Prazosin (CED0002930)

Record Information
Version1.0
Creation Date2016-05-22 06:58:55 UTC
Update Date2026-08-20 03:09:48 UTC
Accession NumberCHEM020290
Identification
Common NamePrazosin
ClassSmall Molecule
Description
Prazosin is an organic compound with the chemical formula C19H21N5O4 and an average molecular weight of 383.40 g/mol. Prazosin belongs to the piperazines, a subclass of diazinanes within the organic compounds. This compound is associated with 14 recorded sources. Within healthcare, pharmaceuticals, and veterinary products, it is used as an antihypertensive. It is also found in food preservation and various household cleaning and consumer products, including tobacco smoke filters, perfumes within detergents and soaps, non electric simulated smoking devices, cigar cigarettes, and other smoking requisites. Additionally, it is released from electrical and electronic equipment, specifically electrodes, antennas, coils, conductors or conductive bodies characterised by the conductive materials, and electrically stimulated smoking devices. The recorded exposure route for this substance is oral. At the molecular level, Prazosin interacts with six recorded protein targets. It acts as an antagonist, binder, or inhibitor of the Alpha-1A adrenergic receptor (ADRA1A), the Alpha-1B adrenergic receptor (ADRA1B), and the Alpha-1D adrenergic receptor (ADRA1D). Furthermore, it targets the voltage-gated inwardly rectifying potassium channel KCNH2 and two other proteins.
Contaminant TypeNot Available
Chemical Structure
Synonyms
ValueSource
1-(4-Amino-6,7-dimethoxy-2-quinazolinyl)-4-(2-furanylcarbonyl)piperazineChEBI
2-(4-(2-Furoyl)piperazin-1-yl)-4-amino-6,7-dimethoxyquinazolineChEBI
PrazosinaChEBI
PrazosineChEBI
PrazosinumChEBI
MinipressKegg
PrazocinHMDB
FurazosinHMDB
Hydrochloride, prazosinHMDB
Pfizer brand OF prazosin hydrochlorideHMDB
Douglas brand OF prazosin hydrochlorideHMDB
Prazosin HCLHMDB
HCL, PrazosinHMDB
PratsiolHMDB
Prazosin hydrochlorideHMDB
Chemical FormulaC19H21N5O4
Average Molecular Mass383.401 g/mol
Monoisotopic Mass383.159 g/mol
CAS Registry Number19216-56-9
IUPAC Name2-[4-(furan-2-carbonyl)piperazin-1-yl]-6,7-dimethoxyquinazolin-4-amine
Traditional Nameprazosin
SMILESCOC1=C(OC)C=C2C(N)=NC(=NC2=C1)N1CCN(CC1)C(=O)C1=CC=CO1
InChI IdentifierInChI=1S/C19H21N5O4/c1-26-15-10-12-13(11-16(15)27-2)21-19(22-17(12)20)24-7-5-23(6-8-24)18(25)14-4-3-9-28-14/h3-4,9-11H,5-8H2,1-2H3,(H2,20,21,22)
InChI KeyIENZQIKPVFGBNW-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as n-arylpiperazines. These are organic compounds containing a piperazine ring where the nitrogen ring atom carries an aryl group.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassDiazinanes
Sub ClassPiperazines
Direct ParentN-arylpiperazines
Alternative Parents
Substituents
  • N-arylpiperazine
  • Quinazolinamine
  • Diazanaphthalene
  • Quinazoline
  • 2-heteroaryl carboxamide
  • Furoic acid or derivatives
  • Anisole
  • Dialkylarylamine
  • Alkyl aryl ether
  • Aminopyrimidine
  • Benzenoid
  • Pyrimidine
  • Imidolactam
  • Tertiary carboxylic acid amide
  • Heteroaromatic compound
  • Furan
  • Carboxamide group
  • Amino acid or derivatives
  • Carboxylic acid derivative
  • Ether
  • Oxacycle
  • Azacycle
  • Organic oxygen compound
  • Amine
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organonitrogen compound
  • Organooxygen compound
  • Primary amine
  • Organopnictogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Organoleptic EffectsNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.69 g/LALOGPS
logP1.93ALOGPS
logP1.65ChemAxon
logS-2.7ALOGPS
pKa (Strongest Basic)7.24ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area106.95 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity104.5 m³·mol⁻¹ChemAxon
Polarizability40.49 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted GC-MSPredicted GC-MS Spectrumsplash10-004s-6964000000-767452811ea10bd5212fNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-001i-0019000000-9cca43997ddcbdd78e84Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-001i-0009000000-9da934e12af818eb0a08Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-001i-0009000000-85316e57dd3fefac386dNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-001i-0019000000-09972bca73a43a1b73abNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0002-1597000000-48d7b8ba991427bab5c2Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0002-7491000000-4258e4db8045e56fe90fNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0002-0093000000-bffbfeafa12bdaf90f1dNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-001i-0009000000-d13122c92100f1c0a02eNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-001i-0009000000-b0b57af432244c705c26Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-000t-1289000000-c6fe1f53648d640102aaNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-000t-3292000000-6907f1985350ad49c47bNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-000t-8490000000-f9e0f1ad0c30225b7de2Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-001i-0009000000-77125e491b72f0b0adaeNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-001i-0029000000-4492a1b0f9df7854cc06Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0f8j-0392000000-b5c53dfdec441c727d1fNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-001r-0149000000-db377c2ba80a2269be91Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-001i-0009000000-b0b57af432244c705c26Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-001i-0009000000-d13122c92100f1c0a02eNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-000t-1289000000-c6fe1f53648d640102aaNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-000t-3292000000-6907f1985350ad49c47bNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-000t-1289000000-6f636f3231dda7f82261Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-014i-0019000000-dfd96213c9e6ff4376efNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-000t-8490000000-f9e0f1ad0c30225b7de2Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-001i-0149000000-f73cca3f923b018c8a1bNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-001i-0029000000-07443e2ca9ed85ab1a8fNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-001i-0009000000-35f8dba4163fc6bc5992Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0f8j-0392000000-b5c53dfdec441c727d1fNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-001i-0019000000-9cca43997ddcbdd78e84Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-001i-0009000000-c6d1daacd75d84cdcd43Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0f89-0009000000-8b8092f98e28585b4426Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0002-1290000000-97e5af08f45209e9c83cNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-001i-0009000000-5a0c9368a651828baa30Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-00lr-2009000000-83a9ee008cd107198d0aNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-014l-6196000000-cf8f424d6bd672c052dcNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-001i-0009000000-126152218112aa602662Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-001i-0009000000-94aaeafec7ae84716857Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0002-3094000000-4617ad3339714d5f48dbNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-001i-0009000000-83c6b2773a3b8c4077aaNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-001i-0019000000-4c5a0c5eeb91f3759e72Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-001r-1459000000-01af7102074580a2c418Not AvailableView Spectrum
Toxicity Profile
Mechanism of ToxicityNot Available
Carcinogenicity (IARC Classification)Not Available
Minimum Risk LevelNot Available
SymptomsNot Available
TreatmentNot Available
Toxicity Values
Toxicity ValueUnitValue RangeOrganismDose DescriptorRoute of ExposurePredicted or ExperimentalReference
1461.0Log mg/kg[820:2600]RatLD50oralpredictedNot Available
Health Effects
Health EffectRelationshipDirectionReference
Exposure Sources
Source IDSourceSectorReference
10InsecticidesAgriculture & land managementNot Available
233BrushesPersonal care & cosmeticsNot Available
289AntihypertensivesHealthcare, pharmaceuticals & veterinary productsNot Available
506AntennasElectrical & Electronic EquipmentNot Available
508CoilsElectrical & Electronic EquipmentNot Available
511Conductors Or Conductive Bodies Characterised By The Conductive MaterialsElectrical & Electronic EquipmentNot Available
518Electrically Stimulated Smoking DevicesElectrical & Electronic EquipmentNot Available
519ElectrodesElectrical & Electronic EquipmentNot Available
524Hybrid CapacitorsElectrical & Electronic EquipmentNot Available
526LoudspeakersElectrical & Electronic EquipmentNot Available
545Food PreservationFood, food processing & cookwareNot Available
556Cigar CigarettesHousehold cleaning & consumer productsNot Available
559Non Electric Simulated Smoking DevicesHousehold cleaning & consumer productsNot Available
560Other Smoking RequisitesHousehold cleaning & consumer productsNot Available
561Perfumes Within Detergents And SoapsHousehold cleaning & consumer productsNot Available
569Tobacco Smoke FiltersHousehold cleaning & consumer productsNot Available
580Manufacture Preparation Of Tobacco ProductsIndustrial manufacturing & chemical processingNot Available
596AcaricidesAgriculture & land managementNot Available
600Herbicides And AlgicidesAgriculture & land managementNot Available
605Pest RepellantsAgriculture & land managementNot Available
606Plant Growth RegulatorsAgriculture & land managementNot Available
610Aftersun ProductsPersonal care & cosmeticsNot Available
611Anti Perspirants Or Body DeoderantsPersonal care & cosmeticsNot Available
614Essential Oils Or PerfumesPersonal care & cosmeticsNot Available
615Eye Makeup ProductsPersonal care & cosmeticsNot Available
617Lip Care ProductsPersonal care & cosmeticsNot Available
618Lip Makeup ProductsPersonal care & cosmeticsNot Available
632ApparelTextiles, leather & furnishingsNot Available
642FootwearTextiles, leather & furnishingsNot Available
Pathways
3 pathways
Targets
StructureProteinUniProt IDOrganismRelationshipDetails
Click to view 3D structureAlpha-1A adrenergic receptorP43140Rattus norvegicusPredicted (SEA)0.0778492
Click to view 3D structureAlpha-1B adrenergic receptorP35368HumansPredicted (SEA)0.233548
Alpha-1A adrenergic receptor structureClick to view 3D structureAlpha-1A adrenergic receptorP35348HumansPredicted (SEA)0.467095
Click to view 3D structureAlpha-1B adrenergic receptorP15823Rattus norvegicusPredicted (SEA)0.155698
Click to view 3D structureD(2) dopamine receptorP61169RatPredicted (SEA)2.49118
Click to view 3D structureAlpha-1D adrenergic receptorP23944Rattus norvegicusPredicted (SEA)0.622794
Click to view 3D structureAlpha-1A adrenergic receptorP18130Bos taurusPredicted (SEA)0.622794
Click to view 3D structureAlpha-1D adrenergic receptorP25100HumansPredicted (SEA)0.311397
Click to view 3D structure5-hydroxytryptamine receptor 1AP19327Rattus norvegicusPredicted (SEA)2.41333
Alpha-2C adrenergic receptor structureClick to view 3D structureAlpha-2C adrenergic receptorP18825HumansPredicted (SEA)1.08989
Alpha-2B adrenergic receptor structureClick to view 3D structureAlpha-2B adrenergic receptorP18089HumansPredicted (SEA)0.778492
Click to view 3D structureBeta-caseinP02665Rattus norvegicusPredicted (SEA)0.0778492
Click to view 3D structure5-hydroxytryptamine receptor 2AP14842Rattus norvegicusPredicted (SEA)4.9045
5-hydroxytryptamine receptor 1A structureClick to view 3D structure5-hydroxytryptamine receptor 1AP08908HumansPredicted (SEA)26.1573
Alpha-2A adrenergic receptor structureClick to view 3D structureAlpha-2A adrenergic receptorP08913HumansPredicted (SEA)7.08428
Click to view 3D structureAlpha-1B adrenergic receptorP18841Mesocricetus auratusPredicted (SEA)1.40129
Voltage-gated inwardly rectifying potassium channel KCNH2 structureClick to view 3D structureVoltage-gated inwardly rectifying potassium channel KCNH2Q12809HumansPredicted (SEA)47.0988
5-hydroxytryptamine receptor 2B structureClick to view 3D structure5-hydroxytryptamine receptor 2BP41595HumansPredicted (SEA)24.4447
Click to view 3D structureAlpha-1A adrenergic receptorO02824Oryctolagus cuniculusPredicted (SEA)0.856341
Interstitial collagenase structureClick to view 3D structureInterstitial collagenaseP03956HumansPredicted (SEA)30.439
Mu-type opioid receptor structureClick to view 3D structureMu-type opioid receptorP35372HumansPredicted (SEA)139.817
Sigma non-opioid intracellular receptor 1 structureClick to view 3D structureSigma non-opioid intracellular receptor 1Q99720HumansPredicted (SEA)64.1478
D(3) dopamine receptor structureClick to view 3D structureD(3) dopamine receptorP35462HumansPredicted (SEA)95.3653
Click to view 3D structureAlpha-2A adrenergic receptorP18871Sus scrofaPredicted (SEA)0.0778492
D(4) dopamine receptor structureClick to view 3D structureD(4) dopamine receptorP21917HumansPredicted (SEA)68.1181
Concentrations
Not Available
External Links
DrugBank IDDB00457
HMDB IDHMDB0014600
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDXRA
Wikipedia LinkPrazosin
Chemspider ID4724
ChEBI ID8364
PubChem Compound ID4893
Kegg Compound IDC07368
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Cushman WC, Ford CE, Cutler JA, Margolis KL, Davis BR, Grimm RH, Black HR, Hamilton BP, Holland J, Nwachuku C, Papademetriou V, Probstfield J, Wright JT Jr, Alderman MH, Weiss RJ, Piller L, Bettencourt J, Walsh SM: Success and predictors of blood pressure control in diverse North American settings: the antihypertensive and lipid-lowering treatment to prevent heart attack trial (ALLHAT). J Clin Hypertens (Greenwich). 2002 Nov-Dec;4(6):393-404.
2. Hiraoka Y, Taniguchi T, Tanaka T, Okada K, Kanamaru H, Muramatsu I: Pharmacological characterization of unique prazosin-binding sites in human kidney. Naunyn Schmiedebergs Arch Pharmacol. 2003 Jul;368(1):49-56. Epub 2003 Jun 25.
3. Bawaskar HS, Bawaskar PH: Utility of scorpion antivenin vs prazosin in the management of severe Mesobuthus tamulus (Indian red scorpion) envenoming at rural setting. J Assoc Physicians India. 2007 Jan;55:14-21.
4. Sigma Aldrich: http://www.sigmaaldrich.com/catalog/search/ProductDetail/SIGMA/P7791
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=20825390