Structure via PubChem · Public domain (PubChem)
vernakalant
Sign in to saveAlso known as RSD1235, (3R)-1-((1R,2R)-2-(2-(3,4-dimethoxyphenyl)ethoxy)cyclohexyl)pyrrolidin-3-ol
Vernakalant, sold under the brand name Brinavess, is a class III antiarrhythmic drug for the acute conversion of atrial fibrillation, in form of an intravenous infusion. It has been approved for use in the European Union and the United Kingdom since 2010. The US Food and Drug Administration denied approval in 2008 and 2019.
Chemical data
- Formula
- C20H31NO4
- Molecular weight
- 349.5 g/mol
- IUPAC name
- (3R)-1-[(1R,2R)-2-[2-(3,4-dimethoxyphenyl)ethoxy]cyclohexyl]pyrrolidin-3-ol
- SMILES
- COC1=C(C=C(C=C1)CCO[C@@H]2CCCC[C@H]2N3CC[C@H](C3)O)OC
- InChIKey
- VBHQKCBVWWUUKN-KZNAEPCWSA-N
- XLogP
- 2.9
- Polar surface area
- 51.2 Ų
- H-bond donors
- 1
- H-bond acceptors
- 5
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Max clinical phase
- Approved
- Molecule type
- Small molecule
- First approval
- 2010
- Indications
- atrial fibrillation, atrial flutter, cardiac arrhythmia
via ChEMBL · EBI
Wikidata facts
- Mass
- 349.225
Show 3 more facts
- chemical formula
- C₂₀H₃₁NO₄
- isomeric SMILES
- COC1=C(C=C(C=C1)CCO[C@@H]2CCCC[C@H]2N3CC[C@H](C3)O)OC
- canonical SMILES
- COC1=C(C=C(C=C1)CCOC2CCCCC2N3CCC(C3)O)OC
Sources (2)
via Wikidata · CC0
~7 min read
Encyclopedic overview
11 sectionsContents
- Medical uses
- Contraindications
- Side effects
- Overdose
- Interactions
- Pharmacology
- Mechanism of action
- Pharmacokinetics and pharmacogenomics
- Chemistry
- History
- References
{{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.svg | image_class = skin-invert-image | alt =
| tradename = Brinavess | pregnancy_AU = | pregnancy_category = | routes_of_administration = Intravenous, | ATC_prefix = C01 | ATC_suffix = BG11
Excerpted from Wikipedia’s “vernakalant” article, available under the CC BY-SA 4.0 licence.