トシル酸ブレチリウム
- 関
- bretylium tosylate
Wikipedia preview
出典(authority):フリー百科事典『ウィキペディア(Wikipedia)』「2016/08/21 01:57:08」(JST)
[Wiki en表示]
Bretylium
|
Systematic (IUPAC) name |
N-(2-bromobenzyl)-N,N-dimethylethanaminium
|
Clinical data |
MedlinePlus |
a682861 |
Pregnancy
category |
- AU: C
- US: C (Risk not ruled out)
|
Routes of
administration |
IV, IM |
Legal status |
Legal status |
|
Pharmacokinetic data |
Bioavailability |
NA |
Protein binding |
NA |
Metabolism |
None |
Biological half-life |
7-8 hours |
Excretion |
Renal |
Identifiers |
CAS Number |
59-41-6 Y |
ATC code |
C01BD02 (WHO) |
PubChem |
CID 2431 |
IUPHAR/BPS |
7130 |
DrugBank |
DB01158 Y |
ChemSpider |
2337 Y |
UNII |
RZR75EQ2KJ Y |
KEGG |
D00645 N |
ChEBI |
CHEBI:3172 Y |
ChEMBL |
CHEMBL1199080 N |
Chemical data |
Formula |
C11H17BrN+ |
Molar 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
|
NY (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 high blood pressure followed by low blood pressure and ventricular ectopy.
Originally introduced in 1959 for the treatment of hypertension.[2] Its use as an antiarrhythmic for ventricular fibrilation was discovered and patented by Marvin Bacaner in 1969 at the University of Minnesota.[3]
The American Heart Association removed Bretylium from their 2000 ECC/ACC guidelines due to its unproven efficacy and ongoing supply problems. Many have cited these supply problems as an issue of raw materials needed in the production of Bretylium. By the release of the AHA 2005 ECC/ACC guidelines there is no mention of Bretylium and it is virtually unavailable throughout most of the world.[4][5]
As of June 8, 2011 Bretylium Tosylate is permanently no longer available in the US after request of Hospira Inc. to withdraw its NDA from the market. Bretylium will remain on the FDA's discontinued drug list since its withdrawal was not the result of a safety or effectiveness concern.[6]
Contents
- 1 Uses
- 2 Experimental Uses
- 3 Synthesis
- 4 References
Uses
It was used in emergency medicine, cardiology, and other specialties throughout the 1980s-1990s for the acute management of ventricular tachycardia and ventricular fibrillation refractory to other first line treatments such as defibrillation or lidocaine.[7]
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.[citation needed]
Experimental Uses
It is used in physiological and pharmacological research as an inhibitor of sympathetic transmission. Its mechanism of action is the inhibition of neurotransmitter release from sympathetic nerve terminals, both by the inhibition of action potentials in the nerve terminals and by other mechanisms.[8] Its specificity for sympathetic nerves is achieved because it is a substrate for the noradrenaline transporter;[9] hence, it accumulates inside nerve terminals which have this transporter.
Synthesis
Bretylium synthesis: Burroughs Wellcome Co. R. Tondeur, F. Binon,
U.S. Patent 3,038,004 (1962).
Quaternization of o-bromo-N,N-dimethylbenzylamine with ethyl-p-toluenesulfonate yields bretylium sulfonate.
References
- ^ Tiku, Patience E.; Nowell, Peter T. (1991). "Selective inhibition of K+-stimulation of Na,K-ATPase by bretylium". British Journal of Pharmacology. 104 (4): 895–900. doi:10.1111/j.1476-5381.1991.tb12523.x. PMC 1908819. PMID 1667290.
- ^ Harington, M (1962). "The drug treatment of hypertension. The results of drug treatment". Proceedings of the Royal Society of Medicine. 55: 283–6. PMC 1896727. PMID 13904707.
- ^ "patent". Retrieved 2014-02-06. [full citation needed]
- ^ Khan, M. Gabriel (December 14, 2005). Encyclopedia of Heart Diseases. Academic Press. p. 221. ISBN 978-0-12-406061-6. Retrieved 2015-07-01.
- ^ Hypothermia~treatment at eMedicine
- ^ https://www.federalregister.gov/articles/2011/12/19/2011-32367/determination-that-bretylium-tosylate-injection-50-milligramsmilliliter-was-not-withdrawn-from-sale[full citation needed]
- ^ "ACS". Archived from the original on September 4, 2006. Retrieved 2008-09-23.
- ^ Brain, K L; Cunnane, T C (2008). "Bretylium abolishes neurotransmitter release without necessarily abolishing the nerve terminal action potential in sympathetic terminals". British Journal of Pharmacology. 153 (4): 831–9. doi:10.1038/sj.bjp.0707623. PMC 2259200. PMID 18071295.
- ^ Boura, A. L. A.; Copp, F. C.; Duncombe, W. G.; Green, A. F.; McCoubrey, A. (1960). "The selective accumulation of bretylium in sympathetic ganglia and their postganglionic nerves". British Journal of Pharmacology and Chemotherapy. 15: 265–70. doi:10.1111/j.1476-5381.1960.tb01242.x. PMC 1481934. PMID 13803289.
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COMT |
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Others
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Precursors |
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|
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Cofactors |
- Ferrous Iron (Fe2+)
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- Nicotinamide → NADPH)
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- Pyridoxamine
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- Vitamin C (Ascorbic acid)
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Neurotoxins |
- DSP-4
- Oxidopamine (6-OHDA)
|
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Others |
- Activity enhancers
- BPAP
- PPAP
|
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- Release blockers
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- See also:
- Dopaminergics
- Melatonergics
- Serotonergics
- List of adrenergic drugs
|
Antiarrhythmic agents (C01B)
|
|
Channel blockers |
class I
(Na+ channel blockers)
|
class Ia (Phase 0→ and Phase 3→)
|
- Ajmaline
- Disopyramide
- Lorajmine
- Prajmaline
- Procainamide#
- Quinidine#
- Sparteine
|
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class Ib (Phase 3←)
|
- IV (Lidocaine#)
- enteral (Aprindine
- Mexiletine
- Tocainide)
|
|
class Ic (Phase 0→)
|
- Encainide‡
- Ethacizine
- Flecainide
- Indecainide‡
- Lorcainide
- Moracizine‡
- Propafenone
|
|
|
class III
(Phase 3→, K+ channel blockers)
|
- Amiodarone
- Bretylium
- Bunaftine
- Celivarone†
- Dofetilide
- Dronedarone
- E-4031†
- Ibutilide
- Nifekalant
- Sotalol
- Tedisamil
- Vernakalant
|
|
class IV
(Phase 4→, Ca2+ channel blockers)
|
|
|
|
Receptor agonists
and antagonists |
class II
(Phase 4→, β blockers)
|
- Nadolol
- Pindolol
- Propranolol
- cardioselective (Acebutolol
- Atenolol
- Esmolol
- Metoprolol)
|
|
A1 agonist
|
- Adenosine
- Benzodiazepines
- Barbiturates
|
|
M2
|
- muscarinic antagonist: Atropine
- Disopyramide
- Quinidine
muscarinic agonist: Digoxin
|
|
α receptors
|
- Amiodarone
- Bretylium
- Quinidine
- Verapamil
|
|
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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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English Journal
- Comparison of the noradrenergic sympathetic nerve contribution during local skin heating at forearm and leg sites in humans.
- Del Pozzi AT1, Hodges GJ.
- European journal of applied physiology.Eur J Appl Physiol.2015 Jan 9. [Epub ahead of print]
- PURPOSE: We investigated the role of noradrenergic sympathetic nerves in the cutaneous circulation at rest and in response to local heating.METHODS: Dorsal forearm and lateral leg sites were each instrumented with 2 microdialysis fibers, 2 local skin heaters, and 2 laser-Doppler probes. All sites we
- PMID 25572497
- To reheat, or to not reheat: that is the question: the efficacy of a local reheating protocol on mechanisms of cutaneous vasodilatation.
- Del Pozzi AT1, Hodges GJ2.
- Microvascular research.Microvasc Res.2015 Jan;97:47-54. doi: 10.1016/j.mvr.2014.09.006. Epub 2014 Oct 2.
- The aim of this study is to determine the effect of repeated bouts of local skin heating on the roles of nitric oxide synthase (NOS) and sympathetic nerves in cutaneous vasodilatation. In 3 repeated-heating protocols skin blood flux of the forearm and leg was measured using laser-Doppler flowmetry a
- PMID 25281012
- Adenosine receptor inhibition attenuates the suppression of postexercise cutaneous blood flow.
- McGinn R1, Fujii N1, Swift B1, Lamarche DT1, Kenny GP2.
- The Journal of physiology.J Physiol.2014 Jun 15;592(Pt 12):2667-78. doi: 10.1113/jphysiol.2014.274068. Epub 2014 Mar 31.
- The time-dependent contributions of active vasodilation (e.g. nitric oxide) and noradrenergic vasoconstriction to the postexercise suppression of cutaneous perfusion despite persistent hyperthermia remain unknown. Moreover, adenosine receptors have been shown to mediate the decrease in cutaneous per
- PMID 24687586
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+ channels and is ...
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