Summary: A group of compounds that are derivatives of methoxybenzene and contain the general formula R-C7H7O.

Top Publications

  1. Kowey P, Dorian P, Mitchell L, Pratt C, Roy D, Schwartz P, et al. Vernakalant hydrochloride for the rapid conversion of atrial fibrillation after cardiac surgery: a randomized, double-blind, placebo-controlled trial. Circ Arrhythm Electrophysiol. 2009;2:652-9 pubmed publisher
    ..There were no deaths. Vernakalant was safe and effective in the rapid conversion of AF to sinus rhythm in patients who had AF after cardiac surgery. Identifier: NCT00125320. ..
  2. Liu L, Fang Y, Xue Z, He Y, Fang R, Li L. Beta-asarone attenuates ischemia-reperfusion-induced autophagy in rat brains via modulating JNK, p-JNK, Bcl-2 and Beclin 1. Eur J Pharmacol. 2012;680:34-40 pubmed publisher
    ..Additionally, ?-asarone can attenuate autophagy in a widespread manner. ..
  3. Liu J, Li C, Xing G, Zhou L, Dong M, Geng Y, et al. Beta-asarone attenuates neuronal apoptosis induced by Beta amyloid in rat hippocampus. Yakugaku Zasshi. 2010;130:737-46 pubmed
    ..Taken together, these results suggest that beta-asarone may be a potential candidate for development as a therapeutic agent for AD. ..
  4. Cialdella P, Pedicino D, Santangeli P. Novel agents for the acute conversion of atrial fibrillation: focus on vernakalant. Recent Pat Cardiovasc Drug Discov. 2011;6:1-8 pubmed
    ..This article will review the recent patents on this novel atrial-selective agent, discussing its mechanisms of action and possible clinical applications in the real-world practice. ..
  5. Jin X, Pare J, Smith Y. Differential localization and function of GABA transporters, GAT-1 and GAT-3, in the rat globus pallidus. Eur J Neurosci. 2011;33:1504-18 pubmed publisher
    ..In conclusion, these data indicate that GAT-1 and GAT-3 represent different target sites through which GABA reuptake may subserve complementary regulation of GABAergic transmission in the rat GP. ..
  6. Lynch J, Regan C, Beatch G, Gleim G, Morabito C. Comparison of the intrinsic vasorelaxant and inotropic effects of the antiarrhythmic agents vernakalant and flecainide in human isolated vascular and cardiac tissues. J Cardiovasc Pharmacol. 2013;61:226-32 pubmed publisher
  7. Fang Y, Shi C, Liu L, Fang R. Pharmacokinetics of beta-asarone in rabbit blood, hippocampus, cortex, brain stem, thalamus and cerebellum. Pharmazie. 2012;67:120-3 pubmed
    ..3801, 1.300, 1.937, 7.142, 2.832 and 8.149 h, respectively. Gender differences do not significantly influence plasma pharmacokinetics of beta-asarone. ..
  8. Geng Y, Li C, Liu J, Xing G, Zhou L, Dong M, et al. Beta-asarone improves cognitive function by suppressing neuronal apoptosis in the beta-amyloid hippocampus injection rats. Biol Pharm Bull. 2010;33:836-43 pubmed
    ..These results suggest that beta-asarone may be a potential candidate for development as a therapeutic agent to manage cognitive impairment associated with conditions such as Alzheimer's disease. ..
  9. Camm A, Toft E, Torp Pedersen C, Vijayaraman P, Juul Moller S, Ip J, et al. Efficacy and safety of vernakalant in patients with atrial flutter: a randomized, double-blind, placebo-controlled trial. Europace. 2012;14:804-9 pubmed publisher
    ..Vernakalant did not restore sinus rhythm in patients with AFL. Vernakalant modestly slowed AFL and ventricular response rates, and was well tolerated. ..

More Information


  1. Tian D, Frishman W. Vernakalant: a new drug to treat patients with acute onset atrial fibrillation. Cardiol Rev. 2011;19:41-4 pubmed publisher
    ..Vernakalant appears to be a safe drug to use, with the most common side-effects being dysgeusia, sneezing, paresthesias, nausea, and hypotension. In the clinical trials, there were minimal drug-induced ventricular arrhythmias observed. ..
  2. Stiell I, Dickinson G, Butterfield N, Clement C, Perry J, Vaillancourt C, et al. Vernakalant hydrochloride: A novel atrial-selective agent for the cardioversion of recent-onset atrial fibrillation in the emergency department. Acad Emerg Med. 2010;17:1175-82 pubmed publisher
    ..Vernakalant rapidly converted recent-onset AF to sinus rhythm in over half of patients, was well tolerated, and has the potential to offer an important therapeutic option for rhythm control of recent-onset AF in the ED. ..
  3. Qiu D, Hou L, Chen Y, Zhou X, Yuan W, Rong W, et al. Beta-asarone inhibits synaptic inputs to airway preganglionic parasympathetic motoneurons. Respir Physiol Neurobiol. 2011;177:313-9 pubmed publisher
    ..These data suggest that the Asarum-caused acute respiratory disturbance involves ?-asarone-induced inhibition of neurotransmission in the medullary respiratory neuronal network. ..
  4. Wettwer E, Christ T, Endig S, Rozmaritsa N, Matschke K, Lynch J, et al. The new antiarrhythmic drug vernakalant: ex vivo study of human atrial tissue from sinus rhythm and chronic atrial fibrillation. Cardiovasc Res. 2013;98:145-54 pubmed publisher
    ..Rate-dependent block of Na(+) channels represents the main antiarrhythmic mechanism of vernakalant in the fibrillating atrium. Open channel block of early transient outward currents and IK,ACh could also contribute. ..
  5. Dobrev D, Nattel S. New antiarrhythmic drugs for treatment of atrial fibrillation. Lancet. 2010;375:1212-23 pubmed publisher
    ..We focus on the basic and clinical pharmacology of newly emerging antiarrhythmic drugs and non-traditional approaches such as upstream therapy for atrial fibrillation. ..
  6. Dvorzhak A, Myakhar O, Unichenko P, Kirmse K, Kirischuk S. Estimation of ambient GABA levels in layer I of the mouse neonatal cortex in brain slices. J Physiol. 2010;588:2351-60 pubmed publisher
  7. Torp Pedersen C, Raev D, Dickinson G, Butterfield N, Mangal B, Beatch G. A randomized, placebo-controlled study of vernakalant (oral) for the prevention of atrial fibrillation recurrence after cardioversion. Circ Arrhythm Electrophysiol. 2011;4:637-43 pubmed publisher
    ..The absence of proarrhythmia and favorable safety profile is an important finding for the drug. URL: Unique identifier: NCT00526136. ..
  8. Camm A, Capucci A, Hohnloser S, Torp Pedersen C, Van Gelder I, Mangal B, et al. A randomized active-controlled study comparing the efficacy and safety of vernakalant to amiodarone in recent-onset atrial fibrillation. J Am Coll Cardiol. 2011;57:313-21 pubmed publisher
    ..Both vernakalant and amiodarone were safe and well tolerated in this study. (A Phase III Superiority Study of Vernakalant vs Amiodarone in Subjects With Recent Onset Atrial Fibrillation [AVRO]; NCT00668759). ..
  9. Duggan S, Scott L. Intravenous vernakalant: a review of its use in the management of recent-onset atrial fibrillation. Drugs. 2011;71:237-52 pubmed publisher
    ..Therefore, intravenous vernakalant provides an effective option for the management of recent-onset atrial fibrillation. ..
  10. Lee S, Kim K, Ryu S, Yoon Y, Hahm D, Kang S, et al. Asarone inhibits adipogenesis and stimulates lipolysis in 3T3-L1 adipocytes. Cell Mol Biol (Noisy-le-grand). 2010;56 Suppl:OL1215-22 pubmed
  11. Li C, Xing G, Dong M, Zhou L, Li J, Wang G, et al. Beta-asarone protection against beta-amyloid-induced neurotoxicity in PC12 cells via JNK signaling and modulation of Bcl-2 family proteins. Eur J Pharmacol. 2010;635:96-102 pubmed publisher
    ..Further, the JNK signaling cascade plays a role in regulating the anti-apoptotic effects of beta-asarone. Thus, our results indicate that beta-asarone might be a potentially therapeutic compound for Alzheimer's disease. ..
  12. Blomstrom Lundqvist C, Blomström P. Safety and efficacy of pharmacological cardioversion of atrial fibrillation using intravenous vernakalant, a new antiarrhythmic drug with atrial selectivity. Expert Opin Drug Saf. 2012;11:671-9 pubmed publisher
  13. Buccelletti F, Iacomini P, Botta G, Marsiliani D, Carroccia A, Gentiloni Silveri N, et al. Efficacy and safety of vernakalant in recent-onset atrial fibrillation after the European medicines agency approval: systematic review and meta-analysis. J Clin Pharmacol. 2012;52:1872-8 pubmed publisher
    ..Further cost-effective analysis and comparison with other antiarrhythmic agents, such as class I antiarrhythmic agents, should be investigated, especially in the emergency department. ..
  14. Pratt C, Roy D, Torp Pedersen C, Wyse D, Toft E, Juul Moller S, et al. Usefulness of vernakalant hydrochloride injection for rapid conversion of atrial fibrillation. Am J Cardiol. 2010;106:1277-83 pubmed publisher
    ..In conclusion, vernakalant demonstrated a rapid and high rate of conversion for short-duration AF and was well tolerated. ..
  15. Ransom C, Wu Y, Richerson G. Postdepolarization potentiation of GABAA receptors: a novel mechanism regulating tonic conductance in hippocampal neurons. J Neurosci. 2010;30:7672-84 pubmed publisher
    ..These properties are well suited to limit excitability during pathophysiological depolarization accompanied by rises in ambient GABA, such as occur during seizures and ischemia. ..
  16. Bash L, Buono J, Davies G, Martin A, Fahrbach K, Phatak H, et al. Systematic review and meta-analysis of the efficacy of cardioversion by vernakalant and comparators in patients with atrial fibrillation. Cardiovasc Drugs Ther. 2012;26:167-79 pubmed publisher
    ..Though best practice methods were used, further research comparing treatments through direct head-to-head comparisons may be warranted to confirm these findings and further inform clinical practice. ..
  17. Löfstrand K, Malmvärn A, Haglund P, Bignert A, Bergman A, Asplund L. Brominated phenols, anisoles, and dioxins present in blue mussels from the Swedish coastline. Environ Sci Pollut Res Int. 2010;17:1460-8 pubmed publisher
    ..PBDDs), together with their potential precursors polybrominated phenols (PBPs) and polybrominated anisoles (PBAs), were analyzed in blue mussels (Mytilus edulis) gathered along the east coast (bordering the Baltic Sea) ..
  18. Kirmse K, Kirischuk S, Grantyn R. Role of GABA transporter 3 in GABAergic synaptic transmission at striatal output neurons. Synapse. 2009;63:921-9 pubmed publisher
    ..Whereas an acute block of GAT-3 under resting conditions is fully compensated for by GAT-1, GAT-3 might provide an additional uptake capacity when neuronal activity and GABA release are increased. ..
  19. Stiell I, Roos J, Kavanagh K, Dickinson G. A multicenter, open-label study of vernakalant for the conversion of atrial fibrillation to sinus rhythm. Am Heart J. 2010;159:1095-101 pubmed publisher
    ..Vernakalant rapidly converted recent-onset AF to SR, was well tolerated, and may be a valuable therapeutic alternative for reestablishing SR in patients with recent-onset AF. ..
  20. Sicouri S, Pourrier M, Gibson J, Lynch J, Antzelevitch C. Comparison of electrophysiological and antiarrhythmic effects of vernakalant, ranolazine, and sotalol in canine pulmonary vein sleeve preparations. Heart Rhythm. 2012;9:422-9 pubmed publisher
    ..This study evaluated the electrophysiological and antiarrhythmic effects of VER, RAN, and SOT in canine PV sleeve preparations in a blinded fashion...
  21. Yamada H, Nakatani K. Odorant-induced hyperpolarization and suppression of cAMP-activated current in newt olfactory receptor neurons. Chem Senses. 2001;26:25-34 pubmed
    ..Given that this inhibitory effect of odorants can affect excitation caused by other odorants, we suggest that it might play a role in coding odorants in olfactory receptor neurons...
  22. Imagawa S, Nakano Y, Obara N, Suzuki N, Doi T, Kodama T, et al. A GATA-specific inhibitor (K-7174) rescues anemia induced by IL-1beta, TNF-alpha, or L-NMMA. FASEB J. 2003;17:1742-4 pubmed
    ..However, the addition of K-7174 reversed these effects. These results raise the possibility of using K-7174 as therapy to treat anemia. ..
  23. Fang Y, Fang R, Fang G, Jiang Y, Fu S. [Effects of beta-asarone on expression of c-fos in kindling epilepsy rat brain]. Zhongguo Zhong Yao Za Zhi. 2008;33:534-6 pubmed
    ..3 +/- 2.6 in model control group, and 95.2 +/- 1.1 in difetoin group, respectively. Beta-asarone can obviously increase the expression of c-fos in epilepsy rat brain. It is one of important response to epilepsy. ..
  24. Conway J, Pink H, Bergquist M, Han B, Depee S, Tadepalli S, et al. Effects of the cFMS kinase inhibitor 5-(3-methoxy-4-((4-methoxybenzyl)oxy)benzyl)pyrimidine-2,4-diamine (GW2580) in normal and arthritic rats. J Pharmacol Exp Ther. 2008;326:41-50 pubmed publisher
    ..In conclusion, GW2580 was effective in preserving joint integrity in the adjuvant arthritis model while showing minimal effects in normal rats...
  25. Kinney G. GAT-3 transporters regulate inhibition in the neocortex. J Neurophysiol. 2005;94:4533-7 pubmed
  26. Conway J, McDonald B, Parham J, Keith B, Rusnak D, Shaw E, et al. Inhibition of colony-stimulating-factor-1 signaling in vivo with the orally bioavailable cFMS kinase inhibitor GW2580. Proc Natl Acad Sci U S A. 2005;102:16078-83 pubmed
    ..The ability of GW2580 to chronically inhibit CSF-1 signaling through cFMS kinase in normal and tumor cells in vivo makes GW2580 a useful tool in assessing the role of cFMS kinase in normal and disease processes. ..
  27. Goswami M, Recio E, Campoy S, Martín J, Coque J. Environmental significance of O-demethylation of chloroanisoles by soil bacterial isolates as a mechanism that improves the overall biodegradation of chlorophenols. Environ Microbiol. 2007;9:2512-21 pubmed
    ..On the contrary O-demethylation of 2,4,6-TCA in P. putida INBP1 is just catalysed by an oxygenase-type NADH/NADPH-dependent O-demethylase, whereas in A. radioresistens INBS1 a THF-dependent O-demethylase activity was detected. ..
  28. Jhumur U, Dötterl S, Jürgens A. Naive and conditioned responses of Culex pipiens pipiens biotype molestus (Diptera: Culicidae) to flower odors. J Med Entomol. 2006;43:1164-70 pubmed
    ..These results indicate that naive mosquitoes are effectively attracted by appropriate floral scent compounds and that learning can increase the attractiveness of these compounds...
  29. Gang D, Lavid N, Zubieta C, Chen F, Beuerle T, Lewinsohn E, et al. Characterization of phenylpropene O-methyltransferases from sweet basil: facile change of substrate specificity and convergent evolution within a plant O-methyltransferase family. Plant Cell. 2002;14:505-19 pubmed
    ..This prediction was confirmed by site-directed mutagenesis, in which the appropriate mutants of CVOMT1 (F260S) and EOMT1 (S261F) were produced that exhibited the opposite substrate preference relative to the respective native enzyme. ..
  30. Oka Y, Omura M, Kataoka H, Touhara K. Olfactory receptor antagonism between odorants. EMBO J. 2004;23:120-6 pubmed
    ..The current study also provides insight into strategies to modulate perceived odorant quality. ..
  31. Wu H, Fang Y. [Pharmacokinetics of beta-asarone in rats]. Yao Xue Xue Bao. 2004;39:836-8 pubmed
    ..The absorption, distribution and elimination of beta-asarone are very rapid, and it is easy to pass through blood brain barrier. Brain is an important organ of distributing of beta-asarone. ..
  32. Barkman T. Evidence for positive selection on the floral scent gene isoeugenol-O-methyltransferase. Mol Biol Evol. 2003;20:168-72 pubmed
    ..Although the selective agent is unknown, the adaptive evolution of this gene may have resulted in increased effectiveness of pollinator attraction or herbivore repellence...
  33. Jeurissen S, Punt A, Boersma M, Bogaards J, Fiamegos Y, Schilter B, et al. Human cytochrome p450 enzyme specificity for the bioactivation of estragole and related alkenylbenzenes. Chem Res Toxicol. 2007;20:798-806 pubmed
  34. Takano Y, Hiramatsu N, Okamura M, Hayakawa K, Shimada T, Kasai A, et al. Suppression of cytokine response by GATA inhibitor K-7174 via unfolded protein response. Biochem Biophys Res Commun. 2007;360:470-5 pubmed
    ..These results suggested a novel, UPR-dependent mechanism underlying the anti-inflammatory potential of K-7174. ..
  35. Huang R, Huang Y, Ou J, Chen C, Hsu F, Chang C. Screening of 25 compounds isolated from Phyllanthus species for anti-human hepatitis B virus in vitro. Phytother Res. 2003;17:449-53 pubmed
    ..3%, 45.3%; 69.6%, 33.9%; 68.1%, 52.3%; 32.1%, 46.6%, respectively. Of these, niranthin (1) showed the best anti-HBsAg activity, while the most potent anti-HBeAg activity was observed with hinokinin (5). ..
  36. Kassuya C, Silvestre A, Menezes de Lima O, Marotta D, Rehder V, Calixto J. Antiinflammatory and antiallodynic actions of the lignan niranthin isolated from Phyllanthus amarus. Evidence for interaction with platelet activating factor receptor. Eur J Pharmacol. 2006;546:182-8 pubmed
    ..Collectively, the present findings suggest that niranthin exhibits antiinflammatory and antiallodynic actions which are probably mediated through its direct antagonistic action on the PAF receptor binding sites...
  37. Chen Y, Wang Q, Liang Y, Fang Y. [Protective effects of beta-asarone on cultured rat cortical neurons damage induced by glutamate]. Zhong Yao Cai. 2007;30:436-9 pubmed
    ..The results suggest that beta-asarone prevents the toxicity of glutamate, and it maybe attribute to its effect of anticalcium. ..
  38. Roy D, Pratt C, Torp Pedersen C, Wyse D, Toft E, Juul Moller S, et al. Vernakalant hydrochloride for rapid conversion of atrial fibrillation: a phase 3, randomized, placebo-controlled trial. Circulation. 2008;117:1518-25 pubmed publisher
    ..The present study assessed the efficacy and safety of vernakalant hydrochloride (RSD1235), a novel compound, for the conversion of atrial fibrillation (AF)...
  39. Cheng J. Vernakalant in the management of atrial fibrillation. Ann Pharmacother. 2008;42:533-42 pubmed publisher
  40. Shimada T, Hiramatsu N, Okamura M, Hayakawa K, Kasai A, Yao J, et al. Unexpected blockade of adipocyte differentiation by K-7174: implication for endoplasmic reticulum stress. Biochem Biophys Res Commun. 2007;363:355-60 pubmed
    ..These results indicated a possibility that ER stress suppresses adipocyte differentiation and that GATA inhibitor K-7174 has the potential for interfering with adipogenesis through induction of ER stress. ..
  41. Scalliet G, Lionnet C, Le Béchec M, Dutron L, Magnard J, Baudino S, et al. Role of petal-specific orcinol O-methyltransferases in the evolution of rose scent. Plant Physiol. 2006;140:18-29 pubmed
    ..These data indicate that up-regulation of OOMT gene expression may have been a critical step in the evolution of scent production in roses...
  42. Scalliet G, Piola F, Douady C, Rety S, Raymond O, Baudino S, et al. Scent evolution in Chinese roses. Proc Natl Acad Sci U S A. 2008;105:5927-32 pubmed publisher
    ..We propose that the emergence of the OOMT1 gene may have been a critical step in the evolution of scent production in Chinese roses. ..
  43. Keros S, Hablitz J. Subtype-specific GABA transporter antagonists synergistically modulate phasic and tonic GABAA conductances in rat neocortex. J Neurophysiol. 2005;94:2073-85 pubmed
    ..Thus neocortical GAT-1 and GAT-2/3 have distinct but overlapping roles in modulating GABA conductances. ..
  44. Luo G, Qato M, Guenthner T. Hydrolysis of the 2',3'-allylic epoxides of allylbenzene, estragole, eugenol, and safrole by both microsomal and cytosolic epoxide hydrolases. Drug Metab Dispos. 1992;20:440-5 pubmed
    ..The susceptibilities of these epoxides to rapid hydrolysis by both epoxide hydrolases may explain their low genotoxic potencies in vivo. ..
  45. Nakano Y, Imagawa S, Matsumoto K, Stockmann C, Obara N, Suzuki N, et al. Oral administration of K-11706 inhibits GATA binding activity, enhances hypoxia-inducible factor 1 binding activity, and restores indicators in an in vivo mouse model of anemia of chronic disease. Blood. 2004;104:4300-7 pubmed
    ..These results raise the possibility of using orally administered K-11706 for treating patients with ACD. ..
  46. Fang Y, Li L, Wu Q. [Effects of beta-asaron on gene expression in mouse brain]. Zhong Yao Cai. 2003;26:650-2 pubmed
    ..beta-asaron has effects on multi-target genes in mouse brain. ..
  47. Jiang X, Martens D, Schramm K, Kettrup A, Xu S, Wang L. Polychlorinated organic compounds (PCOCs) in waters, suspended solids and sediments of the Yangtse River. Chemosphere. 2000;41:901-5 pubmed
    ..HCB and its metabolite (PeCB) presented the highest contamination levels among PCOCs in sediments. ..
  48. Punt A, Freidig A, Delatour T, Scholz G, Boersma M, Schilter B, et al. A physiologically based biokinetic (PBBK) model for estragole bioactivation and detoxification in rat. Toxicol Appl Pharmacol. 2008;231:248-59 pubmed publisher
    ..These results indicate that the relative importance of different metabolic pathways of estragole may vary in a dose-dependent way, leading to a relative increase in bioactiviation of estragole at higher doses. ..
  49. Borden L, Dhar T, Smith K, Branchek T, Gluchowski C, Weinshank R. Cloning of the human homologue of the GABA transporter GAT-3 and identification of a novel inhibitor with selectivity for this site. Receptors Channels. 1994;2:207-13 pubmed
    ..Due to its lipophilicity, (S)-SNAP-5114 is also expected to cross the blood-brain-barrier and therefore, should be an important tool for evaluating the role of GAT-3 in neural function. ..
  50. Iyer L, Ho M, Shinn W, Bradford W, Tanga M, Nath S, et al. Glucuronidation of 1'-hydroxyestragole (1'-HE) by human UDP-glucuronosyltransferases UGT2B7 and UGT1A9. Toxicol Sci. 2003;73:36-43 pubmed
    ..Our results also have toxicogenetic significance, as UGT2B7 is polymorphic and could potentially result in genetic differences in glucuronidation of 1'-HE and, hence, toxicity of estragole. ..
  51. Dorian P, Pinter A, Mangat I, Korley V, Cvitkovic S, Beatch G. The effect of vernakalant (RSD1235), an investigational antiarrhythmic agent, on atrial electrophysiology in humans. J Cardiovasc Pharmacol. 2007;50:35-40 pubmed
  52. Campoy S, Alvarez Rodríguez M, Recio E, Rumbero A, Coque J. Biodegradation of 2,4,6-TCA by the white-rot fungus Phlebia radiata is initiated by a phase I (O-demethylation)-phase II (O-conjugation) reactions system: implications for the chlorine cycle. Environ Microbiol. 2009;11:99-110 pubmed publisher
    ..radiata combines two different degradative mechanisms in order to biodegrade 2,4,6-TCA. The significance of the capability of white-rot fungi to O-demethylate chloroanisoles for the global chlorine cycle is discussed...
  53. Dötterl S, Füssel U, Jürgens A, Aas G. 1,4-Dimethoxybenzene, a floral scent compound in willows that attracts an oligolectic bee. J Chem Ecol. 2005;31:2993-8 pubmed
    ..The strongest antennal responses were triggered by 1,4-dimethoxybenzene, and in field bioassays, this benzenoid attracted females of A. vaga at the beginning of its flight period, but not at the end. ..
  54. Punt A, Delatour T, Scholz G, Schilter B, van Bladeren P, Rietjens I. Tandem mass spectrometry analysis of N2-(trans-Isoestragol-3'-yl)-2'-deoxyguanosine as a strategy to study species differences in sulfotransferase conversion of the proximate carcinogen 1'-hydroxyestragole. Chem Res Toxicol. 2007;20:991-8 pubmed