ドキサゾシン
WordNet
- an antihypertensive drug (trade name Cardura) that works by relaxing blood vessels so that blood passes through them more easily; it is also used to treat benign prostatic hyperplasia (同)Cardura
Wikipedia preview
出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2015/01/01 01:11:42」(JST)
[Wiki en表示]
Doxazosin
|
|
| Systematic (IUPAC) name |
| (RS)-2-[4-(2,3-Dihydro-1,4-benzodioxine-2-carbonyl)piperazin-1-yl]-6,7-dimethoxyquinazolin-4-amine |
| Clinical data |
| Trade names |
Cardura |
| AHFS/Drugs.com |
monograph |
| MedlinePlus |
a693045 |
| Legal status |
|
| Routes |
oral |
| Pharmacokinetic data |
| Bioavailability |
65% |
| Protein binding |
98% |
| Metabolism |
Hepatic |
| Half-life |
22 hours |
| Identifiers |
| CAS number |
74191-85-8 Y |
| ATC code |
C02CA04 |
| PubChem |
CID 3157 |
| DrugBank |
DB00590 |
| ChemSpider |
3045 Y |
| UNII |
NW1291F1W8 Y |
| KEGG |
D07874 Y |
| ChEBI |
CHEBI:4708 Y |
| ChEMBL |
CHEMBL707 Y |
| Chemical data |
| Formula |
C23H25N5O5 |
| Mol. mass |
451.475 g/mol |
SMILES
- O=C(N3CCN(c2nc1cc(OC)c(OC)cc1c(n2)N)CC3)C4Oc5c(OC4)cccc5
|
InChI
-
InChI=1S/C23H25N5O5/c1-30-18-11-14-15(12-19(18)31-2)25-23(26-21(14)24)28-9-7-27(8-10-28)22(29)20-13-32-16-5-3-4-6-17(16)33-20/h3-6,11-12,20H,7-10,13H2,1-2H3,(H2,24,25,26) Y
Key:RUZYUOTYCVRMRZ-UHFFFAOYSA-N Y
|
| Y (what is this?) (verify) |
Doxazosin mesylate, a quinazoline compound sold by Pfizer under the brand names Cardura and Carduran, is an α1-selective alpha blocker used to treat high blood pressure and urinary retention associated with benign prostatic hyperplasia (BPH).
On February 22, 2005, the US FDA approved a sustained release form of doxazosin, to be marketed as Cardura XL.
It is an alpha-1 adrenergic receptor blocker that inhibits the binding of norepinephrine (released from sympathetic nerve terminals) to the alpha-1 receptors on the membrane of vascular smooth muscle cells. The primary effect of this inhibition is relaxed vascular smooth muscle tone (vasodilation), which decreases peripheral vascular resistance, leading to decreased blood pressure.
Doxazosin and similar medications like prazosin have been found to help reduce the intensity of and/or stop posttraumatic stress disorder night terrors and nightmares. The full reasoning of this effect is not understood.
In Egypt, tablet formulation sold as Duracin produced by Biopharm group for research and the drug industry, Dosin by Eipico and Doxazocine by Multi-Apex.
Efficacy
In March 2000, the Antihypertensive and Lipid Lowering Treatment to Prevent Heart Attack Trial (ALLHAT) study stopped its arm of the trial looking at alpha blockers, because doxazosin was less effective than a simple diuretic, and because patients on doxazosin had a 25% higher rate of cardiovascular disease and twice the rate of congestive heart failure as patients on diuretics.[1] Pfizer, aware of the results before publication, launched a marketing campaign in early 2000, and sales were largely unaffected, despite the dangers highlighted by the study.[2][3]
Doxazosin shows potential for treatment of benign prostatic hyperplasia and erectile dysfunction.[4]
Doxazosin has also shown some efficacy in treating chronic epididymitis.[5]
References
- ^ Piller LB, Davis BR, Cutler JA, et al. (2002). "Validation of Heart Failure Events in the Antihypertensive and Lipid Lowering Treatment to Prevent Heart Attack Trial (ALLHAT) Participants Assigned to Doxazosin and Chlorthalidone". Curr Control Trials Cardiovasc Med 3 (1): 10. doi:10.1186/1468-6708-3-10. PMC 149403. PMID 12459039.
- ^ Goldacre, Ben (2012) Bad Pharma How drug companies mislead doctors and harm patients, Fourth Estate, ISBN 0007350740.
- ^ Lenzer, J (2003). "Spin doctors soft pedal data on antihypertensives". BMJ : British Medical Journal 326 (7381): 170. doi:10.1136/bmj.326.7381.170. PMC 1128917.
- ^ "Antihypertensive Drugs and Patients With Erectile Dysfunction". Medscape.
- ^ Zhou, YC; Xia GS; Xue YY; Zhang XD; Zheng LW; Jin BF (2010–2012). "Kidney-tonifying and dampness-expelling Chinese herbal medicine combined with doxazosin for the treatment of chronic epididymitis". Zhonghua Nan Ke Xue (in Chinese) 16 (12): 1143–6. PMID 21348207.
External links
- Information about Cardura from rxlist.com
- Cardura XL product website, run by Pfizer
|
Sympatholytic (and closely related) antihypertensives (C02)
|
|
Sympatholytics
(antagonize α-adrenergic
vasoconstriction) |
|
Central
|
|
α2 agonist
|
- Clonidine
- Guanabenz
- Guanfacine
- Methyldopa#
|
|
|
Adrenergic release inhibitors
|
- Bethanidine
- Bretylium
- Debrisoquine
- Guanadrel
- Guanazodine
- Guanethidine
- Guanoclor
- Guanazodine
- Guanoxabenz
- Guanoxan
|
|
|
Imidazoline receptor agonist
|
|
|
|
Ganglion-blocking/nicotinic antagonist
|
- Mecamylamine
- Pentolinium
- Trimethaphan
|
|
|
|
Peripheral
|
|
Indirect
|
|
MAOI
|
|
|
|
Adrenergic uptake inhibitor
|
- Bietaserpine
- Deserpidine
- Methoserpidine
- Rescinnamine
- Reserpine
|
|
|
Tyrosine hydroxylase inhibitor
|
|
|
|
|
Direct
|
|
α1 blockers
|
- Prazosin
- Indoramin
- Trimazosin
- Doxazosin
- Urapidil
|
|
|
Non-selective α blocker
|
|
|
|
|
|
| Other antagonists |
|
Serotonin antagonist
|
|
|
|
Endothelin antagonist (for PH)
|
- dual (Bosentan, Macitentan)
- selective (Ambrisentan, Sitaxentan)
|
|
|
- #WHO-EM
- ‡Withdrawn from market
- Clinical trials:
- †Phase III
- §Never to phase III
Index of the circulatory system
|
|
| Description |
- Anatomy
- Arteries
- head and neck
- arms
- chest
- abdomen
- legs
- Veins
- head and neck
- arms
- chest
- abdomen and pelvis
- legs
- Lymph vessels
- Development
- Cells
- Physiology
|
|
| Disease |
- Congenital
- Neoplasms and cancer
- Lymphatic vessels
- Injury
- Vasculitis
- Other
- Symptoms and signs
|
|
| Treatment |
- Procedures
- Drugs
- beta blockers
- channel blockers
- diuretics
- nonsympatholytic vasodilatory antihypertensives
- peripheral vasodilators
- renin–angiotensin system
- sympatholytic antihypertensives
- vasoprotectives
|
|
|
|
Drugs used in benign prostatic hypertrophy (G04C)
|
|
| 5α-reductase inhibitors |
|
|
| Alpha blockers (α1) |
- Alfuzosin
- Doxazosin
- Silodosin
- Tamsulosin
- Terazosin
|
|
| Herbals |
- Pygeum africanum
- Saw palmetto extract
|
|
| Other |
|
|
Index of the male reproductive system
|
|
| Description |
- Anatomy
- Physiology
- Development
|
|
| Disease |
- Congenital
- Neoplasms and cancer
- Other
- Symptoms and signs
|
|
| Treatment |
- Procedures
- Drugs
- androgens
- benign prostatic hypertrophy
- erectile dysfunction and premature ejaculation
|
|
|
|
Adrenergics
|
|
|
Receptor ligands
|
|
|
α1
|
- Agonists: 5-FNE
- 6-FNE
- Amidephrine
- Anisodamine
- Anisodine
- Cirazoline
- Dipivefrine
- Dopamine
- Ephedrine
- Epinephrine
- Etilefrine
- Ethylnorepinephrine
- Indanidine
- Levonordefrin
- Metaraminol
- Methoxamine
- Methyldopa
- Midodrine
- Naphazoline
- Norepinephrine
- Octopamine
- Oxymetazoline
- Phenylephrine
- Phenylpropanolamine
- Pseudoephedrine
- Synephrine
- Tetrahydrozoline
Antagonists: Abanoquil
- Adimolol
- Ajmalicine
- Alfuzosin
- Amosulalol
- Arotinolol
- Atiprosin
- Benoxathian
- Buflomedil
- Bunazosin
- Carvedilol
- CI-926
- Corynanthine
- Dapiprazole
- DL-017
- Domesticine
- Doxazosin
- Eugenodilol
- Fenspiride
- GYKI-12,743
- GYKI-16,084
- Hydroxyzine
- Indoramin
- Ketanserin
- L-765,314
- Labetalol
- Mephendioxan
- Metazosin
- Monatepil
- Moxisylyte
- Naftopidil
- Nantenine
- Neldazosin
- Nicergoline
- Niguldipine
- Pelanserin
- Phendioxan
- Phenoxybenzamine
- Phentolamine
- Piperoxan
- Prazosin
- Quinazosin
- Ritanserin
- RS-97,078
- SGB-1,534
- Silodosin
- SL-89.0591
- Spiperone
- Talipexole
- Tamsulosin
- Terazosin
- Tibalosin
- Tiodazosin
- Tipentosin
- Tolazoline
- Trimazosin
- Upidosin
- Urapidil
- WB-4101
- Zolertine
* Note that many TCAs, TeCAs, antipsychotics, ergolines, and some piperazines like buspirone and trazodone all antagonize α1-adrenergic receptors as well, which contributes to their side effects such as orthostatic hypotension.
|
|
|
α2
|
- Agonists: (R)-3-Nitrobiphenyline
- 4-NEMD
- 6-FNE
- Amitraz
- Apraclonidine
- Brimonidine
- Cannabivarin
- Clonidine
- Detomidine
- Dexmedetomidine
- Dihydroergotamine
- Dipivefrine
- Dopamine
- Ephedrine
- Ergotamine
- Epinephrine
- Esproquin
- Etilefrine
- Ethylnorepinephrine
- Guanabenz
- Guanfacine
- Guanoxabenz
- Levonordefrin
- Lofexidine
- Medetomidine
- Methyldopa
- Mivazerol
- Naphazoline
- Norepinephrine
- Oxymetazoline
- Phenylpropanolamine
- Piperoxan
- Pseudoephedrine
- Rilmenidine
- Romifidine
- Talipexole
- Tetrahydrozoline
- Tizanidine
- Tolonidine
- Urapidil
- Xylazine
- Xylometazoline
Antagonists: 1-PP
- Adimolol
- Aptazapine
- Atipamezole
- BRL-44408
- Buflomedil
- Cirazoline
- Efaroxan
- Esmirtazapine
- Fenmetozole
- Fluparoxan
- GYKI-12,743
- GYKI-16,084
- Idazoxan
- Mianserin
- Mirtazapine
- MK-912
- NAN-190
- Olanzapine
- Phentolamine
- Phenoxybenzamine
- Piperoxan
- Piribedil
- Rauwolscine
- Rotigotine
- SB-269,970
- Setiptiline
- Spiroxatrine
- Sunepitron
- Tolazoline
- Yohimbine
* Note that many atypical antipsychotics and azapirones like buspirone (via metabolite 1-PP) antagonize α2-adrenergic receptors as well.
|
|
|
β
|
|
|
|
|
|
Reuptake inhibitors
|
|
|
NET
|
- Selective norepinephrine reuptake inhibitors: Amedalin
- Atomoxetine (Tomoxetine)
- Ciclazindol
- Daledalin
- Edivoxetine
- Esreboxetine
- Lortalamine
- Mazindol
- Nisoxetine
- Reboxetine
- Talopram
- Talsupram
- Tandamine
- Viloxazine; Norepinephrine-dopamine reuptake inhibitors: Amineptine
- Bupropion
- Fencamine
- Fencamfamine
- Hydroxybupropion
- Lefetamine
- Levophacetoperane
- LR-5182
- Manifaxine
- Methylphenidate
- Nomifensine
- O-2172
- Radafaxine; Serotonin-norepinephrine reuptake inhibitors: Bicifadine
- Desvenlafaxine
- Duloxetine
- Eclanamine
- Levomilnacipran
- Milnacipran
- Sibutramine
- Venlafaxine; Serotonin-norepinephrine-dopamine reuptake inhibitors: Brasofensine
- Diclofensine
- DOV-102,677
- DOV-21,947
- DOV-216,303
- JNJ-7925476
- JZ-IV-10
- Liafensine
- Methylnaphthidate
- Naphyrone
- NS-2359
- Perafensine
- PRC200-SS
- SEP-225,289
- SEP-227,162
- Tesofensine; Tricyclic antidepressants: Amitriptyline
- Butriptyline
- Cianopramine
- Clomipramine
- Desipramine
- Dosulepin
- Doxepin
- Imipramine
- Lofepramine
- Melitracen
- Nortriptyline
- Protriptyline
- Trimipramine; Tetracyclic antidepressants: Amoxapine
- Maprotiline
- Mianserin
- Oxaprotiline
- Setiptiline; Others: Cocaine
- CP-39,332
- Ethanol
- EXP-561
- Fezolamine
- Ginkgo biloba
- Indeloxazine
- Nefazodone
- Nefopam
- Pridefrine
- Tapentadol
- Tedatioxetine
- Teniloxazine
- Tofenacin
- Tramadol
- Ziprasidone
|
|
|
VMAT
|
- Ibogaine
- Reserpine
- Tetrabenazine
|
|
|
|
|
|
|
|
Enzyme inhibitors
|
|
|
Anabolism
|
|
PAH
|
|
|
|
TH
|
- 3-Iodotyrosine
- Aquayamycin
- Bulbocapnine
- Metirosine
- Oudenone
|
|
|
AAAD
|
- Benserazide
- Carbidopa
- DFMD
- Genistein
- Methyldopa
|
|
|
DBH
|
- Bupicomide
- Disulfiram
- Dopastin
- Fusaric acid
- Nepicastat
- Phenopicolinic acid
- Tropolone
|
|
|
PNMT
|
- CGS-19281A
- SKF-64139
- SKF-7698
|
|
|
|
Catabolism
|
|
MAO
|
- Nonselective: Benmoxin
- Caroxazone
- Echinopsidine
- Furazolidone
- Hydralazine
- Indantadol
- Iproclozide
- Iproniazid
- Isocarboxazid
- Isoniazid
- Linezolid
- Mebanazine
- Metfendrazine
- Nialamide
- Octamoxin
- Paraxazone
- Phenelzine
- Pheniprazine
- Phenoxypropazine
- Pivalylbenzhydrazine
- Procarbazine
- Safrazine
- Tranylcypromine; MAO-A selective: Amiflamine
- Bazinaprine
- Befloxatone
- Brofaromine
- Cimoxatone
- Clorgiline
- Eprobemide
- Esuprone
- Harmala alkaloids (Harmine,
- Harmaline
- Tetrahydroharmine
- Harman
- Norharman, etc)
- Methylene blue
- Metralindole
- Minaprine
- Moclobemide
- Pirlindole
- Sercloremine
- Tetrindole
- Toloxatone
- Tyrima; MAO-B selective:
- Ladostigil
- Lazabemide
- Milacemide
- Mofegiline
- Pargyline
- Rasagiline
- Safinamide
- Selegiline (also D-Deprenyl)
* Note that MAO-B inhibitors also influence norepinephrine/epinephrine levels since they inhibit the breakdown of their precursor dopamine.
|
|
|
COMT
|
- Entacapone
- Nitecapone
- Tolcapone
|
|
|
|
|
|
Others
|
|
|
Precursors
|
- L-Phenylalanine → L-Tyrosine → L-DOPA (Levodopa) → Dopamine
- L-DOPS (Droxidopa)
|
|
|
Cofactors
|
- Ferrous Iron (Fe2+)
- S-Adenosyl-L-Methionine
- Vitamin B3 (Niacin
- Nicotinamide → NADPH)
- Vitamin B6 (Pyridoxine
- Pyridoxamine
- Pyridoxal → Pyridoxal Phosphate)
- Vitamin B9 (Folic acid → Tetrahydrofolic acid)
- Vitamin C (Ascorbic acid)
- Zinc (Zn2+)
|
|
|
Others
|
- Activity enhancers: BPAP
- PPAP; Release blockers: Bethanidine
- Bretylium
- Guanadrel
- Guanazodine
- Guanclofine
- Guanethidine
- Guanoxan; Toxins: 6-OHDA
|
|
|
|
|
List of adrenergic drugs
|
|
UpToDate Contents
全文を閲覧するには購読必要です。 To read the full text you will need to subscribe.
English Journal
- Highly sensitive spectrofluorimetric method for determination of doxazosin through derivatization with fluorescamine; Application to content uniformity testing.
- Omar MA1, Hammad MA2, Salman BI3, Derayea SM1.
- Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy.Spectrochim Acta A Mol Biomol Spectrosc.2016 Mar 15;157:55-60. doi: 10.1016/j.saa.2015.12.012. Epub 2015 Dec 17.
- A highly sensitive, simple and selective spectrofluorimetric method has been developed and validated for determination of doxazosin mesylate in pure form, pharmaceutical formulations and human plasma. The method is based on the reaction between doxazosin mesylate and fluorescamine in Teorell buffer
- PMID 26716887
- Synthesis, vasorelaxant activity and 2D-QSAR study of some novel pyridazine derivatives.
- George RF1, Saleh DO2.
- European journal of medicinal chemistry.Eur J Med Chem.2016 Jan 27;108:663-73. doi: 10.1016/j.ejmech.2015.12.015. Epub 2015 Dec 12.
- Novel 3,6-disubstituted pyridazines were synthesized by facile method and screened for their vasorelaxant properties utilizing isolated thoracic rat aortic rings. Compounds 8a and 11a exerted potent vasorelaxant activity (IC50 = 198 and 177 μM, respectively) relative to doxazosin mesylate (used
- PMID 26735908
- Reappraisal of Antihypertensive Medicine Doxazosin and Carvedilol as a Potential Therapeutic for Hepatic Fibrosis.
- Paik YH1,2.
- Gut and liver.Gut Liver.2016 Jan 23;10(1):10-1. doi: 10.5009/gnl15576.
- PMID 26696027
Japanese Journal
- Determination of doxazosin and verapamil in human serum by fast LC-MS/MS : Application to document non-compliance of patients
- CHYTIL Lukas,STRAUCH Branislav,CVACKA Josef,MARESOVA Vera,WIDIMSKY Jiri Jr.,HOLAJ Robert,SLANAR Ondrej
- Journal of chromatography. B, Analytical technologies in the biomedical and life sciences 878(30), 3167-3173, 2010-11-15
- NAID 10028044040
- Enantioselective determination of doxazosin in human plasma by liquid chromatography-tandem mass spectrometry using ovomucoid chiral stationary phase
- LIU Ke,ZHONG Dafang,CHEN Xiaoyan
- Journal of chromatography. B, Analytical technologies in the biomedical and life sciences 878(26), 2415-2420, 2010-09-15
- NAID 10028041004
- α-Blockers in the treatment of male voiding dysfunction: how do they work and why do they differ in tolerability? (Forum minireview: The forefront for novel therapeutic agents based on the pathophysiology of lower urinary tract dysfunction)
- Michel Martin C.
- Journal of pharmacological sciences 112(2), 151-157, 2010-02
- NAID 40016992203
Related Links
- Doxazosin official prescribing information for healthcare professionals. Includes: indications, dosage, adverse reactions, pharmacology and more. ... In one fixed-dose study (STUDY 2), Doxazosin mesylate therapy (4 to 8 mg, once ...
- Doxazosin is in a group of drugs called alpha-adrenergic (AL-fa ad-ren-ER-jik) blockers. Doxazosin relaxes your veins and arteries so that blood can more easily pass through them. It also relaxes the muscles in the prostate and ...
Related Pictures
★リンクテーブル★
[★]
- 英
- doxazosin
- 化
- メシル酸ドキサゾシン doxazosin mesilate
- 商
- アルフロシン、カズマリン、カデメシン、カルデナリン、カルドナン、カルバドゲン、カルメゾシン、タツゾシン、ドキサゾシンM、ドキサゾン、ドナシン
- 関
- 血圧降下剤
[★]
- 関
- doxazosin