ブレチリウムトシレート
- 関
- bretylium tosilate
Wikipedia preview
出典(authority):フリー百科事典『ウィキペディア(Wikipedia)』「2012/07/14 01:28:31」(JST)
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Bretylium
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Systematic (IUPAC) name |
N-(2-bromobenzyl)-N,N-dimethylethanaminium |
Clinical data |
MedlinePlus |
a682861 |
Pregnancy cat. |
C (AU) C (US) |
Legal status |
℞-only (US) |
Routes |
IV, IM |
Pharmacokinetic data |
Bioavailability |
NA |
Protein binding |
NA |
Metabolism |
None |
Half-life |
7-8 hours |
Excretion |
Renal |
Identifiers |
CAS number |
59-41-6 Y |
ATC code |
C01BD02 |
PubChem |
CID 2431 |
DrugBank |
DB01158 |
ChemSpider |
2337 Y |
UNII |
RZR75EQ2KJ Y |
KEGG |
D00645 N |
ChEBI |
CHEBI:3172 Y |
ChEMBL |
CHEMBL1199080 N |
Chemical data |
Formula |
C11H17BrN+ |
Mol. mass |
243.163 g/mol |
|
InChI
-
InChI=1S/C11H17BrN/c1-4-13(2,3)9-10-7-5-6-8-11(10)12/h5-8H,4,9H2,1-3H3/q+1 Y
Key:AAQOQKQBGPPFNS-UHFFFAOYSA-N Y
|
N (what is this?) (verify)
|
Bretylium (also bretylium tosylate) is an antiarrhythmic agent.[1] It blocks the release of noradrenaline from nerve terminals. In effect, it decreases output from the peripheral sympathetic nervous system. It also acts by blocking K+ channels and is considered a class III antiarrhythmic. The dose is 5-10 mg/kg and side effects are hypertension followed by hypotension and ventricular ectopy.
It was patented in 1978 by Marvin Bacaner at the University of Minnesota.[2]
Uses
It is used in emergency medicine, cardiology, and other specialties for the acute management of ventricular tachycardia and ventricular fibrillation. [3]
It is contraindicated in patients with AV (atrioventricular) heart block or digoxin toxicity.
Bretylium should be used only in an ICU or Emergency Department setting and should not be used elsewhere due to its dramatic actions and its predominant side effect of hypotension.
References
- ^ Tiku PE, Nowell PT (December 1991). "Selective inhibition of K(+)-stimulation of Na,K-ATPase by bretylium". Br. J. Pharmacol. 104 (4): 895–900. PMC 1908819. PMID 1667290. //www.pubmedcentral.nih.gov/articlerender.fcgi?tool=pmcentrez&artid=1908819.
- ^ "University of Minnesota: Scholars Walk". http://www.scholarswalk.umn.edu/discovery/wall_names.html. Retrieved 2008-09-23.
- ^ "ACS". http://www2.kumc.edu/wichita/meded/intro/modules/ami/reading/RAMI-09.htm. Retrieved 2008-09-23. [dead link]
Adrenergics
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Receptor ligands
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α1
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- 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
- 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
- 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.
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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
- 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.
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β
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Reuptake inhibitors
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NET
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- 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 (Amfebutamone)
- Fencamine
- Fencamfamine
- 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
- Methylnaphthidate
- Naphyrone
- NS-2359
- 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
- EXP-561
- Fezolamine
- Ginkgo biloba
- Indeloxazine
- Nefazodone
- Nefopam
- Pridefrine
- Tapentadol
- Tedatioxetine
- Teniloxazine
- Tofenacin
- Tramadol
- Ziprasidone
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VMAT
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- Ibogaine
- Reserpine
- Tetrabenazine
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Enzyme inhibitors
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Anabolism
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PAH
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TH
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- 3-Iodotyrosine
- Aquayamycin
- Bulbocapnine
- Metirosine
- Oudenone
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AAAD
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- Benserazide
- Carbidopa
- DFMD
- Genistein
- Methyldopa
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DBH
|
- Bupicomide
- Disulfiram
- Dopastin
- Fusaric acid
- Nepicastat
- Phenopicolinic acid
- Tropolone
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PNMT
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- CGS-19281A
- SKF-64139
- SKF-7698
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Catabolism
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MAO
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- 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
- Befol
- Brofaromine
- Cimoxatone
- Clorgiline
- 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.
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COMT
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- Entacapone
- Nitecapone
- Tolcapone
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Others
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Precursors
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- L-Phenylalanine → L-Tyrosine → L-DOPA (Levodopa) → Dopamine
- L-DOPS (Droxidopa)
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Cofactors
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- 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+)
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Others
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- Activity enhancers: BPAP
- PPAP; Release blockers: Bethanidine
- Bretylium
- Guanadrel
- Guanazodine
- Guanclofine
- Guanethidine
- Guanoxan; Toxins: 6-OHDA
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List of adrenergic drugs
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Channel blockers
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Calcium (Ca2+) |
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Potassium (K+) |
- 3,4-Diaminopyridine
- 4-Aminopyridine
- Amiodarone
- Bretylium
- Bunaftine
- Charybdotoxin
- Conotoxins
- Dofetilide
- Dronedarone
- E-4031
- Ibutilide
- Linopirdine
- Maurotoxin
- Nifekalant
- Paxilline
- Sotalol
- Tedisamil
- Tetraethylammonium
- Vernakalant
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Sodium (Na+) |
- Antiarrhythmics: Ajmaline
- Aprindine
- Disopyramide
- Dronedarone
- Encainide
- Flecainide
- Lidocaine
- Lorajmine
- Lorcainide
- Mexiletine
- Moricizine
- Phenytoin
- Pilsicainide
- Prajmaline
- Procainamide
- Propafenone
- Quinidine
- Sparteine
- Tocainide
- Anticonvulsants: Carbamazepine
- Eslicarbazepine acetate
- Ethotoin
- Fosphenytoin
- Licarbazepine
- Mephenytoin
- Oxcarbazepine
- Oxitriptyline
- Phenytoin
- Rufinamide
- Topiramate
- Sodium valproate
- Valnoctamide
- Valproate pivoxil
- Valproate semisodium
- Valproic acid
- Valpromide
- Diuretics: Amiloride
- Benzamil
- Triamterene
- Local anesthetics: pFBT
- Amylocaine
- Articaine
- Benzocaine
- Bupivacaine (Levobupivacaine, Ropivacaine)
- Butacaine
- Butamben
- Chloroprocaine
- Cinchocaine
- Cocaine
- Cyclomethycaine
- Dimethocaine
- Etidocaine
- Hexylcaine
- Iontocaine
- Lidocaine
- Mepivacaine
- Meprylcaine
- Metabutoxycaine
- Orthocaine
- Piperocaine
- Prilocaine
- Procaine
- Propoxycaine
- Proxymetacaine
- Risocaine
- Tetracaine
- Trimecaine
- Toxins: Conotoxins
- Neosaxitoxin
- Saxitoxin
- Tetrodotoxin
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Other |
- Uncategorized: Ethadione
- Paramethadione
- Phenacemide
- Pheneturide
- Trimethadione
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Antiarrhythmic agents (C01B)
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Channel blockers |
class I
(Na+ channel blockers)
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class Ia (Phase 0→ and Phase 3→)
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- Procainamide #
- Quinidine #
- Ajmaline
- Disopyramide
- Prajmaline
- Lorajmine
- Sparteine
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class Ib (Phase 3←)
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- IV (Lidocaine #)
- enteral (Mexiletine
- Tocainide
- Aprindine)
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class Ic (Phase 0→)
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- Encainide‡
- Flecainide
- Lorcainide
- Moracizine‡
- Propafenone
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class III
(Phase 3→, K+ channel blockers)
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- Amiodarone
- Dronedarone
- Bretylium
- Bunaftine
- Dofetilide
- Ibutilide
- Nifekalant
- Sotalol
- Tedisamil
- Vernakalant
- E-4031
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class IV
(Phase 4→, Ca2+ channel blockers)
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Receptor agonists
and antagonists |
class II
(Phase 4→, β blockers)
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- Propranolol
- Nadolol
- Pindolol
- cardioselective (Atenolol
- Metoprolol
- Acebutolol
- Esmolol)
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A1 agonist
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M2
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- muscarinic antagonist: Atropine
- Quinidine
- Disopyramide
muscarinic agonist: Digoxin
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α receptors
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- Quinidine
- Verapamil
- Amiodarone
- Bretylium
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Ion transporters |
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- #WHO-EM
- ‡Withdrawn from market
- Clinical trials:
- †Phase III
- §Never to phase III
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noco/cong/tumr, sysi/epon, injr
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proc, drug (C1A/1B/1C/1D), blte
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UpToDate Contents
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English Journal
- Aging and aerobic fitness affect the contribution of noradrenergic sympathetic nerves to the rapid cutaneous vasodilator response to local heating.
- Tew GA, Saxton JM, Klonizakis M, Moss J, Ruddock AD, Hodges GJ.SourceCentre for Sport and Exercise Science, Sheffield Hallam University, Sheffield, United Kingdom.
- Journal of applied physiology (Bethesda, Md. : 1985).J Appl Physiol.2011 May;110(5):1264-70. Epub 2011 Feb 17.
- Sedentary aging results in a diminished rapid cutaneous vasodilator response to local heating. We investigated whether this diminished response was due to altered contributions of noradrenergic sympathetic nerves by assessing 1) the age-related decline and 2) the effect of aerobic fitness. Using las
- PMID 21330615
- Tetrahydrobiopterin does not affect end-organ responsiveness to norepinephrine-mediated vasoconstriction in aged skin.
- Lang JA, Holowatz LA, Kenney WL.SourcePennsylvania State University, Noll Laboratory, Department of Kinesiology, University Park, Pennsylvania, USA. lang@hendrix.edu
- American journal of physiology. Regulatory, integrative and comparative physiology.Am J Physiol Regul Integr Comp Physiol.2010 Dec;299(6):R1651-5. Epub 2010 Oct 6.
- We have recently demonstrated that tetrahydrobiopterin (BH(4)) augments reflex vasoconstriction (VC) in aged skin. Although this appears to occur through its role in norepinephrine (NE) biosynthesis, the extent with which vascular mechanisms are affected are unknown. We hypothesized that localized B
- PMID 20926766
Japanese Journal
- Oral bretylium tosylate use during pregnancy and subsequent breastfeeding : A case report
- 第3詳抗不整脈剤-sotalol及びbretylium tosylate-の急性心筋虚血時の心室筋に対する電気生理学的検討
- 小倉 敏嗣,徳竹 英一,斎藤 友昭,渡辺 一郎,日比谷 和平,高橋 信博,斎藤 頴,小沢 友紀雄,波多野 道信
- Japanese circulation journal 49回学術集会, 283, 1985-03-01
- NAID 110002566954
Related Links
- Bretylium (also bretylium tosylate) is an antiarrhythmic agent. It blocks the release of noradrenaline from nerve terminals. In effect, it decreases output from the peripheral sympathetic nervous system. It also acts by blocking K+ ...
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