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Substance Name: Prazosin [INN:BAN]
RN: 19216-56-9
UNII: XM03YJ541D
InChIKey: IENZQIKPVFGBNW-UHFFFAOYSA-N

Note

  • A selective adrenergic alpha-1 antagonist used in the treatment of HEART FAILURE; HYPERTENSION; PHEOCHROMOCYTOMA; RAYNAUD DISEASE; PROSTATIC HYPERTROPHY; and URINARY RETENTION.

Molecular Formula

  • C19-H21-N5-O4

Molecular Weight

  • 383.4059
 

Classification Codes

  • Adrenergic Agents
  • Adrenergic alpha-1 Receptor Antagonists
  • Adrenergic alpha-Antagonists
  • Adrenergic Antagonists
  • Antihypertensive Agents
  • Cardiovascular Agents
  • Drug / Therapeutic Agent
  • Human Data
  • Neurotransmitter Agents
  • Reproductive Effect

Names and Synonyms

Name of Substance

  • Prazosin
  • Prazosin [INN:BAN]

MeSH Heading

  • Prazosin

Synonyms

  • 1-(4-Amino-6,7-dimethoxy-2-quinazolinyl)-4-(2-furanylcarbonyl)piperazine
  • 2-(4-(2-Furoyl)piperazin-1-yl)-4-amino-6,7-dimethoxyquinazoline
  • 5-25-13-00365 (Beilstein Handbook Reference)
  • BRN 0768345
  • EINECS 242-885-8
  • Furazosin
  • Piperazine, 1-(4-amino-6,7-dimethoxy-2-quinazolinyl)-4-(2-furanylcarbonyl)-
  • Piperazine, 1-(4-amino-6,7-dimethoxy-2-quinazolinyl)-4-(2-furoyl)-
  • Prazosin
  • Prazosina
  • Prazosina [INN-Spanish]
  • Prazosine
  • Prazosine [INN-French]
  • Prazosinum
  • Prazosinum [INN-Latin]
  • Quinazoline, 4-amino-6,7-dimethoxy-2-(4-(2-furoyl)piperazin-1-yl)-
  • UNII-XM03YJ541D

Systematic Names

  • Piperazine, 1-(4-amino-6,7-dimethoxy-2-quinazolinyl)-4-(2-furanylcarbonyl)-
  • Prazosin
  • Quinazoline, 4-amino-6,7-dimethoxy-2-(4-(2-furoyl)piperazin-1-yl)-

Registry Numbers

CAS Registry Number

  • 19216-56-9

FDA UNII

  • XM03YJ541D

System Generated Number

  • 0019216569

Structure Descriptors

InChI

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)

InChIKey

IENZQIKPVFGBNW-UHFFFAOYSA-N

Smiles

COc1cc2nc(nc(N)c2cc1OC)N3CCN(CC3)C(=O)c4occc4

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
human TDLo oral 280ug/kg (0.28mg/kg) VASCULAR: BP LOWERING NOT CHARACTERIZED IN AUTONOMIC SECTION

BEHAVIORAL: "HALLUCINATIONS, DISTORTED PERCEPTIONS"

BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)
British Medical Journal. Vol. 2, Pg. 508, 1976.
human TDLo oral 1260ug/kg (1.26mg/kg) BEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY)

KIDNEY, URETER, AND BLADDER: OTHER CHANGES
British Medical Journal. Vol. 1, Pg. 622, 1978.
man TDLo oral 1143ug/kg (1.143mg/kg) VASCULAR: BP LOWERING NOT CHARACTERIZED IN AUTONOMIC SECTION Acta Medica Scandinavica. Vol. 213, Pg. 157, 1983.
mouse LD50 intravenous > 400mg/kg (400mg/kg)   Russian Pharmacology and Toxicology Vol. 50, Pg. 182, 1987.
mouse LD50 oral > 4gm/kg (4000mg/kg)   Bollettino Chimico Farmaceutico. Vol. 128, Pg. 129, 1989.
rat LD oral > 3gm/kg (3000mg/kg)   United States Patent Document. Vol. #4734418,
women TDLo oral 20ug/kg (0.02mg/kg) GASTROINTESTINAL: NAUSEA OR VOMITING

VASCULAR: BP LOWERING NOT CHARACTERIZED IN AUTONOMIC SECTION
Annals of Internal Medicine. Vol. 97, Pg. 455, 1982.

Physical Properties

Physical Property Value Units Temp (deg C) Source
Melting Point 279 deg C   EXP
log P (octanol-water) 1.280 (none)   EST
Atmospheric OH Rate Constant 2.84E-10 cm3/molecule-sec 25 EST

Physical property data is provided to ChemIDplus by SRC, Inc.