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

Stem definitionDrug idCAS RN
antihypertensive substances, prazosin derivatives 4209 19216-56-9

Description:

MoleculeDescription

Molfile Inchi Smiles

Synonyms:

  • prazosin
  • prazosin hydrochloride
  • furazosin
  • prazosin HCl
A selective adrenergic alpha-1 antagonist used in the treatment of HEART FAILURE; HYPERTENSION; PHEOCHROMOCYTOMA; RAYNAUD DISEASE; PROSTATIC HYPERTROPHY; and URINARY RETENTION.
  • Molecular weight: 383.41
  • Formula: C19H21N5O4
  • CLOGP: 2.03
  • LIPINSKI: 0
  • HAC: 9
  • HDO: 1
  • TPSA: 106.95
  • ALOGS: -2.74
  • ROTB: 4

  • Status: OFP

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

Drug dosage:

DoseUnitRoute
5 mg O

ADMET properties:

PropertyValueReference
BDDCS (Biopharmaceutical Drug Disposition Classification System) 1 Benet LZ, Broccatelli F, Oprea TI
S (Water solubility) 1.40 mg/mL Benet LZ, Broccatelli F, Oprea TI
EoM (Fraction excreted unchanged in urine) 0.50 % Benet LZ, Broccatelli F, Oprea TI
MRTD (Maximum Recommended Therapeutic Daily Dose) 1.49 ┬ÁM/kg/day Contrera JF, Matthews EJ, Kruhlak NL, Benz RD
BA (Bioavailability) 68 % Kim MT, Sedykh A, Chakravarti SK, Saiakhov RD, Zhu H
Vd (Volume of distribution) 0.73 L/kg Lombardo F, Berellini G, Obach RS
CL (Clearance) 4.70 mL/min/kg Lombardo F, Berellini G, Obach RS
fu (Fraction unbound in plasma) 0.06 % Lombardo F, Berellini G, Obach RS
t_half (Half-life) 2 hours Lombardo F, Berellini G, Obach RS

Approvals:

DateAgencyCompanyOrphan
June 23, 1976 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
Atrioventricular block first degree 113.91 16.68 37 4791 6149 46675085
Unmasking of previously unidentified disease 48.90 16.68 12 4816 719 46680515
Sinus bradycardia 45.25 16.68 24 4804 13758 46667476
Circulatory collapse 45.07 16.68 28 4800 21596 46659638
Electrocardiogram ST segment elevation 40.46 16.68 15 4813 3680 46677554
Posterior reversible encephalopathy syndrome 40.42 16.68 23 4805 15118 46666116
Norepinephrine increased 40.20 16.68 7 4821 73 46681161
Electrocardiogram repolarisation abnormality 37.89 16.68 11 4817 1254 46679980
Systolic dysfunction 37.48 16.68 11 4817 1303 46679931
Ventricular hypokinesia 32.01 16.68 13 4815 4065 46677169
Electrocardiogram QRS complex prolonged 31.56 16.68 14 4814 5435 46675799
Toxicity to various agents 31.17 16.68 68 4760 211698 46469536
Hypotension 27.98 16.68 69 4759 232520 46448714
Cardiac arrest 27.59 16.68 40 4788 90359 46590875
Hypertrichosis 27.39 16.68 8 4820 932 46680302
Cardiac hypertrophy 26.46 16.68 8 4820 1049 46680185
Cardiotoxicity 25.78 16.68 13 4815 6709 46674525
Overdose 25.31 16.68 41 4787 101938 46579296
Drug withdrawal syndrome 23.94 16.68 21 4807 27363 46653871
Metabolic acidosis 22.99 16.68 24 4804 38756 46642478
Bradycardia 22.69 16.68 31 4797 66267 46614967
Ventricular extrasystoles 22.22 16.68 14 4814 11049 46670185
Suicidal ideation 21.82 16.68 28 4800 56354 46624880
Cardio-respiratory arrest 20.49 16.68 28 4800 59841 46621393
Dissociative identity disorder 20.49 16.68 4 4824 81 46681153
Haemophagocytic lymphohistiocytosis 20.47 16.68 12 4816 8330 46672904
Hypertensive crisis 19.58 16.68 14 4814 13601 46667633
Status epilepticus 19.25 16.68 14 4814 13965 46667269
Electrocardiogram QRS complex shortened 19.25 16.68 5 4823 377 46680857
Electrocardiogram QT prolonged 19.09 16.68 25 4803 51300 46629934
Stress cardiomyopathy 18.58 16.68 11 4817 7773 46673461
Withdrawal syndrome 18.08 16.68 15 4813 18119 46663115
Acute kidney injury 17.63 16.68 59 4769 235796 46445438
Coma scale abnormal 17.23 16.68 9 4819 4997 46676237
Hypovolaemic shock 16.93 16.68 9 4819 5174 46676060

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
Priapism 83.85 15.64 31 4924 4712 29942811
Parasomnia 76.81 15.64 16 4939 278 29947245
Antidepressant drug level above therapeutic 67.12 15.64 13 4942 153 29947370
Analgesic drug level above therapeutic 62.08 15.64 13 4942 232 29947291
Abnormal sleep-related event 47.50 15.64 12 4943 502 29947021
Serotonin syndrome 44.86 15.64 31 4924 17860 29929663
Suicidal behaviour 44.06 15.64 14 4941 1348 29946175
Vasoplegia syndrome 32.75 15.64 11 4944 1260 29946263
Drug interaction 31.60 15.64 88 4867 199480 29748043
Sudden cardiac death 30.26 15.64 14 4941 3738 29943785
Orthostatic hypotension 26.90 15.64 26 4929 23953 29923570
Somnambulism 25.94 15.64 12 4943 3202 29944321
Compartment syndrome 25.40 15.64 11 4944 2516 29945007
Sinus bradycardia 24.11 15.64 18 4937 11677 29935846
Spleen tuberculosis 24.01 15.64 4 4951 18 29947505
Syncope 20.38 15.64 44 4911 84859 29862664
Hyperlactacidaemia 18.79 15.64 9 4946 2597 29944926
Pulmonary congestion 17.03 15.64 15 4940 12272 29935251
Electrocardiogram QT prolonged 16.94 15.64 25 4930 35810 29911713
Aspiration 16.91 15.64 14 4941 10537 29936986
Suicidal ideation 16.80 15.64 25 4930 36089 29911434
Food interaction 16.50 15.64 6 4949 869 29946654
Overdose 16.15 15.64 40 4915 84297 29863226

Pharmacologic Action:

SourceCodeDescription
ATC C02CA01 CARDIOVASCULAR SYSTEM
ANTIHYPERTENSIVES
ANTIADRENERGIC AGENTS, PERIPHERALLY ACTING
Alpha-adrenoreceptor antagonists
ATC C02LE01 CARDIOVASCULAR SYSTEM
ANTIHYPERTENSIVES
ANTIHYPERTENSIVES AND DIURETICS IN COMBINATION
Alpha-adrenoreceptor antagonists and diuretics
FDA MoA N0000000099 Adrenergic alpha-Antagonists
FDA EPC N0000175553 alpha-Adrenergic Blocker
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
CHEBI has role CHEBI:35674 antihypertensive
CHEBI has role CHEBI:37890 alpha-adrenoceptor antagonists
CHEBI has role CHEBI:76779 prolyl oligopeptidase (ec 3.4.21.26) inhibitor

Drug Use (View source of the data)

DiseaseRelationSNOMED_IDDOID
Hypertensive disorder indication 38341003 DOID:10763
Benign prostatic hyperplasia off-label use 266569009
PTSD related nightmares off-label use 428687006
Chronic Post Traumatic Stress Disorder with Trauma-related Nightmares off-label use
End stage renal disease contraindication 46177005 DOID:784
Narcolepsy contraindication 60380001 DOID:8986
Cataract surgery contraindication 110473004
Micturition syncope contraindication 234168001
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-1A adrenergic receptor GPCR INVERSE AGONIST Ki 10.40 CHEMBL IUPHAR
Alpha-1B adrenergic receptor GPCR INVERSE AGONIST Ki 9.68 CHEMBL IUPHAR
Alpha-1D adrenergic receptor GPCR INVERSE AGONIST Ki 9.70 CHEMBL IUPHAR
5-hydroxytryptamine receptor 2A GPCR Ki 7.73 WOMBAT-PK
Solute carrier family 22 member 1 Transporter IC50 5 CHEMBL
Solute carrier family 22 member 2 Transporter IC50 4.87 CHEMBL
Alpha-2A adrenergic receptor GPCR Ki 6.68 CHEMBL
D(4) dopamine receptor GPCR Ki 5.08 CHEMBL
5-hydroxytryptamine receptor 1D GPCR Ki 9.48 CHEMBL
Potassium voltage-gated channel subfamily H member 2 Ion channel IC50 5.80 CHEMBL
Alpha-2B adrenergic receptor GPCR Ki 7.89 CHEMBL
Alpha-2C adrenergic receptor GPCR Ki 7.62 CHEMBL
Multidrug and toxin extrusion protein 2 Transporter IC50 4.42 CHEMBL
Multidrug and toxin extrusion protein 1 Transporter IC50 5.80 CHEMBL
Adenosine receptor A3 GPCR IC50 9.07 CHEMBL
Sodium channel alpha subunits; brain (Types I, II, III) Ion channel IC50 5 CHEMBL
Ribosyldihydronicotinamide dehydrogenase [quinone] Enzyme IC50 8.11 CHEMBL
5-hydroxytryptamine receptor 2B GPCR Ki 5.58 DRUG MATRIX
Matrix metalloproteinase-9 Enzyme IC50 5.16 DRUG MATRIX
Interstitial collagenase Enzyme IC50 5.39 DRUG MATRIX
Alpha-1B adrenergic receptor GPCR Ki 9.08 CHEMBL
Serotonin 2 (5-HT2) receptor GPCR IC50 4.38 CHEMBL
Adrenergic receptor alpha-2 GPCR Ki 9.40 CHEMBL
Alpha-2A adrenergic receptor GPCR Ki 5.78 CHEMBL
Alpha-1D adrenergic receptor GPCR Ki 9.70 CHEMBL
Alpha-2A adrenergic receptor GPCR Ki 5.39 CHEMBL
Alpha-2 adrenergic receptor GPCR Ki 7.89 CHEMBL
5-hydroxytryptamine receptor 2A GPCR Ki 5.82 CHEMBL
Adrenergic receptor alpha-1 GPCR Kd 10.99 CHEMBL
Alpha-1A adrenergic receptor GPCR Ki 9.77 CHEMBL
Alpha-2A adrenergic receptor GPCR Ki 6.97 CHEMBL
Alpha-1A adrenergic receptor GPCR Ki 10.15 CHEMBL
5-hydroxytryptamine receptor 1A GPCR Ki 5.63 CHEMBL
Alpha-1B adrenergic receptor GPCR Ki 10 CHEMBL
D(2) dopamine receptor GPCR IC50 4.96 CHEMBL
Mu-type opioid receptor GPCR Ki 9.70 CHEMBL
Beta-casein Unclassified Ki 9.44 CHEMBL

External reference:

IDSource
4019901 VUID
N0000147986 NUI
D00609 KEGG_DRUG
19237-84-4 SECONDARY_CAS_RN
4018850 VANDF
4019901 VANDF
C0032912 UMLSCUI
CHEBI:8364 CHEBI
XRA PDB_CHEM_ID
CHEMBL2 ChEMBL_ID
CHEMBL1558 ChEMBL_ID
D011224 MESH_DESCRIPTOR_UI
DB00457 DRUGBANK_ID
503 IUPHAR_LIGAND_ID
2593 INN_ID
XM03YJ541D UNII
4893 PUBCHEM_CID
203210 RXNORM
2426 MMSL
5345 MMSL
d00138 MMSL
000635 NDDF
004491 NDDF
387283005 SNOMEDCT_US
387433003 SNOMEDCT_US
76058001 SNOMEDCT_US

Pharmaceutical products:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
Minipress HUMAN PRESCRIPTION DRUG LABEL 1 0069-4310 CAPSULE 1 mg ORAL NDA 22 sections
Minipress HUMAN PRESCRIPTION DRUG LABEL 1 0069-4370 CAPSULE 2 mg ORAL NDA 22 sections
Minipress HUMAN PRESCRIPTION DRUG LABEL 1 0069-4380 CAPSULE 5 mg ORAL NDA 22 sections
Prazosin Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0093-4067 CAPSULE 1 mg ORAL ANDA 21 sections
Prazosin Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0093-4068 CAPSULE 2 mg ORAL ANDA 21 sections
Prazosin Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0093-4069 CAPSULE 5 mg ORAL ANDA 21 sections
Prazosin Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0378-1101 CAPSULE 1 mg ORAL ANDA 21 sections
Prazosin Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0378-2302 CAPSULE 2 mg ORAL ANDA 21 sections
Prazosin Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0378-3205 CAPSULE 5 mg ORAL ANDA 21 sections
Prazosin Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0904-7020 CAPSULE 1 mg ORAL ANDA 20 sections
Prazosin Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0904-7021 CAPSULE 2 mg ORAL ANDA 20 sections
Prazosin Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0904-7022 CAPSULE 5 mg ORAL ANDA 20 sections
Prazosin Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 10135-666 CAPSULE 1 mg ORAL ANDA 21 sections
Prazosin Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 10135-667 CAPSULE 2 mg ORAL ANDA 21 sections
Prazosin Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 10135-668 CAPSULE 5 mg ORAL ANDA 21 sections
Prazosin Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 33261-860 CAPSULE 1 mg ORAL ANDA 21 sections
Prazosin Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 33261-861 CAPSULE 2 mg ORAL ANDA 21 sections
Prazosin Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 43063-248 CAPSULE 5 mg ORAL ANDA 21 sections
Prazosin Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 43063-260 CAPSULE 2 mg ORAL ANDA 21 sections
Prazosin Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 43353-035 CAPSULE 2 mg ORAL ANDA 21 sections
Prazosin Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 43353-868 CAPSULE 2 mg ORAL ANDA 22 sections
Prazosin Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 50090-0379 CAPSULE 1 mg ORAL ANDA 21 sections
Prazosin Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 50090-1948 CAPSULE 1 mg ORAL ANDA 21 sections
Prazosin Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 50090-1948 CAPSULE 1 mg ORAL ANDA 21 sections
Prazosin Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 50090-2845 CAPSULE 1 mg ORAL ANDA 21 sections
Prazosin Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 50090-5512 CAPSULE 2 mg ORAL ANDA 21 sections
Prazosin Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 51079-630 CAPSULE 1 mg ORAL ANDA 21 sections
Prazosin Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 51079-631 CAPSULE 2 mg ORAL ANDA 21 sections
Prazosin Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 51079-632 CAPSULE 5 mg ORAL ANDA 21 sections
Prazosin Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 53808-1075 CAPSULE 2 mg ORAL ANDA 21 sections