19216-56-9

19216-56-9 structure

Name: Prazosin
Chemical Name: prazosin
CAS Number: 19216-56-9
Molecular Formula: C₁₉H₂₁N₅O₄
Molecular Weight: 383.40100
Catalog: API Circulatory system medication Antihypertensive drug
Create Date: 2018-06-02 08:00:00
Modify Date: 2024-01-05 15:19:48
Prazosin is an alpha-adrenergic blocker and is a sympatholytic drug used to treat high blood pressure and anxiety, PTSD, and panic disorder.Target: Adrenergic ReceptorPrazosin, is a sympatholytic drug used to treat high blood pressure and anxiety, PTSD, andpanic disorder. It is an alpha-adrenergic blocker that is specific for the alpha-1 receptors. These receptors are found on vascular smooth muscle, where they are responsible for the vasoconstrictive action of norepinephrine. They are also found throughout the central nervous system. As of 2013, prazosin is off-patent in the US, and the FDA has approved at least one generic manufacturer.In addition to its alpha-blocking activity, prazosin is an antagonist of the MT3 receptor (which is not present in humans), with selectivity for this receptor over the MT1 and MT2 receptors.Prazosin is orally active and has a minimal effect on cardiac function due to its alpha-1 receptor selectivity. However, when prazosin is initially started, heart rate and contractility go up in order to maintain the pre-treatment blood pressures because the body has reached homeostasis at its abnormally high blood pressure. The blood pressure lowering effect becomes apparent when prazosin is taken for longer periods of time. The heart rate and contractility go back down over time and blood pressure decreases.

Name	prazosin
Synonyms	[14C]-Prazosin Prazosinum [INN-Latin] Minipress (4-(4-Amino-6,7-dimethoxyquinazolin-2-yl)piperazin-1-yl)(furan-2-yl)methanone [4-(4-amino-6,7-dimethoxyquinazolin-2-yl)piperazin-1-yl]-(furan-2-yl)methanone [125I]-Prazosin Prazosinum 4-(4-amino-6,7-dimethoxyquinazolin-2-yl)piperazinyl furan-2-yl ketone [Bodipyl-FL]-Prazosin Prazosine Prazosina Furazosin Prazosina [INN-Spanish] 2-[4-(2-furoyl)-piperazin-1-yl]-4-amino-6,7-dimethoxy-quinazoline Prazosine [INN-French] Lentopres

Description	Prazosin is an alpha-adrenergic blocker and is a sympatholytic drug used to treat high blood pressure and anxiety, PTSD, and panic disorder.Target: Adrenergic ReceptorPrazosin, is a sympatholytic drug used to treat high blood pressure and anxiety, PTSD, andpanic disorder. It is an alpha-adrenergic blocker that is specific for the alpha-1 receptors. These receptors are found on vascular smooth muscle, where they are responsible for the vasoconstrictive action of norepinephrine. They are also found throughout the central nervous system. As of 2013, prazosin is off-patent in the US, and the FDA has approved at least one generic manufacturer.In addition to its alpha-blocking activity, prazosin is an antagonist of the MT3 receptor (which is not present in humans), with selectivity for this receptor over the MT1 and MT2 receptors.Prazosin is orally active and has a minimal effect on cardiac function due to its alpha-1 receptor selectivity. However, when prazosin is initially started, heart rate and contractility go up in order to maintain the pre-treatment blood pressures because the body has reached homeostasis at its abnormally high blood pressure. The blood pressure lowering effect becomes apparent when prazosin is taken for longer periods of time. The heart rate and contractility go back down over time and blood pressure decreases.
Related Catalog	Signaling Pathways >> GPCR/G Protein >> Adrenergic Receptor Natural Products >> Alkaloid Research Areas >> Cardiovascular Disease
References	[1]. Day HE, et al. Distribution of alpha 1a-, alpha 1b- and alpha 1d-adrenergic receptor mRNA in the rat brain and spinal cord. J Chem Neuroanat. 1997 Jul;13(2):115-39. [2]. Yu CX, et al. Selective MT(2) melatonin receptor antagonist blocks melatonin-induced antinociception in rats. Neurosci Lett. 2000 Mar 24;282(3):161-4.

Density	1.352g/cm3
Boiling Point	638.4ºC at 760mmHg
Melting Point	278-280ºC
Molecular Formula	C₁₉H₂₁N₅O₄
Molecular Weight	383.40100
Flash Point	339.9ºC
Exact Mass	383.15900
PSA	107.68000
LogP	1.71760
Vapour Pressure	3.4E-16mmHg at 25°C
Index of Refraction	1.651

CHEMICAL IDENTIFICATION

RTECS NUMBER :: VA1300000

CHEMICAL NAME :: Quinazoline, 4-amino-6,7-dimethoxy-2-(4-(2-furoyl)piperazin-1-yl)-

CAS REGISTRY NUMBER :: 19216-56-9

BEILSTEIN REFERENCE NO. :: 0768345

LAST UPDATED :: 199703

DATA ITEMS CITED :: 9

MOLECULAR FORMULA :: C19-H21-N5-O4

MOLECULAR WEIGHT :: 383.45

WISWESSER LINE NOTATION :: T66 BN DNJ C- AT6N DNTJ DV- BT5OJ&& EZ HO1 IO1

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Human - woman

DOSE/DURATION :: 20 ug/kg

TOXIC EFFECTS :: Vascular - BP lowering not characterized in autonomic section Gastrointestinal - nausea or vomiting

REFERENCE :: AIMEAS Annals of Internal Medicine. (American College of Physicians, 4200 Pine St., Philadelphia, PA 19104) V.1- 1927- Volume(issue)/page/year: 97,455,1982

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Human - man

DOSE/DURATION :: 1143 ug/kg

TOXIC EFFECTS :: Vascular - BP lowering not characterized in autonomic section

REFERENCE :: AMSVAZ Acta Medica Scandinavica. (Almqvist & Wiksell, POB 45150, S-10430 Stockholm, Sweden) V.52-224, 1919-88. Volume(issue)/page/year: 213,157,1983

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Human

DOSE/DURATION :: 280 ug/kg

TOXIC EFFECTS :: Behavioral - somnolence (general depressed activity) Behavioral - hallucinations, distorted perceptions Vascular - BP lowering not characterized in autonomic section

REFERENCE :: BMJOAE British Medical Journal. (British Medical Assoc., BMA House, Tavistock Sq., London WC1H 9JR, UK) V.1- 1857- Volume(issue)/page/year: 2,508,1976

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Human

DOSE/DURATION :: 1260 ug/kg

TOXIC EFFECTS :: Behavioral - changes in motor activity (specific assay) Kidney, Ureter, Bladder - other changes

REFERENCE :: BMJOAE British Medical Journal. (British Medical Assoc., BMA House, Tavistock Sq., London WC1H 9JR, UK) V.1- 1857- Volume(issue)/page/year: 1,622,1978

TYPE OF TEST :: LD - Lethal dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: >3 gm/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: USXXAM United States Patent Document. (U.S. Patent Office, Box 9, Washington, DC 20231) Volume(issue)/page/year: #4734418

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: >4 gm/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: BCFAAI Bollettino Chimico Farmaceutico. (Societa Editoriale Farmaceutica, Via Ausonio 12, 20123 Milan, Italy) V.33- 1894- Volume(issue)/page/year: 128,129,1989

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: >400 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: RPTOAN Russian Pharmacology and Toxicology (English Translation). Translation of FATOAO. (Euromed Pub., 33, Woodlands Rd., Surbiton, Surrey, UK) V.30- 1967- Volume(issue)/page/year: 50,182,1987 ** OTHER MULTIPLE DOSE TOXICITY DATA **

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 30 mg/kg/60D-I

TOXIC EFFECTS :: Cardiac - changes in heart weight Vascular - BP lowering not characterized in autonomic section Endocrine - changes in adrenal weight

REFERENCE :: ETPAEK Experimental and Toxicologic Pathology. (Gustav Fischer Verlag Jena, Postfach 100537, D-07705 Jena, Germany) V.44- 1992- Volume(issue)/page/year: 45,109,1993 ** REPRODUCTIVE DATA **

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 2571 ug/kg

SEX/DURATION :: male 60 day(s) pre-mating

TOXIC EFFECTS :: Reproductive - Paternal Effects - testes, epididymis, sperm duct

REFERENCE :: AMSVAZ Acta Medica Scandinavica. (Almqvist & Wiksell, POB 45150, S-10430 Stockholm, Sweden) V.52-224, 1919-88. Volume(issue)/page/year: 213,319,1983