urapidil ๐Ÿถ Veterinary Use | Indications/Contra | FAERs-F | FAERs-M | Orange Bk | BioActivity |

Stem definitionDrug idCAS RN
vasodilators 2796 34661-75-1

Description:

MoleculeDescription

Molfile Inchi Smiles

Synonyms:

  • urapidil
  • ebrantil
  • eupressyl
  • mediatensyl
  • uraprene
  • uropidil
  • urapidil hydrochloride
  • urapidil HCl
  • Molecular weight: 387.48
  • Formula: C20H29N5O3
  • CLOGP: 2.25
  • LIPINSKI: 0
  • HAC: 8
  • HDO: 1
  • TPSA: 68.36
  • ALOGS: -2.86
  • ROTB: 7

Drug dosage:

DoseUnitRoute
0.12 g O
50 mg P

ADMET properties:

PropertyValueReference
BDDCS (Biopharmaceutical Drug Disposition Classification System) 1 Benet LZ, Broccatelli F, Oprea TI
S (Water solubility) 19 mg/mL Benet LZ, Broccatelli F, Oprea TI
EoM (Fraction excreted unchanged in urine) 15 % Benet LZ, Broccatelli F, Oprea TI
MRTD (Maximum Recommended Therapeutic Daily Dose) 6.64 ยตM/kg/day Contrera JF, Matthews EJ, Kruhlak NL, Benz RD
BA (Bioavailability) 78 % Kim MT, Sedykh A, Chakravarti SK, Saiakhov RD, Zhu H
Vd (Volume of distribution) 0.75 L/kg Lombardo F, Berellini G, Obach RS
CL (Clearance) 3.10 mL/min/kg Lombardo F, Berellini G, Obach RS
t_half (Half-life) 3.50 hours Lombardo F, Berellini G, Obach RS

Approvals:

DateAgencyCompanyOrphan
Jan. 1, 1981 YEAR INTRODUCED

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
Acute kidney injury 221.75 25.47 187 5650 263228 63219957
Hyponatraemia 143.00 25.47 102 5735 111798 63371387
Hyperkalaemia 139.23 25.47 77 5760 54126 63429059
Product prescribing error 98.05 25.47 48 5789 26241 63456944
Bradycardia 87.14 25.47 64 5773 73163 63410022
Mixed liver injury 64.78 25.47 22 5815 4713 63478472
Product monitoring error 61.85 25.47 21 5816 4495 63478690
Fall 58.51 25.47 118 5719 392216 63090969
Anaemia 58.46 25.47 100 5737 293330 63189855
Shock haemorrhagic 52.24 25.47 23 5814 9872 63473313
Pain 50.38 25.47 5 5832 740623 62742562
Hypotension 49.20 25.47 89 5748 272515 63210670
Patent ductus arteriosus 47.55 25.47 17 5820 4233 63478952
Ischaemic stroke 47.38 25.47 26 5811 17931 63465254
Haematoma 47.27 25.47 33 5804 34787 63448398
General physical health deterioration 45.91 25.47 73 5764 201329 63281856
Polyuria 45.57 25.47 20 5817 8522 63474663
Rhabdomyolysis 44.69 25.47 35 5802 43916 63439269
Diabetic metabolic decompensation 44.57 25.47 13 5824 1697 63481488
Labelled drug-drug interaction medication error 39.82 25.47 21 5816 13378 63469807
Renal impairment 38.57 25.47 44 5793 88311 63394874
Hyperlactacidaemia 38.04 25.47 13 5824 2836 63480349
Lactic acidosis 37.86 25.47 30 5807 38257 63444928
Walking disability 37.86 25.47 11 5826 1416 63481769
Acute generalised exanthematous pustulosis 37.61 25.47 19 5818 11080 63472105
Hypoglycaemia 37.09 25.47 36 5801 60029 63423156
Drug interaction 36.55 25.47 71 5766 229060 63254125
Resting tremor 34.09 25.47 9 5828 814 63482371
Pancreatic pseudoaneurysm 33.94 25.47 6 5831 78 63483107
Myoclonus 33.85 25.47 20 5817 15848 63467337
Premature baby 33.75 25.47 22 5815 20713 63462472
Bradyarrhythmia 33.60 25.47 11 5826 2104 63481081
Hypertensive crisis 31.91 25.47 19 5818 15267 63467918
Pyelonephritis 31.75 25.47 20 5817 17758 63465427
Haematoma muscle 31.21 25.47 9 5828 1128 63482057
Toxic encephalopathy 30.61 25.47 14 5823 6565 63476620
Haemorrhagic transformation stroke 30.48 25.47 9 5828 1226 63481959
Hepatocellular injury 30.44 25.47 23 5814 27358 63455827
Rash maculo-papular 29.42 25.47 24 5813 31872 63451313
Multiple organ dysfunction syndrome 27.75 25.47 30 5807 56722 63426463
Hypokalaemia 26.94 25.47 40 5797 103764 63379421
Left ventricular hypertrophy 26.91 25.47 12 5825 5303 63477882
Adenocarcinoma metastatic 26.12 25.47 5 5832 103 63483082
Metabolic acidosis 25.94 25.47 26 5811 45043 63438142
Hyperglycaemia 25.66 25.47 25 5812 41842 63441343
Agranulocytosis 25.50 25.47 20 5817 25114 63458071

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
Acute kidney injury 139.15 21.56 208 5579 304780 34646364
Toxic epidermal necrolysis 118.63 21.56 62 5725 21584 34929560
Coma 67.95 21.56 58 5729 45620 34905524
Rash maculo-papular 61.42 21.56 45 5742 28406 34922738
Hepatic cytolysis 61.29 21.56 35 5752 14461 34936683
Ureteric compression 60.33 21.56 13 5774 267 34950877
Eosinophilia 55.52 21.56 41 5746 26181 34924963
General physical health deterioration 50.35 21.56 82 5705 128187 34822957
Drug reaction with eosinophilia and systemic symptoms 49.23 21.56 42 5745 32970 34918174
Hyperkalaemia 49.23 21.56 59 5728 69330 34881814
Haematoma muscle 43.98 21.56 14 5773 1354 34949790
Hyperthermia 43.27 21.56 25 5762 10552 34940592
Pyelocaliectasis 42.34 21.56 13 5774 1117 34950027
Hypoglycaemia 39.62 21.56 47 5740 54593 34896551
Fungal endocarditis 35.74 21.56 9 5778 371 34950773
Leukocytosis 34.61 21.56 30 5757 24035 34927109
Postrenal failure 34.13 21.56 9 5778 446 34950698
Histology abnormal 32.55 21.56 8 5779 298 34950846
Anaemia 32.17 21.56 98 5689 233237 34717907
Blood pressure ambulatory increased 31.86 21.56 6 5781 60 34951084
Cardiac autonomic neuropathy 31.60 21.56 6 5781 63 34951081
Shock haemorrhagic 31.59 21.56 21 5766 11333 34939811
Agranulocytosis 30.88 21.56 28 5759 23793 34927351
Chylothorax 29.32 21.56 9 5778 772 34950372
Disturbance in attention 28.84 21.56 28 5759 25917 34925227
Cerebral haemorrhage 28.59 21.56 32 5755 34905 34916239
Retinal disorder 27.34 21.56 9 5778 968 34950176
Haematuria 26.72 21.56 37 5750 50029 34901115
Supine hypertension 26.45 21.56 7 5780 352 34950792
Altered state of consciousness 25.99 21.56 25 5762 22868 34928276
Pancytopenia 25.97 21.56 52 5735 95105 34856039
Drug interaction 25.79 21.56 89 5698 225857 34725287
Haematochezia 25.75 21.56 35 5752 46499 34904645
Hypotension 25.02 21.56 87 5700 221562 34729582
Death 24.74 21.56 18 5769 398031 34553113
Proteinuria 24.33 21.56 22 5765 18620 34932524
Drug ineffective 23.17 21.56 25 5762 456726 34494418
Metabolic acidosis 22.88 21.56 32 5755 43648 34907496
Hypoglycaemic encephalopathy 22.84 21.56 6 5781 293 34950851
Vascular purpura 22.08 21.56 9 5778 1769 34949375
Encephalopathy 21.75 21.56 28 5759 35291 34915853
Septic shock 21.71 21.56 41 5746 71793 34879351

FDA Adverse Event Reporting System (Geriatric)

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
Acute kidney injury 334.25 20.42 390 11057 519014 79213927
Hyperkalaemia 162.22 20.42 133 11314 114265 79618676
Hyponatraemia 112.56 20.42 133 11314 177715 79555226
Toxic epidermal necrolysis 106.44 20.42 71 11376 44510 79688431
Bradycardia 93.47 20.42 106 11341 135451 79597490
Product prescribing error 89.62 20.42 64 11383 44749 79688192
Rash maculo-papular 87.46 20.42 69 11378 56009 79676932
General physical health deterioration 86.16 20.42 147 11300 275091 79457850
Anaemia 85.01 20.42 193 11254 444822 79288119
Shock haemorrhagic 76.20 20.42 43 11404 20017 79712924
Hypoglycaemia 72.66 20.42 81 11366 101513 79631428
Haematoma muscle 72.05 20.42 23 11424 2592 79730349
Hepatic cytolysis 69.06 20.42 45 11402 27106 79705835
Hypotension 66.98 20.42 175 11272 440142 79292799
Fall 63.43 20.42 183 11264 487446 79245495
Ureteric compression 62.04 20.42 13 11434 270 79732671
Pain 61.71 20.42 13 11434 703789 79029152
Eosinophilia 60.59 20.42 51 11396 45294 79687647
Drug interaction 59.05 20.42 161 11286 415022 79317919
Drug reaction with eosinophilia and systemic symptoms 57.98 20.42 58 11389 64186 79668755
Coma 56.63 20.42 71 11376 100578 79632363
Pyelocaliectasis 55.92 20.42 15 11432 918 79732023
Agranulocytosis 54.78 20.42 48 11399 44982 79687959
Mixed liver injury 54.48 20.42 25 11422 7553 79725388
Labelled drug-drug interaction medication error 51.86 20.42 38 11409 27612 79705329
Hypertensive crisis 49.36 20.42 33 11414 20737 79712204
Disturbance in attention 46.08 20.42 46 11401 50755 79682186
Product monitoring error 44.77 20.42 23 11424 8883 79724058
Metabolic acidosis 44.48 20.42 57 11390 82472 79650469
Hyperthermia 43.68 20.42 29 11418 18008 79714933
Hepatocellular injury 41.16 20.42 42 11405 47551 79685390
Septic shock 40.20 20.42 67 11380 122734 79610207
Acute generalised exanthematous pustulosis 40.00 20.42 27 11420 17227 79715714
Pancytopenia 39.73 20.42 79 11368 165666 79567275
Encephalopathy 38.62 20.42 48 11399 67349 79665592
Lactic acidosis 38.55 20.42 49 11398 70310 79662631
Cerebral haemorrhage 37.84 20.42 44 11403 57629 79675312
Postrenal failure 36.44 20.42 10 11437 667 79732274
Rhabdomyolysis 36.09 20.42 58 11389 103073 79629868
Diabetic metabolic decompensation 33.76 20.42 14 11433 3318 79729623
Haemorrhagic transformation stroke 33.10 20.42 13 11434 2679 79730262
Fungal endocarditis 32.73 20.42 9 11438 605 79732336
Cardiac autonomic neuropathy 32.36 20.42 6 11441 64 79732877
Blood pressure ambulatory increased 32.36 20.42 6 11441 64 79732877
Resting tremor 32.34 20.42 11 11436 1510 79731431
Renal impairment 31.73 20.42 70 11377 157713 79575228
Pyelonephritis acute 31.56 20.42 16 11431 6007 79726934
Pancreatic pseudoaneurysm 31.27 20.42 6 11441 78 79732863
Leukopenia 30.93 20.42 58 11389 116455 79616486
Death 30.71 20.42 22 11425 566492 79166449
Myoclonus 30.69 20.42 28 11419 27632 79705309
Eczema 29.93 20.42 33 11414 40785 79692156
Inappropriate antidiuretic hormone secretion 29.91 20.42 27 11420 26286 79706655
Altered state of consciousness 29.69 20.42 34 11413 43788 79689153
Haematoma 29.62 20.42 37 11410 52158 79680783
Anuria 28.86 20.42 24 11423 20939 79712002
Proteinuria 28.68 20.42 29 11418 32473 79700468
Walking disability 28.66 20.42 11 11436 2132 79730809
Joint swelling 28.14 20.42 4 11443 288642 79444299
Cholestasis 28.08 20.42 36 11411 52073 79680868
Hypertriglyceridaemia 27.32 20.42 19 11428 12721 79720220
Haematuria 27.26 20.42 41 11406 68795 79664146
Polyuria 26.73 20.42 20 11427 14994 79717947
Thrombocytopenia 26.48 20.42 91 11356 265168 79467773
Ischaemic stroke 26.42 20.42 28 11419 33103 79699838
Supine hypertension 26.28 20.42 7 11440 417 79732524
Haematochezia 26.27 20.42 46 11401 87599 79645342
Nasopharyngitis 26.00 20.42 3 11444 253878 79479063
Subarachnoid haemorrhage 25.66 20.42 24 11423 24441 79708500
Product administration error 25.55 20.42 27 11420 31819 79701122
Hypernatriuria 25.17 20.42 4 11443 15 79732926
Leukocytosis 24.97 20.42 31 11416 43424 79689517
Pemphigoid 24.19 20.42 19 11428 15296 79717645
Hyperlactacidaemia 24.00 20.42 13 11434 5582 79727359
Peripheral swelling 23.52 20.42 5 11442 269612 79463329
Pyelonephritis 23.33 20.42 21 11426 20367 79712574
Acute pulmonary oedema 23.22 20.42 18 11429 14212 79718729
Completed suicide 22.61 20.42 4 11443 245763 79487178
Hypersensitivity 22.60 20.42 5 11442 262234 79470707
Headache 22.55 20.42 37 11410 653735 79079206
Posterior reversible encephalopathy syndrome 22.37 20.42 23 11424 26258 79706683
Bradyarrhythmia 21.69 20.42 11 11436 4135 79728806
Pallor 21.53 20.42 31 11416 50031 79682910
Adenocarcinoma metastatic 21.06 20.42 5 11442 186 79732755
Dermatitis exfoliative generalised 20.89 20.42 13 11434 7228 79725713
Alopecia 20.78 20.42 4 11443 231351 79501590
Victim of crime 20.77 20.42 6 11441 482 79732459
Fatigue 20.48 20.42 67 11380 929660 78803281

FDA Adverse Event Reporting System (Pediatric)

None

Pharmacologic Action:

SourceCodeDescription
ATC C02CA06 CARDIOVASCULAR SYSTEM
ANTIHYPERTENSIVES
ANTIADRENERGIC AGENTS, PERIPHERALLY ACTING
Alpha-adrenoreceptor antagonists
MeSH PA D018663 Adrenergic Agents
MeSH PA D058668 Adrenergic alpha-1 Receptor Antagonists
MeSH PA D000317 Adrenergic alpha-Antagonists
MeSH PA D018674 Adrenergic Antagonists
MeSH PA D000959 Antihypertensive Agents
MeSH PA D002317 Cardiovascular Agents
MeSH PA D018377 Neurotransmitter Agents
MeSH PA D018490 Serotonin Agents
MeSH PA D017366 Serotonin Receptor Agonists
MeSH PA D014665 Vasodilator Agents

Drug Use | Suggest Off label Use Form| |View source of the data|

DiseaseRelationSNOMED_IDDOID
Hypertensive emergency indication 132721000119104




๐Ÿถ Veterinary Drug Use

None

๐Ÿถ Veterinary products

None

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation levelDissociation constantType (acidic/basic)
pKa1 6.85 Basic
pKa2 2.48 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
Alpha-1A adrenergic receptor GPCR ANTAGONIST Ki 8.85 WOMBAT-PK KEGG DRUG
Alpha-1D adrenergic receptor GPCR ANTAGONIST Ki 7.90 WOMBAT-PK KEGG DRUG
Alpha-1B adrenergic receptor GPCR ANTAGONIST Ki 7.10 WOMBAT-PK KEGG DRUG
5-hydroxytryptamine receptor 1A GPCR Ki 9.46 WOMBAT-PK

External reference:

IDSource
D01333 KEGG_DRUG
C0077857 UMLSCUI
CHEBI:32278 CHEBI
CHEMBL279229 ChEMBL_ID
DB12661 DRUGBANK_ID
C015568 MESH_SUPPLEMENTAL_RECORD_UI
5639 PUBCHEM_CID
3169 INN_ID
64887-14-5 SECONDARY_CAS_RN
A78GF17HJS UNII
39230 RXNORM
005866 NDDF
005867 NDDF
698807007 SNOMEDCT_US
734449004 SNOMEDCT_US
CHEMBL1256716 ChEMBL_ID

Pharmaceutical products:

None