Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C20H31NO4 |
Molecular Weight | 349.4644 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 3 / 3 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
COC1=CC=C(CCO[C@@H]2CCCC[C@H]2N3CC[C@@H](O)C3)C=C1OC
InChI
InChIKey=VBHQKCBVWWUUKN-KZNAEPCWSA-N
InChI=1S/C20H31NO4/c1-23-19-8-7-15(13-20(19)24-2)10-12-25-18-6-4-3-5-17(18)21-11-9-16(22)14-21/h7-8,13,16-18,22H,3-6,9-12,14H2,1-2H3/t16-,17-,18-/m1/s1
Molecular Formula | C20H31NO4 |
Molecular Weight | 349.4644 |
Charge | 0 |
Count |
|
Stereochemistry | ABSOLUTE |
Additional Stereochemistry | No |
Defined Stereocenters | 3 / 3 |
E/Z Centers | 0 |
Optical Activity | UNSPECIFIED |
DescriptionSources: https://www.ncbi.nlm.nih.gov/pubmed/21135602Curator's Comment: Description was created based on several sources, including
http://adisinsight.springer.com/drugs/800015306 | http://www.ema.europa.eu/docs/en_GB/document_library/EPAR_-_Public_assessment_report/human/001215/WC500097150.pdf
Sources: https://www.ncbi.nlm.nih.gov/pubmed/21135602
Curator's Comment: Description was created based on several sources, including
http://adisinsight.springer.com/drugs/800015306 | http://www.ema.europa.eu/docs/en_GB/document_library/EPAR_-_Public_assessment_report/human/001215/WC500097150.pdf
Vernakalant is a new antiarrhythmic drug that acts selectively in the atrium, targeting atrial specific channels. Vernakalant is an anti-arrhythmic medicine that acts preferentially in the atria by prolonging atrial refractoriness and by rate-dependently slowing impulse conduction. These anti-fibrillatory actions on refractoriness and conduction are thought to suppress reentry, and are potentiated in the atria during atrial fibrillation. The preferential effects of vernakalant on the atria are postulated to result from its block of currents that are expressed in the atria (e.g., the ultra-rapid delayed rectifier potassium current; and the acetylcholine-activated potassium current), but not in the ventricles, as well as the unique electrophysiologic condition of the fibrillating atria. An oral formulation of vernakalant is in phase II development as a long-term maintenance therapy for patients with atrial fibrillation. An intravenous formulation of vernakalant has been launched in most countries in Europe and Latin America, and in Hong Kong, for the acute conversion of atrial fibrillation. The product has been approved for the acute conversion of atrial fibrillation in South Africa, Iceland, Turkey and is awaiting approval for the same indication in Canada. Phase III development of the IV formulation is ongoing at sites in Asia, and development is currently on hold in the US.
Originator
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL4306 |
13.0 µM [IC50] | ||
Target ID: CHEMBL5885 Sources: https://www.ncbi.nlm.nih.gov/pubmed/16302909 |
38.0 µM [IC50] | ||
Target ID: CHEMBL1964 Sources: https://www.ncbi.nlm.nih.gov/pubmed/16302909 |
30.0 µM [IC50] | ||
Target ID: CHEMBL240 Sources: https://www.ncbi.nlm.nih.gov/pubmed/16302909 |
21.0 µM [IC50] | ||
Target ID: CHEMBL1980 Sources: https://www.ncbi.nlm.nih.gov/pubmed/16302909 |
9.0 µM [IC50] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | BRINAVESS Approved UseBRINAVESS 20 mg/ml concentrate for solution for infusion
(vernakalant hydrochloride) is indicated for rapid conversion of recent onset atrial fibrillation to sinus rhythm in adults Launch Date1.28321284E12 |
PubMed
Title | Date | PubMed |
---|---|---|
The effect of vernakalant (RSD1235), an investigational antiarrhythmic agent, on atrial electrophysiology in humans. | 2007 Jul |
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New antiarrhythmic treatment of atrial fibrillation. | 2007 Jul |
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Vernakalant in the management of atrial fibrillation. | 2008 Apr |
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[Amiodaron for treatment of perioperative cardiac arrythmia: a broad spectrum antiarrythmetic agent?]. | 2008 Dec |
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The cardiac persistent sodium current: an appealing therapeutic target? | 2008 Mar |
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Vernakalant: pharmacology electrophysiology, safety and efficacy. | 2008 May |
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New antiarrhythmic drugs for atrial fibrillation: focus on dronedarone and vernakalant. | 2008 Oct |
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Kv1.5 blockers for the treatment of atrial fibrillation: approaches to optimization of potency and selectivity and translation to in vivo pharmacology. | 2009 |
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Novel approaches for pharmacological management of atrial fibrillation. | 2009 |
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Pharmacologic management of atrial fibrillation: established and emerging options. | 2009 Aug |
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Vernakalant hydrochloride for the rapid conversion of atrial fibrillation after cardiac surgery: a randomized, double-blind, placebo-controlled trial. | 2009 Dec |
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Vernakalant hydrochloride for the treatment of atrial fibrillation. | 2009 Dec |
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Atrial-selective pharmacological therapy for atrial fibrillation: hype or hope? | 2009 Jan |
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Recent advances in the pharmacological treatment of cardiac arrythmias. | 2009 Nov |
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Atrial fibrillation: from ion channels to bedside treatment options. | 2009 Nov-Dec |
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New pharmacological agents for arrhythmias. | 2009 Oct |
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Modeling of high-affinity binding of the novel atrial anti-arrhythmic agent, vernakalant, to Kv1.5 channels. | 2009 Oct |
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[New antiarrhythmic drugs for treatment of atrial fibrillation]. | 2010 |
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[New developments in the antiarrhythmic therapy of atrial fibrillation]. | 2010 Dec |
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A multicenter, open-label study of vernakalant for the conversion of atrial fibrillation to sinus rhythm. | 2010 Jun |
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New and emerging antiarrhythmic and anticoagulant agents for atrial fibrillation. | 2010 May 1 |
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Usefulness of vernakalant hydrochloride injection for rapid conversion of atrial fibrillation. | 2010 Nov 1 |
|
Vernakalant, a mixed sodium and potassium ion channel antagonist that blocks K(v)1.5 channels, for the potential treatment of atrial fibrillation. | 2010 Sep |
Patents
Sample Use Guides
BRINAVESS is dosed by patient body weight, with a maximum calculated dose based upon 113 kg.
The recommended initial infusion is 3 mg/kg to be infused over a 10 minute period. For patients
weighing ≥ 113 kg, the maximum initial dose of 339 mg (84.7 ml of 4 mg/ml solution) should not
exceeded. If conversion to sinus rhythm does not occur within 15 minutes after the end of the initial
infusion, a second 10 minute infusion of 2 mg/kg may be administered. For patients weighing
≥ 113 kg, the maximum second infusion of 226 mg (56.5 ml of 4 mg/ml solution) should not exceeded
.Cumulative doses of greater than 5 mg/kg should not be administered within 24 hours. Cumulative
doses above 565 mg have not been evaluated.
Route of Administration:
Intravenous
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/22019863
3-30 μM Vernakalant in canine pulmonary vein sleeve preparations produced small (10-15 ms) increases in action potential duration and suppressed delayed afterdepolarization-mediated triggered activity induced by isoproterenol and high calcium.
Substance Class |
Chemical
Created
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on
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Record UNII |
9G468C8B13
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Record Status |
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C47793
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C01BG11
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C93038
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