Vernakalant

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Vernakalant
Vernakalant.svg
Systematic (IUPAC) name
(3R)-1-{(1R,2R)-2-[2-(3,4-dimethoxyphenyl)
ethoxy]cyclohexyl}pyrrolidin-3-ol
Clinical data
Licence data EMA:Link
Legal status
  • ℞ (Prescription only)
Routes of
administration		 Intravenous, oral
Identifiers
CAS Number 794466-70-9 YesY
Template:CAS (HCl)
ATC code C01BG11 (WHO)
PubChem CID: 9930049
ChemSpider 8105680 N
UNII 9G468C8B13 YesY
Chemical data
Formula C20H31NO4
Molecular mass 349.464 g/mol
  • O(c1ccc(cc1OC)CCO[C@@H]3CCCC[C@H]3N2CC[C@@H](O)C2)C
  • 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 N
  • Key:VBHQKCBVWWUUKN-KZNAEPCWSA-N N
 NYesY (what is this?)  (verify)

Vernakalant (INN; codenamed RSD1235, proposed tradenames Kynapid and Brinavess) is an investigational drug under regulatory review for the acute conversion of atrial fibrillation. It was initially developed by Cardiome Pharma, and the intravenous formulation was bought for further development by Merck in April 2009.[1] In September 2012, Merck terminated its agreements with Cardiome and has consequently returned all rights of the drug back to Cardiome.

On 11 December 2007, the Cardiovascular and Renal Drugs Advisory Committee of the US Food and Drug Administration (FDA) voted to recommend the approval of vernakalant,[2] but in August 2008 the FDA judged that additional information was necessary for approval.[1] The drug (under brand name Brinavess) was approved in Europe on 1 September 2010.[3]

An oral formulation underwent Phase II clinical trials between 2005 and 2008.[4][5]

Mechanism of action

Like other class III antiarrhythmics, vernakalant blocks atrial potassium channels, thereby prolonging repolarization. It differs from typical class III agents by blocking a certain type of potassium channel, the cardiac transient outward potassium current, with increased potency as the heart rate increases. This means that it is more effective at high heart rates, while other class III agents tend to lose effectiveness under these circumstances. It also slightly blocks the hERG potassium channel, leading to a prolonged QT interval. This may theoretically increase the risk of ventricular tachycardia, though this does not seem to be clinically relevant.[6]

The drug also blocks atrial sodium channels.[6]

References

  1. ↑ 1.0 1.1 Lua error in package.lua at line 80: module 'strict' not found.
  2. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  3. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  4. ↑ Clinical trial number NCT00267930 for "Study of RSD1235-SR for the Prevention of Atrial Fibrillation/Atrial Flutter Recurrence" at ClinicalTrials.gov
  5. ↑ Clinical trial number NCT00526136 for "Vernakalant (Oral) Prevention of Atrial Fibrillation Recurrence Post-Conversion Study" at ClinicalTrials.gov
  6. ↑ 6.0 6.1 Lua error in package.lua at line 80: module 'strict' not found.
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