Details of the Drug

General Information of Drug (ID: DMOQ81Y)

Drug Name

Vernakalant

Synonyms

Vernakalant; 794466-70-9; UNII-9G468C8B13; Vemakalant; RSD1235; 9G468C8B13; (3R)-1-((1R,2R)-2-(2-(3,4-dimethoxyphenyl)ethoxy)cyclohexyl)pyrrolidin-3-ol; 3-Pyrrolidinol,1-[(1R,2R)-2-[2-(3,4-dimethoxyphenyl)ethoxy]cyclohexyl]-, (3R)-; RSD-1235; Vernakalant [INN:BAN]; SCHEMBL410062; CHEMBL2111112; DTXSID60229659; VBHQKCBVWWUUKN-KZNAEPCWSA-N; CHEBI:135956; EX-A2465; ZINC22010910; 4151AH; AKOS027326205; DB06217; SB16873; CS-0276; API0014187; RL05068; 3-Pyrrolidinol, 1-((1R,2R)-2-(2-(3,4-dimethoxyphenyl)ethoxy)cyclohexyl)-, (3R)-

Indication

Disease Entry	ICD 11	Status	REF
Atrial fibrillation	BC81.3	Phase 3	[1]

Drug Type

Small molecular drug

Structure

3D MOL

2D MOL

#Ro5 Violations (Lipinski): 0

Molecular Weight (mw)

349.5

Topological Polar Surface Area (xlogp)

2.9

Rotatable Bond Count (rotbonds)

Hydrogen Bond Donor Count (hbonddonor)

Hydrogen Bond Acceptor Count (hbondacc)

ADMET Property

Absorption Cmax: The maximum plasma concentration (Cmax) of drug is 3.9 mg/L [2]
Absorption Tmax: The time to maximum plasma concentration (Tmax) is 10 min [2]
Clearance: The total body clearance of drug is 0.41 L/h/kg [3]
Half-life: The concentration or amount of drug in body reduced by one-half in 3 hours [4]
Metabolism: The drug is metabolized via the CYP2D6 mediated O-demethylation [5]
Vd: The volume of distribution (Vd) of drug is approximately 2 L/kg [3]

Chemical Identifiers

Formula: C20H31NO4
IUPAC Name: (3R)-1-[(1R,2R)-2-[2-(3,4-dimethoxyphenyl)ethoxy]cyclohexyl]pyrrolidin-3-ol
Canonical SMILES: COC1=C(C=C(C=C1)CCO[C@@H]2CCCC[C@H]2N3CC[C@H](C3)O)OC
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
InChIKey: VBHQKCBVWWUUKN-KZNAEPCWSA-N

Cross-matching ID

PubChem CID: 9930049
ChEBI ID: CHEBI:135956
CAS Number: 794466-70-9
DrugBank ID: DB06217
TTD ID: D00OTL
INTEDE ID: DR1682

Molecular Interaction Atlas of This Drug

Drug-Metabolizing Enzyme (DME)

DME Name	DME ID	UniProt ID	MOA	REF
Cytochrome P450 2D6 (CYP2D6)_{Main DME}	DECB0K3	CP2D6_HUMAN	Substrate	[6]

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Molecular Interaction Atlas (MIA)

MIA Detail

Jump to Detail Molecular Interaction Atlas of This Drug

References

1	Vernakalant hydrochloride for rapid conversion of atrial fibrillation: a phase 3, randomized, placebo-controlled trial. Circulation. 2008 Mar 25;117(12):1518-25.
2	European Medicines Agency Summary of product characteristics
3	An FDA phase I clinical trial of quinacrine sterilization (QS). Int J Gynaecol Obstet. 2003 Oct;83 Suppl 2:S45-9.
4	Trend Analysis of a Database of Intravenous Pharmacokinetic Parameters in Humans for 1352 Drug Compounds
5	FDA approval: ado-trastuzumab emtansine for the treatment of patients with HER2-positive metastatic breast cancer. Clin Cancer Res. 2014 Sep 1;20(17):4436-41.
6	Pharmacokinetics of novel atrial-selective antiarrhythmic agent vernakalant hydrochloride injection (RSD1235): influence of CYP2D6 expression and other factors. J Clin Pharmacol. 2009 Jan;49(1):17-29.
7	Inhibitory effects of anticancer drugs on dextromethorphan-O-demethylase activity in human liver microsomes. Cancer Chemother Pharmacol. 1993;32(6):491-5.
8	Effect of genetic polymorphism on the metabolism of endogenous neuroactive substances, progesterone and p-tyramine, catalyzed by CYP2D6. Brain Res Mol Brain Res. 2004 Oct 22;129(1-2):117-23.
9	CYP2D6 polymorphisms and tamoxifen metabolism: clinical relevance. Curr Oncol Rep. 2010 Jan;12(1):7-15.
10	Metabolic interactions between acetaminophen (paracetamol) and two flavonoids, luteolin and quercetin, through in-vitro inhibition studies. J Pharm Pharmacol. 2017 Dec;69(12):1762-1772.
11	Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675.
12	Inhibition of cytochrome P450 2D6: structure-activity studies using a series of quinidine and quinine analogues. Chem Res Toxicol. 2003 Apr;16(4):450-9.
13	Effects of propofol on human hepatic microsomal cytochrome P450 activities. Xenobiotica. 1998 Sep;28(9):845-53.
14	Pharmacogenetics of schizophrenia. Am J Med Genet. 2000 Spring;97(1):98-106.
15	Roles of CYP2A6 and CYP2B6 in nicotine C-oxidation by human liver microsomes. Arch Toxicol. 1999 Mar;73(2):65-70.
16	Structure-activity relationship for human cytochrome P450 substrates and inhibitors. Drug Metab Rev. 2002 Feb-May;34(1-2):69-82.