Doxazosin Mesylate

HCID 62978CAS 77883-43-3

Grundinformationen

Standard-SMILES
COc1cc2nc(N3CCN(C(=O)C4COc5ccccc5O4)CC3)nc(N)c2cc1OC.CS(=O)(=O)O
InChIKey
VJECBOKJABCYMF-UHFFFAOYSA-N
Summenformel
C24H29N5O8S
Durchschnittliche Molmasse
547,6 g/mol
Monoisotopische Masse
547,17368407

Namen und Bezeichner

Bevorzugter Name
Doxazosin Mesylate
IUPAC
[4-(4-amino-6,7-dimethoxyquinazolin-2-yl)piperazin-1-yl]-(2,3-dihydro-1,4-benzodioxin-3-yl)methanone;methanesulfonic acid
Englischer Name
Doxazosin mesylate
Summenformel
C24H29N5O8S
Molmasse
547.58

Namen und Synonyme

Doxazosin mesylate77883-43-3AlfadilCardura XLDoxazosin mesilateDoxazosin (as mesilate)DTXSID5045598Doxazosin methanesulfonate86P6PQK0MUNSC-759284UK-33274-27UK-33,274-27
Weitere Namen anzeigen
CARDURA1-(4-amino-6,7-dimethoxy-2-quinazolinyl)-4-(1,4-benzodioxan-2-ylcarbonyl) piperazine methanesulfonate1-(4-AMINO-6,7-DIMETHOXY-2-QUINAZOLINYL)-4-[4-(1,4-BENZODIOXAN-2-YL)CARPIPERAZIN-1-YL)]-6,7-DIMETHOXYQUINAZOLINE MESYLATECardranBeyacinCardularCarduranDiblocinCaldular
DTXCID3025598Piperazine, 1-(4-amino-6,7-dimethoxy-2-quinazolinyl)-4-((2,3-dihydro-1,4-benzodioxin-2-yl)carbonyl)-, monomethanesulfonateCHEBI:4709DoxaduraCascorCardozin xlDoxzogen xlOxandosin xl

Datenbank-Bezeichner

CAS
77883-43-3
PubChem CID
62978
DTXSID
DTXSID5045598
ChEMBL
CHEMBL1200561
UNII
86P6PQK0MU
EC Number
616-536-9、643-013-2

Eigenschaften

Berechnete Struktureigenschaften

Polarare Oberfläche (TPSA)
175 Ų
H-Brücken-Donoren
2
H-Brücken-Akzeptoren
12
Frei drehbare Bindungen
4
Schwere Atome
38

Experimentelle und physikochemische Eigenschaften

Solubility... Freely soluble in dimethylsulfoxide, soluble in dimethylformamide, slightly soluble in methanol, ethanol, and water (0.8 percent at 25 °C), and very slighlty soluble in acetone and methylene chloride.
Collision Cross Section203.3 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
Other Experimental Properties · 2 Einträge

Crystals, mp 289-290 °C /Hydrochloride/

Molecular weight: 451.47 /Doxazosin/

Physikochemische Eigenschaften

Schmelzpunkt
275 · 275-277°C
storage temp.
2 · 2-8°C
Löslichkeit
15 volumes · Slightly soluble in water, soluble in a mixture of 15 volumes of water and 35 volumes of tetrahydrofuran, slightly soluble in methanol, practically insoluble in acetone. It shows polymorphism (5.9), some forms may be hygroscopic
Aggregatzustand
powder
Farbe
white
BCS Class
1 · 1

Sicherheit und Regulatorisches

GHS-Klassifizierung

GHS Classification · 6 Einträge

This chemical does not meet GHS hazard criteria for 2% (2 of 100) of reports.

Warning

H373 (95%): May causes damage to organs through prolonged or repeated exposure [Warning Specific target organ toxicity, repeated exposure];H411 (95%): Toxic to aquatic life with long lasting effects [Hazardous to the aquatic environment, long-term hazard]

P260, P273, P319, P391, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 100 reports by companies from 10 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.;Reported as not meeting GHS hazard criteria per 2 of 100 reports by companies.;There are 9 notifications provided by 98 of 100 reports by companies with hazard statement code(s).;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

Regulatory InformationDoxazosin mesylate: Does not have an individual approval but may be used under an appropriate group standard
FDA Requirements · 1 Eintrag

The Approved Drug Products with Therapeutic Equivalence Evaluations List identifies currently marketed prescription drug products, incl doxazosin mesylate, approved on the basis of safety and effectiveness by FDA under sections 505 of the Federal Food, Drug, and Cosmetic Act.

Hazard Classes and Categories · 2 Einträge

STOT RE 2 (95%);Aquatic Chronic 2 (95%)

Aquatic Chronic 2 (100%)

Sicherheit und Schutzausrüstung

Disposal Methods · 1 Eintrag

SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.

Toxikologische Informationen

Interactions · 5 Einträge

Antihypertensive effects of doxazosin may be reduced when the medication is used concurrently with these agents; indomethacin, and possibly other /nonsteroidal anti-inflammatory drugs/ NSAIDs, may antagonize the antihypertensive effect by inhibiting renal prostaglandin synthesis and/or by causing sodium and fluid retention; the patient should be carefully monitored to confirm that the desired effect is being obtained. /Salt not specified/

Concurrent use may slightly increase the serum concentration of doxazosin; however, the clinical significance of this increase is not known. /Salt not specified/

Antihypertensive effects may be potentiated when these medications /other hypertension-producing medications/ are used concurrently with doxazosin; although some antihypertensive and/or diuretic combinations are frequently used to therapeutic advantage, dosage adjustments are necessary during concurrent use. /Salt not specified/

Antihypertensive effects of doxazosin may be reduced when it is used concurrently with these agents /sympathomimetics/; the patient should be carefully monitored to confirm that the desired effect is being obtained. /Salt not specified/

For more Interactions (Complete) data for DOXAZOSIN MESYLATE (9 total), please visit the HSDB record page.

Drug Induced Liver Injury · 6 Einträge

Drug Induced Liver Injury Rank (DILIrank 2.0)

Doxazosin mesylate

vLess-DILI-concern

3

Adverse reactions

DOI:10.1016/j.drudis.2016.02.015

Non-Human Toxicity Excerpts · 4 Einträge

/LABORATORY ANIMALS: Chronic Exposure or Carcinogenicity/ In one 24 month chronic dietary administration study in rats, doxazosin (given at a dose equivalent to 150 times the maximum recommended human dose) produced no evidence of carcinogenicity. In another similarly conducted study done in mice, up to 18 months of dietary administration produced no evidence of carcinogenicity. The latter study, however, did not use a maximally tolerated dose of doxazosin. /Salt not specified/

/LABORATORY ANIMALS: Developmental or Reproductive Toxicity/ Studies in rats given oral doses of 20 mg/kg of body weight per day ... have shown that doxazosin reduces fertility in male rats. The effect was reversible after about 2 weeks of discontinuation of treatment. /Salt not specified/

/LABORATORY ANIMALS: Developmental or Reproductive Toxicity/ Studies in rabbits and rats given daily oral doses of 40 and 20 mg/kg, respectively, have shown no evidence of harm to the fetus. The rabbit study, however, did not use a maximally tolerated dose of doxazosin. Reduced fetal survival was associated with a dosage regimen of 82 mg/kg in rabbits. Following oral administration of labeled doxazosin to pregnant rats, radioactivity was found to cross the placenta. /Salt not specified/

/LABORATORY ANIMALS: Developmental or Reproductive Toxicity/ Studies in perinatal and postnatal rats given 40 or 50 mg/kg per day of doxazosin revealed evidence of delayed postnatal development manifested by slower body weight gain and slightly later appearance of anatomical features and reflexes. /Salt not specified/

Antidote and Emergency Treatment · 1 Eintrag

Treatment of overdose: Treatment of circulatory failure by placing the patient the supine position and elevating the legs is most important; if shock is present, additional measures are necessary. Volume expanders may be used to treat shock, followed, if necessary, by administration of a vasopressor. Symptomatic, supportive treatment and monitoring of fluid and electrolyte status.

Regulatorische Informationen

Regulatory InformationDoxazosin mesylate: Does not have an individual approval but may be used under an appropriate group standard
FDA Requirements · 1 Eintrag

The Approved Drug Products with Therapeutic Equivalence Evaluations List identifies currently marketed prescription drug products, incl doxazosin mesylate, approved on the basis of safety and effectiveness by FDA under sections 505 of the Federal Food, Drug, and Cosmetic Act.

Sicherheitsdaten

wgk
2
hs_code
29349990
RTECS-Nr.
TK8044000
risk_code
36/37/38
hazard_code
Xi
safety_code
26-36/37-24/25

Chemie und Industrie

Pharmakologische Informationen

Mechanism of Action · 5 Einträge

Selective alpha1-adrenergic blocker related to prazosin, q.v. /Salt not specified/

Blocks postsynaptic alpha 1 receptors and cause vasodilation /Salt not specified/

Hypertension: Blockade of alpha1-adrenergic receptors by doxazosin results in peripheral vasodilation, which produces a fall in blood pressure because of decreased peripheral vascular resistance. Benign prostatic hyperplasia: Relaxation of smooth muscle in the bladder neck, prostate, and prostate capsule produced by alpha1-adrenergic blockade results in a reduction in urethral resistance and pressure, bladder outlet resistance, and urinary symptoms. /Salt not specified/

Previous studies have demonstrated that the alpha(1)-adrenergic receptor antagonist doxazosin (Dox) inhibits multiple mitogenic signaling pathways in human vascular smooth muscle cells. This broad antiproliferative activity of Dox occurs through a novel mechanism unrelated to its blocking the alpha(1)-adrenergic receptor. Flow cytometry demonstrated that Dox prevents mitogen-induced G(1)-->S progression of human coronary artery smooth muscle cells (CASMCs) in a dose-dependent manner, with a maximal reduction of S-phase transition by 88+/-10.5% in 20 ng/mL platelet-derived growth factor and 1 micromol/L insulin (P+I)-stimulated cells (P<0.01 for 10 micromol/L Dox versus P+I alone) and 52+/-18.7% for 10% FBS-induced mitogenesis (P<0.05 for 10 micromol/L Dox versus 10% FBS alone). Inhibition of G(1) exit by Dox was accompanied by a significant blockade of retinoblastoma protein (Rb) phospstimulated quiescent CASMCs to progress through G(1) and enter the S phase. E2F-mediated G(1) exit was not affected by Dox, suggesting that it targets events upstream from Rb hyperphosphorylation. Downregulation of the cyclin-dependent kinase inhibitory protein p27 is important for maximal activation of G(1) cyclin/cyclin-dependent kinase holoenzymes to overcome the cell cycle inhibitory activity of Rb. In Western blot analysis, p27 levels decreased after mitogenic stimulation (after P+I, 43+/-1.8% of quiescent cells [P<0.01 versus quiescent cells]; after 10% FBS, 55+/-7.7% of quiescent cells [P<0. 05 versus quiescent cells]), whereas the addition of Dox (10 micromol/L) markedly attenuated its downregulation (after P+I, 90+/-8.3% of quiescent cells [P<0.05 versus P+I alone]; after 10% FBS, 78+/-8.3% of quiescent cells [P<0.05 versus 10% FBS alone]). Furthermore, Dox inhibited cyclin A expression, an E2F regulated gene that is essential for cell cycle progression into the S phase. The present study demonstrates that Dox inhibits CASMC proliferation by blocking cell

For more Mechanism of Action (Complete) data for DOXAZOSIN MESYLATE (6 total), please visit the HSDB record page.

Biological Half-Life · 2 Einträge

The half-life of doxazosin is approximately 20 hours ... /Salt not specified/

Elimination /half life/: 19 to 22 hours; does not appear to be significantly influenced by age or mild to moderate renal impairment. /Salt not specified/

Metabolism/Metabolites · 1 Eintrag

Metabolized extensively in the liver. Although several active and inactive metabolites have been identified (2-piperazinyl, 6' and 7'-hydroxy,6' and 7'-O-desmethyl, and 2-amino), there is no evidence that they are present in substantial amounts. /Salt not specified/

FDA Pharmacological Classification · 2 Einträge

DOXAZOSIN MESYLATE

alpha-Adrenergic Blocker [EPC]; Adrenergic alpha-Antagonists [MoA]

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 · 3 Einträge

Most doxazosin metabolites are eliminated in the feces. /Salt not specified/

Well absorbed from gastrointestinal tract; bioavailability is about 65%. /Salt not specified/

Elimination: Fecal: Unchanged drug, about 5%; metabolites, 63 to 65%. Renal: 9%. /Salt not specified/

Verwendung und Herstellung

UsesMEDICATION
Methods of ManufacturingPrepn: S.F. Campbell, DE 2847623; idem, US 4188390 (1979, 1980 both to Pfizer). /Doxazosin/
Formulations/PreparationsAlfadil; Benur; Cardenalin; Cardular; Cardura; Carduran; Diblocin; Normothen; Supressin; Zoxan.

Anwendungen

VerwendenA selective a-1-adrenergicblocker related to prazosin

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