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

Stem definitionDrug idCAS RN
antihypertensive substances, prazosin derivatives 954 74191-85-8

Description:

MoleculeDescription

Molfile Inchi Smiles

Synonyms:

  • doxazosin
  • doxazosin mesylate
  • doxazosine
  • doxazosin mesilate
A prazosin-related compound that is a selective alpha-1-adrenergic blocker.
  • Molecular weight: 451.48
  • Formula: C23H25N5O5
  • CLOGP: 3.53
  • LIPINSKI: 0
  • HAC: 10
  • HDO: 1
  • TPSA: 112.27
  • ALOGS: -2.76
  • ROTB: 4

  • Status: OFP

  • Legend:
    OFP - off patent
    OFM - off market
    ONP - on patent

Drug dosage:

DoseUnitRoute
4 mg O

ADMET properties:

PropertyValueReference
BDDCS (Biopharmaceutical Drug Disposition Classification System) 1 Benet LZ, Broccatelli F, Oprea TI
MRTD (Maximum Recommended Therapeutic Daily Dose) 0.59 ┬ÁM/kg/day Contrera JF, Matthews EJ, Kruhlak NL, Benz RD
Vd (Volume of distribution) 1.30 L/kg Lombardo F, Berellini G, Obach RS
CL (Clearance) 1.60 mL/min/kg Lombardo F, Berellini G, Obach RS
fu (Fraction unbound in plasma) 0.02 % Lombardo F, Berellini G, Obach RS
t_half (Half-life) 10 hours Lombardo F, Berellini G, Obach RS

Approvals:

DateAgencyCompanyOrphan
Nov. 2, 1990 FDA PFIZER

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
Hypotension 287.70 35.93 97 939 32339 2324710
Syncope 246.53 35.93 74 962 16801 2340248
Orthostatic hypotension 228.62 35.93 49 987 2830 2354219
Dizziness 201.53 35.93 88 948 58577 2298472
Hypertensive crisis 156.07 35.93 35 1001 2478 2354571
Hypertension 155.04 35.93 59 977 27302 2329747
Urinary incontinence 152.90 35.93 38 998 4195 2352854
Blood pressure increased 130.83 35.93 46 990 16940 2340109
Loss of consciousness 122.61 35.93 45 991 18722 2338327
Renin increased 119.19 35.93 16 1020 41 2357008
Presyncope 116.74 35.93 30 1006 3773 2353276
Dyspnoea 106.04 35.93 63 973 78670 2278379
Renal artery stenosis 94.43 35.93 16 1020 252 2356797
Drug ineffective 91.27 35.93 63 973 101561 2255488
Drug interaction 90.45 35.93 41 995 29122 2327927
Headache 77.23 35.93 52 984 80127 2276922
Drug hypersensitivity 74.94 35.93 42 994 46601 2310448
Angioedema 73.17 35.93 25 1011 8371 2348678
Left ventricular hypertrophy 72.95 35.93 15 1021 696 2356353
Vomiting 70.23 35.93 47 989 71555 2285494
Acute kidney injury 70.00 35.93 34 1002 28088 2328961
Sinus bradycardia 66.35 35.93 17 1019 2099 2354950
Bradycardia 65.22 35.93 24 1012 9957 2347092
Joint swelling 62.83 35.93 27 1009 16792 2340257
Hyperkalaemia 57.04 35.93 19 1017 5874 2351175
Hypertensive angiopathy 56.67 35.93 7 1029 6 2357043
Fall 53.58 35.93 34 1002 47065 2309984
Atrial fibrillation 51.05 35.93 22 1014 13746 2343303
Overdose 49.24 35.93 24 1012 19883 2337166
Asthenia 48.73 35.93 32 1004 46894 2310155
Palpitations 47.28 35.93 22 1014 16434 2340615
Abdominal pain 47.17 35.93 28 1008 34346 2322703
Renal impairment 47.07 35.93 19 1017 10073 2346976
Abdominal distension 46.50 35.93 19 1017 10392 2346657
Hyperlipidaemia 44.25 35.93 13 1023 2661 2354388
Hypoglycaemia 43.28 35.93 17 1019 8390 2348659
Oedema peripheral 42.40 35.93 23 1013 23740 2333309
Abdominal tenderness 40.72 35.93 10 1026 1037 2356012
Tumour rupture 40.47 35.93 6 1030 37 2357012
Nausea 40.06 35.93 41 995 112148 2244901
Drug abuse 37.41 35.93 17 1019 12009 2345040
Blood pressure inadequately controlled 37.05 35.93 9 1027 891 2356158
Completed suicide 36.51 35.93 20 1016 21014 2336035
Hypokalaemia 36.13 35.93 16 1020 10638 2346411

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
Hypotension 636.79 44.33 213 1294 29441 1715833
Syncope 450.33 44.33 138 1369 14031 1731243
Orthostatic hypotension 417.66 44.33 97 1410 3334 1741940
Loss of consciousness 269.23 44.33 95 1412 14780 1730494
Dizziness 213.67 44.33 102 1405 34259 1711015
Drug interaction 201.49 44.33 92 1415 27866 1717408
Hypertension 185.33 44.33 78 1429 19370 1725904
Acute kidney injury 173.12 44.33 89 1418 34855 1710419
Bradycardia 166.36 44.33 61 1446 10473 1734801
Overdose 145.67 44.33 63 1444 16638 1728636
Hypertensive crisis 122.58 44.33 31 1476 1496 1743778
Dyspnoea 115.43 44.33 79 1428 51980 1693294
Asthenia 115.18 44.33 68 1439 34602 1710672
Drug ineffective 114.36 44.33 85 1422 63716 1681558
Renal failure 113.35 44.33 56 1451 19961 1725313
Presyncope 109.51 44.33 32 1475 2666 1742608
Blood lactic acid increased 106.63 44.33 25 1482 874 1744400
Cardiomegaly 105.03 44.33 30 1477 2304 1742970
Hyperkalaemia 104.04 44.33 41 1466 8506 1736768
Nocturia 100.27 44.33 25 1482 1136 1744138
Circulatory collapse 97.44 44.33 31 1476 3436 1741838
Floppy iris syndrome 91.93 44.33 16 1491 114 1745160
Toxicity to various agents 85.84 44.33 53 1454 29088 1716186
Cardiac failure 85.57 44.33 40 1467 12562 1732712
Drug hypersensitivity 84.51 44.33 42 1465 15093 1730181
Left ventricular hypertrophy 81.90 44.33 20 1487 832 1744442
Fatigue 80.38 44.33 63 1444 50718 1694556
Fall 78.85 44.33 49 1458 27165 1718109
Chest pain 76.37 44.33 43 1464 19871 1725403
Malaise 75.12 44.33 49 1458 29516 1715758
Oedema peripheral 74.70 44.33 39 1468 15511 1729763
Pulmonary oedema 74.52 44.33 30 1477 6556 1738718
Metabolic acidosis 73.04 44.33 28 1479 5374 1739900
Blood pressure increased 72.55 44.33 34 1473 10719 1734555
Nausea 71.37 44.33 59 1448 51137 1694137
Mouth breathing 69.57 44.33 11 1496 39 1745235
Blood pressure inadequately controlled 67.19 44.33 16 1491 597 1744677
Cough 64.36 44.33 38 1469 19159 1726115
Crystalluria 63.86 44.33 11 1496 73 1745201
Vomiting 63.66 44.33 49 1458 38266 1707008
Completed suicide 61.87 44.33 35 1472 16277 1728997
Shock 61.40 44.33 23 1484 4138 1741136
Troponin I increased 60.26 44.33 13 1494 308 1744966
Vertigo 60.08 44.33 23 1484 4390 1740884
Hypoxia 60.05 44.33 25 1482 5938 1739336
Suicide attempt 58.10 44.33 26 1481 7355 1737919
Renal impairment 56.56 44.33 30 1477 12284 1732990
Tricuspid valve incompetence 55.93 44.33 16 1491 1230 1744044
Headache 54.95 44.33 43 1464 34333 1710941
Blood creatinine increased 53.06 44.33 30 1477 13916 1731358
Mitral valve incompetence 53.00 44.33 17 1490 1925 1743349
Therapy non-responder 52.29 44.33 23 1484 6243 1739031
Lower respiratory tract infection 52.16 44.33 20 1487 3831 1741443
Left ventricular dysfunction 51.89 44.33 15 1492 1196 1744078
Blood uric acid increased 50.00 44.33 14 1493 995 1744279
Osmolar gap abnormal 49.52 44.33 7 1500 8 1745266
Urinary tract discomfort 48.65 44.33 7 1500 10 1745264
Angioedema 48.51 44.33 25 1482 9639 1735635
Atrial fibrillation 48.21 44.33 29 1478 15082 1730192
Mitral valve thickening 47.51 44.33 7 1500 13 1745261
Bradyarrhythmia 47.25 44.33 11 1496 371 1744903
Oedema 46.89 44.33 22 1485 6926 1738348
Ventricular hyperkinesia 45.95 44.33 7 1500 18 1745256
Right atrial enlargement 44.91 44.33 7 1500 22 1745252
Blood pressure decreased 44.89 44.33 22 1485 7624 1737650

Pharmacologic Action:

SourceCodeDescription
ATC C02CA04 CARDIOVASCULAR SYSTEM
ANTIHYPERTENSIVES
ANTIADRENERGIC AGENTS, PERIPHERALLY ACTING
Alpha-adrenoreceptor antagonists
MeSH PA D018663 Adrenergic Agents
MeSH PA D058668 Adrenergic alpha-1 Receptor Antagonists
FDA EPC N0000175553 alpha-Adrenergic Blocker
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
CHEBI has role CHEBI:35674 antihypertensive agent
CHEBI has role CHEBI:37890 alpha-adrenergic antagonist
CHEBI has role CHEBI:35610 antineoplastic agent
CHEBI has role CHEBI:35620 vasodilator agent
CHEBI has role CHEBI:59844 antihyperplasia drug

Drug Use (View source of the data)

DiseaseRelationSNOMED_IDDOID
Hypertensive disorder indication 38341003 DOID:10763
Benign prostatic hyperplasia indication 266569009
Priapism contraindication 6273006 DOID:9286
Stenosis of intestine contraindication 23065003
Orthostatic hypotension contraindication 28651003
Low blood pressure contraindication 45007003
Hepatic failure contraindication 59927004
Chronic idiopathic constipation contraindication 82934008
Cataract surgery contraindication 110473004
Disease of liver contraindication 235856003 DOID:409
Pyloric obstruction contraindication 244815007
Syncope contraindication 271594007
Intraoperative floppy iris syndrome contraindication 418801006

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation levelDissociation constantType (acidic/basic)
pKa1 7.22 Basic
pKa2 0.72 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-1D adrenergic receptor GPCR ANTAGONIST Ki 8.85 WOMBAT-PK CHEMBL
Alpha-1A adrenergic receptor GPCR ANTAGONIST Ki 8.80 WOMBAT-PK CHEMBL
Alpha-1B adrenergic receptor GPCR ANTAGONIST Ki 9.10 WOMBAT-PK CHEMBL
5-hydroxytryptamine receptor 2B GPCR Ki 6.63 DRUG MATRIX
5-hydroxytryptamine receptor 2C GPCR Ki 6.55 DRUG MATRIX
Sodium-dependent dopamine transporter Transporter Ki 6.83 DRUG MATRIX
Interstitial collagenase Enzyme IC50 5.24 DRUG MATRIX
Potassium voltage-gated channel subfamily H member 2 Ion channel IC50 6.23 WOMBAT-PK
Multidrug resistance protein 1 Transporter Ki 5 WOMBAT-PK
Alpha-2A adrenergic receptor GPCR Ki 6.14 CHEMBL
Alpha-2C adrenergic receptor GPCR Ki 6.55 CHEMBL
Beta-2 adrenergic receptor GPCR Ki 5.72 DRUG MATRIX
Sodium-dependent serotonin transporter Transporter Ki 5.85 DRUG MATRIX
5-hydroxytryptamine receptor 4 GPCR Ki 6.90 DRUG MATRIX
Alpha-1B adrenergic receptor GPCR Ki 9.38 DRUG MATRIX
Alpha-1A adrenergic receptor GPCR IC50 8.81 CHEMBL

External reference:

IDSource
4019735 VUID
N0000147827 NUI
C0114873 UMLSCUI
D00608 KEGG_DRUG
108556006 SNOMEDCT_US
4019735 VANDF
004493 NDDF
49276 RXNORM
372508002 SNOMEDCT_US
d00726 MMSL
86P6PQK0MU UNII
77883-43-3 SECONDARY_CAS_RN
CHEMBL707 ChEMBL_ID
DB00590 DRUGBANK_ID
CHEMBL1200561 ChEMBL_ID
5143 INN_ID
CHEBI:4708 CHEBI
7170 IUPHAR_LIGAND_ID
D017292 MESH_DESCRIPTOR_UI
3157 PUBCHEM_CID

Pharmaceutical products:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
Cardura HUMAN PRESCRIPTION DRUG LABEL 1 0049-2710 TABLET, MULTILAYER, EXTENDED RELEASE 4 mg ORAL NDA 19 sections
Cardura HUMAN PRESCRIPTION DRUG LABEL 1 0049-2720 TABLET, MULTILAYER, EXTENDED RELEASE 8 mg ORAL NDA 19 sections
Cardura HUMAN PRESCRIPTION DRUG LABEL 1 0049-2750 TABLET 1 mg ORAL NDA 18 sections
Cardura HUMAN PRESCRIPTION DRUG LABEL 1 0049-2760 TABLET 2 mg ORAL NDA 18 sections
Cardura HUMAN PRESCRIPTION DRUG LABEL 1 0049-2770 TABLET 4 mg ORAL NDA 18 sections
Cardura HUMAN PRESCRIPTION DRUG LABEL 1 0049-2780 TABLET 8 mg ORAL NDA 18 sections
Doxazosin HUMAN PRESCRIPTION DRUG LABEL 1 0093-2067 TABLET 8 mg ORAL ANDA 17 sections
Doxazosin HUMAN PRESCRIPTION DRUG LABEL 1 0093-2068 TABLET 4 mg ORAL ANDA 17 sections
Doxazosin HUMAN PRESCRIPTION DRUG LABEL 1 0093-2069 TABLET 2 mg ORAL ANDA 17 sections
Doxazosin HUMAN PRESCRIPTION DRUG LABEL 1 0093-2070 TABLET 1 mg ORAL ANDA 17 sections
Doxazosin HUMAN PRESCRIPTION DRUG LABEL 1 0378-4021 TABLET 1 mg ORAL ANDA 17 sections
Doxazosin HUMAN PRESCRIPTION DRUG LABEL 1 0378-4022 TABLET 2 mg ORAL ANDA 17 sections
Doxazosin HUMAN PRESCRIPTION DRUG LABEL 1 0378-4024 TABLET 4 mg ORAL ANDA 17 sections
Doxazosin HUMAN PRESCRIPTION DRUG LABEL 1 0378-4028 TABLET 8 mg ORAL ANDA 17 sections
Doxazosin HUMAN PRESCRIPTION DRUG LABEL 1 0615-5536 TABLET 1 mg ORAL ANDA 13 sections
Doxazosin HUMAN PRESCRIPTION DRUG LABEL 1 0615-5537 TABLET 8 mg ORAL ANDA 13 sections
Doxazosin HUMAN PRESCRIPTION DRUG LABEL 1 0615-6570 TABLET 2 mg ORAL ANDA 13 sections
Doxazosin HUMAN PRESCRIPTION DRUG LABEL 1 0615-6571 TABLET 4 mg ORAL ANDA 13 sections
Doxazosin HUMAN PRESCRIPTION DRUG LABEL 1 0832-0356 TABLET 1 mg ORAL ANDA 18 sections
Doxazosin HUMAN PRESCRIPTION DRUG LABEL 1 0832-0357 TABLET 2 mg ORAL ANDA 18 sections
Doxazosin HUMAN PRESCRIPTION DRUG LABEL 1 0832-1358 TABLET 4 mg ORAL ANDA 18 sections
Doxazosin HUMAN PRESCRIPTION DRUG LABEL 1 0832-1359 TABLET 8 mg ORAL ANDA 18 sections
Doxazosin HUMAN PRESCRIPTION DRUG LABEL 1 0904-5522 TABLET 1 mg ORAL ANDA 17 sections
Doxazosin HUMAN PRESCRIPTION DRUG LABEL 1 0904-5523 TABLET 2 mg ORAL ANDA 17 sections
Doxazosin HUMAN PRESCRIPTION DRUG LABEL 1 0904-5524 TABLET 4 mg ORAL ANDA 17 sections
Doxazosin Mesylate HUMAN PRESCRIPTION DRUG LABEL 1 10544-292 TABLET 4 mg ORAL ANDA 12 sections
Doxazosin Mesylate HUMAN PRESCRIPTION DRUG LABEL 1 10544-629 TABLET 1 mg ORAL ANDA 12 sections
Doxazosin HUMAN PRESCRIPTION DRUG LABEL 1 16590-274 TABLET 4 mg ORAL ANDA 12 sections
Doxazosin HUMAN PRESCRIPTION DRUG LABEL 1 16729-211 TABLET 1 mg ORAL ANDA 17 sections
Doxazosin HUMAN PRESCRIPTION DRUG LABEL 1 16729-212 TABLET 2 mg ORAL ANDA 17 sections