Vernakalant: Difference between revisions

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Created page with "__NOTOC__ {{SI}} {{CMG}} {{Drugbox | Watchedfields = changed | verifiedrevid = 446573380 | IUPAC_name = (3''R'')-1-{(1''R'',2''R'')-2-[2-(3,4-dimethoxyphenyl)<br>ethoxy]cyclo..."
 
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__NOTOC__
{{SI}}
{{CMG}}


{{Drugbox
{{Drugbox
| Verifiedfields = changed
| Watchedfields = changed
| Watchedfields = changed
| verifiedrevid = 446573380
| verifiedrevid = 446573380
| IUPAC_name = (3''R'')-1-{(1''R'',2''R'')-2-[2-(3,4-dimethoxyphenyl)<br>ethoxy]cyclohexyl}pyrrolidin-3-ol
| IUPAC_name = (3''R'')-1-{(1''R'',2''R'')-2-[2-(3,4-dimethoxyphenyl)<br>ethoxy]cyclohexyl}pyrrolidin-3-ol
| image = Vernakalant.svg
| image = Vernakalant.png


<!--Clinical data-->
<!--Clinical data-->
Line 31: Line 29:


<!--Identifiers-->
<!--Identifiers-->
| CAS_number_Ref = {{cascite|correct|??}}
| CAS_number = 794466-70-9
| CAS_number = 794466-70-9
| CAS_supplemental = <br />{{CAS|748810-28-8}} ([[hydrochloride|HCl]])
| CAS_supplemental = <br />{{CAS|748810-28-8}} ([[hydrochloride|HCl]])
Line 40: Line 39:
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 9G468C8B13
| UNII = 9G468C8B13
| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}
| ChemSpiderID      = 8105680
| ChemSpiderID      = 8105680
| smiles            = O(c1ccc(cc1OC)CCO[C@@H]3CCCC[C@H]3N2CC[C@@H](O)C2)C
| smiles            = O(c1ccc(cc1OC)CCO[C@@H]3CCCC[C@H]3N2CC[C@@H](O)C2)C
| InChI            = 1/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
| InChI            = 1/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
| InChIKey          = VBHQKCBVWWUUKN-KZNAEPCWBT
| InChIKey          = VBHQKCBVWWUUKN-KZNAEPCWBT
| StdInChI_Ref = {{stdinchicite|changed|chemspider}}
| StdInChI          = 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
| StdInChI          = 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
| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}
| StdInChIKey      = VBHQKCBVWWUUKN-KZNAEPCWSA-N
| StdInChIKey      = VBHQKCBVWWUUKN-KZNAEPCWSA-N


<!--Chemical data-->
<!--Chemical data-->
| C=20 | H=31 | N=1 | O=4
| C=20 | H=31 | N=1 | O=4  
| molecular_weight = 349.464 g/mol
| molecular_weight = 349.464 g/mol
}}
}}
__NOTOC__
{{SI}}
{{CMG}}


==Overview==
==Overview==
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[[Category:Antiarrhythmic agents]]
[[Category:Antiarrhythmic agents]]
[[Category:Phenol ethers]]
[[Category:Cardiovascular Drugs]]
[[Category:Pyrrolidines]]
[[Category:Drug]]
[[Category:Alcohols]]
 
 
{{cardiovascular-drug-stub}}
 
[[fr:Vernakalant]]
[[it:Vernakalant]]
[[hu:Vernakalant]]

Revision as of 22:34, 23 July 2014

{{Drugbox | Verifiedfields = changed | Watchedfields = changed | verifiedrevid = 446573380 | IUPAC_name = (3R)-1-{(1R,2R)-2-[2-(3,4-dimethoxyphenyl)
ethoxy]cyclohexyl}pyrrolidin-3-ol | image = Vernakalant.png

| tradename = | licence_EU = Brinavess | licence_US = | pregnancy_AU = | pregnancy_US = | pregnancy_category = | legal_AU = | legal_CA = | legal_UK = | legal_US = | legal_status = Rx-only | routes_of_administration = Intravenous, oral

| bioavailability = | protein_bound = | metabolism = | elimination_half-life = | excretion =

| CAS_number_Ref =  ☑Y | CAS_number = 794466-70-9 | CAS_supplemental =
748810-28-8 (HCl) | ATC_prefix = C01 | ATC_suffix = BG11 | PubChem = 9930049 | DrugBank_Ref =  ☑Y | DrugBank = | UNII_Ref =  ☑Y | UNII = 9G468C8B13 | ChemSpiderID_Ref =  ☒N | ChemSpiderID = 8105680 | smiles = O(c1ccc(cc1OC)CCO[C@@H]3CCCC[C@H]3N2CC[C@@H](O)C2)C | InChI = 1/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 | InChIKey = VBHQKCBVWWUUKN-KZNAEPCWBT | StdInChI_Ref =  ☒N | StdInChI = 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 | StdInChIKey_Ref =  ☒N | StdInChIKey = VBHQKCBVWWUUKN-KZNAEPCWSA-N

| C=20 | H=31 | N=1 | O=4 | molecular_weight = 349.464 g/mol }}


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Editor-In-Chief: C. Michael Gibson, M.S., M.D. [1]

Overview

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 has been bought for further development by Merck in April 2009.[1]

On December 11, 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 was approved in Europe on September 1, 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 "Merck and Cardiome Pharma Sign License Agreement for Vernakalant, an Investigational Drug for Treatment of Atrial Fibrillation". FierceBiotech. 9 April 2009. Retrieved 12 October 2010.
  2. ↑ "FDA Advisory Committee Recommends Approval of Kynapid for Acute Atrial Fibrillation". Drugs.com. Retrieved 2008-03-15.
  3. ↑ "BRINAVESS (vernakalant) for Infusion Approved in the European Union for Rapid Conversion of Recent Onset Atrial Fibrillation" (Press release). Merck & Co., Inc. 2010-09-01. Retrieved September 28, 2010.
  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 Template:Cite

Template:Antiarrhythmic agents

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