urapidil 🐶 Veterinary Use | Indications/Contra | FAERs-F | FAERs-M | Orange Bk | PK/Tox | Related Drugs | 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 µM/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

Predicted pharmacokinetic/toxicological properties (PK-AZ):

PropertyDescriptionValueUnitConfidenceSimilarity
azlogd74 LogD at pH 7.4 1.159 High 1
caco2-efflux Caco-2 efflux ratio (BA/AB) 13.213 High 1
caco2-intrinsic-papp Caco-2 intrinsic apparent permeability 6.982 10^-6 cm/s High 1
dh-clint Dog hepatocyte intrinsic clearance 3.273 uL/min/10^6 cells High 1
dppb Dog plasma protein binding (% unbound) 57.090 % High 1
fcs-ppb Fetal calf serum protein binding (% unbound) 62.080 % High 1
herg hERG pIC50 4.626 pIC50 High 1
hh-clint Human hepatocyte intrinsic clearance 1.426 uL/min/10^6 cells High 1
hlm-clint Human liver microsomal intrinsic clearance 9.204 uL/min/mg protein High 1
hppb Human plasma protein binding (% unbound) 39.450 % High 1
kinase-safety-class ACVR2A,ACVR2B,ALK,AURKA,AXL,BRAF,BTK,CAMK2B,CAMK2D,CDK5,CDK9,DDR1,DYRK1B,EGFR,EIF2AK3,EPHB4,ERBB2,FLT3,GRK2,ITK,JAK1,JAK2,MAP3K21,MAP3K7,MAPK10,MAPK7,MAPK9,MARK4,MET,MTOR,NTRK2,PDK2,PDK4,PIK3CB,PIK3CD,PIM2,PRKCD,PRKDC,SIK2,SIK3,STK33,TEK,TTK,ULK1 44
kinase-selectivity-class AXL,BRAF,CDK9,GRK2,MAPK7,PRKDC,SIK2,STK33,TEK 9
mdck-mdr1-efflux MDCK-MDR1 efflux ratio 12.972 High 1
mh-clint Mouse hepatocyte intrinsic clearance 21.928 High 1
mppb Mouse plasma protein binding (% unbound) 56.360 High 1
nih-mdck-mdr1-efflux NIH MDCK-MDR1 efflux ratio 22.233 High 1
pfas-class PFAS structural alert (1 = True, 0 = False) 0
pppb Pig plasma protein binding (% unbound) 68.480 % High 1
rh-clint Rat hepatocyte intrinsic clearance 5.861 uL/min/10^6 cells High 1
rh-fuinc Rat hepatocyte fraction unbound in incubation 84.420 % High 1
rppb Rat plasma protein binding (% unbound) 47.300 % High 1
solubility-dd Solubility at pH 7.4 in DMSO 920.450 uM High 1

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 291.69 24.35 220 6658 320167 90301402
Hyperkalaemia 182.71 24.35 92 6786 64872 90556697
Hyponatraemia 175.27 24.35 115 6763 133423 90488146
Product prescribing error 100.53 24.35 48 6830 30097 90591472
Fall 96.40 24.35 148 6730 481662 90139907
Bradycardia 90.34 24.35 64 6814 83783 90537786
Product monitoring error 65.67 24.35 21 6857 4523 90617046
Anaemia 64.33 24.35 104 6774 352698 90268871
Hepatocellular injury 64.15 24.35 35 6843 28923 90592646
Mixed liver injury 62.32 24.35 23 6855 7600 90613969
Shock haemorrhagic 58.28 24.35 25 6853 12220 90609349
Hypotension 55.35 24.35 93 6785 325304 90296265
Rhabdomyolysis 54.88 24.35 39 6839 51217 90570352
Haematoma 54.45 24.35 35 6843 39013 90582556
Lactic acidosis 53.12 24.35 38 6840 50425 90571144
Polyuria 52.78 24.35 22 6856 10018 90611551
Scleroedema 51.69 24.35 9 6869 131 90621438
Drug interaction 51.03 24.35 82 6796 276371 90345198
Diabetic metabolic decompensation 49.81 24.35 14 6864 1943 90619626
Ischaemic stroke 49.67 24.35 27 6851 22139 90599430
Patent ductus arteriosus 49.54 24.35 17 6861 4552 90617017
Posterior reversible encephalopathy syndrome 49.48 24.35 27 6851 22312 90599257
Hypoglycaemia 48.27 24.35 41 6837 69807 90551762
Pain 47.78 24.35 9 6869 996332 89625237
Renal impairment 46.12 24.35 48 6830 105373 90516196
Toxic encephalopathy 45.52 24.35 19 6859 8680 90612889
Pneumonia staphylococcal 45.21 24.35 15 6863 3626 90617943
Rash maculo-papular 43.48 24.35 31 6847 40902 90580667
Labelled drug-drug interaction medication error 41.94 24.35 21 6857 14561 90607008
Septic shock 41.71 24.35 41 6837 84119 90537450
Acute generalised exanthematous pustulosis 40.20 24.35 20 6858 13683 90607886
Hyperlactacidaemia 39.50 24.35 14 6864 4122 90617447
Walking disability 39.44 24.35 11 6867 1484 90620085
Hypertensive crisis 38.02 24.35 21 6857 17763 90603806
Multiple organ dysfunction syndrome 37.08 24.35 35 6843 68301 90553268
Resting tremor 35.17 24.35 9 6869 874 90620695
Cerebral haemorrhage 34.05 24.35 25 6853 34497 90587072
Bradyarrhythmia 34.03 24.35 11 6867 2450 90619119
Myoclonus 33.90 24.35 20 6858 19148 90602421
Pancreatic pseudoaneurysm 33.87 24.35 6 6872 97 90621472
Premature baby 33.78 24.35 22 6856 25055 90596514
Hypokalaemia 32.95 24.35 45 6833 131071 90490498
Haematoma muscle 32.81 24.35 10 6868 1840 90619729
General physical health deterioration 32.03 24.35 78 6800 355037 90266532
Pyelonephritis 31.94 24.35 20 6858 21296 90600273
Haemorrhagic transformation stroke 31.73 24.35 9 6869 1290 90620279
Pneumonia respiratory syncytial viral 31.38 24.35 9 6869 1342 90620227
Renal failure 29.99 24.35 43 6835 130964 90490605
Agranulocytosis 29.33 24.35 23 6855 34979 90586590
Pyelonephritis acute 28.87 24.35 12 6866 5420 90616149
Cholestasis 28.59 24.35 23 6855 36276 90585293
HELLP syndrome 27.79 24.35 8 6870 1209 90620360
Left ventricular hypertrophy 27.45 24.35 12 6866 6132 90615437
Hyperglycaemia 27.44 24.35 26 6852 50944 90570625
Hepatic cytolysis 27.40 24.35 21 6857 30895 90590674
Simple partial seizures 26.89 24.35 7 6871 728 90620841
Pemphigoid 25.96 24.35 13 6865 9013 90612556
Metabolic acidosis 25.50 24.35 26 6852 55650 90565919
Aplasia 25.28 24.35 10 6868 3981 90617588
Dermatitis exfoliative generalised 25.24 24.35 11 6867 5582 90615987
Hyperplasia adrenal 25.16 24.35 4 6874 32 90621537
Anuria 25.00 24.35 15 6863 14803 90606766
Pancreatitis acute 24.56 24.35 20 6858 32095 90589474

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 173.51 22.60 257 6923 367080 42247075
Toxic epidermal necrolysis 115.93 22.60 66 7114 26684 42587471
Eosinophilia 95.91 22.60 63 7117 32836 42581319
Rash maculo-papular 93.08 22.60 65 7115 37438 42576717
Hepatic cytolysis 87.11 22.60 55 7125 26789 42587366
Coma 74.59 22.60 66 7114 53488 42560667
Hyperkalaemia 62.03 22.60 72 7108 80386 42533769
Hyperthermia 59.80 22.60 33 7147 12541 42601614
Ureteric compression 58.75 22.60 13 7167 298 42613857
Drug reaction with eosinophilia and systemic symptoms 56.87 22.60 51 7129 42024 42572131
Leukocytosis 56.76 22.60 44 7136 29664 42584491
General physical health deterioration 46.83 22.60 88 7092 151158 42462997
Cerebral haemorrhage 42.61 22.60 42 7138 38924 42575231
Oral mucosal eruption 39.90 22.60 10 7170 397 42613758
Pyelocaliectasis 39.29 22.60 13 7167 1396 42612759
Agranulocytosis 39.18 22.60 36 7144 30576 42583579
Fungal endocarditis 38.60 22.60 10 7170 454 42613701
Haematoma muscle 37.54 22.60 14 7166 2136 42612019
Cardiac autonomic neuropathy 37.05 22.60 7 7173 70 42614085
Blood pressure ambulatory increased 36.96 22.60 7 7173 71 42614084
Hypoglycaemia 35.53 22.60 47 7133 59807 42554348
Postrenal failure 31.76 22.60 9 7171 574 42613581
Hypotension 31.43 22.60 105 7075 257526 42356629
Histology abnormal 31.35 22.60 8 7172 342 42613813
Supine hypertension 30.59 22.60 8 7172 377 42613778
Product administration error 30.39 22.60 25 7155 18318 42595837
Hyponatraemia 28.86 22.60 57 7123 101405 42512750
Shock haemorrhagic 28.73 22.60 23 7157 16219 42597936
Hepatocellular injury 28.66 22.60 27 7153 23651 42590504
Disturbance in attention 28.64 22.60 30 7150 29836 42584319
Drug interaction 28.40 22.60 104 7076 266895 42347260
Victim of crime 27.84 22.60 8 7172 537 42613618
Nervous system disorder 27.58 22.60 23 7157 17172 42596983
Eczema 27.06 22.60 31 7149 34055 42580100
Septic shock 26.67 22.60 52 7128 91620 42522535
Metabolic acidosis 26.66 22.60 38 7142 51820 42562335
Drug ineffective 26.46 22.60 41 7139 630156 41983999
Pancytopenia 26.36 22.60 60 7120 117683 42496472
Death 25.70 22.60 25 7155 471160 42142995
Chylothorax 25.56 22.60 9 7171 1165 42612990
Retinal disorder 25.56 22.60 9 7171 1166 42612989
Victim of homicide 24.78 22.60 6 7174 206 42613949
Anaemia 24.78 22.60 103 7077 280175 42333980
Cholestasis 24.59 22.60 29 7151 32850 42581305
Altered state of consciousness 23.88 22.60 27 7153 29232 42584923
Hypertensive crisis 23.69 22.60 17 7163 10189 42603966
Haematuria 23.54 22.60 38 7142 57761 42556394
Drug diversion 23.16 22.60 8 7172 979 42613176

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 448.39 21.38 468 13308 634962 109940561
Hyperkalaemia 217.17 21.38 160 13616 135636 110439887
Hyponatraemia 158.97 21.38 164 13612 217489 110358034
Rash maculo-papular 138.18 21.38 96 13680 74126 110501397
Eosinophilia 122.27 21.38 81 13695 57855 110517668
Toxic epidermal necrolysis 109.39 21.38 75 13701 56652 110518871
Hepatic cytolysis 109.04 21.38 74 13702 54979 110520544
Product prescribing error 104.06 21.38 70 13706 51261 110524262
Bradycardia 100.70 21.38 110 13666 155407 110420116
Fall 90.02 21.38 218 13558 603264 109972259
Hypotension 86.56 21.38 197 13579 523652 110051871
Anaemia 86.29 21.38 202 13574 546884 110028639
Hepatocellular injury 83.83 21.38 61 13715 50581 110524942
Cerebral haemorrhage 82.84 21.38 67 13709 64901 110510622
Hypoglycaemia 81.97 21.38 86 13690 116018 110459505
Drug interaction 81.40 21.38 187 13589 499996 110075527
Shock haemorrhagic 79.98 21.38 47 13729 27200 110548323
Coma 77.37 21.38 84 13692 117785 110457738
Drug reaction with eosinophilia and systemic symptoms 71.18 21.38 68 13708 82027 110493496
Haematoma muscle 68.99 21.38 24 13752 4066 110571457
Agranulocytosis 68.98 21.38 59 13717 61701 110513822
Pain 67.34 21.38 18 13758 954937 109620586
Hyperthermia 65.89 21.38 38 13738 21234 110554289
Septic shock 65.36 21.38 89 13687 157439 110418084
General physical health deterioration 64.76 21.38 155 13621 425140 110150383
Ureteric compression 62.53 21.38 13 13763 301 110575222
Hypertensive crisis 61.11 21.38 38 13738 24334 110551189
Mixed liver injury 58.34 21.38 29 13747 12050 110563473
Pyelocaliectasis 55.33 21.38 15 13761 1104 110574419
Labelled drug-drug interaction medication error 54.72 21.38 38 13738 29264 110546259
Lactic acidosis 53.78 21.38 62 13714 92749 110482774
Haemorrhagic transformation stroke 51.91 21.38 18 13758 3019 110572504
Metabolic acidosis 51.79 21.38 63 13713 99681 110475842
Leukocytosis 51.29 21.38 47 13729 53781 110521742
Disturbance in attention 51.18 21.38 50 13726 61945 110513578
Product monitoring error 47.80 21.38 23 13753 8904 110566619
Cholestasis 47.68 21.38 49 13727 64469 110511054
Rhabdomyolysis 46.89 21.38 66 13710 120335 110455188
Pancytopenia 46.39 21.38 89 13687 209524 110365999
Scleroedema 45.65 21.38 9 13767 158 110575365
Pancreatitis acute 43.14 21.38 45 13731 60229 110515294
Encephalopathy 41.76 21.38 51 13725 81004 110494519
Hyperlactacidaemia 40.33 21.38 20 13756 8266 110567257
Acute generalised exanthematous pustulosis 40.23 21.38 28 13748 21636 110553887
Postrenal failure 39.86 21.38 11 13765 865 110574658
Hypokalaemia 39.79 21.38 77 13699 182371 110393152
Posterior reversible encephalopathy syndrome 39.13 21.38 33 13743 33828 110541695
Cardiac autonomic neuropathy 39.07 21.38 7 13769 71 110575452
Blood pressure ambulatory increased 38.72 21.38 7 13769 75 110575448
Joint swelling 38.25 21.38 5 13771 442840 110132683
Eczema 38.07 21.38 46 13730 72247 110503276
Haematoma 37.17 21.38 41 13735 58435 110517088
Diabetic metabolic decompensation 36.98 21.38 15 13761 3874 110571649
Pyelonephritis acute 36.86 21.38 18 13758 7195 110568328
Pneumonia staphylococcal 36.63 21.38 17 13759 6074 110569449
Product administration error 36.43 21.38 33 13743 37184 110538339
Infusion related reaction 36.27 21.38 3 13773 381159 110194364
Myoclonus 35.77 21.38 31 13745 32967 110542556
Fungal endocarditis 35.75 21.38 10 13766 826 110574697
Nasopharyngitis 35.17 21.38 4 13772 394357 110181166
Dermatitis exfoliative generalised 35.05 21.38 20 13756 10952 110564571
Renal impairment 34.53 21.38 74 13702 188371 110387152
Thrombocytopenia 33.92 21.38 108 13668 348777 110226746
Drug hypersensitivity 33.00 21.38 8 13768 454082 110121441
Altered state of consciousness 32.54 21.38 38 13738 57588 110517935
Resting tremor 32.52 21.38 11 13765 1712 110573811
Proteinuria 32.51 21.38 32 13744 39986 110535537
Subarachnoid haemorrhage 32.39 21.38 28 13748 29674 110545849
Oral mucosal eruption 32.38 21.38 10 13766 1167 110574356
Supine hypertension 31.73 21.38 8 13768 443 110575080
Pancreatic pseudoaneurysm 30.96 21.38 6 13770 96 110575427
Polyuria 30.79 21.38 22 13754 17716 110557807
Peripheral swelling 29.59 21.38 7 13769 404027 110171496
Hypersensitivity 29.59 21.38 7 13769 403991 110171532
Alopecia 29.46 21.38 5 13771 364748 110210775
Inappropriate antidiuretic hormone secretion 29.25 21.38 28 13748 33823 110541700
Anuria 28.70 21.38 24 13752 24317 110551206
Fatigue 28.47 21.38 69 13707 1215889 109359634
Walking disability 28.41 21.38 11 13765 2517 110573006
Hypertriglyceridaemia 27.95 21.38 20 13756 16134 110559389
Leukopenia 27.91 21.38 59 13717 148732 110426791
Haematuria 27.25 21.38 42 13734 82963 110492560
Rheumatoid arthritis 26.80 21.38 3 13773 299610 110275913
Drug diversion 26.80 21.38 9 13767 1371 110574152
Victim of crime 26.78 21.38 9 13767 1374 110574149
Acute respiratory distress syndrome 26.63 21.38 33 13743 53165 110522358
Renal failure 26.60 21.38 75 13701 226499 110349024
Ischaemic stroke 26.34 21.38 29 13747 41234 110534289
Death 26.30 21.38 29 13747 698840 109876683
Swelling 25.86 21.38 6 13770 351035 110224488
Haematochezia 25.47 21.38 49 13727 115475 110460048
Victim of homicide 25.30 21.38 6 13770 257 110575266
Nervous system disorder 25.09 21.38 25 13751 31696 110543827
Atrioventricular block 24.94 21.38 19 13757 16858 110558665
Headache 24.88 21.38 45 13731 882332 109693191
Hepatic enzyme increased 24.62 21.38 5 13771 320887 110254636
Toxic encephalopathy 24.42 21.38 18 13758 15196 110560327
Pemphigoid 24.42 21.38 20 13756 19687 110555836
Arthralgia 23.59 21.38 38 13738 779594 109795929
Hypernatriuria 23.53 21.38 4 13772 29 110575494
Stevens-Johnson syndrome 23.32 21.38 29 13747 46872 110528651
Chronic kidney disease 22.82 21.38 37 13739 76254 110499269
Acute pulmonary oedema 22.65 21.38 18 13758 16978 110558545
Toxic skin eruption 22.34 21.38 22 13754 27493 110548030
Cerebral aspergillosis 22.31 21.38 9 13767 2293 110573230
Pallor 22.04 21.38 31 13745 56436 110519087
Lip oedema 22.01 21.38 13 13763 7587 110567936
Hyperplasia adrenal 21.95 21.38 4 13772 45 110575478
Cardio-respiratory arrest 21.80 21.38 46 13730 115790 110459733
Aplasia 21.58 21.38 13 13763 7860 110567663

FDA Adverse Event Reporting System (Pediatric)

None

Pharmacologic Action:

SourceCodeDescription
ATC C02CA06 CARDIOVASCULAR SYSTEM
ANTIHYPERTENSIVES
ANTIADRENERGIC AGENTS, PERIPHERALLY ACTING
Alpha-adrenoreceptor antagonists
MeSH PA D000317 Adrenergic alpha-Antagonists
MeSH PA D000959 Antihypertensive Agents
MeSH PA D002317 Cardiovascular Agents
MeSH PA D014665 Vasodilator Agents
MeSH PA D017366 Serotonin Receptor Agonists
MeSH PA D018377 Neurotransmitter Agents
MeSH PA D018490 Serotonin Agents
MeSH PA D018663 Adrenergic Agents
MeSH PA D018674 Adrenergic Antagonists
MeSH PA D058668 Adrenergic alpha-1 Receptor Antagonists
CHEBI has role CHEBI:35674 antihypertensive agent

Related Drugs by ATC class:

C02CA Alpha-adrenoreceptor antagonists 4 drugs
doxazosinindoraminprazosintrimazosin

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

DiseaseRelationSNOMED_IDDOID
Hypertensive emergency indication 132721000119104




🐶 Veterinary Drug Use

None

🐶 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
CHEMBL1256716 ChEMBL_ID
C015568 MESH_SUPPLEMENTAL_RECORD_UI
5639 PUBCHEM_CID
13357 IUPHAR_LIGAND_ID
3169 INN_ID
64887-14-5 SECONDARY_CAS_RN
A78GF17HJS UNII
39230 RXNORM
005866 NDDF
005867 NDDF
698807007 SNOMEDCT_US
734449004 SNOMEDCT_US
A78GF17HJS INXIGHT DRUGS

Pharmaceutical products:

None