StartseiteMCPWorkbenchSkills
StartseiteWorkbenchBenachrichtigungenMein Bereich
Huagongshe Open Project:[email protected]KI-Anbindung: llms.txt · MCP-AnleitungDatenschutz · Nutzungsbedingungen · Supportv1.7.8
  1. Startseite
  2. /Verbindung

Prazosin

HCID 4893
NotizenReaktionen
GrundinformationenNamen und BezeichnerEigenschaftenSicherheit und RegulatorischesChemie und IndustrieZugehörige ReaktionenNotizen zur Verbindung
TeilstruktursucheÄhnliche Strukturen suchen

Grundinformationen

CAS
19216-56-9
Standard-SMILES
COc1cc2nc(N3CCN(C(=O)c4ccco4)CC3)nc(N)c2cc1OC
InChIKey
IENZQIKPVFGBNW-UHFFFAOYSA-N
Summenformel
C19H21N5O4
Durchschnittliche Molmasse
383,4 g/mol
Monoisotopische Masse
383,15935417

Namen und Bezeichner

Bevorzugter Name
Prazosin
IUPAC
[4-(4-amino-6,7-dimethoxyquinazolin-2-yl)piperazin-1-yl]-(furan-2-yl)methanone
Lokaler Name
Prazosin
Englischer Name
Prazosin
Summenformel
C19H21N5O4
Molmasse
383.4

Namen und Synonyme

prazosin19216-56-9FurazosinPrazosinePrazosinaPrazosinum1-(4-Amino-6,7-dimethoxy-2-quinazolinyl)-4-(2-furanylcarbonyl)piperazine2-(4-(2-Furoyl)piperazin-1-yl)-4-amino-6,7-dimethoxyquinazolineDTXSID4049082Piperazine, 1-(4-amino-6,7-dimethoxy-2-quinazolinyl)-4-(2-furanylcarbonyl)-XM03YJ541DCP-122991
Weitere Namen anzeigen
pressinminipressAKOS B020009PrazosinBaseTerazosin-010Prazosin USP/EP/BPART-CHEM-BB B020009
CHEBI:8364DTXCID0029008Piperazine, 1-(4-amino-6,7-dimethoxy-2-quinazolinyl)-4-(2-furoyl)-2-{4-[(furan-2-yl)carbonyl]piperazin-1-yl}-6,7-dimethoxyquinazolin-4-amine2-[4-(2-Furoyl)piperazin-1-yl]-4-amino-6,7-dimethoxyquinazoline(4-(4-amino-6,7-dimethoxyquinazolin-2-yl)piperazin-1-yl)-furan-2-ylmethanone[4-(4-amino-6,7-dimethoxyquinazolin-2-yl)piperazin-1-yl]-furan-2-ylmethanone2-(4-((furan-2-yl)carbonyl)piperazin-1-yl)-6,7-dimethoxyquinazolin-4-amine

Datenbank-Bezeichner

CAS
19216-56-9

Eigenschaften

Berechnete Struktureigenschaften

XLogP
2
Polarare Oberfläche (TPSA)
107 Ų
H-Brücken-Donoren
1
H-Brücken-Akzeptoren
8
Frei drehbare Bindungen
4
Schwere Atome
28
Formalladung
0
Komplexität
544

Experimentelle und physikochemische Eigenschaften

LogP · 2 Einträge

1.3

1.3

Solubility · 2 Einträge

1.4

6.93e-01 g/L

Boiling Point638.366
Melting Point · 2 Einträge

277-280

279 °C

Physical DescriptionSolid
Dissociation Constants6.54
Collision Cross Section · 2 Einträge

192.7 Ų [M+H]+ [CCS Type: TW; Method: Major Mix IMS/Tof Calibration Kit (Waters)]

192 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards];186.41 Ų [M+Na]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards];187.83 Ų [M+K]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]

Physikochemische Eigenschaften

Sicherheit und Regulatorisches

Sicherheitsangaben dienen nur zur Orientierung und ersetzen weder das Sicherheitsdatenblatt (SDB) des Lieferanten noch geltende Vorschriften oder eine fachliche Bewertung.

GHS-Klassifizierung

GHS Classification · 5 Einträge

Warning

H302 (50%): Harmful if swallowed [Warning Acute toxicity, oral];H315 (50%): Causes skin irritation [Warning Skin corrosion/irritation];H319 (100%): Causes serious eye irritation [Warning Serious eye damage/eye irritation];H335 (50%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract irritation]

P261, P264, P264+P265, P270, P271, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P319, P321, P330, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 2 reports by companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.;Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown. For more detailed information, please visit ECHA C&L website.

Gefahrenhinweise

Other Safety Information · 1 Eintrag

IMAP assessments - Piperazine, 1-(4-amino-6,7-dimethoxy-2-quinazolinyl)-4-(2-furanylcarbonyl)-: Environment tier I assessment;IMAP assessments - Piperazine, 1-(4-amino-6,7-dimethoxy-2-quinazolinyl)-4-(2-furanylcarbonyl)-: Human health tier I assessment

Hazard Classes and CategoriesAcute Tox. 4 (50%);Skin Irrit. 2 (50%);Eye Irrit. 2 (100%);STOT SE 3 (50%)

Toxikologische Informationen

Hepatotoxicity · 1 Eintrag

Prazosin has been associated with a low rate of serum aminotransferase elevations that in controlled trials was no higher than with placebo therapy. These elevations were transient and did not require dose modification. No instances of clinically apparent acute liver injury due to prazosin have been published in the literature, but reports of cholestatic hepatitis have been received by the sponsor. Among the alpha adrenergic receptor antagonists, the most frequently implicated agent in causing liver injury has been alfuzosin with only single, and not well documented cases linked to other alpha blockers. Thus, acute symptomatic liver injury due to prazosin is quite rare, and severe hepatotoxicity must be exceeding rare, if it occurs at all.;Likelihood score: E* (unproven but suspected rare cause of clinically apparent liver injury).

Chemie und Industrie

Pharmakologische Informationen

ATC Code · 3 Einträge

C02CA01

C - Cardiovascular system;C02 - Antihypertensives;C02C - Antiadrenergic agents, peripherally acting;C02CA - Alpha-adrenoreceptor antagonists;C02CA01 - Prazosin

QC - Cardiovascular system;QC02 - Antihypertensives;QC02C - Antiadrenergic agents, peripherally acting;QC02CA - Alpha-adrenoreceptor antagonists;QC02CA01 - Prazosin

Protein BindingHighly bound to proteins with 97% binding to albumin and alpha 1-acid glycoprotein. Prazosin is thought to be mostly (about 80-90%) bound to albumin.
Pharmacodynamics · 1 Eintrag

**Effects on blood pressure** The pharmacodynamic and therapeutic effect of this drug includes is a decrease in blood pressure as well as clinically significant decreases in cardiac output, heart rate, blood flow to the kidney, and glomerular filtration rate. The decrease in blood pressure may occur in both standing and supine positions. Many of the above effects are due to vasodilation of blood vessels caused by prazosin, resulting in decreased peripheral resistance,. Peripheral resistance refers to the level resistance of the blood vessels to blood that flows through them. As the blood vessels constrict (narrow), the resistance increases and as they dilate (widen), and peripheral resistance decreases, lowering blood pressure. **Effects on sleep disturbance related to post-traumatic stress disorder (PTSD)** Some studies have suggested that this drug improves sleep in patients suffering from insomnia related to nightmares and post-traumatic stress disorder, caused by hyperarousal. This effect likely occurs through the inhibition of adrenergic stimulation found in states of hyperarousal.

Mechanism of Action · 1 Eintrag

Alpha-adrenergic receptors are essential for the regulation of blood pressure in humans. Two types of alpha receptors, alpha 1 and alpha 2, both play a role in regulating blood pressure. Alpha-1 receptors are postsynaptic (located after the nerve junction, or space between a nerve fiber and target tissue). In this case, the target tissue is the vascular smooth muscle. These receptors, when activated, increase blood pressure. Prazosin inhibits the postsynaptic alpha-1 adrenoceptors. This inhibition blocks the vasoconstricting (narrowing) effect of catecholamines (epinephrine and norepinephrine) on the vessels, leading to peripheral blood vessel dilation. Through blood vessel constriction by adrenergic receptor activation, epinephrine and norepinephrine normally act to increase blood pressure.

Zugehörige Reaktionen

10
Reaktionsaufzeichnung erstellen
Reaktionsgleichung von HRID 372680
HRID 372680als Produktuspto-grants-1978_05
Reaktionsgleichung von HRID 461331
HRID 461331als Produktuspto-grants-1977_12
Reaktionsgleichung von HRID 461336
HRID 461336als Produktuspto-grants-1977_12
Reaktionsgleichung von HRID 826660
HRID 826660als ProduktTest data from https://doi.org/10.1039/C8SC04228D
Reaktionsgleichung von HRID 840093
HRID 840093als Produktuspto-grants-2002_04
Reaktionsgleichung von HRID 979728
HRID 979728als Eduktuspto-grants-1987_05
Reaktionsgleichung von HRID 1576327
HRID 1576327als Produktuspto-grants-1976_09
Reaktionsgleichung von HRID 1580969
HRID 1580969als Produktuspto-grants-1976_01
Seite 1 von 2

Notizen zur Verbindung

Wird geladen…

Auf dieser SeiteGrundinformationenNamen und BezeichnerEigenschaftenSicherheit und RegulatorischesChemie und IndustrieZugehörige ReaktionenNotizen zur Verbindung
PubChem CID
4893
DTXSID
DTXSID4049082
ChEMBL
CHEMBL2
ChEBI
CHEBI:8364
UNII
XM03YJ541D
EC Number
242-885-8
Nikkaji
J10.000E
Schmelzpunkt
278 · 278-280°C
Siedepunkt
510.33 °C · 510.33°C (rough estimate)
Dichte
1.3275 · 1.3275 (rough estimate)
Brechungsindex
1.76 · 1.7600 (estimate)
storage temp.
2 · 2-8°C
Löslichkeit
DMSO (Slightly), Methanol (Slightly, Heated)
Aggregatzustand
Solid
pka
6.54 · pKa 6.54(50% EtOH) (Uncertain)
Farbe
White to Off-White
Wasserlöslichkeit
3.2 mg/L · 3.2mg/L(22.5 ºC)
InChI
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
C(N1CCN(C2=NC(N)=C3C(=N2)C=C(OC)C(OC)=C3)CC1)(C1=CC=CO1)=O
Adverse Effects · 1 Eintrag

Serious Adverse Effects;Serious adverse effects include first-dose hypotension, and therefore it is recommended to take the initial dose at night. Also, patients may develop orthostatic hypotension and syncope. In cataract surgeries, patients taking prazosin may develop intraoperative floppy iris syndrome (IFIS) due to the drug's effect on the alpha receptors on the iris dilator muscle. However, some patients develop IFIS without using alpha-adrenergic receptor antagonists prior to surgery . Other serious adverse effects include priapism.;Common side effects found in 5 to 10% of patients are dizziness, headaches, drowsiness, lack of energy, weakness, palpitations, and nausea. An extensive list of side effects can be found below with their occurrence rates.;Serious Adverse Effects;* First dose hypotension;* Orthostatic hypotension;* Intraoperative Floppy iris syndrome;* Priapism;* Syncope;Common Adverse Effects (5 to 10% of patients) (Koola);* Dizziness;* Headache;* Drowsiness;* Lack of energy;* Weakness;* Palpitations;* Nausea;Less Common Adverse Effects (1 to 4%);* Vomiting;* Diarrhea

Toxicity Summary · 1 Eintrag

There is no direct toxicity with this medication. High doses and overdoses could lead to hypotension, and patients should be supported clinically with volume resuscitation if necessary or pressor support.;The literature reports a case of an overdose of prazosin in a pediatric patient with hypotension, which was refractory to volume resuscitation, epinephrine, and norepinephrine support. This patient had concomitant ingestion with naproxen and acetaminophen. Given the hepatic metabolism of both acetaminophen and prazosin, this likely led to the prolonged clearing of the medication. The patient did respond to vasopressin.

Drug Induced Liver Injury · 5 Einträge

Drug-Induced Liver Injury Severity and Toxicity (DILIst)

prazosin

DILI Negative

Oral

DOI:10.1016/j.drudis.2019.09.022

Effects During Pregnancy and Lactation · 1 Eintrag

◉ Summary of Use during Lactation;Because little is available on the use of prazosin during breastfeeding, an alternate drug may be preferred, especially while nursing a newborn or preterm infant.;◉ Effects in Breastfed Infants;Relevant published information was not found as of the revision date.;◉ Effects on Lactation and Breastmilk;Relevant published information in nursing mothers was not found as of the revision date. Prazosin does not affect serum prolactin concentration in patients with hypertension. The prolactin level in a mother with established lactation may not affect her ability to breastfeed.

Sicherheitsdaten

Alarmwort
Warnung
Gefahrenhinweise
Code Gefahrenhinweise Gefahrenklasse Abteilung Alarmwort Symbol P-Code H315
Biological Half-LifeThe plasma half-life is about 2-3 hours.
Metabolism/MetabolitesIn animals, prazosin hydrochloride is heavily metabolized. This occurs through liver demethylation and conjugation. Some studies in humans or human cells in vitro show similar prazosin metabolism.
FDA Pharmacological Classification · 6 Einträge

XM03YJ541D

PRAZOSIN

Mechanisms of Action [MoA] - Adrenergic alpha-Antagonists

Established Pharmacologic Class [EPC] - alpha-Adrenergic Blocker

Prazosin is an alpha-Adrenergic Blocker. The mechanism of action of prazosin is as an Adrenergic alpha-Antagonist.

PRAZOSIN

MeSH Pharmacological Classification · 2 Einträge

Drugs used in the treatment of acute or chronic vascular HYPERTENSION regardless of pharmacological mechanism. Among the antihypertensive agents are DIURETICS; (especially DIURETICS, THIAZIDE); ADRENERGIC BETA-ANTAGONISTS; ADRENERGIC ALPHA-ANTAGONISTS; ANGIOTENSIN-CONVERTING ENZYME INHIBITORS; CALCIUM CHANNEL BLOCKERS; GANGLIONIC BLOCKERS; and VASODILATOR AGENTS.

Drugs that bind to and block the activation of ADRENERGIC ALPHA-1 RECEPTORS.

Absorption, Distribution and Excretion · 4 Einträge

After administration of an oral dose, peak plasma concentrations are attained at approximately 3 hours. There is a linear association between the prazosin dose given and plasma concentration at steady state.

This drug is mainly excreted in the bile and the feces.

About 0.6 L/kg.

In patients with congestive heart failure, the clearance of this drug is decreased. Impairment of renal function does not have relevant effects on elimination.

Cellular LocationsExtracellular;Membrane

Verwendung und Herstellung

UsesUse (kg; approx.) in Germany (2009): >10;Consumption (g per capita; approx.) in Germany (2009): 0.000122;Calculated removal (%): 8.9
Use ClassificationPharmaceuticals
Anwendungen · 2 Einträge

HistoryPrazosin is a drug used to treat hypertension. Prazosin is marketed by Pfizer and was initially approved by the FDA in 1988. It belongs to the class of drugs known as alpha-1 antagonists.According to FDA, in October 2025, New Jersey-based drugmaker Teva Pharmaceuticals USA and drug distributor Amerisource Health Services issued voluntary nationwide recalls of over half a million bottles of various strengths of prazosine capsules, which may include a cancer-causing chemical.

VerwendenPrazosin is used for treating mid-to-moderate hypertension. When using this drug, blood pressure is reduced without any significant change in indicators of cardiac function such as frequency, coronary flow, or cardiac output.

Vor- und nachgelagerte Produkte

Vorgelagerte Rohstoffe

1-(2-Furoyl)piperazinBenzonitrilAmmonia-ammonium chlorideMethyljodidThioharnstoffAmmoniak, wasserfrei2-Furoylchlorid2-Chlor-6,7-dimethoxychinazolin-4-aminPiperazin2,4-Dichloro-6,7-dihydro-5H-cyclopentapyrimidine

Nachgelagerte Produkte

Bunazosin

Anbieter82 Anbieter

北京华美互利生物化工010-56205725 · [email protected]
苏州道澜生物医药科技有限公司15952404857 · [email protected]
武汉英诺医药科技有限公司+86-027-59232304 15387063101 · [email protected]
艾吉析科技(上海)有限公司17717235263 · [email protected]
上海麦克林生化科技股份有限公司021-50706066 15221275939 · [email protected]
合肥翰刚医药科技有限公司+8618062405514 · [email protected]
咸宁深蓝生物医药研发有限公司18171815831 · [email protected]
湖北金梭生物科技有限公司00123456789 · [email protected]
普善实业(陕西)有限公司029-81310890 18165209495 · [email protected]
南京世洲生物科技有限公司025-025-85560043 17301488900 · [email protected]
上海海皋科技有限公司021-57646680 18306277365 · [email protected]
LGM Pharma1-(800)-881-8210 · [email protected]
Syntechem Co.,Ltd[email protected]
梯希爱(上海)化工贸易有限公司021-61109150 · [email protected]
欧利希(湖北)医药科技有限公司17316404525 17316404525 · [email protected]
上海诗丹德标准技术服务有限公司021-021-57127007-6622-6622 17621252073 · [email protected]
United Life Science020-82099279 18988941402 · [email protected]
西安泽邦生物科技有限公司[email protected]
銳迪國際科技有限公司18024082417 · [email protected]
上海艾梯西生物科技有限公司18721763493
MedChemexpress LLC021-58955995 · [email protected]
BOC Sciences1-631-485-4226; 16314854226 · [email protected]
Moxin Chemicals+86-17320513646 +86-17320513646 · [email protected]
上海皓鸿生物医药科技有限公司400-8210725 4008210725 · [email protected]
深圳振强药物研发有限公司0755-66853366 13670046396 · [email protected]
广州爱纯医药科技有限公司020-39119399 18927568969 · [email protected]
山东博洛达生物科技有限公司0531-68659041 · [email protected]
武汉鹏胤药业有限公司13163333255 · [email protected]
HBCChem, Inc.+1-510-219-6317 · [email protected]
日照力德士化工有限公司010-51268198 · [email protected]
天津普西唐生物医药科技有限公司010-60605840 · [email protected]
常州翔龙医药科技有限公司18915873328 18915873328 · [email protected]
青岛海智微元生物科技有限公司18317699790 18317699790 · [email protected]
深圳振强药物研发有限公司+86-0755-66853366 +86-13670046396 · [email protected]
上海陶术生物科技股份有限公司+1-781-999-5354; +1-00000000000 · [email protected]
安耐吉化学&3A(安徽泽升科技股份有限公司)400-0056266 · [email protected]
sgtlifesciences pvt ltd+91-8790379245 · [email protected]
上海阿拉丁生化科技股份有限公司6206333 13167063860 · [email protected]
武汉多普乐生物医药有限公司+86-02787215551 19945035818 · [email protected]
风咏生物(AbMole)021-10000000 13000000000 · [email protected]
陕西缔都医药化工有限公司+86-29-81139210 +86-17392587031 · [email protected]
成都大道三灵生物科技有限公司18108108965 18108108965 · [email protected]
上海源叶生物科技有限公司13636370518 · [email protected]
武汉沃格达生物科技有限公司15071299552 · [email protected]
河北贞佳新材料有限公司0319-5925599 13315915972
深圳市祥根生物医药有限公司0755-28967200 13631290199 · [email protected]
成都诺维尔生物医药有限公司028-85255396 18302801538 · [email protected]
陕西缔都医药化工有限公司029-81154043 17391733319 · [email protected]
杭州洁汉化工有限公司+86-571-86217390; +8618058761490 · [email protected]
Musechem+1-800-259-7612 · [email protected]

Ergänzende Hinweise

DefinitionChEBI: A member of the class of piperazines that is piperazine substituted by a furan-2-ylcarbonyl group and a 4-amino-6,7-dimethoxyquinazolin-2-yl group at positions 1 and 4 respectively.