Identification

Name
Azimilide
Accession Number
DB04957
Type
Small Molecule
Groups
Investigational
Description

Azimilide is an investigational class III anti-arrhythmic drug that blocks fast and slow components of the delayed rectifier cardiac potassium channels. It is not approved for use in any country, but is currently in clinical trials in the United States.

Structure
Thumb
Synonyms
Not Available
International/Other Brands
Stedicor
Categories
UNII
74QU6P2934
CAS number
149908-53-2
Weight
Average: 457.96
Monoisotopic: 457.1880675
Chemical Formula
C23H28ClN5O3
InChI Key
MREBEPTUUMTTIA-UHFFFAOYSA-N
InChI
InChI=1S/C23H28ClN5O3/c1-26-12-14-27(15-13-26)10-2-3-11-28-22(30)17-29(23(28)31)25-16-20-8-9-21(32-20)18-4-6-19(24)7-5-18/h4-9,16H,2-3,10-15,17H2,1H3
IUPAC Name
1-({[5-(4-chlorophenyl)furan-2-yl]methylidene}amino)-3-[4-(4-methylpiperazin-1-yl)butyl]imidazolidine-2,4-dione
SMILES
CN1CCN(CCCCN2C(=O)CN(N=CC3=CC=C(O3)C3=CC=C(Cl)C=C3)C2=O)CC1

Pharmacology

Indication

Investigated for use/treatment in arrhythmia and atrial fibrillation.

Structured Indications
Not Available
Pharmacodynamics

Azimilide is a new class III anti-arrhythmic agent. It is distinguished by a relative lack of reverse use-dependence, excellent oral absorption, no need for dose titration, an option for out-patient initiation, no need for adjustment associated with renal or liver failure and a lack of interaction with warfarin or digoxin. It carries some risk of torsade de pointes and rarely, neutropoenia.

Mechanism of action

The mechanism of action of azimilide is to block both the slowly conducting (I(Ks)) and rapidly conducting (I(Kr)) rectifier potassium currents in cardiac cells. This differs from other class III agents that block I(Kr) exclusively or in combination with sodium, calcium, or transient outward (I(to)) potassium current channels. It also has blocking effects on sodium (I(Na)) and calcium currents (I(CaL)). Its effects on reentrant circuits in infarct border zones causing ventricular tachyarrhythmias are unknown.

TargetActionsOrganism
UPotassium voltage-gated channel subfamily E member 1Not AvailableHuman
UPotassium voltage-gated channel subfamily KQT member 1Not AvailableHuman
UPotassium voltage-gated channel subfamily H member 2Not AvailableHuman
Absorption

Excellent oral absorption.

Volume of distribution
Not Available
Protein binding
Not Available
Metabolism

The metabolic fate of azimilide in man is unusual as it undergoes a cleavage in vivo resulting in the formation of two classes of structurally distinct metabolites. One study has shown that a cleaved metabolite, 4-chloro-2-phenyl furoic acid was present at high concentration in plasma, while other plasma metabolites, azimilide N-oxide, and a cleaved hydantoin metabolite were present at lower concentrations than azimilide. In urine, the cleaved metabolites were the major metabolites, (> 35% of the dose) along with phenols (as conjugates, 7%-8%), azimilide N-oxide (4%-10%), a butanoic acid metabolite (2%-3%), and desmethyl azimilide (2%). A limited investigation of fecal metabolites indicated that azimilide (3%-5%), desmethyl azimilide (1%-3%), and the butanoic acid metabolite (< 1%) were present. Contributing pathways for metabolism of azimilide, identified through in vitro and in-vivo studies, were CYPs 1A1 (est. 28%), 3A4/5 (est. 20%), 2D6 (< 1%), FMO (est. 14%), and cleavage (35%). Enzyme(s) involved in the cleavage of azimilide were not identified.

Route of elimination
Not Available
Half life
Not Available
Clearance
Not Available
Toxicity
Not Available
Affected organisms
  • Humans and other mammals
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteractionDrug group
2-HYDROXY-1,4-NAPHTHOQUINONEThe risk or severity of adverse effects can be increased when 2-HYDROXY-1,4-NAPHTHOQUINONE is combined with Azimilide.Experimental
2-mercaptobenzothiazoleThe risk or severity of adverse effects can be increased when 2-mercaptobenzothiazole is combined with Azimilide.Vet Approved
AlfuzosinAlfuzosin may increase the hypotensive activities of Azimilide.Approved, Investigational
AmobarbitalThe metabolism of Azimilide can be increased when combined with Amobarbital.Approved, Illicit
AmorolfineThe risk or severity of adverse effects can be increased when Amorolfine is combined with Azimilide.Approved, Investigational
Amphotericin BThe risk or severity of adverse effects can be increased when Amphotericin B is combined with Azimilide.Approved, Investigational
AnidulafunginThe risk or severity of adverse effects can be increased when Anidulafungin is combined with Azimilide.Approved, Investigational
ArtemetherThe risk or severity of adverse effects can be increased when Artemether is combined with Azimilide.Approved
AtorvastatinThe risk or severity of adverse effects can be increased when Azimilide is combined with Atorvastatin.Approved
AtosibanThe risk or severity of adverse effects can be increased when Azimilide is combined with Atosiban.Approved, Investigational
Atracurium besylateAzimilide may increase the neuromuscular blocking activities of Atracurium besylate.Approved
Bafilomycin A1The risk or severity of adverse effects can be increased when Bafilomycin A1 is combined with Azimilide.Experimental
BarbexacloneThe metabolism of Azimilide can be increased when combined with Barbexaclone.Experimental
BarbitalThe metabolism of Azimilide can be increased when combined with Barbital.Illicit
Benzoic AcidThe risk or severity of adverse effects can be increased when Benzoic Acid is combined with Azimilide.Approved
BifonazoleThe risk or severity of adverse effects can be increased when Bifonazole is combined with Azimilide.Approved, Investigational
Brefeldin AThe risk or severity of adverse effects can be increased when 1,6,7,8,9,11A,12,13,14,14A-DECAHYDRO-1,13-DIHYDROXY-6-METHYL-4H-CYCLOPENT[F]OXACYCLOTRIDECIN-4-ONE is combined with Azimilide.Experimental
BucindololBucindolol may increase the hypotensive activities of Azimilide.Investigational
BunazosinBunazosin may increase the hypotensive activities of Azimilide.Investigational
ButenafineThe risk or severity of adverse effects can be increased when Butenafine is combined with Azimilide.Approved
ButoconazoleThe risk or severity of adverse effects can be increased when Butoconazole is combined with Azimilide.Approved
CalciumThe therapeutic efficacy of Azimilide can be decreased when used in combination with Calcium.Approved, Nutraceutical
Calcium AcetateThe therapeutic efficacy of Azimilide can be decreased when used in combination with Calcium Acetate.Approved
Calcium CarbonateThe therapeutic efficacy of Azimilide can be decreased when used in combination with Calcium Carbonate.Approved
Calcium CitrateThe therapeutic efficacy of Azimilide can be decreased when used in combination with Calcium Citrate.Approved
Calcium glubionateThe therapeutic efficacy of Azimilide can be decreased when used in combination with Calcium glubionate.Approved
Calcium GluceptateThe therapeutic efficacy of Azimilide can be decreased when used in combination with Calcium Gluceptate.Approved
Calcium gluconateThe therapeutic efficacy of Azimilide can be decreased when used in combination with Calcium gluconate.Approved, Vet Approved
Calcium lactateThe therapeutic efficacy of Azimilide can be decreased when used in combination with Calcium lactate.Approved, Experimental, Investigational, Vet Approved
Calcium lactate gluconateThe therapeutic efficacy of Azimilide can be decreased when used in combination with Calcium lactate gluconate.Experimental
Calcium laevulateThe therapeutic efficacy of Azimilide can be decreased when used in combination with Calcium laevulate.Experimental
Calcium pangamateThe therapeutic efficacy of Azimilide can be decreased when used in combination with Calcium pangamate.Experimental
Calcium PhosphateThe therapeutic efficacy of Azimilide can be decreased when used in combination with Calcium Phosphate.Approved
CandicidinThe risk or severity of adverse effects can be increased when Candicidin is combined with Azimilide.Withdrawn
Capric acidThe risk or severity of adverse effects can be increased when Capric acid is combined with Azimilide.Experimental
CarbomycinThe metabolism of Azimilide can be decreased when combined with Carbomycin.Vet Approved
CarvedilolCarvedilol may increase the hypotensive activities of Azimilide.Approved, Investigational
CaseinThe therapeutic efficacy of Azimilide can be decreased when used in combination with Casein.Approved
CaspofunginThe risk or severity of adverse effects can be increased when Caspofungin is combined with Azimilide.Approved
CerivastatinThe risk or severity of adverse effects can be increased when Azimilide is combined with Cerivastatin.Withdrawn
CeruleninThe risk or severity of adverse effects can be increased when Cerulenin is combined with Azimilide.Approved
ChloroxineThe risk or severity of adverse effects can be increased when Chloroxine is combined with Azimilide.Approved
CiclopiroxThe risk or severity of adverse effects can be increased when Ciclopirox is combined with Azimilide.Approved, Investigational
CimetidineThe serum concentration of Azimilide can be increased when it is combined with Cimetidine.Approved
ClarithromycinThe metabolism of Azimilide can be decreased when combined with Clarithromycin.Approved
ClopidogrelThe therapeutic efficacy of Clopidogrel can be decreased when used in combination with Azimilide.Approved, Nutraceutical
ClotrimazoleThe risk or severity of adverse effects can be increased when Clotrimazole is combined with Azimilide.Approved, Vet Approved
CordycepinThe risk or severity of adverse effects can be increased when Cordycepin is combined with Azimilide.Investigational
CyclosporineThe risk or severity of adverse effects can be increased when Cyclosporine is combined with Azimilide.Approved, Investigational, Vet Approved
DapoxetineDapoxetine may increase the orthostatic hypotensive activities of Azimilide.Investigational
DichloropheneThe risk or severity of adverse effects can be increased when Dichlorophene is combined with Azimilide.Vet Approved
DoxazosinDoxazosin may increase the hypotensive activities of Azimilide.Approved
EconazoleThe risk or severity of adverse effects can be increased when Econazole is combined with Azimilide.Approved
EfavirenzThe serum concentration of Azimilide can be decreased when it is combined with Efavirenz.Approved, Investigational
EfinaconazoleThe risk or severity of adverse effects can be increased when Efinaconazole is combined with Azimilide.Approved
ErythromycinThe metabolism of Azimilide can be decreased when combined with Erythromycin.Approved, Vet Approved
FenticonazoleThe risk or severity of adverse effects can be increased when Fenticonazole is combined with Azimilide.Experimental
FluconazoleThe serum concentration of Azimilide can be increased when it is combined with Fluconazole.Approved
FlucytosineThe risk or severity of adverse effects can be increased when Flucytosine is combined with Azimilide.Approved
FlutrimazoleThe risk or severity of adverse effects can be increased when Flutrimazole is combined with Azimilide.Experimental
FluvastatinThe risk or severity of adverse effects can be increased when Azimilide is combined with Fluvastatin.Approved
FosphenytoinThe serum concentration of Fosphenytoin can be increased when it is combined with Azimilide.Approved
GlyphosateThe risk or severity of adverse effects can be increased when Glyphosate is combined with Azimilide.Experimental
GriseofulvinThe risk or severity of adverse effects can be increased when Griseofulvin is combined with Azimilide.Approved, Vet Approved
HachimycinThe risk or severity of adverse effects can be increased when Hachimycin is combined with Azimilide.Experimental
HaloproginThe risk or severity of adverse effects can be increased when Haloprogin is combined with Azimilide.Approved, Withdrawn
HexetidineThe risk or severity of adverse effects can be increased when Hexetidine is combined with Azimilide.Approved, Investigational
HexobarbitalThe metabolism of Azimilide can be increased when combined with Hexobarbital.Approved
IndoraminIndoramin may increase the hypotensive activities of Azimilide.Withdrawn
IsoconazoleThe risk or severity of adverse effects can be increased when Isoconazole is combined with Azimilide.Approved
ItraconazoleThe risk or severity of adverse effects can be increased when Itraconazole is combined with Azimilide.Approved, Investigational
JosamycinThe metabolism of Azimilide can be decreased when combined with Josamycin.Approved, Investigational
KetoconazoleThe risk or severity of adverse effects can be increased when Ketoconazole is combined with Azimilide.Approved, Investigational
KitasamycinThe metabolism of Azimilide can be decreased when combined with Kitasamycin.Experimental
LabetalolLabetalol may increase the hypotensive activities of Azimilide.Approved
LovastatinThe risk or severity of adverse effects can be increased when Azimilide is combined with Lovastatin.Approved, Investigational
Magnesium HydroxideThe risk or severity of adverse effects can be increased when Azimilide is combined with Magnesium Hydroxide.Approved
Magnesium oxideThe risk or severity of adverse effects can be increased when Azimilide is combined with Magnesium oxide.Approved
Magnesium salicylateThe risk or severity of adverse effects can be increased when Azimilide is combined with Magnesium salicylate.Approved
Magnesium SulfateThe risk or severity of adverse effects can be increased when Azimilide is combined with Magnesium Sulfate.Approved, Vet Approved
MepartricinThe risk or severity of adverse effects can be increased when Mepartricin is combined with Azimilide.Experimental
MethohexitalThe metabolism of Azimilide can be increased when combined with Methohexital.Approved
MethylphenobarbitalThe metabolism of Azimilide can be increased when combined with Methylphenobarbital.Approved
MevastatinThe risk or severity of adverse effects can be increased when Mevastatin is combined with Azimilide.Experimental
MicafunginThe risk or severity of adverse effects can be increased when Micafungin is combined with Azimilide.Approved, Investigational
MiconazoleThe risk or severity of adverse effects can be increased when Miconazole is combined with Azimilide.Approved, Investigational, Vet Approved
MiltefosineThe risk or severity of adverse effects can be increased when Miltefosine is combined with Azimilide.Approved
MivacuriumAzimilide may increase the neuromuscular blocking activities of Mivacurium.Approved
MonensinThe risk or severity of adverse effects can be increased when Monensin is combined with Azimilide.Vet Approved
MyxothiazolThe risk or severity of adverse effects can be increased when Myxothiazol is combined with Azimilide.Experimental
NafcillinThe metabolism of Azimilide can be increased when combined with Nafcillin.Approved
NaftifineThe risk or severity of adverse effects can be increased when Naftifine is combined with Azimilide.Approved
NatamycinThe risk or severity of adverse effects can be increased when Natamycin is combined with Azimilide.Approved
NifuratelThe risk or severity of adverse effects can be increased when Nifuratel is combined with Azimilide.Experimental
Nikkomycin ZThe risk or severity of adverse effects can be increased when Nikkomycin Z is combined with Azimilide.Investigational
NitroprussideAzimilide may increase the hypotensive activities of Nitroprusside.Approved
NitroxolineThe risk or severity of adverse effects can be increased when Nitroxoline is combined with Azimilide.Approved
NystatinThe risk or severity of adverse effects can be increased when Nystatin is combined with Azimilide.Approved, Vet Approved
OleandomycinThe metabolism of Azimilide can be decreased when combined with Oleandomycin.Vet Approved
OmoconazoleThe risk or severity of adverse effects can be increased when Omoconazole is combined with Azimilide.Experimental
OxiconazoleThe risk or severity of adverse effects can be increased when Oxiconazole is combined with Azimilide.Approved
pafuramidineThe risk or severity of adverse effects can be increased when pafuramidine is combined with Azimilide.Investigational
PentamidineThe risk or severity of adverse effects can be increased when Pentamidine is combined with Azimilide.Approved
PentobarbitalThe metabolism of Azimilide can be increased when combined with Pentobarbital.Approved, Vet Approved
PhenobarbitalThe metabolism of Azimilide can be increased when combined with Phenobarbital.Approved
PhenytoinThe serum concentration of Phenytoin can be increased when it is combined with Azimilide.Approved, Vet Approved
PitavastatinThe risk or severity of adverse effects can be increased when Azimilide is combined with Pitavastatin.Approved
PosaconazoleThe risk or severity of adverse effects can be increased when Posaconazole is combined with Azimilide.Approved, Investigational, Vet Approved
PravastatinThe risk or severity of adverse effects can be increased when Azimilide is combined with Pravastatin.Approved
PrazosinPrazosin may increase the hypotensive activities of Azimilide.Approved
PrimidoneThe metabolism of Azimilide can be increased when combined with Primidone.Approved, Vet Approved
PyrrolnitrinThe risk or severity of adverse effects can be increased when Pyrrolnitrin is combined with Azimilide.Experimental
RadicicolThe risk or severity of adverse effects can be increased when Radicicol is combined with Azimilide.Experimental
RapacuroniumAzimilide may increase the neuromuscular blocking activities of Rapacuronium.Withdrawn
RifabutinThe serum concentration of Azimilide can be decreased when it is combined with Rifabutin.Approved
RifampicinThe serum concentration of Azimilide can be decreased when it is combined with Rifampicin.Approved
RifapentineThe serum concentration of Azimilide can be decreased when it is combined with Rifapentine.Approved
RosuvastatinThe risk or severity of adverse effects can be increased when Azimilide is combined with Rosuvastatin.Approved
Salicylhydroxamic AcidThe risk or severity of adverse effects can be increased when Salicylhydroxamic Acid is combined with Azimilide.Experimental
Salicylic acidThe risk or severity of adverse effects can be increased when Salicylic acid is combined with Azimilide.Approved, Vet Approved
SecobarbitalThe metabolism of Azimilide can be increased when combined with Secobarbital.Approved, Vet Approved
SertaconazoleThe risk or severity of adverse effects can be increased when Sertaconazole is combined with Azimilide.Approved
SilodosinSilodosin may increase the hypotensive activities of Azimilide.Approved
SimvastatinThe risk or severity of adverse effects can be increased when Azimilide is combined with Simvastatin.Approved
SinefunginThe risk or severity of adverse effects can be increased when Sinefungin is combined with Azimilide.Experimental
SirolimusThe risk or severity of adverse effects can be increased when Sirolimus is combined with Azimilide.Approved, Investigational
SolithromycinThe metabolism of Azimilide can be decreased when combined with Solithromycin.Investigational
SulconazoleThe risk or severity of adverse effects can be increased when Sulconazole is combined with Azimilide.Approved
TamsulosinTamsulosin may increase the hypotensive activities of Azimilide.Approved, Investigational
TavaboroleThe risk or severity of adverse effects can be increased when Tavaborole is combined with Azimilide.Approved
TelithromycinThe metabolism of Azimilide can be decreased when combined with Telithromycin.Approved
TerazosinTerazosin may increase the hypotensive activities of Azimilide.Approved
TerbinafineThe risk or severity of adverse effects can be increased when Terbinafine is combined with Azimilide.Approved, Investigational, Vet Approved
TerconazoleThe risk or severity of adverse effects can be increased when Terconazole is combined with Azimilide.Approved
ThiamylalThe metabolism of Azimilide can be increased when combined with Thiamylal.Approved, Vet Approved
ThiopentalThe metabolism of Azimilide can be increased when combined with Thiopental.Approved, Vet Approved
ThymolThe risk or severity of adverse effects can be increased when Thymol is combined with Azimilide.Approved
TioconazoleThe risk or severity of adverse effects can be increased when Tioconazole is combined with Azimilide.Approved
TolciclateThe risk or severity of adverse effects can be increased when Tolciclate is combined with Azimilide.Experimental
TolnaftateThe risk or severity of adverse effects can be increased when Tolnaftate is combined with Azimilide.Approved, Vet Approved
TrimazosinTrimazosin may increase the hypotensive activities of Azimilide.Experimental
TrimetrexateThe risk or severity of adverse effects can be increased when Trimetrexate is combined with Azimilide.Approved, Investigational
TylosinThe metabolism of Azimilide can be decreased when combined with Tylosin.Vet Approved
UbidecarenoneThe risk or severity of adverse effects can be increased when Azimilide is combined with Ubidecarenone.Approved, Experimental
UrapidilUrapidil may increase the hypotensive activities of Azimilide.Investigational
VoriconazoleThe risk or severity of adverse effects can be increased when Voriconazole is combined with Azimilide.Approved, Investigational
Food Interactions
Not Available

References

General References
  1. Schmitt H, Cabo C, Coromilas JC, Wit AL: Effects of azimilide, a new class III antiarrhythmic drug, on reentrant circuits causing ventricular tachycardia and fibrillation in a canine model of myocardial infarction. J Cardiovasc Electrophysiol. 2001 Sep;12(9):1025-33. [PubMed:11573692]
  2. Abrol R, Page RL: Azimilide dihydrochloride: a new class III anti-arrhythmic agent. Expert Opin Investig Drugs. 2000 Nov;9(11):2705-15. [PubMed:11060832]
  3. Tran HT: Azimilide dihydrochloride: a unique class III antiarrhythmic agent. Heart Dis. 1999 May-Jun;1(2):114-6. [PubMed:11720612]
  4. Toothaker RD, Corey AE, Valentine SN, Agnew JR, Parekh N, Moehrke W, Thompson GA, Powell JH: Influence of coadministration on the pharmacokinetics of azimilide dihydrochloride and digoxin. J Clin Pharmacol. 2005 Jul;45(7):773-80. [PubMed:15951467]
  5. Riley P, Figary PC, Entwisle JR, Roe AL, Thompson GA, Ohashi R, Ohashi N, Moorehead TJ: The metabolic profile of azimilide in man: in vivo and in vitro evaluations. J Pharm Sci. 2005 Sep;94(9):2084-95. [PubMed:16052551]
External Links
KEGG Compound
C13777
PubChem Compound
9571004
PubChem Substance
175426919
ChemSpider
54906
BindingDB
50117913
Wikipedia
Azimilide

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
3TerminatedTreatmentCardiac Dysrhythmia / Cardiovascular Disease (CVD) / Heart Diseases / Implantable Cardioverter Defibrillator (ICD)1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.0861 mg/mLALOGPS
logP2.91ALOGPS
logP2.59ChemAxon
logS-3.7ALOGPS
pKa (Strongest Acidic)11.95ChemAxon
pKa (Strongest Basic)8.7ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area72.6 Å2ChemAxon
Rotatable Bond Count8ChemAxon
Refractivity124.83 m3·mol-1ChemAxon
Polarizability50.15 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+1.0
Blood Brain Barrier+0.9013
Caco-2 permeable-0.5057
P-glycoprotein substrateSubstrate0.7072
P-glycoprotein inhibitor IInhibitor0.79
P-glycoprotein inhibitor IINon-inhibitor0.5948
Renal organic cation transporterInhibitor0.614
CYP450 2C9 substrateNon-substrate0.7463
CYP450 2D6 substrateNon-substrate0.9116
CYP450 3A4 substrateSubstrate0.7085
CYP450 1A2 substrateNon-inhibitor0.8317
CYP450 2C9 inhibitorNon-inhibitor0.7377
CYP450 2D6 inhibitorNon-inhibitor0.8987
CYP450 2C19 inhibitorInhibitor0.5383
CYP450 3A4 inhibitorNon-inhibitor0.8177
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.8234
Ames testAMES toxic0.5429
CarcinogenicityNon-carcinogens0.7114
BiodegradationNot ready biodegradable0.9967
Rat acute toxicity2.6412 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Strong inhibitor0.8037
hERG inhibition (predictor II)Inhibitor0.5718
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Taxonomy

Description
This compound belongs to the class of organic compounds known as hydantoins. These are heterocyclic compounds containing an imidazolidine substituted by ketone group at positions 2 and 4.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Azolidines
Sub Class
Imidazolidines
Direct Parent
Hydantoins
Alternative Parents
Alpha amino acids and derivatives / N-methylpiperazines / Chlorobenzenes / Semicarbazones / Aryl chlorides / Heteroaromatic compounds / Furans / Dicarboximides / Trialkylamines / Organic carbonic acids and derivatives
show 7 more
Substituents
Hydantoin / Alpha-amino acid or derivatives / Chlorobenzene / Halobenzene / N-methylpiperazine / N-alkylpiperazine / Aryl chloride / Aryl halide / Monocyclic benzene moiety / 1,4-diazinane
show 26 more
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
Not Available

Targets

Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Telethonin binding
Specific Function
Ancillary protein that assembles as a beta subunit with a voltage-gated potassium channel complex of pore-forming alpha subunits. Modulates the gating kinetics and enhances stability of the channel...
Gene Name
KCNE1
Uniprot ID
P15382
Uniprot Name
Potassium voltage-gated channel subfamily E member 1
Molecular Weight
14674.66 Da
References
  1. Schmitt H, Cabo C, Coromilas JC, Wit AL: Effects of azimilide, a new class III antiarrhythmic drug, on reentrant circuits causing ventricular tachycardia and fibrillation in a canine model of myocardial infarction. J Cardiovasc Electrophysiol. 2001 Sep;12(9):1025-33. [PubMed:11573692]
  2. Abrol R, Page RL: Azimilide dihydrochloride: a new class III anti-arrhythmic agent. Expert Opin Investig Drugs. 2000 Nov;9(11):2705-15. [PubMed:11060832]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Voltage-gated potassium channel activity involved in ventricular cardiac muscle cell action potential repolarization
Specific Function
Potassium channel that plays an important role in a number of tissues, including heart, inner ear, stomach and colon (By similarity) (PubMed:10646604). Associates with KCNE beta subunits that modul...
Gene Name
KCNQ1
Uniprot ID
P51787
Uniprot Name
Potassium voltage-gated channel subfamily KQT member 1
Molecular Weight
74697.925 Da
References
  1. Schmitt H, Cabo C, Coromilas JC, Wit AL: Effects of azimilide, a new class III antiarrhythmic drug, on reentrant circuits causing ventricular tachycardia and fibrillation in a canine model of myocardial infarction. J Cardiovasc Electrophysiol. 2001 Sep;12(9):1025-33. [PubMed:11573692]
  2. Abrol R, Page RL: Azimilide dihydrochloride: a new class III anti-arrhythmic agent. Expert Opin Investig Drugs. 2000 Nov;9(11):2705-15. [PubMed:11060832]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Voltage-gated potassium channel activity involved in ventricular cardiac muscle cell action potential repolarization
Specific Function
Pore-forming (alpha) subunit of voltage-gated inwardly rectifying potassium channel. Channel properties are modulated by cAMP and subunit assembly. Mediates the rapidly activating component of the ...
Gene Name
KCNH2
Uniprot ID
Q12809
Uniprot Name
Potassium voltage-gated channel subfamily H member 2
Molecular Weight
126653.52 Da
References
  1. Schmitt H, Cabo C, Coromilas JC, Wit AL: Effects of azimilide, a new class III antiarrhythmic drug, on reentrant circuits causing ventricular tachycardia and fibrillation in a canine model of myocardial infarction. J Cardiovasc Electrophysiol. 2001 Sep;12(9):1025-33. [PubMed:11573692]
  2. Abrol R, Page RL: Azimilide dihydrochloride: a new class III anti-arrhythmic agent. Expert Opin Investig Drugs. 2000 Nov;9(11):2705-15. [PubMed:11060832]

Enzymes

Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Vitamin d 24-hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name
CYP1A1
Uniprot ID
P04798
Uniprot Name
Cytochrome P450 1A1
Molecular Weight
58164.815 Da
References
  1. Riley P, Figary PC, Entwisle JR, Roe AL, Thompson GA, Ohashi R, Ohashi N, Moorehead TJ: The metabolic profile of azimilide in man: in vivo and in vitro evaluations. J Pharm Sci. 2005 Sep;94(9):2084-95. [PubMed:16052551]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Vitamin d3 25-hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation react...
Gene Name
CYP3A4
Uniprot ID
P08684
Uniprot Name
Cytochrome P450 3A4
Molecular Weight
57342.67 Da
References
  1. Riley P, Figary PC, Entwisle JR, Roe AL, Thompson GA, Ohashi R, Ohashi N, Moorehead TJ: The metabolic profile of azimilide in man: in vivo and in vitro evaluations. J Pharm Sci. 2005 Sep;94(9):2084-95. [PubMed:16052551]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Oxygen binding
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name
CYP3A5
Uniprot ID
P20815
Uniprot Name
Cytochrome P450 3A5
Molecular Weight
57108.065 Da
References
  1. Riley P, Figary PC, Entwisle JR, Roe AL, Thompson GA, Ohashi R, Ohashi N, Moorehead TJ: The metabolic profile of azimilide in man: in vivo and in vitro evaluations. J Pharm Sci. 2005 Sep;94(9):2084-95. [PubMed:16052551]

Drug created on October 21, 2007 16:23 / Updated on November 09, 2017 03:49