sildenafil Indications/Contra | FAERs-F | FAERs-M | Orange Bk | BioActivity |

Stem definitionDrug idCAS RN
inhibitors of phosphodiesterase PDE5 with vasodilator action 2441 139755-83-2

Description:

MoleculeDescription

Molfile Inchi Smiles

Synonyms:

  • mysildecard
  • sildenafil
  • sildenafil citrate
  • revatio
A PHOSPHODIESTERASE TYPE-5 INHIBITOR; VASODILATOR AGENT and UROLOGICAL AGENT that is used in the treatment of ERECTILE DYSFUNCTION and PRIMARY PULMONARY HYPERTENSION.
  • Molecular weight: 474.58
  • Formula: C22H30N6O4S
  • CLOGP: 1.98
  • LIPINSKI: 0
  • HAC: 10
  • HDO: 1
  • TPSA: 109.13
  • ALOGS: -3.01
  • ROTB: 6
  • Status: OFP
    • Legend:
    OFP - off patent
    OFM - off market
    ONP - on patent

Drug dosage:

DoseUnitRoute
50 mg O

ADMET properties:

PropertyValueReference
BDDCS (Biopharmaceutical Drug Disposition Classification System) 1 Benet LZ, Broccatelli F, Oprea TI
S (Water solubility) 3.50 mg/mL Benet LZ, Broccatelli F, Oprea TI
EoM (Fraction excreted unchanged in urine) 7.50 % Benet LZ, Broccatelli F, Oprea TI
MRTD (Maximum Recommended Therapeutic Daily Dose) 3.52 µM/kg/day Contrera JF, Matthews EJ, Kruhlak NL, Benz RD
BA (Bioavailability) 38 % Kim MT, Sedykh A, Chakravarti SK, Saiakhov RD, Zhu H
Vd (Volume of distribution) 1.36 L/kg Lombardo F, Berellini G, Obach RS
CL (Clearance) 9 mL/min/kg Lombardo F, Berellini G, Obach RS
fu (Fraction unbound in plasma) 0.04 % Lombardo F, Berellini G, Obach RS
t_half (Half-life) 2.20 hours Lombardo F, Berellini G, Obach RS

Approvals:

DateAgencyCompanyOrphan
March 27, 1998 FDA PFIZER IRELAND

FDA Adverse Event Reporting System (Female)

MedDRA adverse event termLikelihood ratioLikelihood ratio thresholdPatients taking drug having adverse eventPatients taking drug not having adverse eventPatients not taking drug having adverse eventPatients not taking drug not having adverse event
Death 1731.48 30.20 659 3446 80809 2273171
Pulmonary hypertension 1251.05 30.20 280 3825 4838 2349142
Dyspnoea 966.89 30.20 434 3671 78299 2275681
Right ventricular failure 712.77 30.20 153 3952 2120 2351860
Condition aggravated 689.47 30.20 265 3840 31714 2322266
Product use issue 683.08 30.20 207 3898 11962 2342018
Pulmonary arterial hypertension 627.66 30.20 154 3951 3956 2350024
Headache 451.38 30.20 263 3842 79916 2274064
Hypotension 399.97 30.20 181 3924 32255 2321725
Fluid retention 394.86 30.20 120 3985 6926 2347054
Pneumonia 364.57 30.20 194 3911 49102 2304878
Malaise 361.90 30.20 201 3904 55384 2298596
Cardiac failure 327.46 30.20 119 3986 11975 2342005
Oxygen saturation decreased 267.75 30.20 91 4014 7495 2346485
Respiratory failure 257.54 30.20 103 4002 13425 2340555
Disease progression 253.93 30.20 109 3996 16986 2336994
Cardiac failure congestive 243.52 30.20 104 4001 15997 2337983
Oedema peripheral 231.57 30.20 113 3992 23650 2330330
Dizziness 230.89 30.20 154 3951 58511 2295469
Oedema 223.35 30.20 86 4019 10117 2343863
Diarrhoea 216.17 30.20 170 3935 83394 2270586
Hypoxia 209.09 30.20 72 4033 6155 2347825
Cough 207.04 30.20 117 3988 33000 2320980
Fatigue 205.24 30.20 166 3939 84707 2269273
Drug ineffective 203.10 30.20 178 3927 101446 2252534
Fall 198.07 30.20 129 3976 46970 2307010
Nausea 182.18 30.20 175 3930 112014 2241966
Syncope 178.58 30.20 85 4020 16790 2337190
Dyspnoea exertional 176.05 30.20 62 4043 5658 2348322
Off label use 173.53 30.20 142 3963 73456 2280524
Pulmonary oedema 171.58 30.20 65 4040 7298 2346682
Flushing 170.49 30.20 74 4031 11797 2342183
Chest pain 163.87 30.20 95 4010 28042 2325938
Fluid overload 162.03 30.20 49 4056 2757 2351223
Prescribed overdose 159.52 30.20 44 4061 1780 2352200
Nasal congestion 153.32 30.20 59 4046 6907 2347073
Pain in jaw 147.52 30.20 56 4049 6316 2347664
Epistaxis 140.48 30.20 61 4044 9718 2344262
Pulmonary arterial pressure increased 140.10 30.20 30 4075 404 2353576
Chronic obstructive pulmonary disease 127.92 30.20 52 4053 7025 2346955
Deafness 125.73 30.20 40 4065 2661 2351319
Pleural effusion 120.95 30.20 58 4047 11610 2342370
Asthenia 119.70 30.20 95 4010 46831 2307149
Cardiac disorder 119.50 30.20 51 4054 7782 2346198
Pain 118.23 30.20 106 3999 61751 2292229
Blood pressure decreased 114.59 30.20 52 4053 9184 2344796
Vomiting 112.45 30.20 110 3995 71492 2282488
Weight decreased 109.91 30.20 74 4031 28297 2325683
Cardiac arrest 107.42 30.20 58 4047 14872 2339108
Sepsis 103.70 30.20 61 4044 18427 2335553
Myalgia 102.86 30.20 66 4039 23267 2330713
Palpitations 99.45 30.20 57 4048 16399 2337581
Anaemia 98.53 30.20 75 4030 34717 2319263
Renal failure 94.03 30.20 56 4049 17293 2336687
Nasopharyngitis 93.78 30.20 61 4044 21995 2331985
Product use in unapproved indication 90.41 30.20 47 4058 11153 2342827
Scleroderma 90.20 30.20 24 4081 844 2353136
Product dose omission 90.12 30.20 74 4031 38183 2315797
Feeling abnormal 90.06 30.20 61 4044 23520 2330460
Influenza 86.64 30.20 48 4057 12930 2341050
Visual impairment 85.45 30.20 46 4059 11709 2342271
Peripheral swelling 83.05 30.20 52 4053 17545 2336435
General physical health deterioration 77.52 30.20 46 4059 14093 2339887
Hospitalisation 75.43 30.20 46 4059 14807 2339173
Pain in extremity 75.40 30.20 70 4035 42470 2311510
Hypoacusis 75.25 30.20 29 4076 3396 2350584
Heart rate increased 73.91 30.20 41 4064 11064 2342916
Productive cough 72.47 30.20 32 4073 5289 2348691
Interstitial lung disease 72.39 30.20 36 4069 7776 2346204
Premature delivery 69.96 30.20 27 4078 3173 2350807
Atrial fibrillation 68.27 30.20 42 4063 13726 2340254
Acute respiratory failure 67.73 30.20 26 4079 3012 2350968
Lung disorder 67.73 30.20 32 4073 6180 2347800
Pericardial effusion 67.43 30.20 28 4077 3981 2349999
Weight increased 67.24 30.20 50 4055 22287 2331693
Pre-existing condition improved 66.09 30.20 17 4088 522 2353458
Back pain 65.76 30.20 57 4048 31602 2322378
Abdominal distension 65.36 30.20 37 4068 10374 2343606
Gastrointestinal haemorrhage 64.38 30.20 39 4066 12396 2341584
Drug interaction 63.60 30.20 54 4051 29109 2324871
Catheter site infection 62.73 30.20 17 4088 641 2353339
Cardio-respiratory arrest 61.48 30.20 34 4071 9112 2344868
Multiple organ dysfunction syndrome 61.44 30.20 32 4073 7609 2346371
Abdominal discomfort 59.17 30.20 42 4063 17414 2336566
Vision blurred 58.47 30.20 39 4066 14629 2339351
Decreased appetite 57.93 30.20 51 4054 28840 2325140
Swelling 56.95 30.20 40 4065 16310 2337670
Haemoptysis 53.85 30.20 23 4082 3504 2350476
Orthopnoea 53.67 30.20 15 4090 635 2353345
Intentional product use issue 53.39 30.20 23 4082 3579 2350401
Pulmonary veno-occlusive disease 51.92 30.20 11 4094 140 2353840
Gait disturbance 51.71 30.20 43 4062 22502 2331478
Therapy non-responder 51.39 30.20 29 4076 8075 2345905
Chronic kidney disease 50.43 30.20 23 4082 4095 2349885
Deafness unilateral 50.24 30.20 14 4091 586 2353394
Catheter site erythema 49.22 30.20 14 4091 632 2353348
Chest discomfort 49.18 30.20 35 4070 14560 2339420
Unevaluable event 48.89 30.20 29 4076 8862 2345118
Therapeutic response unexpected 48.67 30.20 22 4083 3837 2350143
Abdominal pain upper 48.31 30.20 41 4064 22059 2331921
Hip fracture 47.47 30.20 23 4082 4689 2349291
Ascites 46.50 30.20 24 4081 5596 2348384
Upper respiratory tract infection 46.41 30.20 28 4077 8823 2345157
Pneumonia aspiration 46.14 30.20 21 4084 3721 2350259
Device related infection 45.65 30.20 20 4085 3239 2350741
Haemorrhage 45.54 30.20 30 4075 11009 2342971
Infusion site pain 45.21 30.20 15 4090 1137 2352843
Arthralgia 44.93 30.20 60 4045 54225 2299755
Lung transplant 44.67 30.20 13 4092 637 2353343
Pulmonary haemorrhage 44.30 30.20 15 4090 1210 2352770
Bronchitis 44.17 30.20 32 4073 13682 2340298
Gastritis hypertrophic 44.01 30.20 7 4098 13 2353967
Dyspepsia 43.67 30.20 28 4077 9816 2344164
Acute kidney injury 43.53 30.20 43 4062 28079 2325901
Myocardial infarction 43.04 30.20 36 4069 18977 2335003
Pulmonary fibrosis 42.91 30.20 18 4087 2622 2351358
Hypertension 42.65 30.20 42 4063 27319 2326661
Rhinorrhoea 42.64 30.20 25 4080 7475 2346505
Drug intolerance 41.90 30.20 31 4074 13686 2340294
Right ventricular dilatation 41.70 30.20 8 4097 59 2353921
Loss of consciousness 41.38 30.20 35 4070 18732 2335248
Urinary tract infection 41.27 30.20 43 4062 29899 2324081
Thrombocytopenia 40.79 30.20 35 4070 19096 2334884
Sinus congestion 40.56 30.20 16 4089 1991 2351989
End stage renal disease 39.48 30.20 11 4094 460 2353520
Pyrexia 39.37 30.20 56 4049 53652 2300328
Catheterisation cardiac 39.26 30.20 12 4093 697 2353283
Pulseless electrical activity 38.97 30.20 13 4092 1002 2352978
Haemoglobin decreased 38.28 30.20 33 4072 18118 2335862
Sudden death 38.19 30.20 15 4090 1845 2352135
Product administered to patient of inappropriate age 38.07 30.20 12 4093 772 2353208
Cardiogenic shock 37.22 30.20 16 4089 2475 2351505
Catheter site pain 37.07 30.20 11 4094 577 2353403
Sinusitis 36.79 30.20 31 4074 16495 2337485
Body height decreased 36.41 30.20 13 4092 1228 2352752
Respiratory arrest 36.19 30.20 21 4084 6157 2347823
Dehydration 36.19 30.20 35 4070 22260 2331720
Exercise tolerance decreased 36.00 30.20 11 4094 638 2353342
Platelet count decreased 35.90 30.20 30 4075 15783 2338197
Right ventricular systolic pressure increased 35.25 30.20 7 4098 63 2353917
Anxiety 34.90 30.20 39 4066 29320 2324660
Cor pulmonale 34.45 30.20 9 4096 294 2353686
Pulmonary congestion 33.96 30.20 14 4091 1951 2352029
Hepatic function abnormal 33.82 30.20 20 4085 6072 2347908
Renal disorder 33.80 30.20 18 4087 4470 2349510
Insomnia 33.68 30.20 36 4069 25751 2328229
Blood creatinine increased 32.60 30.20 24 4081 10509 2343471
Swelling face 32.51 30.20 23 4082 9470 2344510
Infection 32.49 30.20 30 4075 17999 2335981
Immobile 32.41 30.20 10 4095 599 2353381
Migraine 32.35 30.20 24 4081 10629 2343351
Expired product administered 32.27 30.20 12 4093 1272 2352708
Oxygen consumption increased 31.73 30.20 9 4096 402 2353578
Blindness 31.52 30.20 16 4089 3602 2350378
Constipation 31.48 30.20 32 4073 21597 2332383
Generalised oedema 31.25 30.20 14 4091 2389 2351591
Sneezing 31.23 30.20 14 4091 2392 2351588
Concomitant disease progression 31.02 30.20 9 4096 436 2353544
Device related sepsis 31.00 30.20 9 4096 437 2353543
Cardiac failure chronic 30.94 30.20 9 4096 440 2353540
Visual field defect 30.33 30.20 12 4093 1504 2352476

FDA Adverse Event Reporting System (Male)

MedDRA adverse event termLikelihood ratioLikelihood ratio thresholdPatients taking drug having adverse eventPatients taking drug not having adverse eventPatients not taking drug having adverse eventPatients not taking drug not having adverse event
Drug ineffective 2861.03 27.42 1150 5298 62651 1677682
Death 678.51 27.42 500 5948 86943 1653390
Optic ischaemic neuropathy 676.20 27.42 135 6313 404 1739929
Headache 546.27 27.42 310 6138 34066 1706267
Pulmonary hypertension 457.94 27.42 135 6313 2607 1737726
Cyanopsia 408.77 27.42 70 6378 51 1740282
Visual impairment 392.91 27.42 147 6301 6071 1734262
Vision blurred 332.95 27.42 142 6306 8281 1732052
Blindness unilateral 331.94 27.42 84 6364 882 1739451
Erectile dysfunction 327.14 27.42 118 6330 4379 1735954
Flushing 323.51 27.42 128 6320 6151 1734182
Erection increased 301.47 27.42 63 6385 250 1740083
Condition aggravated 297.98 27.42 177 6271 20973 1719360
Blindness 255.51 27.42 87 6361 2709 1737624
Product use issue 244.23 27.42 115 6333 8456 1731877
Visual field defect 242.28 27.42 68 6380 1088 1739245
Nasal congestion 231.24 27.42 83 6365 3028 1737305
Dyspnoea 226.61 27.42 215 6233 51844 1688489
Hypotension 223.01 27.42 168 6280 29486 1710847
Cardiac failure 218.73 27.42 121 6327 12481 1727852
Intentional product misuse 216.60 27.42 101 6347 7257 1733076
Priapism 213.51 27.42 65 6383 1399 1738934
Visual acuity reduced 181.81 27.42 74 6374 3814 1736519
Right ventricular failure 164.98 27.42 51 6397 1156 1739177
Pulmonary arterial hypertension 163.76 27.42 54 6394 1516 1738817
Drug interaction 161.95 27.42 136 6312 27822 1712511
Therapeutic product effect decreased 159.51 27.42 78 6370 6219 1734114
Deafness 159.49 27.42 56 6392 1910 1738423
Therapeutic product effect incomplete 154.72 27.42 73 6375 5375 1734958
Prostate cancer 153.30 27.42 69 6379 4557 1735776
Syncope 152.15 27.42 100 6348 14069 1726264
Cerebrovascular accident 151.52 27.42 109 6339 17757 1722576
Suspected counterfeit product 148.27 27.42 31 6417 123 1740210
Malaise 145.34 27.42 131 6317 29434 1710899
Retinal vein occlusion 144.18 27.42 37 6411 411 1739922
Dizziness 132.26 27.42 133 6315 34228 1706105
Blindness transient 128.29 27.42 36 6412 574 1739759
Pre-existing condition improved 119.62 27.42 29 6419 250 1740083
Cardiac arrest 118.81 27.42 90 6358 15840 1724493
Therapeutic response unexpected 116.23 27.42 47 6401 2377 1737956
Retinal artery occlusion 114.47 27.42 30 6418 364 1739969
Chest pain 113.33 27.42 96 6352 19818 1720515
Tinnitus 113.32 27.42 50 6398 3145 1737188
Product quality issue 106.87 27.42 59 6389 6034 1734299
Blood pressure decreased 102.09 27.42 62 6386 7584 1732749
Completed suicide 99.74 27.42 82 6366 16230 1724103
Chromatopsia 99.51 27.42 21 6427 88 1740245
Myocardial infarction 96.82 27.42 101 6347 27073 1713260
Deafness unilateral 94.64 27.42 27 6421 458 1739875
Fall 93.12 27.42 99 6349 27115 1713218
Expired product administered 91.38 27.42 29 6419 717 1739616
Palpitations 90.30 27.42 55 6393 6759 1733574
Cardiac failure congestive 89.67 27.42 75 6373 15195 1725138
Atrial fibrillation 88.28 27.42 74 6374 15037 1725296
Peyronie's disease 86.51 27.42 21 6427 182 1740151
Intentional product use issue 85.10 27.42 39 6409 2680 1737653
Hypoacusis 84.84 27.42 38 6410 2475 1737858
Cardiac disorder 84.18 27.42 55 6393 7636 1732697
Blood testosterone decreased 81.60 27.42 29 6419 1023 1739310
Self-medication 81.42 27.42 26 6422 656 1739677
Feeling abnormal 80.78 27.42 62 6386 11104 1729229
Hypertension 75.95 27.42 76 6372 19372 1720961
Blood cholesterol increased 75.10 27.42 37 6411 2989 1737344
Oxygen saturation decreased 73.11 27.42 45 6403 5630 1734703
Oedema peripheral 72.48 27.42 67 6381 15483 1724850
Onychomycosis 72.39 27.42 20 6428 300 1740033
Loss of consciousness 71.09 27.42 65 6383 14810 1725523
Macular degeneration 70.45 27.42 22 6426 515 1739818
Retinal haemorrhage 70.43 27.42 27 6421 1182 1739151
Renal failure 68.72 27.42 73 6375 19944 1720389
Hypoxia 68.58 27.42 44 6404 5919 1734414
Off label use 68.46 27.42 101 6347 38470 1701863
Dyspepsia 67.99 27.42 41 6407 4944 1735389
Pneumonia 66.76 27.42 110 6338 46072 1694261
Drug ineffective for unapproved indication 66.05 27.42 29 6419 1800 1738533
Back pain 64.98 27.42 65 6383 16548 1723785
Ischaemic stroke 64.27 27.42 34 6414 3188 1737145
Acute myocardial infarction 62.78 27.42 48 6400 8539 1731794
Insomnia 62.40 27.42 63 6385 16213 1724120
Cataract 60.83 27.42 32 6416 2966 1737367
Penis disorder 60.45 27.42 18 6430 357 1739976
Gastrooesophageal reflux disease 60.24 27.42 37 6411 4610 1735723
Pulmonary oedema 59.88 27.42 42 6406 6544 1733789
Drug hypersensitivity 58.78 27.42 59 6389 15076 1725257
Spinal cord infarction 58.60 27.42 13 6435 72 1740261
Nausea 58.51 27.42 110 6338 51086 1689247
Macrophages increased 57.94 27.42 10 6438 8 1740325
Optic atrophy 56.60 27.42 16 6432 262 1740071
Dyspnoea exertional 56.16 27.42 34 6414 4127 1736206
Papilloedema 54.80 27.42 19 6429 622 1739711
Ventricular fibrillation 54.73 27.42 29 6419 2727 1737606
Coronary artery occlusion 53.50 27.42 26 6422 2037 1738296
Heart rate increased 53.40 27.42 39 6409 6471 1733862
Blood pressure increased 53.33 27.42 48 6400 10705 1729628
Photopsia 52.28 27.42 17 6431 455 1739878
Chronic obstructive pulmonary disease 51.88 27.42 37 6411 5916 1734417
Cardio-respiratory arrest 51.12 27.42 44 6404 9249 1731084
Eye pain 50.49 27.42 26 6422 2305 1738028
Product counterfeit 49.84 27.42 12 6436 100 1740233
Scar 48.97 27.42 19 6429 859 1739474
Visual brightness 48.80 27.42 10 6438 35 1740298
Painful erection 48.63 27.42 12 6436 112 1740221
Fluid retention 48.53 27.42 30 6418 3779 1736554
Glaucoma 47.98 27.42 20 6428 1091 1739242
Optic disc disorder 47.95 27.42 10 6438 39 1740294
Cardiomegaly 47.60 27.42 25 6423 2309 1738024
Retinal vascular occlusion 47.55 27.42 10 6438 41 1740292
Ejaculation disorder 47.53 27.42 16 6432 478 1739855
Chest discomfort 47.14 27.42 38 6410 7293 1733040
Therapeutic product effect delayed 46.85 27.42 14 6434 281 1740052
Incorrect dose administered 46.79 27.42 38 6410 7371 1732962
Pain in extremity 45.84 27.42 57 6391 18415 1721918
Sudden death 44.84 27.42 26 6422 2914 1737419
Blood ethanol increased 44.25 27.42 10 6438 61 1740272
Amnesia 44.00 27.42 31 6417 4860 1735473
Retinal detachment 43.96 27.42 19 6429 1134 1739199
Pulmonary arterial pressure increased 43.80 27.42 12 6436 174 1740159
Circulatory collapse 43.39 27.42 27 6421 3440 1736893
Toxicity to various agents 42.80 27.42 70 6378 29071 1711262
Photophobia 42.72 27.42 19 6429 1215 1739118
Depression 42.26 27.42 52 6396 16617 1723716
Haemoptysis 41.78 27.42 30 6418 4846 1735487
Pulmonary congestion 41.61 27.42 21 6427 1784 1738549
Transient global amnesia 41.57 27.42 10 6438 83 1740250
Weight decreased 40.88 27.42 60 6388 22693 1717640
Disease progression 40.81 27.42 52 6396 17211 1723122
Nasopharyngitis 40.64 27.42 40 6408 9970 1730363
Overdose 40.58 27.42 51 6397 16650 1723683
Ventilation perfusion mismatch 39.73 27.42 8 6440 25 1740308
Cholestasis 39.56 27.42 26 6422 3639 1736694
Feeling hot 39.25 27.42 24 6424 2963 1737370
Respiratory arrest 39.10 27.42 31 6417 5808 1734525
Chorioretinopathy 38.66 27.42 13 6435 387 1739946
Diabetes mellitus 38.57 27.42 33 6415 6875 1733458
Weight increased 38.18 27.42 41 6407 11316 1729017
Deafness neurosensory 37.95 27.42 14 6434 550 1739783
Pain 37.74 27.42 63 6385 26594 1713739
Hot flush 37.63 27.42 22 6426 2503 1737830
Diplopia 37.27 27.42 22 6426 2548 1737785
Macular oedema 36.28 27.42 15 6433 801 1739532
Fluid overload 36.27 27.42 20 6428 2035 1738298
Arrhythmia 36.18 27.42 30 6418 5986 1734347
Vomiting 36.07 27.42 76 6372 38239 1702094
Retinopathy 35.57 27.42 13 6435 497 1739836
Epistaxis 35.23 27.42 34 6414 8272 1732061
Implant site extravasation 35.07 27.42 10 6438 169 1740164
Cough 35.02 27.42 51 6397 19146 1721187
Retinal disorder 34.84 27.42 11 6437 267 1740066
Respiratory failure 34.76 27.42 44 6404 14461 1725872
Hepatic failure 34.60 27.42 29 6419 5874 1734459
Epstein-Barr virus antibody positive 34.57 27.42 9 6439 106 1740227
Sudden hearing loss 34.49 27.42 11 6437 276 1740057
Heart rate irregular 34.14 27.42 18 6430 1674 1738659
Colour blindness 33.83 27.42 9 6439 116 1740217
Prescribed overdose 33.38 27.42 18 6430 1752 1738581
Ocular vascular disorder 33.08 27.42 8 6440 68 1740265
Fatigue 32.85 27.42 87 6361 50694 1689639
Prescription drug used without a prescription 32.60 27.42 10 6438 220 1740113
Body height decreased 32.37 27.42 12 6436 478 1739855
Abdominal pain upper 32.29 27.42 37 6411 10964 1729369
Acute macular outer retinopathy 31.91 27.42 5 6443 0 1740333
Alcohol poisoning 31.85 27.42 12 6436 500 1739833
Hyperhidrosis 31.70 27.42 39 6409 12449 1727884
Ventricular tachycardia 31.69 27.42 23 6425 3775 1736558
Product use in unapproved indication 31.64 27.42 34 6414 9388 1730945
Stress 31.62 27.42 20 6428 2621 1737712
Product taste abnormal 31.58 27.42 11 6437 365 1739968
Left ventricular failure 31.57 27.42 13 6435 687 1739646
Cerebral infarction 31.38 27.42 26 6422 5183 1735150
Tachycardia 31.36 27.42 39 6409 12589 1727744
Gait disturbance 31.25 27.42 39 6409 12631 1727702
Ocular hyperaemia 31.24 27.42 18 6430 1992 1738341
Cerebral haemorrhage 31.06 27.42 28 6420 6249 1734084
Abdominal discomfort 30.90 27.42 33 6415 9048 1731285
Fracture of penis 30.67 27.42 8 6440 95 1740238
Conjunctival hyperaemia 30.64 27.42 12 6436 556 1739777
Intentional overdose 29.93 27.42 30 6418 7640 1732693
Type 2 diabetes mellitus 29.68 27.42 17 6431 1861 1738472
Anorgasmia 29.56 27.42 9 6439 193 1740140
Maculopathy 29.45 27.42 10 6438 307 1740026
Penile pain 29.41 27.42 10 6438 308 1740025
Atrial flutter 29.15 27.42 17 6431 1925 1738408
Alcohol use 29.13 27.42 13 6435 838 1739495
Cardiac failure chronic 29.11 27.42 12 6436 636 1739697
Transient ischaemic attack 29.03 27.42 24 6424 4767 1735566
Neoplasm malignant 28.97 27.42 23 6425 4316 1736017
Scratch 28.67 27.42 11 6437 482 1739851
Nodular melanoma 28.65 27.42 6 6442 24 1740309
Arthritis 28.55 27.42 22 6426 3953 1736380
Herpes simplex encephalitis 28.40 27.42 7 6441 65 1740268
Road traffic accident 28.16 27.42 21 6427 3592 1736741
Cardiogenic shock 27.93 27.42 18 6430 2436 1737897
Dysuria 27.86 27.42 21 6427 3651 1736682
Retinal toxicity 27.80 27.42 8 6440 140 1740193

Pharmacologic Action:

SourceCodeDescription
ATC G04BE03 GENITO URINARY SYSTEM AND SEX HORMONES
UROLOGICALS
UROLOGICALS
Drugs used in erectile dysfunction
MeSH PA D002317 Cardiovascular Agents
MeSH PA D004791 Enzyme Inhibitors
MeSH PA D058986 Phosphodiesterase 5 Inhibitors
MeSH PA D010726 Phosphodiesterase Inhibitors
CHEBI has role CHEBI:35620 vasodilator agent
FDA EPC N0000175599 Phosphodiesterase 5 Inhibitor
MeSH PA D064804 Urological Agents
MeSH PA D014665 Vasodilator Agents

Drug Use (View source of the data)

DiseaseRelationSNOMED_IDDOID
Pulmonary arterial hypertension indication 11399002
Impotence indication 397803000
Induratio penis plastica contraindication 1335005 DOID:8616
Priapism contraindication 6273006 DOID:9286
Hearing loss contraindication 15188001
Myocardial infarction contraindication 22298006 DOID:5844
Fibrosis of corpus cavernosum contraindication 32608004
Dehydration contraindication 34095006
Low blood pressure contraindication 45007003
Chronic heart failure contraindication 48447003
Acute nephropathy contraindication 58574008
Hepatic failure contraindication 59927004
Aortic valve stenosis contraindication 60573004 DOID:1712
Pulmonary veno-occlusive disease contraindication 89420002 DOID:5453
Leukemia, disease contraindication 93143009 DOID:1240
Multiple myeloma contraindication 109989006 DOID:9538
Hb SS disease contraindication 127040003 DOID:10923
Cerebrovascular accident contraindication 230690007
Penis bent contraindication 249247007
Esophageal dysmotility contraindication 266434009 DOID:9192
Idiopathic hypertrophic subaortic stenosis contraindication 360465008
Acute coronary syndrome contraindication 394659003
Anterior ischemic optic neuropathy contraindication 404659001
Hypertensive urgency contraindication 443482000
Pigmentary Retinopathy contraindication
Severe Autonomic Insufficiency contraindication
Hereditary Degeneration of Retina contraindication
Life-Threatening Cardiac Arrhythmias contraindication

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation levelDissociation constantType (acidic/basic)
pKa1 9.35 acidic
pKa2 7.72 Basic
pKa3 3.61 Basic
pKa4 2.92 Basic

Orange Book patent data (new drug applications)

None

Orange Book exclusivity data (new drug applications)

None

Bioactivity Summary:

TargetClassPharosUniProtActionTypeActivity value
(-log[M])		Mechanism
action		Bioact sourceMoA source
cGMP-specific 3',5'-cyclic phosphodiesterase Enzyme INHIBITOR IC50 9 IUPHAR CHEMBL
Adenosine receptor A1 GPCR Ki 6.06 DRUG MATRIX
Rod cGMP-specific 3',5'-cyclic phosphodiesterase subunit alpha Enzyme WOMBAT-PK
Solute carrier organic anion transporter family member 1B3 Transporter INHIBITOR IC50 6.10 IUPHAR
High affinity cAMP-specific 3',5'-cyclic phosphodiesterase 7A Enzyme IC50 5.33 CHEMBL
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A Enzyme IC50 5.47 CHEMBL
Phosphodiesterase 4 Enzyme IC50 5.11 CHEMBL
Potassium voltage-gated channel subfamily H member 2 Ion channel IC50 5.48 CHEMBL
cAMP-specific 3',5'-cyclic phosphodiesterase 4D Enzyme IC50 4.70 CHEMBL
Multidrug resistance-associated protein 5 Transporter Ki 5.92 CHEMBL
Adenosine receptor A2a GPCR Ki 6.70 CHEMBL
Cone cGMP-specific 3',5'-cyclic phosphodiesterase subunit alpha' Enzyme IC50 7.41 CHEMBL
Phosphodiesterase 1 Enzyme IC50 6.57 CHEMBL
Phosphodiesterase 3 Enzyme IC50 5.15 CHEMBL
Dual 3',5'-cyclic-AMP and -GMP phosphodiesterase 11A Enzyme IC50 5.64 CHEMBL
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Enzyme IC50 5.51 CHEMBL
High affinity cAMP-specific and IBMX-insensitive 3',5'-cyclic phosphodiesterase 8A Enzyme IC50 4 CHEMBL
cGMP-dependent 3',5'-cyclic phosphodiesterase Enzyme IC50 4.20 CHEMBL
Alpha-1B adrenergic receptor GPCR Ki 6.09 DRUG MATRIX
cGMP-specific 3',5'-cyclic phosphodiesterase Enzyme Ki 8.74 CHEMBL
Uncharacterized protein Enzyme IC50 5.04 CHEMBL
cGMP-specific 3',5'-cyclic phosphodiesterase Enzyme IC50 9 CHEMBL
Phosphodiesterase 1 Enzyme IC50 6.59 CHEMBL
Indoleamine 2,3-dioxygenase 2 Enzyme IC50 5.35 CHEMBL
Rod cGMP-specific 3',5'-cyclic phosphodiesterase subunit alpha Enzyme IC50 6.85 CHEMBL
Phosphodiesterase 1 Enzyme IC50 6.40 CHEMBL
Phosphodiesterase 6 Enzyme IC50 7.70 CHEMBL
Phosphodiesterase 2A Unclassified IC50 4.37 CHEMBL
Phosphodiesterase 4 Enzyme IC50 5.34 CHEMBL
Cone cGMP-specific 3',5'-cyclic phosphodiesterase subunit alpha' Enzyme IC50 7.48 CHEMBL
cGMP-specific 3',5'-cyclic phosphodiesterase Enzyme IC50 8.22 CHEMBL

External reference:

IDSource
D000068677 MESH_DESCRIPTOR_UI
4024110 VUID
N0000022115 NUI
C0529793 UMLSCUI
D02229 KEGG_DRUG
3M7OB98Y7H UNII
7374 INN_ID
109123009 SNOMEDCT_US
147641 MMSL
4024110 VANDF
26866 MMSL
007448 NDDF
d04299 MMSL
136411 RXNORM
372572000 SNOMEDCT_US
171599-83-0 SECONDARY_CAS_RN
CHEMBL192 ChEMBL_ID
DB00203 DRUGBANK_ID
CHEMBL1737 ChEMBL_ID
VIA PDB_CHEM_ID
CHEBI:9139 CHEBI
135398744 PUBCHEM_CID
4743 IUPHAR_LIGAND_ID

Pharmaceutical products:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
Revatio HUMAN PRESCRIPTION DRUG LABEL 1 0069-0336 POWDER, FOR SUSPENSION 10 mg ORAL NDA 19 sections
Revatio HUMAN PRESCRIPTION DRUG LABEL 1 0069-0338 INJECTION, SOLUTION 0.80 mg INTRAVENOUS NDA 19 sections
Revatio HUMAN PRESCRIPTION DRUG LABEL 1 0069-4190 TABLET, FILM COATED 20 mg ORAL NDA 19 sections
Viagra HUMAN PRESCRIPTION DRUG LABEL 1 0069-4200 TABLET, FILM COATED 25 mg ORAL NDA 19 sections
Viagra HUMAN PRESCRIPTION DRUG LABEL 1 0069-4210 TABLET, FILM COATED 50 mg ORAL NDA 19 sections
Viagra HUMAN PRESCRIPTION DRUG LABEL 1 0069-4220 TABLET, FILM COATED 100 mg ORAL NDA 19 sections
Sildenafil HUMAN PRESCRIPTION DRUG LABEL 1 0093-5341 TABLET, FILM COATED 25 mg ORAL ANDA 18 sections
Sildenafil HUMAN PRESCRIPTION DRUG LABEL 1 0093-5342 TABLET, FILM COATED 50 mg ORAL ANDA 18 sections
Sildenafil HUMAN PRESCRIPTION DRUG LABEL 1 0093-5343 TABLET, FILM COATED 100 mg ORAL ANDA 18 sections
Sildenafil HUMAN PRESCRIPTION DRUG LABEL 1 0093-5517 TABLET, FILM COATED 20 mg ORAL ANDA 17 sections
Sildenafil HUMAN PRESCRIPTION DRUG LABEL 1 0179-0160 TABLET, FILM COATED 20 mg ORAL NDA authorized generic 19 sections
Sildenafil HUMAN PRESCRIPTION DRUG LABEL 1 0378-1657 TABLET, FILM COATED 20 mg ORAL ANDA 18 sections
Sildenafil HUMAN PRESCRIPTION DRUG LABEL 1 0378-1658 TABLET, FILM COATED 25 mg ORAL ANDA 18 sections
Sildenafil HUMAN PRESCRIPTION DRUG LABEL 1 0378-1659 TABLET, FILM COATED 50 mg ORAL ANDA 18 sections
Sildenafil HUMAN PRESCRIPTION DRUG LABEL 1 0378-1660 TABLET, FILM COATED 100 mg ORAL ANDA 18 sections
SILDENAFIL CITRATE HUMAN PRESCRIPTION DRUG LABEL 1 0904-6671 TABLET 20 mg ORAL ANDA 17 sections
SILDENAFIL CITRATE HUMAN PRESCRIPTION DRUG LABEL 1 13668-185 TABLET 20 mg ORAL ANDA 17 sections
SILDENAFIL CITRATE HUMAN PRESCRIPTION DRUG LABEL 1 13668-186 TABLET, FILM COATED 25 mg ORAL ANDA 18 sections
SILDENAFIL CITRATE HUMAN PRESCRIPTION DRUG LABEL 1 13668-187 TABLET, FILM COATED 50 mg ORAL ANDA 18 sections
SILDENAFIL CITRATE HUMAN PRESCRIPTION DRUG LABEL 1 13668-188 TABLET, FILM COATED 100 mg ORAL ANDA 18 sections
Sildenafil HUMAN PRESCRIPTION DRUG LABEL 1 17224-460 TABLET, FILM COATED 20 mg ORAL ANDA 17 sections
Sildenafil Citrate HUMAN PRESCRIPTION DRUG LABEL 1 17856-8100 TABLET, FILM COATED 20 mg ORAL ANDA 19 sections
Viagra HUMAN PRESCRIPTION DRUG LABEL 1 21695-157 TABLET, FILM COATED 50 mg ORAL NDA 13 sections
Viagra HUMAN PRESCRIPTION DRUG LABEL 1 21695-158 TABLET, FILM COATED 100 mg ORAL NDA 13 sections
Sildenafil Citrate HUMAN PRESCRIPTION DRUG LABEL 1 27241-067 TABLET, FILM COATED 25 mg ORAL ANDA 18 sections
Sildenafil Citrate HUMAN PRESCRIPTION DRUG LABEL 1 27241-068 TABLET, FILM COATED 50 mg ORAL ANDA 18 sections
Sildenafil Citrate HUMAN PRESCRIPTION DRUG LABEL 1 27241-069 TABLET, FILM COATED 100 mg ORAL ANDA 18 sections
Sildenafil HUMAN PRESCRIPTION DRUG LABEL 1 27241-124 TABLET 20 mg ORAL ANDA 18 sections
Sildenafil HUMAN PRESCRIPTION DRUG LABEL 1 27241-175 POWDER, FOR SUSPENSION 10 mg ORAL ANDA 17 sections
Sildenafil HUMAN PRESCRIPTION DRUG LABEL 1 31722-709 TABLET, FILM COATED 25 mg ORAL ANDA 18 sections