KEGG   DRUG: Tadalafil
Entry
D02008                      Drug                                   
Name
Tadalafil (JAN/USP/INN);
Adcirca (TN);
Cialis (TN);
Zalutia (TN)
Product
ADCIRCA (United Therapeutics Corporation), CIALIS (Eli Lilly and Company), TADLIQ (CMP Pharma)
  Generic
ALYQ (AvKARE), ALYQ (Teva Pharmaceuticals USA), ALYQ (Teva Pharmaceuticals), TADALAFIL (A-S Medication Solutions), TADALAFIL (A-S Medication Solutions), TADALAFIL (A-S Medication Solutions), TADALAFIL (A-S Medication Solutions), TADALAFIL (A-S Medication Solutions), TADALAFIL (A-S Medication Solutions), TADALAFIL (ANI Pharmaceuticals), TADALAFIL (Accord Healthcare), TADALAFIL (Ajanta Pharma USA), TADALAFIL (Ajanta Pharma USA), TADALAFIL (Alembic Pharmaceuticals Limited), TADALAFIL (Alembic Pharmaceuticals), TADALAFIL (Amneal Pharmaceuticals NY LLC), TADALAFIL (Amneal Pharmaceuticals NY LLC), TADALAFIL (Aphena Pharma Solutions - Tennessee), TADALAFIL (Aphena Pharma Solutions - Tennessee), TADALAFIL (Aphena Pharma Solutions - Tennessee), TADALAFIL (Aphena Pharma Solutions - Tennessee), TADALAFIL (Aphena Pharma Solutions - Tennessee), TADALAFIL (Aphena Pharma Solutions - Tennessee), TADALAFIL (Asclemed USA), TADALAFIL (Asclemed USA), TADALAFIL (Asclemed USA), TADALAFIL (Asclemed USA), TADALAFIL (Aurobindo Pharma Limited), TADALAFIL (Aurobindo Pharma Limited), TADALAFIL (AvKARE), TADALAFIL (AvPAK), TADALAFIL (Bryant Ranch Prepack), TADALAFIL (Bryant Ranch Prepack), TADALAFIL (Bryant Ranch Prepack), TADALAFIL (Bryant Ranch Prepack), TADALAFIL (Bryant Ranch Prepack), TADALAFIL (Bryant Ranch Prepack), TADALAFIL (Burel Pharmaceuticals), TADALAFIL (Burel Pharmaceuticals), TADALAFIL (Camber Pharmaceuticals), TADALAFIL (Camber Pharmaceuticals), TADALAFIL (Cipla USA), TADALAFIL (Cipla USA), TADALAFIL (Direct_Rx), TADALAFIL (Direct_Rx), TADALAFIL (Dr.Reddys Laboratories), TADALAFIL (Dr.Reddys Laboratories), TADALAFIL (ECI Pharmaceuticals), TADALAFIL (Lupin Pharmaceuticals), TADALAFIL (Lupin Pharmaceuticals), TADALAFIL (Macleods Pharmaceuticals Limited), TADALAFIL (Macleods Pharmaceuticals Limited), TADALAFIL (Medsource Pharmaceuticals), TADALAFIL (NIVAGEN PHARMACEUTICALS), TADALAFIL (NUCARE PHARMACEUTICALS), TADALAFIL (NorthStar RxLLC), TADALAFIL (Northwind Pharmaceuticals), TADALAFIL (Northwind Pharmaceuticals), TADALAFIL (Northwind Pharmaceuticals), TADALAFIL (Northwind Pharmaceuticals), TADALAFIL (NuCare Pharmaceuticals), TADALAFIL (NuCare Pharmaceuticals), TADALAFIL (NuCare Pharmaceuticals), TADALAFIL (NuCare Pharmaceuticals), TADALAFIL (NuCare Pharmaceuticals), TADALAFIL (NuCare Pharmaceuticals), TADALAFIL (NuCare Pharmaceuticals), TADALAFIL (NuCare Pharmaceuticals), TADALAFIL (NuCare Pharmaceuticals), TADALAFIL (NuCare Pharmaceuticals), TADALAFIL (NuCare Pharmaceuticals), TADALAFIL (NuCare Pharmaceuticals), TADALAFIL (NuCare Pharmaceuticals), TADALAFIL (PD-RX Pharmaceuticals), TADALAFIL (PD-Rx Pharmaceuticals), TADALAFIL (PD-Rx Pharmaceuticals), TADALAFIL (PD-Rx Pharmaceuticals), TADALAFIL (Preferred Pharmaceuticals), TADALAFIL (Preferred Pharmaceuticals), TADALAFIL (Preferred Pharmaceuticals), TADALAFIL (Preferred Pharmaceuticals), TADALAFIL (Proficient Rx LP), TADALAFIL (Proficient Rx LP), TADALAFIL (Proficient Rx LP), TADALAFIL (Proficient Rx LP), TADALAFIL (Proficient Rx LP), TADALAFIL (Proficient Rx LP), TADALAFIL (Proficient Rx LP), TADALAFIL (Proficient Rx LP), TADALAFIL (Proficient Rx LP), TADALAFIL (Proficient Rx LP), TADALAFIL (Proficient Rx LP), TADALAFIL (Qilu Pharmaceutical), TADALAFIL (Quallent Pharmaceuticals Health LLC), TADALAFIL (Quallent Pharmaceuticals Health LLC), TADALAFIL (REMEDYREPACK), TADALAFIL (REMEDYREPACK), TADALAFIL (REMEDYREPACK), TADALAFIL (REMEDYREPACK), TADALAFIL (REMEDYREPACK), TADALAFIL (REMEDYREPACK), TADALAFIL (REMEDYREPACK), TADALAFIL (Solco Healthcare US), TADALAFIL (Solco Healthcare US), TADALAFIL (Sun Pharmaceutical Industries), TADALAFIL (Teva Pharmaceuticals USA), TADALAFIL (Teva Pharmaceuticals), TADALAFIL (Torrent Pharmaceuticals Limited), TADALAFIL (Torrent Pharmaceuticals Limited), TADALAFIL (Unichem Pharmaceuticals (USA)), TADALAFIL (VKT Pharma Private Limited), TADALAFIL (Zydus Lifesciences Limited), TADALAFIL (Zydus Pharmaceuticals USA), TADALAFIL (direct rx), TADALAFIL (medsource pharmaceuticals)
Formula
C22H19N3O4
Exact mass
389.1376
Mol weight
389.404
Structure
Class
Cardiovascular agent
 DG01509  Phosphodiesterase V inhibitor
Metabolizing enzyme substrate
 DG01633  CYP3A/CYP3A4 substrate
  DG02913  CYP3A4 substrate
Remark
Therapeutic category: 2190 2590
ATC code: G04BE08
Product: D02008<JP/US>
Product (mixture): D12486<US>
Efficacy
Antihypertensive, Impotence therapy, Phosphodiesterase V inhibitor
  Disease
Pulmonary arterial hypertension [DS:H01621]
Comment
Treatment of male erectile and female sexual dysfunction
Target
PDE5 [HSA:8654] [KO:K13762]
  Pathway
hsa00230  Purine metabolism
Metabolism
Enzyme: CYP3A4 [HSA:1576]
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
     G04BE08 Tadalafil
      D02008  Tadalafil (JAN/USP/INN) <JP/US>
USP drug classification [BR:br08302]
 Genitourinary Agents
  Benign Prostatic Hypertrophy Agents
   Tadalafil
    D02008  Tadalafil (JAN/USP/INN)
 Respiratory Tract/Pulmonary Agents
  Pulmonary Antihypertensives
   Phosphodiesterase-5 (PDE5) Inhibitors
    Tadalafil
     D02008  Tadalafil (JAN/USP/INN)
 Sexual Disorder Agents
  Sexual Disorder Agents (Male)
   Tadalafil
    D02008  Tadalafil (JAN/USP/INN)
Therapeutic category of drugs in Japan [BR:br08301]
 2  Agents affecting individual organs
  21  Cardiovascular agents
   219  Miscellaneous
    2190  Miscellaneous
     D02008  Tadalafil (JAN/USP/INN)
  25  Urogenital and anal organ agents
   259  Miscellaneous
    2590  Miscellaneous
     D02008  Tadalafil (JAN/USP/INN)
Drug groups [BR:br08330]
 Cardiovascular agent
  DG01509  Phosphodiesterase V inhibitor
   D02008  Tadalafil
 Metabolizing enzyme substrate
  DG01633  CYP3A/CYP3A4 substrate
   DG02913  CYP3A4 substrate
    D02008  Tadalafil
Target-based classification of drugs [BR:br08310]
 Enzymes
  Hydrolases (EC3)
   Phosphodiesterases
    PDE5
     D02008  Tadalafil (JAN/USP/INN) <JP/US>
New drug approvals in the USA [br08319.html]
 New molecular entities and new therapeutic biological products
  D02008
New drug approvals in Europe [br08329.html]
 European public assessment reports (EPAR) authorised medicine
  D02008
New drug approvals in Japan [br08318.html]
 Drugs with new active ingredients
  D02008
New drug approvals in the USA, Europe and Japan [br08328.html]
 Approval dates by FDA, EMA and PMDA
  D02008
Drug metabolizing enzymes and transporters [br08309.html]
 Drug metabolizing enzymes
  D02008
Other DBs
CAS: 171596-29-5
PubChem: 7849070
ChEBI: 71940
PDB-CCD: CIA[PDBj]
LigandBox: D02008
NIKKAJI: J1.662.659G
KCF data

ATOM        29
            1   N1y N    29.4582  -12.6733
            2   C1x C    30.1741  -13.7777
            3   C5x C    29.5963  -15.0632
            4   N1y N    28.2326  -15.0448
            5   C1y C    27.4708  -14.1585
            6   C5x C    28.0566  -12.6389
            7   C1y C    27.6549  -16.4236
            8   C8y C    26.2912  -16.4518
            9   C1x C    26.1152  -14.1159
            10  C8y C    25.5294  -15.3555
            11  O5x O    27.2788  -11.5908
            12  O5x O    30.4201  -16.2432
            13  C8y C    28.4706  -17.5343
            14  C8x C    29.8722  -17.4755
            15  C8x C    30.6960  -18.6089
            16  C8y C    30.0724  -19.9725
            17  C8y C    28.6250  -19.9694
            18  C8x C    27.8471  -18.8281
            19  O2x O    30.5829  -21.1851
            20  C1x C    29.5192  -22.1306
            21  O2x O    28.3012  -21.3988
            22  C1a C    30.0900  -11.4256
            23  C8y C    24.1928  -15.8284
            24  C8y C    24.2058  -17.2380
            25  N4x N    25.5595  -17.6699
            26  C8x C    22.9827  -15.1426
            27  C8x C    21.7866  -15.8747
            28  C8x C    21.8003  -17.2924
            29  C8x C    23.0561  -17.9701
BOND        34
            1     1   2 1
            2     2   3 1
            3     3   4 1
            4     4   5 1
            5     5   6 1
            6     1   6 1
            7     4   7 1
            8     7   8 1
            9     5   9 1
            10   10   8 2
            11    9  10 1
            12    6  11 2
            13    3  12 2
            14    7  13 1 #Down
            15   13  14 2
            16   14  15 1
            17   15  16 2
            18   16  17 1
            19   17  18 2
            20   13  18 1
            21   16  19 1
            22   19  20 1
            23   20  21 1
            24   17  21 1
            25    1  22 1
            26   10  23 1
            27   23  24 1
            28   24  25 1
            29   25   8 1
            30   23  26 2
            31   26  27 1
            32   27  28 2
            33   28  29 1
            34   24  29 2

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Ontology (10)   
   KEGG BRITE (10)   
Disease (1)   
   KEGG DISEASE (1)   
Drug (4)   
   KEGG DGROUP (2)   
   LigandBox (1)   
   SIDER (1)   
Chemical substance (6)   
   PubChem (1)   
   ChEBI (1)   
   HMDB (1)   
   HSDB (1)   
   NIKKAJI (1)   
   PDB-CCD (1)   
Gene (2)   
   KEGG ORTHOLOGY (1)   
   KEGG GENES (1)   
All databases (23)   

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