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Doxazosin mesylate

Description Pharmacological effects Synthetic route Usage and dosage Pharmacokinetics Side effects Precautions Application References
Doxazosin mesylate
Doxazosin mesylate structure
CAS No.
77883-43-3
Chemical Name:
Doxazosin mesylate
Synonyms
Cardran;ALFADIL;CARDURA;Diblocin;Carduran;Cardular;Caldular;Supressin;Normothen;CARDENALIN
CBNumber:
CB3285710
Molecular Formula:
C24H29N5O8S
Formula Weight:
547.58
MOL File:
77883-43-3.mol

Doxazosin mesylate Properties

Melting point:
275-277°C
storage temp. 
Desiccate at RT
solubility 
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
form 
powder
color 
white
Stability:
Protect from light
InChIKey
VJECBOKJABCYMF-UHFFFAOYSA-N
CAS DataBase Reference
77883-43-3(CAS DataBase Reference)

SAFETY

Hazard Codes  Xi
Risk Statements  36/37/38
Safety Statements  26-36/37-24/25
WGK Germany  2
RTECS  TK8044000
HS Code  29349990
Hazardous Substances Data 77883-43-3(Hazardous Substances Data)

Doxazosin mesylate price More Price(9)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich D9815 Doxazosin mesylate ≥97% (HPLC), powder 77883-43-3 50mg $116 2018-11-13 Buy
Sigma-Aldrich 1225419 Doxazosin mesylate United States Pharmacopeia (USP) Reference Standard 77883-43-3 200mg $348 2018-11-13 Buy
TCI Chemical D4126 Doxazosin Mesylate >98.0%(HPLC)(N) 77883-43-3 1g $209 2018-11-22 Buy
TCI Chemical D4126 Doxazosin Mesylate >98.0%(HPLC)(N) 77883-43-3 100mg $55 2018-11-22 Buy
Cayman Chemical 18633 Doxazosin (mesylate) ≥98% 77883-43-3 100mg $35 2018-11-13 Buy

Doxazosin mesylate Chemical Properties,Uses,Production

Description

Doxazosin mesylate is a quinazoline compound that is a selective inhibitor of the alpha1 subtype of alpha adrenergic receptors. The chemical name of doxazosin mesylate is 1-(4-amino-6,7-dimethoxy-2-quinazolinyl)-4-(1,4-benzodioxan-2-ylcarbonyl) piperazine methanesulfonate.The empirical formula for doxazosin mesylate is C23H25N505 • CH4O3S and the molecular weight is 547.6.
Doxazosin mesylate is freely soluble in dimethylsulfoxide, soluble in dimethylformamide, slightly soluble in methanol, ethanol, and water (0.8% at 25°C), and very slightly soluble in acetone and methylene chloride. Each doxazosin mesylate tablet, for oral administration, contains 1 mg, 2 mg, 4 mg and 8 mg of doxazosin as the free base.
Doxazosin mesylate is a new generation of quinazolone α1 receptor blocker developed by the Pfizer company (United States), It has a long half-life, exerting its effects of dilating the blood vessels, reducing the vascular resistance and lowering the blood pressure through blocking the a 1 receptor. It selectively blocks the a1 adrenergic receptor of the prostate smooth muscle matrix, capsule and bladder neck, alleviating the symptoms of patients of benign prostatic hyperplasia, while having good curing effect on the dysuria caused by simple prostatic hyperplasia. In 1988, doxazosin, as a drug for the treatment of hypertension, had been listed in Denmark. In 1995, the US FDA had approved it for the treatment of benign prostatic hyperplasia. In 2002 September, Doxazosin controlled release tablets had been listed in China, providing a new option for the domestic treatment of benign prostatic hyperplasia. It has been recommended abroad as first-line clinical drugs of anti-hypertension and treatment of prostate disease.

Pharmacological effects

This product is a new highly selective α1 receptor blockers, having a significant effect of causing reduction in blood pressure while having good effect of alleviating lipid metabolism. It can significantly reduce serum triglycerides and total cholesterol; it can also selectively block the a1 adrenergic receptor of prostate smooth muscle matrix, capsule and bladder neck, alleviating the symptoms of benign prostatic hyperplasia patients, further significantly slowing down the effect of benign prostatic hyperplasia, especially having good effect on the treatment of dysuria caused by simple prostatic hyperplasia. It has a long half-life.

Synthetic route

1. Reaction bottle was added of catechol and sodium hydroxide solution, stir evenly and dropped of epichlorohydrin at 50 ℃. The dripping process can be finished within 0.5 h. After the completion of dripping, the solution was refluxed at 85 ℃ for 2.5 h, after which the solution turned from dark green to brown oil. It is further extracted with chloroform, and the organic phases are combined, followed by being dried over anhydrous sodium sulfate, filtered, and the filtrate is concentrated under reduced pressure, and the residue is cooled to crystallize, filtered. The filter cake is further washed with a small amount of cold carbon tetrachloride and dried at below 50 ℃ to obtain a white solid compound 2.
2. Potassium permanganate and potassium hydroxide solution were added to the reaction flask, and the pyridine solution of Intermediate 2 was added dropwise at 0-10 °C. After the completion of the dropping, the reaction was continued for 24 h at room temperature. The reaction mixture was filtered. The filtrate has its pH adjusted by concentrated ammonia to 7, concentrated to half, added of chloroform after cooling. The concentrated hydrochloric acid was added dropwise of concentrated hydrogen chloride and adjusted to pH = 1. It is then extracted with chloroform. The organic phases were combined, dried over anhydrous sodium sulfate, filtered and the filtrate was concentrated under reduced pressure to give Compound 3 as a pale yellow solid.
3. The reaction flask was added with intermediate 3, toluene solution and DMF. The mixture was heated to 50 ° C, stirred and dissolved, and thionyl chloride was added dropwise. The reaction mixture was refluxed for 4 hours. The toluene and the remaining thionyl chloride were distilled off under reduced pressure to give the crude compound 4.
4. Add piperazine, methanol and water to the reaction flask, stir the mixture evenly, add the ethyl acetate solution of Intermediate 4 dropwise at 10-20 ℃, continue the reaction for 2 hours, extract the reaction mixture with methylene chloride. The organic phase was extracted twice with water and the aqueous phase was adjusted to pH 10 with concentrated aqueous ammonia. The organic phase was extracted three times with dichloromethane. The organic phases were combined, washed twice with water, dried over anhydrous sodium sulfate, filtered and evaporated of methylene chloride under reduced pressure to give the compound 5 as a pale yellow solid.
5. The reaction flask was added with 2-chloro-4-amino-6, 7-dimethoxyquinazoline, intermediate 5 and n-butanol, stirred and refluxed for 4 hours. After completion of the reaction, the crystals were cooled and washed with n-butanol, and dried to obtain Compound 6 as a white crystalline powder.
6 is placed into the beaker, adjusted to pH = 10 with ammonia; extract it with dichloromethane; remove the water layer; wash the organic phase with water; slowly add methanesulfonic acid and gradually precipitate of white crystals, apply cooling crystallization, filtration and drying to obtain the crude product 1.
7. The crude product is added to the methanol, heated to dissolve all; cool and crystallize it; filter, wash with cold methanol once, dry to obtain the refined product 1.
synthesis route of doxazosin mesylate

Figure 1 shows the synthesis route of doxazosin mesylate

Usage and dosage

  • Commonly adult oral dose, apply an initial dose of 1mg, once a day. After 1-2 weeks, adjust the dosage according to the clinical response and tolerance; for first dose and dose adjustment, it is preferably taken at bedtime. Maintenance dose of 1-8mg, once a day, but over 4 mg can cause orthostatic hypotension. Foreign research data suggest that the maximum dose of this product to 16mg/day.
  • Pediatric dose has not been determined.

Pharmacokinetics

The product should be administrated orally with oral bioavailability of 62% to 69%, protein binding rate of 98% to 99%, peak time of 1.7 to 3.6 hours, elimination half-life of 16 to 22 hours. It should subject to liver metabolism. About 65% of the drug was eliminated by metabolites via fecal, and only about 5% of the prototype was excreted by urine.

Side effects

There may be dizziness, dry mouth, headache, palpitations, fatigue, the symptoms are mild, bearable, disappear within about 1 week, without special treatment. No postural hypotension occurred.

Precautions

Patients allergic to this product should be disabled. During the postmarketing experience of treatment of hypertension, there are reports of tachycardia, palpitations, chest pain, angina pectoris, myocardial infarction, cerebrovascular accident and arrhythmia, but in general, those symptoms can’t be distinguished from those of patients don’t take doxazosin. Application of this product may affect the capability of driver and the mechanical operator, especially during the initial drug phase.

Application

Patients of primary mild to moderate hypertension, and hypertensive patients with benign prostatic hypertrophy; For patients who have difficulty controlling blood pressure with a single drug, doxazosin can be administered in combination with thiazide diuretics and beta-blockers, calcium antagonists, or angiotensin converting enzyme inhibitors. It can be used for treatment of high blood pressure.
The outline, synthetic route, usage, dosage, pharmacokinetics and adverse reaction of doxazosin mesylate were compiled by Baoquan of Chemicalbook. (2016-04-09)

References

https://dailymed.nlm.nih.gov/dailymed/archives/fdaDrugInfo.cfm?archiveid=51901
https://www.drugs.com/doxazosin.html

Chemical Properties

White or almost white crystalline powder.

Uses

A selective a-1-adrenergicblocker related to prazosin

Uses

A selective α-1-adrenergicblocker related to prazosin.

Uses

antihypertensive

Uses

Doxazosin is a selective α1-adrenoceptor antagonist. Doxazosin relaxes smooth muscles of the prostate.

Uses

Doxazosin ER is indicated for the treatment of the signs and symptoms of benign prostatic hyperplasia

brand name

Cardura (Pfizer).

Biological Activity

Selective α 1 -adrenoceptor antagonist (pK i values are 9.0, 8.5 and 8.4 for human α 1B , α 1A and α 1D receptors respectively). Displays antihypertensive activity.

Doxazosin mesylate Preparation Products And Raw materials

Raw materials

Preparation Products


Doxazosin mesylate Suppliers

Global( 255)Suppliers
Supplier Tel Fax Email Country ProdList Advantage
Shenzhen Sendi Biotechnology Co.Ltd.
0755-23311925 18102838259
0755-23311925 Abel@chembj.com CHINA 3203 55
Henan DaKen Chemical CO.,LTD.
+86-371-55531817
info@dakenchem.com CHINA 21922 58
Beijing Cooperate Pharmaceutical Co.,Ltd.
+86-10-60279497 +86(0)15646567669
+86-10-60279497 sales01@cooperate-pharm.com CHINA 1530 55
Henan Tianfu Chemical Co.,Ltd.
0371-55170693
0371-55170693 info@tianfuchem.com CHINA 20680 55
Mainchem Co., Ltd.
+86-0592-6210733
+86-0592-6210733 sales@mainchem.com CHINA 32457 55
Xiamen AmoyChem Co., Ltd
+86 (0)592-605 1114
sales@amoychem.com CHINA 6374 58
career henan chemical co
+86-371-86658258
sales@coreychem.com CHINA 20580 58
Chemwill Asia Co.,Ltd.
86-21-51086038
86-21-51861608 chemwill_asia@126.com;sales@chemwill.com;chemwill@hotmail.com;chemwill@gmail.com CHINA 23982 58
Hubei Jusheng Technology Co.,Ltd.
86-188-71490254
peter@hubeijusheng.com CHINA 20094 58
QUALITY CONTROL CHEMICALS INC.
(323) 306-3136
(626) 453-0409 orders@qcchemical.com United States 8409 58

View Lastest Price from Doxazosin mesylate manufacturers

Image Release date Product Price Min. Order Purity Supply Ability Manufacturer
2018-12-24 Doxazosin mesylate
77883-43-3
US $2.00 / kg 1kg 99% 100kg career henan chemical co

77883-43-3(Doxazosin mesylate )Related Search:


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  • DOXAZOSIN METHANESUFONATE
  • Cardran
  • Cardular
  • Cardura (pharmaceutical)
  • Carduran
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  • doxazolazine mesylate
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  • Supressin
  • DOXAPRAMHYDROCHLORIDE
  • 1-(4-Amino-6,7-dimethoxy-2-quinazolinyl)-4-[4-(1,4-benzodioxan-2-yl)carpiperazin-1-yl)]-6,7-dimethoxyquinazoline mesylate
  • 1-(4-AMINO-6,7-DIMETHOXY-2-QUINAZOLINYL)-4-[4-(1,4-BENZODIOXAN-2-YL)CARPIPERAZIN-1-YL)]-6,7-DIMETHOXYQUINAZOLINE MESYLATE
  • 1-(4-amino-6,7-dimethoxy-2-quinazolinyl)-4-(1,4-benzodioxan-2-ylcarbonyl) piperazine methanesulfonate
  • ALFADIL
  • CARDURA
  • CARDENALIN
  • 1-(4-Amino-6,7-dimethoxy-2-quinazolinyl)-4-(1,4-benzodioxan-2-ylcarbonyl)piperazine mesylate
  • Caldular
  • Piperazine, 1-(4-amino-6,7-dimethoxy-2-quinazolinyl)-4-[(2,3-dihydro-1,4-be
  • DOXAZOSIN MESYlLATE
  • 4-Amino-2-[4-(1,4-benzodioxan-2-carbonyl)piperazin-1-yl]-6,7-dimethoxyquinazolinemethanesulfonate
  • Doxazosin Mesylate (200 mg)
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  • (4-(4-aMino-6,7-diMethoxyquinazolin-2-yl)piperazin-1-yl)(2,3-dihydrobenzo[b][1,4]dioxin-2-yl)Methanone Methanesulfonate
  • Methanone, [4-(4-amino-6,7-dimethoxy-2-quinazolinyl)-1-piperazinyl](2,3-dihydro-1,4-benzodioxin-2-yl)-, methanesulfonate
  • -
  • 77883-43-3
  • DOXAZOSIN MESYLATE
  • DOXAZOSIN METHANESULFONATE
  • UK-33274-27
  • doxazosinmesylate(patented-nosupply)
  • piperazine,1-(4-amino-6,7-dimethoxy-2-quinazolinyl)-4-((2,3-dihydro-1,4-benzod
  • DOXAZOSIN MEYLATE
  • Doxazosin monomethanesulfonate
  • UK-33274-27, Alfadil, Cardenalin,
  • C23H25N5O5CH3SO3H
  • C23H25N5O5CH4SO3
  • Doxazosin mesylate, >=99%
  • Mesylate sandy azole lamictal
  • 1-(4-Amino-6,7-dimethoxyquinazolin-2-yl)-4-[(2RS)-2,3-dihydro-1,4-benzodioxin-2-ylcarbonyl]piperazine methanesulphonate
  • Inhibitors
  • C23H25N5O5CH3SO3HC24H29N5O8S
  • C24H29N5O8S
  • C23H25N5O5CH4O3S
  • C23H25N5O5xCH4O3S
  • C23H25N5O5CH3SO3HC24H
  • Active Pharmaceutical Ingredients
  • Antihypertensive
  • Intermediates & Fine Chemicals
  • Pharmaceuticals
  • Adrenoceptor
  • CARDURA
  • Cardiovascular APIs
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