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 Date2010 |
PubMed
Title | Date | PubMed |
---|---|---|
The molecular basis of high-affinity binding of the antiarrhythmic compound vernakalant (RSD1235) to Kv1.5 channels. | 2007 Dec |
|
The effect of vernakalant (RSD1235), an investigational antiarrhythmic agent, on atrial electrophysiology in humans. | 2007 Jul |
|
New antiarrhythmic treatment of atrial fibrillation. | 2007 Jul |
|
The cardiac persistent sodium current: an appealing therapeutic target? | 2008 Mar |
|
Vernakalant hydrochloride for rapid conversion of atrial fibrillation: a phase 3, randomized, placebo-controlled trial. | 2008 Mar 25 |
|
Vernakalant--a promising therapy for conversion of recent-onset atrial fibrillation. | 2008 May |
|
Vernakalant (RSD1235) in the management of atrial fibrillation: a review of pharmacological properties, clinical efficacy and safety. | 2008 Nov |
|
Kv1.5 blockers for the treatment of atrial fibrillation: approaches to optimization of potency and selectivity and translation to in vivo pharmacology. | 2009 |
|
Novel approaches for pharmacological management of atrial fibrillation. | 2009 |
|
Pharmacologic management of atrial fibrillation: established and emerging options. | 2009 Aug |
|
Cardioversion for atrial fibrillation: treatment options and advances. | 2009 Aug |
|
Vernakalant hydrochloride for the treatment of atrial fibrillation. | 2009 Dec |
|
Pharmacokinetics of novel atrial-selective antiarrhythmic agent vernakalant hydrochloride injection (RSD1235): influence of CYP2D6 expression and other factors. | 2009 Jan |
|
Atrial fibrillation: from ion channels to bedside treatment options. | 2009 Nov-Dec |
|
New and emerging antiarrhythmic drugs for atrial fibrillation: what may become available to the clinician in the near future. | 2009 Oct |
|
New pharmacological agents for arrhythmias. | 2009 Oct |
|
Modeling of high-affinity binding of the novel atrial anti-arrhythmic agent, vernakalant, to Kv1.5 channels. | 2009 Oct |
|
[New antiarrhythmic drugs for treatment of atrial fibrillation]. | 2010 |
|
New antiarrhythmic drugs for treatment of atrial fibrillation. | 2010 Apr 3 |
|
Advances in the treatment of atrial fibrillation. | 2010 Dec |
|
Vernakalant. | 2010 Dec |
|
[New developments in the antiarrhythmic therapy of atrial fibrillation]. | 2010 Dec |
|
Beta1-adrenoceptor polymorphism predicts flecainide action in patients with atrial fibrillation. | 2010 Jul 2 |
|
Atrial Ca2+ signaling in atrial fibrillation as an antiarrhythmic drug target. | 2010 Mar |
|
[Vernakalant: a novel antiarrhythmic drug for the rapid conversion of atrial fibrillation to sinus rhythm]. | 2010 May |
|
New and emerging antiarrhythmic and anticoagulant agents for atrial fibrillation. | 2010 May 1 |
|
Vernakalant hydrochloride: A novel atrial-selective agent for the cardioversion of recent-onset atrial fibrillation in the emergency department. | 2010 Nov |
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
by
admin
on
Edited
Fri Dec 15 15:28:39 GMT 2023
by
admin
on
Fri Dec 15 15:28:39 GMT 2023
|
Record UNII |
9G468C8B13
|
Record Status |
Validated (UNII)
|
Record Version |
|
-
Download
Name | Type | Language | ||
---|---|---|---|---|
|
Official Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Systematic Name | English | ||
|
Common Name | English | ||
|
Systematic Name | English |
Classification Tree | Code System | Code | ||
---|---|---|---|---|
|
NCI_THESAURUS |
C47793
Created by
admin on Fri Dec 15 15:28:39 GMT 2023 , Edited by admin on Fri Dec 15 15:28:39 GMT 2023
|
||
|
WHO-ATC |
C01BG11
Created by
admin on Fri Dec 15 15:28:39 GMT 2023 , Edited by admin on Fri Dec 15 15:28:39 GMT 2023
|
||
|
WHO-VATC |
QC01BG11
Created by
admin on Fri Dec 15 15:28:39 GMT 2023 , Edited by admin on Fri Dec 15 15:28:39 GMT 2023
|
||
|
NCI_THESAURUS |
C93038
Created by
admin on Fri Dec 15 15:28:39 GMT 2023 , Edited by admin on Fri Dec 15 15:28:39 GMT 2023
|
Code System | Code | Type | Description | ||
---|---|---|---|---|---|
|
9930049
Created by
admin on Fri Dec 15 15:28:39 GMT 2023 , Edited by admin on Fri Dec 15 15:28:39 GMT 2023
|
PRIMARY | |||
|
9G468C8B13
Created by
admin on Fri Dec 15 15:28:39 GMT 2023 , Edited by admin on Fri Dec 15 15:28:39 GMT 2023
|
PRIMARY | |||
|
8733
Created by
admin on Fri Dec 15 15:28:39 GMT 2023 , Edited by admin on Fri Dec 15 15:28:39 GMT 2023
|
PRIMARY | |||
|
C524581
Created by
admin on Fri Dec 15 15:28:39 GMT 2023 , Edited by admin on Fri Dec 15 15:28:39 GMT 2023
|
PRIMARY | |||
|
VERNAKALANT
Created by
admin on Fri Dec 15 15:28:39 GMT 2023 , Edited by admin on Fri Dec 15 15:28:39 GMT 2023
|
PRIMARY | |||
|
DTXSID60229659
Created by
admin on Fri Dec 15 15:28:39 GMT 2023 , Edited by admin on Fri Dec 15 15:28:39 GMT 2023
|
PRIMARY | |||
|
C152864
Created by
admin on Fri Dec 15 15:28:39 GMT 2023 , Edited by admin on Fri Dec 15 15:28:39 GMT 2023
|
PRIMARY | |||
|
794466-70-9
Created by
admin on Fri Dec 15 15:28:39 GMT 2023 , Edited by admin on Fri Dec 15 15:28:39 GMT 2023
|
PRIMARY | |||
|
SUB127269
Created by
admin on Fri Dec 15 15:28:39 GMT 2023 , Edited by admin on Fri Dec 15 15:28:39 GMT 2023
|
PRIMARY | |||
|
DB06217
Created by
admin on Fri Dec 15 15:28:39 GMT 2023 , Edited by admin on Fri Dec 15 15:28:39 GMT 2023
|
PRIMARY | |||
|
CHEMBL2111112
Created by
admin on Fri Dec 15 15:28:39 GMT 2023 , Edited by admin on Fri Dec 15 15:28:39 GMT 2023
|
PRIMARY | |||
|
4365
Created by
admin on Fri Dec 15 15:28:39 GMT 2023 , Edited by admin on Fri Dec 15 15:28:39 GMT 2023
|
PRIMARY | |||
|
m11427
Created by
admin on Fri Dec 15 15:28:39 GMT 2023 , Edited by admin on Fri Dec 15 15:28:39 GMT 2023
|
PRIMARY | Merck Index | ||
|
100000153301
Created by
admin on Fri Dec 15 15:28:39 GMT 2023 , Edited by admin on Fri Dec 15 15:28:39 GMT 2023
|
PRIMARY |
Related Record | Type | Details | ||
---|---|---|---|---|
|
TARGET -> INHIBITOR |
|
||
|
SALT/SOLVATE -> PARENT |
|
||
|
TARGET -> INHIBITOR |
|
Related Record | Type | Details | ||
---|---|---|---|---|
|
ACTIVE MOIETY |
|