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Also known as: 794466-70-9, Vemakalant, Rsd1235, Rsd-1235, (3r)-1-((1r,2r)-2-(2-(3,4-dimethoxyphenyl)ethoxy)cyclohexyl)pyrrolidin-3-ol, 9g468c8b13

Molecular Formula

C₂₀H₃₁NO₄

Molecular Weight

349.5 g/mol

InChI Key

VBHQKCBVWWUUKN-KZNAEPCWSA-N

FDA UNII

9G468C8B13

Vernakalant was developed by Cardiome Pharma as as an antiarrhythmic drug intended for rapid conversion of atrial fibrillation to sinus rhythm. It acts as an atypical class III antiarrhythmic drug that potentiates its effect in higher heart rates. Intravenous formulation was approved in Europe in September 2010 as Brinavess and in Canada in April 2017. It is an investigational drug under regulatory review by FDA.

1 2D Structure

Vernakalant

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

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

2.1.2 InChI

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

2.1.3 InChI Key

VBHQKCBVWWUUKN-KZNAEPCWSA-N

2.1.4 Canonical SMILES

COC1=C(C=C(C=C1)CCOC2CCCCC2N3CCC(C3)O)OC

2.1.5 Isomeric SMILES

COC1=C(C=C(C=C1)CCO[C@@H]2CCCC[C@H]2N3CC[C@H](C3)O)OC

2.2 Other Identifiers

2.2.1 UNII

9G468C8B13

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Rsd 1235

2. Rsd-1235

3. Rsd1235

2.3.2 Depositor-Supplied Synonyms

1. 794466-70-9

2. Vemakalant

3. Rsd1235

4. Rsd-1235

5. (3r)-1-((1r,2r)-2-(2-(3,4-dimethoxyphenyl)ethoxy)cyclohexyl)pyrrolidin-3-ol

6. 9g468c8b13

7. (3r)-1-[(1r,2r)-2-[2-(3,4-dimethoxyphenyl)ethoxy]cyclohexyl]pyrrolidin-3-ol

8. 3-pyrrolidinol, 1-((1r,2r)-2-(2-(3,4-dimethoxyphenyl)ethoxy)cyclohexyl)-, (3r)-

9. 3-pyrrolidinol,1-[(1r,2r)-2-[2-(3,4-dimethoxyphenyl)ethoxy]cyclohexyl]-, (3r)-

10. Vernakalant [inn]

11. Vernakalant [inn:ban]

12. Unii-9g468c8b13

13. Vernakalant [mi]

14. Vernakalant [who-dd]

15. Schembl410062

16. Chembl2111112

17. Dtxsid60229659

18. Chebi:135956

19. Ex-a2465

20. Zinc22010910

21. Cs-0276

22. Db06217

23. Ncgc00378872-01

24. Ac-35850

25. As-56235

26. Hy-14182

27. A864860

28. Q665725

29. J-513102

30. (r)-1-((1r,2r)-2-(3,4-dimethoxyphenethoxy)cyclohexyl)pyrrolidin-3-ol

31. (r,r)-1-{2-[2-(3,4-dimethoxy-phenyl)-ethoxy]-cyclohexyl}-pyrrolidin-3-(r)-ol

2.4 Create Date

2006-10-25

3 Chemical and Physical Properties

Molecular Formula	C₂₀H₃₁NO₄
Molecular Weight	349.5 g/mol
XLogP3	2.9
Hydrogen Bond Donor Count	1
Hydrogen Bond Acceptor Count	5
Rotatable Bond Count	7
Exact Mass	349.22530847 g/mol
Monoisotopic Mass	349.22530847 g/mol
Topological Polar Surface Area	51.2 Å²
Heavy Atom Count	25
Formal Charge	0
Complexity	394
Isotope Atom Count	0
Defined Atom Stereocenter Count	3
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

4 Drug and Medication Information

4.1 Drug Indication

Indicated for the rapid conversion of recent onset of atrial fibrillation to sinus rhythm in adults for non-surgery patients that lasts for less than 7 days of duration and post-cardiac surgery patients with atrial fibrillation lasting less than 3 days of duration.

5 Pharmacology and Biochemistry

5.1 Pharmacology

Vernakalant blocks currents in all phases of atrial action potential including atria-specific potassium currents (the ultra-rapid delayed rectifier and the acetylcholine dependent potassium currents) and prolongs the refractory period. It dose-dependently prolongs atrial refractoriness, prolongs AV nodal conduction and refractoriness, and slightly prolongs QRS duration without significantly affecting ventricular refractory period. Vernakalant has a high affinity to ion channels specifically involved in repolarization of atrial tissue and is thought to have a low proarrhythmic potential.

5.2 ATC Code

C01BG11

S76 | LUXPHARMA | Pharmaceuticals Marketed in Luxembourg | Pharmaceuticals marketed in Luxembourg, as published by d'Gesondheetskeess (CNS, la caisse nationale de sante, www.cns.lu), mapped by name to structures using CompTox by R. Singh et al. (in prep.). List downloaded from https://cns.public.lu/en/legislations/textes-coordonnes/liste-med-comm.html. Dataset DOI:10.5281/zenodo.4587355

C - Cardiovascular system

C01 - Cardiac therapy

C01B - Antiarrhythmics, class i and iii

C01BG - Other antiarrhythmics, class i and iii

C01BG11 - Vernakalant

5.3 Absorption, Distribution and Excretion

Absorption

In patients, average peak plasma concentrations of vernakalant were 3.9 g/ml following a single 10 minute infusion of 3 mg/kg vernakalant hydrochloride, and 4.3 g/ml following a second infusion of 2 mg/kg with a 15 minute interval between doses.

Route of Elimination

Mainly eliminated via renal excretion.

Volume of Distribution

Approximately 2L/kg.

Clearance

The typical total body clearance of vernakalant was estimated to be 0.41 l/hr/kg.

5.4 Metabolism/Metabolites

Vernakalant is mainly eliminated by CYP2D6 mediated O-demethylation in CYP2D6 extensive metabolisers. Glucuronidation is the main metabolism pathway in CYP2D6 poor metabolisers.

5.5 Biological Half-Life

Elimination half life in CYP2D6 extensive metabolizers is 3 hours and 5.5 hours in poor metabolizers.

5.6 Mechanism of Action

Vernakalant blocks atrial voltage-gated sodium channels in a dose and frequency-dependent manner and inhibits late sodium current (INa)which confers its effect on intra-atrial conduction. This current blockade enhance and onset of drug action accelerates in higher heart rate as the affinity of vernakalant for INa also increases. Its binding offset is quick once the heart rate slows. It also blocks Kv 1.5 channel and its early activating potassium channels (IKur) and inhibits acetylcholine-activated potassium channels (IKAch), which are specific to the atrium and cause prolongation of atrial refractoriness. Vernakalant also blocks Kv4.3 channel and its cardiac transient outward potassium current (Ito), which is involved more with atrial than ventricular refractoriness. Vernakalant minimally blocks hERG channels and its rapidly activating/delayed rectifying potassium current (IKr) which accounts for mild QT prolongation. QRS widening due to INa blockade also contributes to QT prolongation.

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