Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C20H31NO4.ClH |
Molecular Weight | 385.925 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 3 / 3 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
Cl.COC1=CC=C(CCO[C@@H]2CCCC[C@H]2N3CC[C@@H](O)C3)C=C1OC
InChI
InChIKey=JMHYCBFEEFHTMK-IIUXMCBISA-N
InChI=1S/C20H31NO4.ClH/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;1H/t16-,17-,18-;/m1./s1
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 |
---|---|---|
Vernakalant (RSD1235): a novel, atrial-selective antifibrillatory agent. | 2007 Apr |
|
Anti-arrhythmic drug therapy for atrial fibrillation: current anti-arrhythmic drugs, investigational agents, and innovative approaches. | 2008 Jun |
|
Vernakalant hydrochloride for rapid conversion of atrial fibrillation: a phase 3, randomized, placebo-controlled trial. | 2008 Mar 25 |
|
Atrial-selective pharmacological therapy for atrial fibrillation: hype or hope? | 2009 Jan |
|
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 Apr 3 |
|
Vernakalant. | 2010 Dec |
|
[New developments in the antiarrhythmic therapy of atrial fibrillation]. | 2010 Dec |
|
A multicenter, open-label study of vernakalant for the conversion of atrial fibrillation to sinus rhythm. | 2010 Jun |
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.
Name | Type | Language | ||
---|---|---|---|---|
|
Official Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Systematic Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Code | English | ||
|
Brand Name | English | ||
|
Common Name | English | ||
|
Brand Name | English | ||
|
Code | English |
Classification Tree | Code System | Code | ||
---|---|---|---|---|
|
NCI_THESAURUS |
C47793
Created by
admin on Fri Dec 15 15:56:45 GMT 2023 , Edited by admin on Fri Dec 15 15:56:45 GMT 2023
|
||
|
EMA ASSESSMENT REPORTS |
BRINAVESS (AUTHORIZED: ATRIAL FIBRILLATION)
Created by
admin on Fri Dec 15 15:56:45 GMT 2023 , Edited by admin on Fri Dec 15 15:56:45 GMT 2023
|
||
|
NCI_THESAURUS |
C93038
Created by
admin on Fri Dec 15 15:56:45 GMT 2023 , Edited by admin on Fri Dec 15 15:56:45 GMT 2023
|
Code System | Code | Type | Description | ||
---|---|---|---|---|---|
|
748810-28-8
Created by
admin on Fri Dec 15 15:56:45 GMT 2023 , Edited by admin on Fri Dec 15 15:56:45 GMT 2023
|
PRIMARY | |||
|
100000115500
Created by
admin on Fri Dec 15 15:56:45 GMT 2023 , Edited by admin on Fri Dec 15 15:56:45 GMT 2023
|
PRIMARY | |||
|
DBSALT002376
Created by
admin on Fri Dec 15 15:56:45 GMT 2023 , Edited by admin on Fri Dec 15 15:56:45 GMT 2023
|
PRIMARY | |||
|
7G4J1ZD9UQ
Created by
admin on Fri Dec 15 15:56:45 GMT 2023 , Edited by admin on Fri Dec 15 15:56:45 GMT 2023
|
PRIMARY | |||
|
m11427
Created by
admin on Fri Dec 15 15:56:45 GMT 2023 , Edited by admin on Fri Dec 15 15:56:45 GMT 2023
|
PRIMARY | Merck Index | ||
|
C152865
Created by
admin on Fri Dec 15 15:56:45 GMT 2023 , Edited by admin on Fri Dec 15 15:56:45 GMT 2023
|
PRIMARY | |||
|
SUB30707
Created by
admin on Fri Dec 15 15:56:45 GMT 2023 , Edited by admin on Fri Dec 15 15:56:45 GMT 2023
|
PRIMARY | |||
|
9930048
Created by
admin on Fri Dec 15 15:56:45 GMT 2023 , Edited by admin on Fri Dec 15 15:56:45 GMT 2023
|
PRIMARY | |||
|
RR-36
Created by
admin on Fri Dec 15 15:56:45 GMT 2023 , Edited by admin on Fri Dec 15 15:56:45 GMT 2023
|
PRIMARY | |||
|
CHEMBL2111112
Created by
admin on Fri Dec 15 15:56:45 GMT 2023 , Edited by admin on Fri Dec 15 15:56:45 GMT 2023
|
PRIMARY |
ACTIVE MOIETY
SUBSTANCE RECORD