Entry

D02008                      Drug

Name

Tadalafil (JAN/USP/INN);
Adcirca (TN);
Cialis (TN);
Zalutia (TN)

Product

CIALIS (Aphena Pharma Solutions - Tennessee), ADCIRCA (Aphena Pharma Solutions - Tennessee), CIALIS (Aphena Pharma Solutions - Tennessee), TADLIQ (CMP Pharma), CIALIS (Eli Lilly and Company), ADCIRCA (United Therapeutics Corporation)

Generic

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 (A-S Medication Solutions), TADALAFIL (A-S Medication Solutions), TADALAFIL (A-S Medication Solutions), TADALAFIL (Accord Healthcare), TADALAFIL (Ajanta Pharma USA), TADALAFIL (Ajanta Pharma USA), TADALAFIL (Alembic Pharmaceuticals), TADALAFIL (Alembic Pharmaceuticals Limited), 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 (Aphena Pharma Solutions - Tennessee), TADALAFIL (Aphena Pharma Solutions - Tennessee), TADALAFIL (Aphena Pharma Solutions - Tennessee), TADALAFIL (Asclemed USA), TADALAFIL (Aurobindo Pharma Limited), TADALAFIL (Aurobindo Pharma Limited), TADALAFIL (AvKARE), ALYQ (AvKARE), TADALAFIL (AvKARE), TADALAFIL (AvPAK), TADALAFIL (Avkare), 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 (Bryant Ranch Prepack), 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 (Cadila Healthcare Limited), 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 (GLENMARK PHARMACEUTICALS), TADALAFIL (HEC Pharm USA), TADALAFIL (Lupin Pharmaceuticals), TADALAFIL (Lupin Pharmaceuticals), TADALAFIL (Macleods Pharmaceuticals Limited), TADALAFIL (Macleods Pharmaceuticals Limited), TADALAFIL (NIVAGEN PHARMACEUTICALS), TADALAFIL (NUCARE PHARMACEUTICALS), TADALAFIL (NorthStar RxLLC), 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 (NuCare Pharmaceuticals), TADALAFIL (NuCare Pharmaceuticals), TADALAFIL (PD-Rx Pharmaceuticals), TADALAFIL (PD-Rx 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 (Qilu Pharmaceutical), 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), ALYQ (Teva Pharmaceuticals USA), TADALAFIL (Torrent Pharmaceuticals Limited), TADALAFIL (Torrent Pharmaceuticals Limited), TADALAFIL (UNYTER ENTERPRISES), TADALAFIL (Unichem Pharmaceuticals (USA)), TADALAFIL (Unit Dose Services), TADALAFIL (VKT Pharma Private 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>

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)
    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