmaceuticals), SILDENAFIL (PD-Rx Pharmaceuticals), SILDENAFIL (Preferred Pharmaceuticals), SILDENAFIL (Preferred Pharmaceuticals), SILDENAFIL (Preferred Pharmaceuticals), SILDENAFIL (Preferred Pharmaceuticals), SILDENAFIL (Proficient Rx LP), SILDENAFIL (Proficient Rx LP), SILDENAFIL CITRATE (Proficient Rx LP), SILDENAFIL (Proficient Rx LP), SILDENAFIL (Proficient Rx LP), SILDENAFIL (Proficient Rx LP), SILDENAFIL (Proficient Rx LP), SILDENAFIL (Proficient Rx LP), SILDENAFIL (Proficient Rx LP), SILDENAFIL (Proficient Rx LP), SILDENAFIL CITRATE (Proficient Rx LP), SILDENAFIL (Proficient Rx LP), SILDENAFIL CITRATE (Proficient Rx LP), SILDENAFIL (REMEDYREPACK), SILDENAFIL (REMEDYREPACK), SILDENAFIL (REMEDYREPACK), SILDENAFIL CITRATE (REMEDYREPACK), SILDENAFIL (REMEDYREPACK), SILDENAFIL (RPK Pharmaceuticals), SILDENAFIL (RPK Pharmaceuticals), SILDENAFIL (Reyoung Corporation), SILDENAFIL (Teva Pharmaceuticals USA), SILDENAFIL (Teva Pharmaceuticals USA), SILDENAFIL CITRATE (Torrent Pharmaceuticals Limited), SILDENAFIL (TruPharma LLC), SILDENAFIL CITRATE (TruPharma LLC), SILDENAFIL (Unit Dose Services), SILDENAFIL (Unit Dose Services), SILDENAFIL (Unit Dose Services), SILDENAFIL (Unit Dose Services), SILDENAFIL (Virtus Pharmaceuticals), SILDENAFIL (XLCARE Pharmaceuticals), SILDENAFIL (XLCare Pharmaceuticals), SILDENAFIL CITRATE (A-S Medication Solutions), SILDENAFIL (Aphena Pharma Solutions - Tennessee), SILDENAFIL CITRATE (Ascend Laboratories), SILDENAFIL (AuroMedics Pharma LLC), SILDENAFIL FOR ORAL SUSPENSION (Cipla USA), SILDENAFIL CITRATE (Major Pharmaceuticals), SILDENAFIL CITRATE (NIVAGEN PHARMACEUTICALS), SILDENAFIL CITRATE (Novadoz Pharmaceuticals LLC), SILDENAFIL (Novitium Pharma LLC), SILDENAFIL CITRATE (Proficient Rx LP), SILDENAFIL (Taro Pharmaceuticals U.S.A.), SILDENAFIL CITRATE (Torrent Pharmaceuticals Limited), SILDENAFIL (Tris Pharma), SILDENAFIL (Unit Dose Services), SILDENAFIL (Camber Pharmaceuticals), SILDENAFIL (Denton Pharma), SILDENAFIL (Mylan Pharmaceuticals)
Formula
C22H30N6O4S. C6H8O7
Exact mass
666.2319
Mol weight
666.6999
Structure
Class
Cardiovascular agent
 DG01509  Phosphodiesterase V inhibitor
Metabolizing enzyme substrate
 DG01642  CYP2C9 substrate
 DG01633  CYP3A/CYP3A4 substrate
  DG02913  CYP3A4 substrate
Remark
Therapeutic category: 2190 2590
ATC code: G04BE03
Chemical structure group: DG00484
Product (DG00484): D02229<JP/US>
Efficacy
Vasodilator, Impotence therapy, Phosphodiesterase V inhibitor
  Disease
Pulmonary arterial hypertension [DS:H01621]
Target
PDE5 [HSA:8654] [KO:K13762]
  Pathway
hsa04022  cGMP-PKG signaling pathway
Metabolism
Enzyme: CYP3A4 [HSA:1576]; CYP2C9 [HSA:1559]
Interaction
Brite
Anatomical Therapeutic Chemical (ATC) classification [BR:br08303]
 G GENITO URINARY SYSTEM AND SEX HORMONES
  G04 UROLOGICALS
   G04B UROLOGICALS
    G04BE Drugs used in erectile dysfunction
     G04BE03 Sildenafil
      D02229  Sildenafil citrate (JAN/USP) <JP/US>
USP drug classification [BR:br08302]
 Respiratory Tract/Pulmonary Agents
  Pulmonary Antihypertensives
   Phosphodiesterase-5 (PDE5)
    Sildenafil
     D02229  Sildenafil citrate (JAN/USP)
 Sexual Disorder Agents
  Sexual Disorder Agents (Male)
   Sildenafil
    D02229  Sildenafil citrate (JAN/USP)
Therapeutic category of drugs in Japan [BR:br08301]
 2  Agents affecting individual organs
  21  Cardiovascular agents
   219  Miscellaneous
    2190  Miscellaneous
     D02229  Sildenafil citrate (JAN/USP)
  25  Urogenital and anal organ agents
   259  Miscellaneous
    2590  Miscellaneous
     D02229  Sildenafil citrate (JAN/USP)
Drug groups [BR:br08330]
 Cardiovascular agent
  DG01509  Phosphodiesterase V inhibitor
   DG00484  Sildenafil
    D02229  Sildenafil citrate
 Metabolizing enzyme substrate
  DG01642  CYP2C9 substrate
   DG00484  Sildenafil
    D02229  Sildenafil citrate
  DG01633  CYP3A/CYP3A4 substrate
   DG02913  CYP3A4 substrate
    DG00484  Sildenafil
     D02229  Sildenafil citrate
Target-based classification of drugs [BR:br08310]
 Enzymes
  Hydrolases (EC3)
   Phosphodiesterases
    PDE5
     D02229  Sildenafil citrate (JAN/USP) <JP/US>
New drug approvals in Europe [br08329.html]
 European public assessment reports (EPAR) authorised medicine
  D02229
Drug metabolizing enzymes and transporters [br08309.html]
 Drug metabolizing enzymes
  D02229
Drug groups [BR:br08330]
 Cardiovascular agent
  DG01509  Phosphodiesterase V inhibitor
   DG00484  Sildenafil
 Metabolizing enzyme substrate
  DG01642  CYP2C9 substrate
   DG00484  Sildenafil
  DG01633  CYP3A/CYP3A4 substrate
   DG02913  CYP3A4 substrate
    DG00484  Sildenafil
Other DBs
CAS: 171599-83-0
PubChem: 7849288
ChEBI: 58987
LigandBox: D02229
NIKKAJI: J974.104F
KCF data

ATOM        46
            1   C8y C    19.6408  -17.9141
            2   C8y C    20.8539  -17.2084
            3   C8y C    19.6408  -19.3198
            4   C8x C    18.4275  -17.2200
            5   N5x N    22.0613  -17.9083
            6   N4x N    20.8423  -15.8085
            7   C8x C    18.4275  -20.0196
            8   O2a O    20.8423  -20.0139
            9   C8y C    17.2201  -17.9141
            10  C8y C    23.2804  -17.2141
            11  C8y C    22.0613  -15.1086
            12  C8x C    17.2144  -19.3139
            13  C1b C    22.0496  -19.3139
            14  S4a S    16.0128  -17.2141
            15  C8y C    23.3444  -15.8143
            16  C8y C    24.6102  -17.6399
            17  O5x O    22.0613  -13.7030
            18  C1a C    23.2511  -20.0139
            19  N1y N    14.8055  -17.9083
            20  O3c O    17.0043  -16.2168
            21  O3c O    15.0096  -16.2168
            22  N4y N    24.6044  -15.3711
            23  N5x N    25.4385  -16.5025
            24  C1b C    25.0359  -18.9640
            25  C1x C    14.8055  -19.3082
            26  C1x C    13.5923  -17.2025
            27  C1a C    25.0419  -14.0353
            28  C1b C    26.3950  -19.2498
            29  C1x C    13.5923  -20.0081
            30  C1x C    12.3792  -17.9083
            31  C1a C    26.8265  -20.5797
            32  N1y N    12.3792  -19.3082
            33  C1a C    11.1718  -20.0139
            34  C1d C    31.4778  -17.1503
            35  C1b C    30.2633  -17.8509
            36  C1b C    32.6923  -17.8509
            37  C6a C    32.1785  -15.9358
            38  O1a O    30.7771  -15.9358
            39  C6a C    29.0489  -17.1970
            40  C6a C    32.6923  -19.2523
            41  O6a O    31.4778  -14.7213
            42  O6a O    33.5798  -15.9358
            43  O6a O    27.8344  -17.8976
            44  O6a O    29.0489  -15.7957
            45  O6a O    33.9067  -19.9529
            46  O6a O    31.4778  -19.9529
BOND        48
            1     1   2 1
            2     1   3 1
            3     1   4 2
            4     2   5 2
            5     2   6 1
            6     3   7 2
            7     3   8 1
            8     4   9 1
            9     5  10 1
            10    6  11 1
            11    7  12 1
            12    8  13 1
            13    9  14 1
            14   10  15 2
            15   10  16 1
            16   11  17 2
            17   13  18 1
            18   14  19 1
            19   14  20 2
            20   14  21 2
            21   15  22 1
            22   16  23 2
            23   16  24 1
            24   19  25 1
            25   19  26 1
            26   22  27 1
            27   24  28 1
            28   25  29 1
            29   26  30 1
            30   28  31 1
            31   29  32 1
            32   32  33 1
            33    9  12 2
            34   11  15 1
            35   22  23 1
            36   30  32 1
            37   34  35 1
            38   34  36 1
            39   34  37 1
            40   34  38 1
            41   35  39 1
            42   36  40 1
            43   37  41 1
            44   37  42 2
            45   39  43 1
            46   39  44 2
            47   40  45 1
            48   40  46 2