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
Hypotension 131.69 57.48 37 188 32399 2325461
Posterior reversible encephalopathy syndrome 77.50 57.48 15 210 2465 2355395
Overdose 76.83 57.48 22 203 19885 2337975
Atrioventricular block first degree 70.53 57.48 12 213 955 2356905
Electrocardiogram QT prolonged 65.44 57.48 16 209 7798 2350062
Acute kidney injury 61.05 57.48 20 205 28102 2329758
Circulatory collapse 60.00 57.48 13 212 3707 2354153
Status epilepticus 59.26 57.48 12 213 2466 2355394
Metabolic acidosis 59.02 57.48 14 211 5984 2351876

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 117.22 55.18 22 267 1442 1745050
Hypotension 76.36 55.18 29 260 29625 1716867
Syncope 75.90 55.18 24 265 14145 1732347
Vasoplegia syndrome 72.54 55.18 11 278 191 1746301
Completed suicide 68.55 55.18 23 266 16289 1730203
Acute respiratory distress syndrome 65.87 55.18 16 273 3535 1742957
Aspiration 59.06 55.18 13 276 1857 1744635
Sinus bradycardia 58.63 55.18 13 276 1920 1744572

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
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

Drug Use (View source of the data)

DiseaseRelationSNOMED_IDDOID
Hypertensive disorder indication 38341003 DOID:10763
Benign prostatic hyperplasia off-label use 266569009
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
C0032912 UMLSCUI
D00609 KEGG_DRUG
76058001 SNOMEDCT_US
4019901 VANDF
8629 RXNORM
387433003 SNOMEDCT_US
d00138 MMSL
387283005 SNOMEDCT_US
004491 NDDF
CHEMBL2 ChEMBL_ID
CHEMBL1558 ChEMBL_ID
DB00457 DRUGBANK_ID
XRA PDB_CHEM_ID
CHEBI:8364 CHEBI
X0Z7454B90 UNII
19237-84-4 SECONDARY_CAS_RN
2593 INN_ID
D011224 MESH_DESCRIPTOR_UI
4893 PUBCHEM_CID
503 IUPHAR_LIGAND_ID

Pharmaceutical products:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
Minipress HUMAN PRESCRIPTION DRUG LABEL 1 0069-4310 CAPSULE 1 mg ORAL NDA 13 sections
Minipress HUMAN PRESCRIPTION DRUG LABEL 1 0069-4370 CAPSULE 2 mg ORAL NDA 13 sections
Minipress HUMAN PRESCRIPTION DRUG LABEL 1 0069-4380 CAPSULE 5 mg ORAL NDA 13 sections
Prazosin Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0093-4067 CAPSULE 1 mg ORAL ANDA 12 sections
Prazosin Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0093-4068 CAPSULE 2 mg ORAL ANDA 12 sections
Prazosin Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0093-4069 CAPSULE 5 mg ORAL ANDA 12 sections
Prazosin Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0378-1101 CAPSULE 1 mg ORAL ANDA 12 sections
Prazosin Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0378-2302 CAPSULE 2 mg ORAL ANDA 12 sections
Prazosin Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0378-3205 CAPSULE 5 mg ORAL ANDA 12 sections
Prazosin Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 10135-666 CAPSULE 1 mg ORAL ANDA 13 sections
Prazosin Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 10135-667 CAPSULE 2 mg ORAL ANDA 13 sections
Prazosin Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 10135-668 CAPSULE 5 mg ORAL ANDA 13 sections
Prazosin Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 33261-860 CAPSULE 1 mg ORAL ANDA 12 sections
Prazosin Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 33261-861 CAPSULE 2 mg ORAL ANDA 12 sections
Prazosin Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 43063-248 CAPSULE 5 mg ORAL ANDA 12 sections
Prazosin Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 43063-260 CAPSULE 2 mg ORAL ANDA 12 sections
Prazosin Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 43353-035 CAPSULE 2 mg ORAL ANDA 13 sections
Prazosin Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 43353-868 CAPSULE 2 mg ORAL ANDA 13 sections
Prazosin Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 50090-1948 CAPSULE 1 mg ORAL ANDA 12 sections
Prazosin Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 51079-630 CAPSULE 1 mg ORAL ANDA 12 sections
Prazosin Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 51079-631 CAPSULE 2 mg ORAL ANDA 12 sections
Prazosin Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 51079-632 CAPSULE 5 mg ORAL ANDA 12 sections
Prazosin Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 53808-1075 CAPSULE 2 mg ORAL ANDA 12 sections
Prazosin Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 54868-1547 CAPSULE 2 mg ORAL ANDA 12 sections
Prazosin Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 55154-4391 CAPSULE 1 mg ORAL ANDA 12 sections
Prazosin Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 55154-8181 CAPSULE 1 mg ORAL ANDA 13 sections
Prazosin Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 55289-536 CAPSULE 1 mg ORAL ANDA 12 sections
Prazosin HUMAN PRESCRIPTION DRUG LABEL 1 59762-5310 CAPSULE 1 mg ORAL NDA AUTHORIZED GENERIC 13 sections
Prazosin HUMAN PRESCRIPTION DRUG LABEL 1 59762-5320 CAPSULE 2 mg ORAL NDA AUTHORIZED GENERIC 13 sections
Prazosin HUMAN PRESCRIPTION DRUG LABEL 1 59762-5350 CAPSULE 5 mg ORAL NDA AUTHORIZED GENERIC 13 sections