Vernakalant HCl | RSD1235 | CAS#748810-28-8 | CAS#794466-70-9 | Potassium Channel Inhibitor

MedKoo Cat#: 3268820 | Name: Vernakalant HCl

Description:

WARNING: This product is for research use only, not for human or veterinary use.

Vernakalant HCl, also known as RSD1235, is an investigational drug for the acute conversion of atrial fibrillation. 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. Vernakalant also blocks atrial sodium channels.

Chemical Structure

Vernakalant HCl

CAS#748810-28-8

Theoretical Analysis

MedKoo Cat#: 3268820

Name: Vernakalant HCl

CAS#: 748810-28-8

Chemical Formula: C20H32ClNO4

Exact Mass:

Molecular Weight: 385.93

Elemental Analysis: C, 62.24; H, 8.36; Cl, 9.19; N, 3.63; O, 16.58

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.

Bulk Inquiry

Related CAS #

748810-28-8 (HCl) 794466-70-9 (free)

Synonym

RSD1235, RSD-1235, RSD 1235, Vernakalant HCl, Kynapid, Brinavess

IUPAC/Chemical Name

(3R)-1-((1R,2R)-2-(2-(3,4-dimethoxyphenyl)ethoxy)cyclohexyl)pyrrolidin-3-ol hydrochloride

InChi Key

JMHYCBFEEFHTMK-IIUXMCBISA-N

InChi Code

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

SMILES Code

O[C@H]1CN([C@H]2[C@H](OCCC3=CC=C(OC)C(OC)=C3)CCCC2)CC1.[H]Cl

Appearance

Solid powder

Purity

>98% (or refer to the Certificate of Analysis)

Shipping Condition

Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition

Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility

Soluble in DMSO

Shelf Life

>2 years if stored properly

Drug Formulation

This drug may be formulated in DMSO

Stock Solution Storage

0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code

2934.99.9001

More Info

Related CAS# CAS#748810-28-8 (Vernakalant hydrochloride) CAS#794466-70-9 (Vernakalant free base))

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 385.93 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

1: Frommeyer G, Ellermann C, Dechering DG, Kochhäuser S, Bögeholz N, Güner F, Leitz P, Pott C, Eckardt L. Ranolazine and Vernakalant Prevent Ventricular Arrhythmias in an Experimental Whole-Heart Model of Short QT Syndrome. J Cardiovasc Electrophysiol. 2016 Jun 10. doi: 10.1111/jce.13029. [Epub ahead of print] PubMed PMID: 27283775. 2: Juliá J, López-Gil M, Villagraz L, Lozano Á, Fontenla A, Arribas F. The Usefulness of Vernakalant in Maintaining Sinus Rhythm During Ablation Procedures. Rev Esp Cardiol (Engl Ed). 2016 Jul;69(7):708-9. doi: 10.1016/j.rec.2016.03.017. Epub 2016 May 24. English, Spanish. PubMed PMID: 27235290. 3: Beatch GN, Mangal B. Safety and efficacy of vernakalant for the conversion of atrial fibrillation to sinus rhythm; a phase 3b randomized controlled trial. BMC Cardiovasc Disord. 2016 May 28;16:113. doi: 10.1186/s12872-016-0289-0. PubMed PMID: 27233239; PubMed Central PMCID: PMC4884402. 4: Cosin-Sales J, Loscos A, Peiró A, Sorando MR, Buendía F, Ruescas L. Real-world Data on the Efficacy of Vernakalant for Pharmacological Cardioversion in Patients With Recent-onset Atrial Fibrillation. Rev Esp Cardiol (Engl Ed). 2016 Jun;69(6):619-20. doi: 10.1016/j.rec.2016.02.020. Epub 2016 May 4. English, Spanish. PubMed PMID: 27131972. 5: Simon A, Niederdoeckl J, Skyllouriotis E, Schuetz N, Herkner H, Weiser C, Laggner AN, Domanovits H, Spiel AO. Vernakalant is superior to ibutilide for achieving sinus rhythm in patients with recent-onset atrial fibrillation: a randomized controlled trial at the emergency department. Europace. 2016 Mar 22. pii: euw052. [Epub ahead of print] PubMed PMID: 27009186. 6: van Hunnik A, Lau DH, Zeemering S, Kuiper M, Verheule S, Schotten U. Antiarrhythmic effect of vernakalant in electrically remodeled goat atria is caused by slowing of conduction and prolongation of postrepolarization refractoriness. Heart Rhythm. 2016 Apr;13(4):964-72. doi: 10.1016/j.hrthm.2015.12.009. Epub 2015 Dec 8. PubMed PMID: 26681610. 7: Seoane L, Baranchuk A, Conde D. [Vernakalant for the conversion of atrial fibrillation of recent onset]. Medicina (B Aires). 2015;75(4):239-44. Review. Spanish. PubMed PMID: 26339882. 8: Chen S, Liu S, Purerfellner H. Vernakalant as a Novel Anti-Arrhythmic Agent for Converting of Atrial Fibrillation, Molecular Mechanism, Updated Clinical Efficacy, and Future Development. Curr Pharm Des. 2015;21(30):4400-8. PubMed PMID: 26234795. 9: Garad DN, Tanpure SD, Mhaske SB. Radical-mediated dehydrative preparation of cyclic imides using (NH4)2S2O8-DMSO: application to the synthesis of vernakalant. Beilstein J Org Chem. 2015 Jun 12;11:1008-16. doi: 10.3762/bjoc.11.113. eCollection 2015. PubMed PMID: 26199655; PubMed Central PMCID: PMC4505096. 10: Müssigbrodt A, John S, Kosiuk J, Richter S, Hindricks G, Bollmann A. Vernakalant-facilitated electrical cardioversion: comparison of intravenous vernakalant and amiodarone for drug-enhanced electrical cardioversion of atrial fibrillation after failed electrical cardioversion. Europace. 2016 Jan;18(1):51-6. doi: 10.1093/europace/euv194. Epub 2015 Jun 7. PubMed PMID: 26056189. 11: Costabel JP, Lambardi F, Aragón M, Campos R, Urdapilleta M, Ariznavarreta P, Vergara JM, Conde D. Predictors of conversion of recent-onset atrial fibrillation treated with vernakalant. Pacing Clin Electrophysiol. 2015 Feb;38(2):196-200. doi: 10.1111/pace.12548. Epub 2014 Dec 2. PubMed PMID: 25469647. 12: Lamotte M, Gerlier L, Caekelbergh K, Lalji K, Polifka J, Lee E. Impact Of A Pharmacological Cardioversion With Vernakalant On The Management Cost Of Recent Atrial Fibrillation In Belgium. Value Health. 2014 Nov;17(7):A490. doi: 10.1016/j.jval.2014.08.1447. Epub 2014 Oct 26. PubMed PMID: 27201454. 13: Seyler C, Schweizer PA, Zitron E, Katus HA, Thomas D. Vernakalant activates human cardiac K(2P)17.1 background K(+) channels. Biochem Biophys Res Commun. 2014 Aug 29;451(3):415-20. doi: 10.1016/j.bbrc.2014.07.133. Epub 2014 Aug 7. PubMed PMID: 25108155. 14: Guerra F, Matassini MV, Scappini L, Urbinati A, Capucci A. Intravenous vernakalant for the rapid conversion of recent onset atrial fibrillation: systematic review and meta-analysis. Expert Rev Cardiovasc Ther. 2014 Sep;12(9):1067-75. doi: 10.1586/14779072.2014.943662. Epub 2014 Aug 5. Review. PubMed PMID: 25096598. 15: Frommeyer G, Schulze Grotthoff J, Fischer C, Bogossian H, Reinke F, Kochhäuser S, Dechering DG, Fehr M, Milberg P, Eckardt L. Vernakalant in an experimental model of pacing-induced heart failure: lack of proarrhythmia despite prolongation of repolarization. J Card Fail. 2014 Oct;20(10):786-92. doi: 10.1016/j.cardfail.2014.07.013. Epub 2014 Jul 30. PubMed PMID: 25084217. 16: Mochalina N, Juhlin T, Öhlin B, Carlson J, Holmqvist F, Platonov PG. Predictors of successful cardioversion with vernakalant in patients with recent-onset atrial fibrillation. Ann Noninvasive Electrocardiol. 2015 Mar;20(2):140-7. doi: 10.1111/anec.12178. Epub 2014 Jul 9. PubMed PMID: 25040826. 17: Reiffel JA. Are we at the goal line with the novel oral anticoagulants and have we reached the end of the line for dronedarone and vernakalant--or is there more to come? Curr Cardiol Rev. 2014 Nov;10(4):315-6. PubMed PMID: 25004988; PubMed Central PMCID: PMC4101195. 18: Rudiger A, Breitenstein A, Arrigo M, Salzberg SP, Bettex D. Suitability, efficacy, and safety of vernakalant for new onset atrial fibrillation in critically ill patients. Crit Care Res Pract. 2014;2014:826286. doi: 10.1155/2014/826286. Epub 2014 May 12. PubMed PMID: 24900920; PubMed Central PMCID: PMC4036718. 19: Camm AJ. The vernakalant story: how did it come to approval in Europe and what is the delay in the U.S.A? Curr Cardiol Rev. 2014 Nov;10(4):309-14. Review. PubMed PMID: 24821654; PubMed Central PMCID: PMC4101194. 20: Limanto J, Ashley ER, Yin J, Beutner GL, Grau BT, Kassim AM, Kim MM, Klapars A, Liu Z, Strotman HR, Truppo MD. A highly efficient asymmetric synthesis of vernakalant. Org Lett. 2014 May 16;16(10):2716-9. doi: 10.1021/ol501002a. Epub 2014 May 1. PubMed PMID: 24786635.