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Identification
NameAmiloride
Accession NumberDB00594  (APRD00790, EXPT00514)
TypeSmall Molecule
GroupsApproved
DescriptionA pyrazine compound inhibiting sodium reabsorption through sodium channels in renal epithelial cells. This inhibition creates a negative potential in the luminal membranes of principal cells, located in the distal convoluted tubule and collecting duct. Negative potential reduces secretion of potassium and hydrogen ions. Amiloride is used in conjunction with diuretics to spare potassium loss. (From Gilman et al., Goodman and Gilman's The Pharmacological Basis of Therapeutics, 9th ed, p705)
Structure
Thumb
Synonyms
3,5-Diamino-N-carbamimidoyl-6-chloropyrazine-2-carboxamide
Amilorid
Amilorida
Amiloridum
Amipramidin
Amipramidine
Amyloride
N-amidino-3,5-diamino-6-chloropyrazinecarboxamide
External Identifiers
  • MK 870
Approved Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Amiloride HydrochlorideTablet5 mg/1OralPhysicians Total Care, Inc.2005-01-28Not applicableUs
Amiloride Hydrochloride Tablets, USPTablet5 mgOralOrbus Pharma IncNot applicableNot applicableCanada
Amiloride HydroclorideTablet5 mg/1OralPaddock Laboratories, LLC2009-04-06Not applicableUs
MidamorTablet5.0 mgOralAa Pharma Inc2004-06-18Not applicableCanada
Midamor Tablets 5mgTablet5 mgOralOrbus Pharma Inc1981-12-312010-06-16Canada
Approved Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Amiloride HydrochlorideTablet5 mg/1OralAv Pak2013-01-28Not applicableUs
Amiloride HydrochlorideTablet5 mg/1OralAv Kare, Inc.2012-03-28Not applicableUs
Amiloride HydrochlorideTablet5 mg/1OralGolden State Medical Supply, Inc.2015-08-31Not applicableUs
Amiloride HydrochlorideTablet5 mg/1OralRising Pharmaceuticals, Inc2009-05-01Not applicableUs
Amiloride HydrochlorideTablet5 mg/1OralCarilion Materials Management1986-01-22Not applicableUs
Amiloride HydrochlorideTablet5 mg/1OralCadila Healthcare Limited2015-09-14Not applicableUs
Amiloride HydrochlorideTablet5 mg/1OralPar Pharmaceutical Inc.1986-01-22Not applicableUs
Amiloride HydrochlorideTablet5 mg/1OralZydus Pharmaceuticals (USA) Inc.2015-09-14Not applicableUs
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International Brands
NameCompany
ArumilSharp & Dohme
KalurilAlphapharm
ModamideMerck
ModureticMerck
Brand mixtures
NameLabellerIngredients
Alti-amiloride HctzAltimed Pharma Inc.
Ami-hydro TabPro Doc Limitee
Amiloride Hydrochloride and HydrochlorothiazideMylan Pharmaceuticals Inc.
Apo-amilzide TabApotex Inc
ModuretPrempharm Inc
Mylan-amilazideMylan Pharmaceuticals Ulc
NovamilorTeva Canada Limited
Nu-amilzide 5/50 Mg TabNu Pharm Inc
Penta-amiloride Hctz TabletsPentapharm Ltd.
Riva-amilzide 5/50 mgLaboratoire Riva Inc
Salts
Name/CASStructureProperties
Amiloride hydrochloride
2016-88-8
Thumb
  • InChI Key: ACHKKGDWZVCSNH-UHFFFAOYSA-N
  • Monoisotopic Mass: 265.0245633
  • Average Mass: 266.09
DBSALT001807
Amiloride hydrochloride dihydrate
17440-83-4
Thumb
  • InChI Key: LTKVFMLMEYCWMK-UHFFFAOYSA-N
  • Monoisotopic Mass: 301.045692731
  • Average Mass: 302.119
DBSALT000270
Categories
UNII7DZO8EB0Z3
CAS number2609-46-3
WeightAverage: 229.627
Monoisotopic: 229.04788562
Chemical FormulaC6H8ClN7O
InChI KeyXSDQTOBWRPYKKA-UHFFFAOYSA-N
InChI
InChI=1S/C6H8ClN7O/c7-2-4(9)13-3(8)1(12-2)5(15)14-6(10)11/h(H4,8,9,13)(H4,10,11,14,15)
IUPAC Name
3,5-diamino-6-chloro-N-(diaminomethylidene)pyrazine-2-carboxamide
SMILES
NC(N)=NC(=O)C1=C(N)N=C(N)C(Cl)=N1
Pharmacology
IndicationFor use as adjunctive treatment with thiazide diuretics or other kaliuretic-diuretic agents in congestive heart failure or hypertension.
Structured Indications
PharmacodynamicsAmiloride, an antikaliuretic-diuretic agent, is a pyrazine-carbonyl-guanidine that is unrelated chemically to other known antikaliuretic or diuretic agents. It is an antihypertensive, potassium-sparing diuretic that was first approved for use in 1967 and helps to treat hypertension and congestive heart failure. The drug is often used in conjunction with thiazide or loop diuretics. Due to its potassium-sparing capacities, hyperkalemia (high blood potassium levels) are occasionally observed in patients taking amiloride. The risk is high in concurrent use of ACE inhibitors or spironolactone. Patients are also advised not to use potassium-containing salt replacements.
Mechanism of actionAmiloride works by inhibiting sodium reabsorption in the distal convoluted tubules and collecting ducts in the kidneys by binding to the amiloride-sensitive sodium channels. This promotes the loss of sodium and water from the body, but without depleting potassium. Amiloride exerts its potassium sparing effect through the inhibition of sodium reabsorption at the distal convoluted tubule, cortical collecting tubule and collecting duct; this decreases the net negative potential of the tubular lumen and reduces both potassium and hydrogen secretion and their subsequent excretion. Amiloride is not an aldosterone antagonist and its effects are seen even in the absence of aldosterone.
TargetKindPharmacological actionActionsOrganismUniProt ID
Amiloride-sensitive sodium channel subunit alphaProteinyes
inhibitor
HumanP37088 details
Amiloride-sensitive sodium channel subunit betaProteinyes
inhibitor
HumanP51168 details
Amiloride-sensitive sodium channel subunit gammaProteinyes
inhibitor
HumanP51170 details
Amiloride-sensitive sodium channel subunit deltaProteinyes
inhibitor
HumanP51172 details
Amiloride-sensitive amine oxidase [copper-containing]Proteinunknown
inhibitor
HumanP19801 details
Acid-sensing ion channel 2Proteinunknown
inhibitor
HumanQ16515 details
Acid-sensing ion channel 1Proteinunknown
inhibitor
HumanP78348 details
Sodium/hydrogen exchanger 1Proteinunknown
inhibitor
HumanP19634 details
Urokinase-type plasminogen activatorProteinunknown
inhibitor
HumanP00749 details
Related Articles
AbsorptionReadily absorbed following oral administration.
Volume of distributionNot Available
Protein bindingNot Available
Metabolism

Amiloride is not metabolized by the liver but is excreted unchanged by the kidneys.

Route of eliminationAmiloride HCl is not metabolized by the liver but is excreted unchanged by the kidneys. About 50 percent of a 20 mg dose of amiloride HCl is excreted in the urine and 40 percent in the stool within 72 hours.
Half lifePlasma half-life varies from 6 to 9 hours.
ClearanceNot Available
ToxicityNo data are available in regard to overdosage in humans. The oral LD50 of amiloride hydrochloride (calculated as the base) is 56 mg/kg in mice and 36 to 85 mg/kg in rats, depending on the strain. The most likely signs and symptoms to be expected with overdosage are dehydration and electrolyte imbalance.
Affected organisms
  • Humans and other mammals
Pathways
PathwayCategorySMPDB ID
Amiloride Action PathwayDrug actionSMP00133
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
Interactions
Drug Interactions
DrugInteractionDrug group
AcebutololThe risk or severity of adverse effects can be increased when Amiloride is combined with Acebutolol.Approved
AceclofenacAceclofenac may decrease the antihypertensive activities of Amiloride.Approved
AcetazolamideThe risk or severity of adverse effects can be increased when Amiloride is combined with Acetazolamide.Approved, Vet Approved
AcetovanilloneAcetovanillone may decrease the antihypertensive activities of Amiloride.Investigational
AcetyldigitoxinThe therapeutic efficacy of Acetyldigitoxin can be decreased when used in combination with Amiloride.Approved
Acetylsalicylic acidAcetylsalicylic acid may decrease the antihypertensive activities of Amiloride.Approved, Vet Approved
AdapaleneAdapalene may decrease the antihypertensive activities of Amiloride.Approved
AldesleukinThe risk or severity of adverse effects can be increased when Aldesleukin is combined with Amiloride.Approved
AlfentanilThe risk or severity of adverse effects can be increased when Alfentanil is combined with Amiloride.Approved, Illicit
AliskirenThe risk or severity of adverse effects can be increased when Amiloride is combined with Aliskiren.Approved, Investigational
AlphacetylmethadolThe risk or severity of adverse effects can be increased when Alphacetylmethadol is combined with Amiloride.Experimental, Illicit
AmifostineThe risk or severity of adverse effects can be increased when Amiloride is combined with Amifostine.Approved, Investigational
AmiodaroneThe risk or severity of adverse effects can be increased when Amiloride is combined with Amiodarone.Approved, Investigational
AmlodipineThe risk or severity of adverse effects can be increased when Amlodipine is combined with Amiloride.Approved
Ammonium chlorideThe risk or severity of adverse effects can be increased when Amiloride is combined with Ammonium chloride.Approved, Vet Approved
AmobarbitalAmobarbital may increase the hypotensive activities of Amiloride.Approved, Illicit
Amphotericin BThe risk or severity of adverse effects can be increased when Amiloride is combined with Amphotericin B.Approved, Investigational
Amyl NitriteThe risk or severity of adverse effects can be increased when Amiloride is combined with Amyl Nitrite.Approved
AnisodamineAnisodamine may decrease the antihypertensive activities of Amiloride.Investigational
AntipyrineAntipyrine may decrease the antihypertensive activities of Amiloride.Approved
AnvirzelThe therapeutic efficacy of Anvirzel can be decreased when used in combination with Amiloride.Investigational
ApomorphineThe risk or severity of adverse effects can be increased when Amiloride is combined with Apomorphine.Approved, Investigational
ApraclonidineThe risk or severity of adverse effects can be increased when Amiloride is combined with Apraclonidine.Approved
ApremilastApremilast may decrease the antihypertensive activities of Amiloride.Approved, Investigational
ArdeparinArdeparin may increase the hyperkalemic activities of Amiloride.Approved, Withdrawn
AripiprazoleAripiprazole may increase the hypotensive activities of Amiloride.Approved, Investigational
ArotinololThe risk or severity of adverse effects can be increased when Amiloride is combined with Arotinolol.Approved
Arsenic trioxideThe risk or severity of adverse effects can be increased when Amiloride is combined with Arsenic trioxide.Approved, Investigational
AtenololThe risk or severity of adverse effects can be increased when Atenolol is combined with Amiloride.Approved
AzapropazoneAzapropazone may decrease the antihypertensive activities of Amiloride.Withdrawn
AzelastineAzelastine may decrease the antihypertensive activities of Amiloride.Approved
Azilsartan medoxomilThe risk or severity of adverse effects can be increased when Amiloride is combined with Azilsartan medoxomil.Approved
BalsalazideBalsalazide may decrease the antihypertensive activities of Amiloride.Approved, Investigational
BarbexacloneBarbexaclone may increase the hypotensive activities of Amiloride.Experimental
BarbitalBarbital may increase the hypotensive activities of Amiloride.Illicit
BarnidipineThe risk or severity of adverse effects can be increased when Amiloride is combined with Barnidipine.Approved
BemiparinBemiparin may increase the hyperkalemic activities of Amiloride.Approved
BenazeprilThe risk or severity of adverse effects can be increased when Benazepril is combined with Amiloride.Approved, Investigational
BendroflumethiazideThe risk or severity of adverse effects can be increased when Bendroflumethiazide is combined with Amiloride.Approved
BenoxaprofenBenoxaprofen may decrease the antihypertensive activities of Amiloride.Withdrawn
BepridilThe risk or severity of adverse effects can be increased when Amiloride is combined with Bepridil.Approved, Withdrawn
BetaxololThe risk or severity of adverse effects can be increased when Betaxolol is combined with Amiloride.Approved
Betulinic AcidBetulinic Acid may decrease the antihypertensive activities of Amiloride.Investigational
BezitramideThe risk or severity of adverse effects can be increased when Bezitramide is combined with Amiloride.Experimental, Illicit, Withdrawn
BisoprololThe risk or severity of adverse effects can be increased when Amiloride is combined with Bisoprolol.Approved
BortezomibThe risk or severity of adverse effects can be increased when Amiloride is combined with Bortezomib.Approved, Investigational
BretyliumThe risk or severity of adverse effects can be increased when Amiloride is combined with Bretylium.Approved
BrimonidineThe risk or severity of adverse effects can be increased when Brimonidine is combined with Amiloride.Approved
BromfenacBromfenac may decrease the antihypertensive activities of Amiloride.Approved
BromocriptineThe risk or severity of adverse effects can be increased when Amiloride is combined with Bromocriptine.Approved, Investigational
BucillamineBucillamine may decrease the antihypertensive activities of Amiloride.Investigational
BumetanideThe risk or severity of adverse effects can be increased when Amiloride is combined with Bumetanide.Approved
BupivacaineThe risk or severity of adverse effects can be increased when Amiloride is combined with Bupivacaine.Approved, Investigational
BuprenorphineThe risk or severity of adverse effects can be increased when Buprenorphine is combined with Amiloride.Approved, Illicit, Investigational, Vet Approved
ButorphanolThe risk or severity of adverse effects can be increased when Butorphanol is combined with Amiloride.Approved, Illicit, Vet Approved
CanagliflozinCanagliflozin may increase the hyperkalemic activities of Amiloride.Approved
CandesartanThe risk or severity of adverse effects can be increased when Amiloride is combined with Candesartan.Approved
CandoxatrilAmiloride may increase the hyperkalemic activities of Candoxatril.Experimental
CaptoprilThe risk or severity of adverse effects can be increased when Amiloride is combined with Captopril.Approved
CarbetocinThe risk or severity of adverse effects can be increased when Amiloride is combined with Carbetocin.Approved
CarfentanilThe risk or severity of adverse effects can be increased when Carfentanil is combined with Amiloride.Illicit, Vet Approved
CarprofenCarprofen may decrease the antihypertensive activities of Amiloride.Approved, Vet Approved, Withdrawn
CarteololThe risk or severity of adverse effects can be increased when Carteolol is combined with Amiloride.Approved
CarvedilolThe risk or severity of adverse effects can be increased when Amiloride is combined with Carvedilol.Approved, Investigational
CastanospermineCastanospermine may decrease the antihypertensive activities of Amiloride.Experimental
CelecoxibCelecoxib may decrease the antihypertensive activities of Amiloride.Approved, Investigational
CertoparinCertoparin may increase the hyperkalemic activities of Amiloride.Approved
ChloroquineChloroquine may decrease the antihypertensive activities of Amiloride.Approved, Vet Approved
ChlorothiazideThe risk or severity of adverse effects can be increased when Amiloride is combined with Chlorothiazide.Approved, Vet Approved
ChlorpromazineThe risk or severity of adverse effects can be increased when Amiloride is combined with Chlorpromazine.Approved, Vet Approved
ChlorthalidoneThe risk or severity of adverse effects can be increased when Chlorthalidone is combined with Amiloride.Approved
CilazaprilThe risk or severity of adverse effects can be increased when Amiloride is combined with Cilazapril.Approved
CilnidipineThe risk or severity of adverse effects can be increased when Amiloride is combined with Cilnidipine.Approved
ClevidipineThe risk or severity of adverse effects can be increased when Amiloride is combined with Clevidipine.Approved
ClofarabineThe risk or severity of adverse effects can be increased when Amiloride is combined with Clofarabine.Approved, Investigational
ClomipramineThe risk or severity of adverse effects can be increased when Amiloride is combined with Clomipramine.Approved, Vet Approved
ClonidineThe risk or severity of adverse effects can be increased when Clonidine is combined with Amiloride.Approved
ClonixinClonixin may decrease the antihypertensive activities of Amiloride.Approved
ClozapineThe risk or severity of adverse effects can be increased when Amiloride is combined with Clozapine.Approved
CodeineThe risk or severity of adverse effects can be increased when Codeine is combined with Amiloride.Approved, Illicit
ConivaptanThe risk or severity of adverse effects can be increased when Amiloride is combined with Conivaptan.Approved, Investigational
CurcuminCurcumin may decrease the antihypertensive activities of Amiloride.Investigational
CyclosporineAmiloride may increase the hyperkalemic activities of Cyclosporine.Approved, Investigational, Vet Approved
D-LimoneneD-Limonene may decrease the antihypertensive activities of Amiloride.Investigational
DalteparinDalteparin may increase the hyperkalemic activities of Amiloride.Approved
DapagliflozinThe risk or severity of adverse effects can be increased when Amiloride is combined with Dapagliflozin.Approved
DesfluraneThe risk or severity of adverse effects can be increased when Amiloride is combined with Desflurane.Approved
DeslanosideThe therapeutic efficacy of Deslanoside can be decreased when used in combination with Amiloride.Approved
DexmedetomidineThe risk or severity of adverse effects can be increased when Amiloride is combined with Dexmedetomidine.Approved, Vet Approved
DextromoramideThe risk or severity of adverse effects can be increased when Dextromoramide is combined with Amiloride.Experimental, Illicit
DextropropoxypheneThe risk or severity of adverse effects can be increased when Dextropropoxyphene is combined with Amiloride.Approved, Illicit, Withdrawn
DezocineThe risk or severity of adverse effects can be increased when Dezocine is combined with Amiloride.Approved
DiclofenacDiclofenac may decrease the antihypertensive activities of Amiloride.Approved, Vet Approved
DiclofenamideThe risk or severity of adverse effects can be increased when Amiloride is combined with Diclofenamide.Approved
DiflunisalDiflunisal may decrease the antihypertensive activities of Amiloride.Approved
DigitoxinThe therapeutic efficacy of Digitoxin can be decreased when used in combination with Amiloride.Approved
DigoxinThe therapeutic efficacy of Digoxin can be decreased when used in combination with Amiloride.Approved
DihydrocodeineThe risk or severity of adverse effects can be increased when Dihydrocodeine is combined with Amiloride.Approved, Illicit
DihydroetorphineThe risk or severity of adverse effects can be increased when Dihydroetorphine is combined with Amiloride.Experimental, Illicit
DihydromorphineThe risk or severity of adverse effects can be increased when Dihydromorphine is combined with Amiloride.Experimental, Illicit
DiltiazemThe risk or severity of adverse effects can be increased when Diltiazem is combined with Amiloride.Approved
DinutuximabThe risk or severity of adverse effects can be increased when Amiloride is combined with Dinutuximab.Approved
DiphenoxylateThe risk or severity of adverse effects can be increased when Diphenoxylate is combined with Amiloride.Approved, Illicit
DipyridamoleThe risk or severity of adverse effects can be increased when Amiloride is combined with Dipyridamole.Approved
DofetilideThe serum concentration of Dofetilide can be increased when it is combined with Amiloride.Approved
DoxazosinThe risk or severity of adverse effects can be increased when Doxazosin is combined with Amiloride.Approved
DPDPEThe risk or severity of adverse effects can be increased when DPDPE is combined with Amiloride.Investigational
DrospirenoneDrospirenone may increase the hyperkalemic activities of Amiloride.Approved
DroxicamDroxicam may decrease the antihypertensive activities of Amiloride.Approved
DuloxetineAmiloride may increase the orthostatic hypotensive activities of Duloxetine.Approved
DuvelisibDuvelisib may decrease the antihypertensive activities of Amiloride.Investigational
E6201E6201 may decrease the antihypertensive activities of Amiloride.Investigational
EbselenEbselen may decrease the antihypertensive activities of Amiloride.Investigational
EfonidipineThe risk or severity of adverse effects can be increased when Amiloride is combined with Efonidipine.Approved
EmpagliflozinThe risk or severity of adverse effects can be increased when Amiloride is combined with Empagliflozin.Approved
EnalaprilThe risk or severity of adverse effects can be increased when Enalapril is combined with Amiloride.Approved, Vet Approved
EnalaprilatAmiloride may increase the hyperkalemic activities of Enalaprilat.Approved
EnoxaparinEnoxaparin may increase the hyperkalemic activities of Amiloride.Approved
EpirizoleEpirizole may decrease the antihypertensive activities of Amiloride.Approved
EplerenoneEplerenone may increase the hyperkalemic activities of Amiloride.Approved
EpoprostenolThe risk or severity of adverse effects can be increased when Amiloride is combined with Epoprostenol.Approved
EprosartanThe risk or severity of adverse effects can be increased when Amiloride is combined with Eprosartan.Approved
EsmololThe risk or severity of adverse effects can be increased when Esmolol is combined with Amiloride.Approved
Etacrynic acidThe risk or severity of adverse effects can be increased when Amiloride is combined with Etacrynic acid.Approved
EtanerceptEtanercept may decrease the antihypertensive activities of Amiloride.Approved, Investigational
EthylmorphineThe risk or severity of adverse effects can be increased when Ethylmorphine is combined with Amiloride.Approved, Illicit
EtodolacEtodolac may decrease the antihypertensive activities of Amiloride.Approved, Investigational, Vet Approved
EtofenamateEtofenamate may decrease the antihypertensive activities of Amiloride.Approved
EtoricoxibEtoricoxib may decrease the antihypertensive activities of Amiloride.Approved, Investigational
EtorphineThe risk or severity of adverse effects can be increased when Etorphine is combined with Amiloride.Illicit, Vet Approved
Evening primrose oilEvening primrose oil may decrease the antihypertensive activities of Amiloride.Approved
exisulindexisulind may decrease the antihypertensive activities of Amiloride.Investigational
FelodipineThe risk or severity of adverse effects can be increased when Amiloride is combined with Felodipine.Approved, Investigational
FenbufenFenbufen may decrease the antihypertensive activities of Amiloride.Approved
FenoldopamThe risk or severity of adverse effects can be increased when Amiloride is combined with Fenoldopam.Approved
FenoprofenFenoprofen may decrease the antihypertensive activities of Amiloride.Approved
FentanylThe risk or severity of adverse effects can be increased when Fentanyl is combined with Amiloride.Approved, Illicit, Investigational, Vet Approved
FimasartanThe risk or severity of adverse effects can be increased when Amiloride is combined with Fimasartan.Approved
FloctafenineFloctafenine may decrease the antihypertensive activities of Amiloride.Approved, Withdrawn
FlunixinFlunixin may decrease the antihypertensive activities of Amiloride.Vet Approved
FlurbiprofenFlurbiprofen may decrease the antihypertensive activities of Amiloride.Approved, Investigational
ForasartanForasartan may increase the hyperkalemic activities of Amiloride.Experimental
FosinoprilThe risk or severity of adverse effects can be increased when Fosinopril is combined with Amiloride.Approved
FurosemideThe risk or severity of adverse effects can be increased when Amiloride is combined with Furosemide.Approved, Vet Approved
GuanfacineThe risk or severity of adverse effects can be increased when Amiloride is combined with Guanfacine.Approved, Investigational
HalothaneThe risk or severity of adverse effects can be increased when Amiloride is combined with Halothane.Approved, Vet Approved
HeparinHeparin may increase the hyperkalemic activities of Amiloride.Approved, Investigational
HeroinThe risk or severity of adverse effects can be increased when Heroin is combined with Amiloride.Approved, Illicit
HexobarbitalHexobarbital may increase the hypotensive activities of Amiloride.Approved
HigenamineHigenamine may decrease the antihypertensive activities of Amiloride.Investigational
HMPL-004HMPL-004 may decrease the antihypertensive activities of Amiloride.Investigational
HydralazineThe risk or severity of adverse effects can be increased when Amiloride is combined with Hydralazine.Approved
HydrochlorothiazideThe risk or severity of adverse effects can be increased when Amiloride is combined with Hydrochlorothiazide.Approved, Vet Approved
HydrocodoneThe risk or severity of adverse effects can be increased when Hydrocodone is combined with Amiloride.Approved, Illicit
HydroflumethiazideThe risk or severity of adverse effects can be increased when Amiloride is combined with Hydroflumethiazide.Approved
HydromorphoneThe risk or severity of adverse effects can be increased when Hydromorphone is combined with Amiloride.Approved, Illicit
IbuprofenIbuprofen may decrease the antihypertensive activities of Amiloride.Approved
IbuproxamIbuproxam may decrease the antihypertensive activities of Amiloride.Withdrawn
IcatibantIcatibant may decrease the antihypertensive activities of Amiloride.Approved
IloprostThe risk or severity of adverse effects can be increased when Amiloride is combined with Iloprost.Approved, Investigational
ImidaprilThe risk or severity of adverse effects can be increased when Amiloride is combined with Imidapril.Investigational
ImipramineThe risk or severity of adverse effects can be increased when Amiloride is combined with Imipramine.Approved
IndapamideThe risk or severity of adverse effects can be increased when Amiloride is combined with Indapamide.Approved
IndomethacinIndomethacin may decrease the antihypertensive activities of Amiloride.Approved, Investigational
IndoprofenIndoprofen may decrease the antihypertensive activities of Amiloride.Withdrawn
IndoraminThe risk or severity of adverse effects can be increased when Amiloride is combined with Indoramin.Withdrawn
IrbesartanThe risk or severity of adverse effects can be increased when Amiloride is combined with Irbesartan.Approved, Investigational
IsocarboxazidThe risk or severity of adverse effects can be increased when Amiloride is combined with Isocarboxazid.Approved
IsofluraneThe risk or severity of adverse effects can be increased when Amiloride is combined with Isoflurane.Approved, Vet Approved
Isosorbide DinitrateThe risk or severity of adverse effects can be increased when Amiloride is combined with Isosorbide Dinitrate.Approved
Isosorbide MononitrateThe risk or severity of adverse effects can be increased when Amiloride is combined with Isosorbide Mononitrate.Approved
IsoxicamIsoxicam may decrease the antihypertensive activities of Amiloride.Withdrawn
IsoxsuprineThe risk or severity of adverse effects can be increased when Amiloride is combined with Isoxsuprine.Approved, Withdrawn
IsradipineThe risk or severity of adverse effects can be increased when Isradipine is combined with Amiloride.Approved
KebuzoneKebuzone may decrease the antihypertensive activities of Amiloride.Experimental
KetobemidoneThe risk or severity of adverse effects can be increased when Ketobemidone is combined with Amiloride.Approved
KetoprofenKetoprofen may decrease the antihypertensive activities of Amiloride.Approved, Vet Approved
KetorolacKetorolac may decrease the antihypertensive activities of Amiloride.Approved
LabetalolThe risk or severity of adverse effects can be increased when Amiloride is combined with Labetalol.Approved
LacidipineThe risk or severity of adverse effects can be increased when Amiloride is combined with Lacidipine.Approved
LeflunomideLeflunomide may decrease the antihypertensive activities of Amiloride.Approved, Investigational
LercanidipineThe risk or severity of adverse effects can be increased when Amiloride is combined with Lercanidipine.Approved, Investigational
LevobunololThe risk or severity of adverse effects can be increased when Amiloride is combined with Levobunolol.Approved
LevobupivacaineThe risk or severity of adverse effects can be increased when Amiloride is combined with Levobupivacaine.Approved
LevodopaAmiloride may increase the orthostatic hypotensive activities of Levodopa.Approved
Levomethadyl AcetateThe risk or severity of adverse effects can be increased when Levomethadyl Acetate is combined with Amiloride.Approved
LevorphanolThe risk or severity of adverse effects can be increased when Levorphanol is combined with Amiloride.Approved
LevosimendanThe risk or severity of adverse effects can be increased when Amiloride is combined with Levosimendan.Approved, Investigational
LisinoprilThe risk or severity of adverse effects can be increased when Amiloride is combined with Lisinopril.Approved, Investigational
LisofyllineLisofylline may decrease the antihypertensive activities of Amiloride.Investigational
LofentanilThe risk or severity of adverse effects can be increased when Lofentanil is combined with Amiloride.Illicit
LofexidineThe risk or severity of adverse effects can be increased when Amiloride is combined with Lofexidine.Approved, Investigational
LornoxicamLornoxicam may decrease the antihypertensive activities of Amiloride.Approved
LosartanThe risk or severity of adverse effects can be increased when Amiloride is combined with Losartan.Approved
LoxoprofenLoxoprofen may decrease the antihypertensive activities of Amiloride.Approved
LumiracoxibLumiracoxib may decrease the antihypertensive activities of Amiloride.Approved, Investigational
Magnesium salicylateMagnesium salicylate may decrease the antihypertensive activities of Amiloride.Approved
MannitolThe risk or severity of adverse effects can be increased when Amiloride is combined with Mannitol.Approved, Investigational
MasoprocolMasoprocol may decrease the antihypertensive activities of Amiloride.Approved
MecamylamineThe risk or severity of adverse effects can be increased when Amiloride is combined with Mecamylamine.Approved
Meclofenamic acidMeclofenamic acid may decrease the antihypertensive activities of Amiloride.Approved, Vet Approved
Mefenamic acidMefenamic acid may decrease the antihypertensive activities of Amiloride.Approved
MeloxicamMeloxicam may decrease the antihypertensive activities of Amiloride.Approved, Vet Approved
MesalazineMesalazine may decrease the antihypertensive activities of Amiloride.Approved
MetamizoleMetamizole may decrease the antihypertensive activities of Amiloride.Withdrawn
MethadoneThe risk or severity of adverse effects can be increased when Methadone is combined with Amiloride.Approved
Methadyl AcetateThe risk or severity of adverse effects can be increased when Methadyl Acetate is combined with Amiloride.Approved, Illicit
MethazolamideThe risk or severity of adverse effects can be increased when Amiloride is combined with Methazolamide.Approved
MethohexitalMethohexital may increase the hypotensive activities of Amiloride.Approved
MethyclothiazideThe risk or severity of adverse effects can be increased when Methyclothiazide is combined with Amiloride.Approved
MethyldopaThe risk or severity of adverse effects can be increased when Amiloride is combined with Methyldopa.Approved
MethylphenobarbitalMethylphenobarbital may increase the hypotensive activities of Amiloride.Approved
MetipranololThe risk or severity of adverse effects can be increased when Amiloride is combined with Metipranolol.Approved
MetolazoneThe risk or severity of adverse effects can be increased when Metolazone is combined with Amiloride.Approved
MetoprololThe risk or severity of adverse effects can be increased when Metoprolol is combined with Amiloride.Approved, Investigational
MinoxidilThe risk or severity of adverse effects can be increased when Minoxidil is combined with Amiloride.Approved
MizoribineMizoribine may decrease the antihypertensive activities of Amiloride.Investigational
MoexiprilThe risk or severity of adverse effects can be increased when Amiloride is combined with Moexipril.Approved
MorphineThe risk or severity of adverse effects can be increased when Morphine is combined with Amiloride.Approved, Investigational
MoxonidineThe risk or severity of adverse effects can be increased when Amiloride is combined with Moxonidine.Approved
Mycophenolate mofetilMycophenolate mofetil may decrease the antihypertensive activities of Amiloride.Approved, Investigational
Mycophenolic acidMycophenolic acid may decrease the antihypertensive activities of Amiloride.Approved
NabiloneThe risk or severity of adverse effects can be increased when Amiloride is combined with Nabilone.Approved, Investigational
NabumetoneNabumetone may decrease the antihypertensive activities of Amiloride.Approved
NadololThe risk or severity of adverse effects can be increased when Amiloride is combined with Nadolol.Approved
NadroparinNadroparin may increase the hyperkalemic activities of Amiloride.Approved
NafamostatNafamostat may decrease the antihypertensive activities of Amiloride.Investigational
NaftifineNaftifine may decrease the antihypertensive activities of Amiloride.Approved
NalbuphineThe risk or severity of adverse effects can be increased when Nalbuphine is combined with Amiloride.Approved
NaproxenNaproxen may decrease the antihypertensive activities of Amiloride.Approved, Vet Approved
NCX 4016NCX 4016 may decrease the antihypertensive activities of Amiloride.Investigational
NebivololThe risk or severity of adverse effects can be increased when Amiloride is combined with Nebivolol.Approved, Investigational
NepafenacNepafenac may decrease the antihypertensive activities of Amiloride.Approved
NesiritideThe risk or severity of adverse effects can be increased when Amiloride is combined with Nesiritide.Approved, Investigational
NicardipineThe risk or severity of adverse effects can be increased when Amiloride is combined with Nicardipine.Approved
NicorandilNicorandil may increase the hypotensive activities of Amiloride.Approved
NifedipineThe risk or severity of adverse effects can be increased when Amiloride is combined with Nifedipine.Approved
Niflumic AcidNiflumic Acid may decrease the antihypertensive activities of Amiloride.Approved
NilvadipineThe risk or severity of adverse effects can be increased when Amiloride is combined with Nilvadipine.Approved
NimesulideNimesulide may decrease the antihypertensive activities of Amiloride.Approved, Withdrawn
NimodipineThe risk or severity of adverse effects can be increased when Nimodipine is combined with Amiloride.Approved
NisoldipineThe risk or severity of adverse effects can be increased when Nisoldipine is combined with Amiloride.Approved
NitrendipineThe risk or severity of adverse effects can be increased when Amiloride is combined with Nitrendipine.Approved
Nitric OxideThe risk or severity of adverse effects can be increased when Amiloride is combined with Nitric Oxide.Approved
NitroaspirinNitroaspirin may decrease the antihypertensive activities of Amiloride.Investigational
NitroglycerinThe risk or severity of adverse effects can be increased when Amiloride is combined with Nitroglycerin.Approved, Investigational
NitroprussideThe risk or severity of adverse effects can be increased when Nitroprusside is combined with Amiloride.Approved
NormethadoneThe risk or severity of adverse effects can be increased when Normethadone is combined with Amiloride.Approved, Illicit
ObinutuzumabThe risk or severity of adverse effects can be increased when Amiloride is combined with Obinutuzumab.Approved
OlmesartanThe risk or severity of adverse effects can be increased when Olmesartan is combined with Amiloride.Approved, Investigational
OlopatadineOlopatadine may decrease the antihypertensive activities of Amiloride.Approved
OlsalazineOlsalazine may decrease the antihypertensive activities of Amiloride.Approved
OmapatrilatAmiloride may increase the hyperkalemic activities of Omapatrilat.Investigational
OpiumThe risk or severity of adverse effects can be increased when Opium is combined with Amiloride.Approved, Illicit
OrgoteinOrgotein may decrease the antihypertensive activities of Amiloride.Vet Approved
OuabainThe therapeutic efficacy of Ouabain can be decreased when used in combination with Amiloride.Approved
OxaprozinOxaprozin may decrease the antihypertensive activities of Amiloride.Approved
OxprenololThe risk or severity of adverse effects can be increased when Amiloride is combined with Oxprenolol.Approved
OxycodoneThe risk or severity of adverse effects can be increased when Oxycodone is combined with Amiloride.Approved, Illicit, Investigational
OxymorphoneThe risk or severity of adverse effects can be increased when Oxymorphone is combined with Amiloride.Approved, Investigational, Vet Approved
OxyphenbutazoneOxyphenbutazone may decrease the antihypertensive activities of Amiloride.Withdrawn
PaclitaxelThe risk or severity of adverse effects can be increased when Amiloride is combined with Paclitaxel.Approved, Vet Approved
PapaverineThe risk or severity of adverse effects can be increased when Amiloride is combined with Papaverine.Approved
ParecoxibParecoxib may decrease the antihypertensive activities of Amiloride.Approved
ParnaparinParnaparin may increase the hyperkalemic activities of Amiloride.Approved
PenbutololThe risk or severity of adverse effects can be increased when Amiloride is combined with Penbutolol.Approved, Investigational
PentazocineThe risk or severity of adverse effects can be increased when Pentazocine is combined with Amiloride.Approved, Vet Approved
PentobarbitalPentobarbital may increase the hypotensive activities of Amiloride.Approved, Vet Approved
PerindoprilThe risk or severity of adverse effects can be increased when Amiloride is combined with Perindopril.Approved
PethidineThe risk or severity of adverse effects can be increased when Pethidine is combined with Amiloride.Approved
PhenelzineThe risk or severity of adverse effects can be increased when Amiloride is combined with Phenelzine.Approved
PhenobarbitalPhenobarbital may increase the hypotensive activities of Amiloride.Approved
PhenoxybenzamineThe risk or severity of adverse effects can be increased when Amiloride is combined with Phenoxybenzamine.Approved
PhentolamineThe risk or severity of adverse effects can be increased when Amiloride is combined with Phentolamine.Approved
PhenylbutazonePhenylbutazone may decrease the antihypertensive activities of Amiloride.Approved, Vet Approved
PimecrolimusPimecrolimus may decrease the antihypertensive activities of Amiloride.Approved, Investigational
PindololThe risk or severity of adverse effects can be increased when Amiloride is combined with Pindolol.Approved
PipamperoneThe risk or severity of adverse effects can be increased when Amiloride is combined with Pipamperone.Approved
PirfenidonePirfenidone may decrease the antihypertensive activities of Amiloride.Investigational
PiritramideThe risk or severity of adverse effects can be increased when Piritramide is combined with Amiloride.Investigational
PiroxicamPiroxicam may decrease the antihypertensive activities of Amiloride.Approved, Investigational
PramipexoleThe risk or severity of adverse effects can be increased when Amiloride is combined with Pramipexole.Approved, Investigational
PrazosinThe risk or severity of adverse effects can be increased when Prazosin is combined with Amiloride.Approved
PrimidonePrimidone may increase the hypotensive activities of Amiloride.Approved, Vet Approved
PropacetamolPropacetamol may decrease the antihypertensive activities of Amiloride.Approved
PropofolThe risk or severity of adverse effects can be increased when Amiloride is combined with Propofol.Approved, Investigational, Vet Approved
PropranololThe risk or severity of adverse effects can be increased when Propranolol is combined with Amiloride.Approved, Investigational
PTC299PTC299 may decrease the antihypertensive activities of Amiloride.Investigational
QuetiapineThe risk or severity of adverse effects can be increased when Amiloride is combined with Quetiapine.Approved
QuinaprilThe risk or severity of adverse effects can be increased when Amiloride is combined with Quinapril.Approved, Investigational
QuinidineThe therapeutic efficacy of Quinidine can be decreased when used in combination with Amiloride.Approved
RamiprilThe risk or severity of adverse effects can be increased when Ramipril is combined with Amiloride.Approved
RasagilineThe risk or severity of adverse effects can be increased when Amiloride is combined with Rasagiline.Approved
RemifentanilThe risk or severity of adverse effects can be increased when Remifentanil is combined with Amiloride.Approved
RescinnamineAmiloride may increase the hyperkalemic activities of Rescinnamine.Approved
ReserpineThe risk or severity of adverse effects can be increased when Reserpine is combined with Amiloride.Approved
ResveratrolResveratrol may decrease the antihypertensive activities of Amiloride.Experimental, Investigational
ReviparinReviparin may increase the hyperkalemic activities of Amiloride.Approved
RiociguatThe risk or severity of adverse effects can be increased when Amiloride is combined with Riociguat.Approved
RisperidoneAmiloride may increase the hypotensive activities of Risperidone.Approved, Investigational
RofecoxibRofecoxib may decrease the antihypertensive activities of Amiloride.Investigational, Withdrawn
RopiniroleThe risk or severity of adverse effects can be increased when Amiloride is combined with Ropinirole.Approved, Investigational
RopivacaineThe risk or severity of adverse effects can be increased when Amiloride is combined with Ropivacaine.Approved
RotigotineThe risk or severity of adverse effects can be increased when Amiloride is combined with Rotigotine.Approved
SacubitrilSacubitril may increase the hyperkalemic activities of Amiloride.Approved
SalicylamideSalicylamide may decrease the antihypertensive activities of Amiloride.Approved
Salicylic acidSalicylic acid may decrease the antihypertensive activities of Amiloride.Approved, Vet Approved
SalsalateSalsalate may decrease the antihypertensive activities of Amiloride.Approved
SaprisartanSaprisartan may increase the hyperkalemic activities of Amiloride.Experimental
SaralasinSaralasin may increase the hyperkalemic activities of Amiloride.Investigational
SecobarbitalSecobarbital may increase the hypotensive activities of Amiloride.Approved, Vet Approved
SelegilineThe risk or severity of adverse effects can be increased when Amiloride is combined with Selegiline.Approved, Investigational, Vet Approved
SeratrodastSeratrodast may decrease the antihypertensive activities of Amiloride.Approved, Investigational
SevofluraneThe risk or severity of adverse effects can be increased when Amiloride is combined with Sevoflurane.Approved, Vet Approved
Sodium NitriteThe risk or severity of adverse effects can be increased when Amiloride is combined with Sodium Nitrite.Approved
SotalolThe risk or severity of adverse effects can be increased when Sotalol is combined with Amiloride.Approved
SpiraprilAmiloride may increase the hyperkalemic activities of Spirapril.Approved
SpironolactoneAmiloride may increase the hyperkalemic activities of Spironolactone.Approved
SRT501SRT501 may decrease the antihypertensive activities of Amiloride.Investigational
StreptokinaseThe risk or severity of adverse effects can be increased when Amiloride is combined with Streptokinase.Approved
SufentanilThe risk or severity of adverse effects can be increased when Sufentanil is combined with Amiloride.Approved, Investigational
SulfasalazineSulfasalazine may decrease the antihypertensive activities of Amiloride.Approved
SulindacSulindac may decrease the antihypertensive activities of Amiloride.Approved
SuprofenSuprofen may decrease the antihypertensive activities of Amiloride.Approved, Withdrawn
TacrolimusAmiloride may increase the hyperkalemic activities of Tacrolimus.Approved, Investigational
TamsulosinThe risk or severity of adverse effects can be increased when Amiloride is combined with Tamsulosin.Approved, Investigational
TapentadolThe risk or severity of adverse effects can be increased when Tapentadol is combined with Amiloride.Approved
TasosartanTasosartan may increase the hyperkalemic activities of Amiloride.Approved
TelmisartanThe risk or severity of adverse effects can be increased when Amiloride is combined with Telmisartan.Approved, Investigational
TemocaprilAmiloride may increase the hyperkalemic activities of Temocapril.Experimental, Investigational
TenoxicamTenoxicam may decrease the antihypertensive activities of Amiloride.Approved
TepoxalinTepoxalin may decrease the antihypertensive activities of Amiloride.Vet Approved
TerazosinThe risk or severity of adverse effects can be increased when Amiloride is combined with Terazosin.Approved
TeriflunomideTeriflunomide may decrease the antihypertensive activities of Amiloride.Approved
ThalidomideThe risk or severity of adverse effects can be increased when Amiloride is combined with Thalidomide.Approved, Investigational, Withdrawn
ThiamylalThiamylal may increase the hypotensive activities of Amiloride.Approved, Vet Approved
ThiopentalThiopental may increase the hypotensive activities of Amiloride.Approved, Vet Approved
ThioridazineThe risk or severity of adverse effects can be increased when Amiloride is combined with Thioridazine.Approved
Tiaprofenic acidTiaprofenic acid may decrease the antihypertensive activities of Amiloride.Approved
TimololThe risk or severity of adverse effects can be increased when Timolol is combined with Amiloride.Approved
TinoridineTinoridine may decrease the antihypertensive activities of Amiloride.Investigational
TinzaparinTinzaparin may increase the hyperkalemic activities of Amiloride.Approved
TizanidineThe risk or severity of adverse effects can be increased when Amiloride is combined with Tizanidine.Approved
TolazolineThe risk or severity of adverse effects can be increased when Amiloride is combined with Tolazoline.Approved, Vet Approved
TolcaponeThe risk or severity of adverse effects can be increased when Amiloride is combined with Tolcapone.Approved, Withdrawn
Tolfenamic AcidTolfenamic Acid may decrease the antihypertensive activities of Amiloride.Approved
TolmetinTolmetin may decrease the antihypertensive activities of Amiloride.Approved
TolvaptanTolvaptan may increase the hyperkalemic activities of Amiloride.Approved
TorasemideThe risk or severity of adverse effects can be increased when Torasemide is combined with Amiloride.Approved
TramadolThe risk or severity of adverse effects can be increased when Tramadol is combined with Amiloride.Approved, Investigational
TrandolaprilThe risk or severity of adverse effects can be increased when Trandolapril is combined with Amiloride.Approved
TranilastTranilast may decrease the antihypertensive activities of Amiloride.Approved, Investigational
TranylcypromineThe risk or severity of adverse effects can be increased when Amiloride is combined with Tranylcypromine.Approved
TretinoinThe risk or severity of adverse effects can be increased when Amiloride is combined with Tretinoin.Approved, Investigational, Nutraceutical
TriamtereneThe risk or severity of adverse effects can be increased when Triamterene is combined with Amiloride.Approved
Trisalicylate-cholineTrisalicylate-choline may decrease the antihypertensive activities of Amiloride.Approved
ValdecoxibValdecoxib may decrease the antihypertensive activities of Amiloride.Investigational, Withdrawn
ValsartanThe risk or severity of adverse effects can be increased when Valsartan is combined with Amiloride.Approved, Investigational
VerapamilThe risk or severity of adverse effects can be increased when Amiloride is combined with Verapamil.Approved
ZaltoprofenZaltoprofen may decrease the antihypertensive activities of Amiloride.Approved
ZileutonZileuton may decrease the antihypertensive activities of Amiloride.Approved, Investigational, Withdrawn
ZomepiracZomepirac may decrease the antihypertensive activities of Amiloride.Withdrawn
Food Interactions
  • Avoid drastic changes in dietary habit.
  • Avoid natural licorice.
  • Avoid salt substitutes containing potassium.
  • Take with food to reduce irritation.
References
Synthesis Reference

Cragoe, E.J., Jr.; US. Patent 3,313,813; April 11,1967; assigned to Merck 81 Co., Inc.

General ReferencesNot Available
External Links
ATC CodesC03DB01
AHFS Codes
  • 40:28.16
PDB Entries
FDA labelDownload (377 KB)
MSDSDownload (39.3 KB)
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9408
Blood Brain Barrier+0.7193
Caco-2 permeable-0.8957
P-glycoprotein substrateNon-substrate0.7207
P-glycoprotein inhibitor INon-inhibitor0.9282
P-glycoprotein inhibitor IINon-inhibitor0.9677
Renal organic cation transporterNon-inhibitor0.8122
CYP450 2C9 substrateNon-substrate0.8253
CYP450 2D6 substrateNon-substrate0.8778
CYP450 3A4 substrateNon-substrate0.6687
CYP450 1A2 substrateInhibitor0.9107
CYP450 2C9 inhibitorNon-inhibitor0.9577
CYP450 2D6 inhibitorNon-inhibitor0.9231
CYP450 2C19 inhibitorNon-inhibitor0.9295
CYP450 3A4 inhibitorNon-inhibitor0.9733
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9605
Ames testAMES toxic0.9107
CarcinogenicityNon-carcinogens0.9119
BiodegradationNot ready biodegradable1.0
Rat acute toxicity2.5469 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9838
hERG inhibition (predictor II)Non-inhibitor0.8945
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Pharmacoeconomics
Manufacturers
  • Par pharmaceutical inc
  • Sigmapharm laboratories llc
  • Paddock laboratories inc
Packagers
Dosage forms
FormRouteStrength
TabletOral
TabletOral5 mg/1
TabletOral5.0 mg
TabletOral5 mg
Prices
Unit descriptionCostUnit
Amiloride hcl powder5.6USD g
Amiloride hcl 5 mg tablet1.49USD tablet
Midamor 5 mg tablet1.19USD tablet
Apo-Amiloride 5 mg Tablet0.28USD tablet
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
PatentsNot Available
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point240.5-241.5Cragoe, E.J., Jr.; US. Patent 3,313,813; April 11,1967; assigned to Merck 81 Co., Inc.
water solubilitySlightly solubleNot Available
logP-0.3Not Available
pKa8.7Not Available
Predicted Properties
PropertyValueSource
Water Solubility1.22 mg/mLALOGPS
logP-0.72ALOGPS
logP-0.89ChemAxon
logS-2.3ALOGPS
pKa (Strongest Acidic)16.46ChemAxon
pKa (Strongest Basic)3.29ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area159.29 Å2ChemAxon
Rotatable Bond Count1ChemAxon
Refractivity56.69 m3·mol-1ChemAxon
Polarizability19.99 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as pyrazinecarboxamides. These are compounds containing a pyrazine ring which bears a carboxamide.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassDiazines
Sub ClassPyrazines
Direct ParentPyrazinecarboxamides
Alternative Parents
Substituents
  • Pyrazinecarboxamide
  • Aminopyrazine
  • Acylguanidine
  • Imidolactam
  • Primary aromatic amine
  • Aryl halide
  • Aryl chloride
  • Heteroaromatic compound
  • Vinylogous amide
  • Guanidine
  • Carboxamide group
  • Azacycle
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Carboximidamide
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Organochloride
  • Organohalogen compound
  • Carbonyl group
  • Amine
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors

Targets

Kind
Protein
Organism
Human
Pharmacological action
yes
Actions
inhibitor
General Function:
Ww domain binding
Specific Function:
Sodium permeable non-voltage-sensitive ion channel inhibited by the diuretic amiloride. Mediates the electrodiffusion of the luminal sodium (and water, which follows osmotically) through the apical membrane of epithelial cells. Plays an essential role in electrolyte and blood pressure homeostasis, but also in airway surface liquid homeostasis, which is important for proper clearance of mucus. C...
Gene Name:
SCNN1A
Uniprot ID:
P37088
Molecular Weight:
75703.08 Da
References
  1. Kelly O, Lin C, Ramkumar M, Saxena NC, Kleyman TR, Eaton DC: Characterization of an amiloride binding region in the alpha-subunit of ENaC. Am J Physiol Renal Physiol. 2003 Dec;285(6):F1279-90. Epub 2003 Aug 19. [PubMed:12928313 ]
  2. Ji HL, Benos DJ: Degenerin sites mediate proton activation of deltabetagamma-epithelial sodium channel. J Biol Chem. 2004 Jun 25;279(26):26939-47. Epub 2004 Apr 14. [PubMed:15084585 ]
  3. Otulakowski G, Duan W, Gandhi S, O'brodovich H: Steroid and oxygen effects on eIF4F complex, mTOR, and ENaC translation in fetal lung epithelia. Am J Respir Cell Mol Biol. 2007 Oct;37(4):457-66. Epub 2007 Jun 7. [PubMed:17556672 ]
  4. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
Kind
Protein
Organism
Human
Pharmacological action
yes
Actions
inhibitor
General Function:
Ww domain binding
Specific Function:
Sodium permeable non-voltage-sensitive ion channel inhibited by the diuretic amiloride. Mediates the electrodiffusion of the luminal sodium (and water, which follows osmotically) through the apical membrane of epithelial cells. Plays an essential role in electrolyte and blood pressure homeostasis, but also in airway surface liquid homeostasis, which is important for proper clearance of mucus. C...
Gene Name:
SCNN1B
Uniprot ID:
P51168
Molecular Weight:
72658.485 Da
References
  1. Lebowitz J, An B, Edinger RS, Zeidel ML, Johnson JP: Effect of altered Na+ entry on expression of apical and basolateral transport proteins in A6 epithelia. Am J Physiol Renal Physiol. 2003 Sep;285(3):F524-31. Epub 2003 May 13. [PubMed:12746257 ]
  2. Planes C, Leyvraz C, Uchida T, Angelova MA, Vuagniaux G, Hummler E, Matthay M, Clerici C, Rossier B: In vitro and in vivo regulation of transepithelial lung alveolar sodium transport by serine proteases. Am J Physiol Lung Cell Mol Physiol. 2005 Jun;288(6):L1099-109. Epub 2005 Jan 28. [PubMed:15681398 ]
  3. Yamagata T, Yamagata Y, Nishimoto T, Nakanishi M, Nakanishi H, Minakata Y, Mune M, Yukawa S: The impact of phorbol ester on the regulation of amiloride-sensitive epithelial sodium channel in alveolar type ii epithelial cells. Exp Lung Res. 2002 Oct-Nov;28(7):543-62. [PubMed:12396248 ]
  4. Brooks HL, Allred AJ, Beutler KT, Coffman TM, Knepper MA: Targeted proteomic profiling of renal Na(+) transporter and channel abundances in angiotensin II type 1a receptor knockout mice. Hypertension. 2002 Feb;39(2 Pt 2):470-3. [PubMed:11882592 ]
  5. Kamide K, Tanaka C, Takiuchi S, Miwa Y, Yoshii M, Horio T, Kawano Y, Miyata T: Six missense mutations of the epithelial sodium channel beta and gamma subunits in Japanese hypertensives. Hypertens Res. 2004 May;27(5):333-8. [PubMed:15198480 ]
Kind
Protein
Organism
Human
Pharmacological action
yes
Actions
inhibitor
General Function:
Ww domain binding
Specific Function:
Sodium permeable non-voltage-sensitive ion channel inhibited by the diuretic amiloride. Mediates the electrodiffusion of the luminal sodium (and water, which follows osmotically) through the apical membrane of epithelial cells. Plays an essential role in electrolyte and blood pressure homeostasis, but also in airway surface liquid homeostasis, which is important for proper clearance of mucus. C...
Gene Name:
SCNN1G
Uniprot ID:
P51170
Molecular Weight:
74269.62 Da
References
  1. Viemann M, Peter M, Lopez-Siguero JP, Simic-Schleicher G, Sippell WG: Evidence for genetic heterogeneity of pseudohypoaldosteronism type 1: identification of a novel mutation in the human mineralocorticoid receptor in one sporadic case and no mutations in two autosomal dominant kindreds. J Clin Endocrinol Metab. 2001 May;86(5):2056-9. [PubMed:11344206 ]
  2. Iwai N, Baba S, Mannami T, Katsuya T, Higaki J, Ogihara T, Ogata J: Association of sodium channel gamma-subunit promoter variant with blood pressure. Hypertension. 2001 Jul;38(1):86-9. [PubMed:11463765 ]
  3. Yamagata T, Yamagata Y, Nishimoto T, Nakanishi M, Nakanishi H, Minakata Y, Mune M, Yukawa S: The impact of phorbol ester on the regulation of amiloride-sensitive epithelial sodium channel in alveolar type ii epithelial cells. Exp Lung Res. 2002 Oct-Nov;28(7):543-62. [PubMed:12396248 ]
  4. Akcay A, Yavuz T, Semiz S, Bundak R, Demirdoven M: Pseudohypoaldosteronism type 1 and respiratory distress syndrome. J Pediatr Endocrinol Metab. 2002 Nov-Dec;15(9):1557-61. [PubMed:12503866 ]
  5. Ludwig M, Bidlingmaier F, Reissinger A: Pseudohypoaldosteronism type 1 and the genes encoding prostasin, alpha-spectrin, and Nedd4. Int J Mol Med. 2004 Dec;14(6):1101-4. [PubMed:15547682 ]
Kind
Protein
Organism
Human
Pharmacological action
yes
Actions
inhibitor
General Function:
Ligand-gated sodium channel activity
Specific Function:
Sodium permeable non-voltage-sensitive ion channel inhibited by the diuretic amiloride. Mediates the electrodiffusion of the luminal sodium (and water, which follows osmotically) through the apical membrane of epithelial cells. Controls the reabsorption of sodium in kidney, colon, lung and sweat glands. Also plays a role in taste perception.
Gene Name:
SCNN1D
Uniprot ID:
P51172
Molecular Weight:
70214.195 Da
References
  1. Yamamura H, Ugawa S, Ueda T, Nagao M, Shimada S: Protons activate the delta-subunit of the epithelial Na+ channel in humans. J Biol Chem. 2004 Mar 26;279(13):12529-34. Epub 2004 Jan 15. [PubMed:14726523 ]
  2. Ji HL, Bishop LR, Anderson SJ, Fuller CM, Benos DJ: The role of Pre-H2 domains of alpha- and delta-epithelial Na+ channels in ion permeation, conductance, and amiloride sensitivity. J Biol Chem. 2004 Feb 27;279(9):8428-40. Epub 2003 Dec 2. [PubMed:14660613 ]
  3. Ji HL, Su XF, Kedar S, Li J, Barbry P, Smith PR, Matalon S, Benos DJ: Delta-subunit confers novel biophysical features to alpha beta gamma-human epithelial sodium channel (ENaC) via a physical interaction. J Biol Chem. 2006 Mar 24;281(12):8233-41. Epub 2006 Jan 19. [PubMed:16423824 ]
  4. Yamamura H, Ugawa S, Ueda T, Nagao M, Shimada S: Icilin activates the delta-subunit of the human epithelial Na+ channel. Mol Pharmacol. 2005 Oct;68(4):1142-7. Epub 2005 Jul 20. [PubMed:16033954 ]
  5. Yamamura H, Ugawa S, Ueda T, Shimada S: Evans blue is a specific antagonist of the human epithelial Na+ channel delta-subunit. J Pharmacol Exp Ther. 2005 Nov;315(2):965-9. Epub 2005 Aug 17. [PubMed:16107516 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
inhibitor
General Function:
Zinc ion binding
Specific Function:
Catalyzes the degradation of compounds such as putrescine, histamine, spermine, and spermidine, substances involved in allergic and immune responses, cell proliferation, tissue differentiation, tumor formation, and possibly apoptosis. Placental DAO is thought to play a role in the regulation of the female reproductive function.
Gene Name:
AOC1
Uniprot ID:
P19801
Molecular Weight:
85377.1 Da
References
  1. Padiglia A, Medda R, Lorrai A, Murgia B, Pedersen JZ, Finazzi Agro A, Floris G: Interaction of Pig Kidney and Lentil Seedling Copper-Containing Amine Oxidases with Guanidinium Compounds. J Enzyme Inhib. 1999 Nov;15(1):91-100. [PubMed:10938536 ]
  2. Padiglia A, Medda R, Lorrai A, Murgia B, Pedersen JZ, Agro AF, Floris G: Interaction of pig kidney and lentil seedling copper-containing amine oxidases with guanidinium compounds. J Enzyme Inhib. 2000;15(1):91-100. [PubMed:10850957 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
inhibitor
General Function:
Ligand-gated sodium channel activity
Specific Function:
Cation channel with high affinity for sodium, which is gated by extracellular protons and inhibited by the diuretic amiloride. Also permeable for Li(+) and K(+). Generates a biphasic current with a fast inactivating and a slow sustained phase. Heteromeric channel assembly seems to modulate.
Gene Name:
ASIC2
Uniprot ID:
Q16515
Molecular Weight:
57708.515 Da
References
  1. Berdiev BK, Xia J, McLean LA, Markert JM, Gillespie GY, Mapstone TB, Naren AP, Jovov B, Bubien JK, Ji HL, Fuller CM, Kirk KL, Benos DJ: Acid-sensing ion channels in malignant gliomas. J Biol Chem. 2003 Apr 25;278(17):15023-34. Epub 2003 Feb 12. [PubMed:12584187 ]
  2. Ugawa S, Yamamoto T, Ueda T, Ishida Y, Inagaki A, Nishigaki M, Shimada S: Amiloride-insensitive currents of the acid-sensing ion channel-2a (ASIC2a)/ASIC2b heteromeric sour-taste receptor channel. J Neurosci. 2003 May 1;23(9):3616-22. [PubMed:12736332 ]
  3. Ugawa S: Identification of sour-taste receptor genes. Anat Sci Int. 2003 Dec;78(4):205-10. [PubMed:14686475 ]
  4. Peng BG, Ahmad S, Chen S, Chen P, Price MP, Lin X: Acid-sensing ion channel 2 contributes a major component to acid-evoked excitatory responses in spiral ganglion neurons and plays a role in noise susceptibility of mice. J Neurosci. 2004 Nov 10;24(45):10167-75. [PubMed:15537887 ]
  5. Vila-Carriles WH, Kovacs GG, Jovov B, Zhou ZH, Pahwa AK, Colby G, Esimai O, Gillespie GY, Mapstone TB, Markert JM, Fuller CM, Bubien JK, Benos DJ: Surface expression of ASIC2 inhibits the amiloride-sensitive current and migration of glioma cells. J Biol Chem. 2006 Jul 14;281(28):19220-32. Epub 2006 May 16. [PubMed:16704974 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
inhibitor
General Function:
Ligand-gated sodium channel activity
Specific Function:
Isoform 2 and isoform 3 function as proton-gated sodium channels; they are activated by a drop of the extracellular pH and then become rapidly desensitized. The channel generates a biphasic current with a fast inactivating and a slow sustained phase. Has high selectivity for sodium ions and can also transport lithium ions with high efficiency. Isoform 2 can also transport potassium, but with lo...
Gene Name:
ASIC1
Uniprot ID:
P78348
Molecular Weight:
59908.915 Da
References
  1. Petruska JC, Napaporn J, Johnson RD, Cooper BY: Chemical responsiveness and histochemical phenotype of electrophysiologically classified cells of the adult rat dorsal root ganglion. Neuroscience. 2002;115(1):15-30. [PubMed:12401318 ]
  2. Jones NG, Slater R, Cadiou H, McNaughton P, McMahon SB: Acid-induced pain and its modulation in humans. J Neurosci. 2004 Dec 1;24(48):10974-9. [PubMed:15574747 ]
  3. Sugiura T, Dang K, Lamb K, Bielefeldt K, Gebhart GF: Acid-sensing properties in rat gastric sensory neurons from normal and ulcerated stomach. J Neurosci. 2005 Mar 9;25(10):2617-27. [PubMed:15758172 ]
  4. Wang W, Duan B, Xu H, Xu L, Xu TL: Calcium-permeable acid-sensing ion channel is a molecular target of the neurotoxic metal ion lead. J Biol Chem. 2006 Feb 3;281(5):2497-505. Epub 2005 Nov 29. [PubMed:16319075 ]
  5. Xiong ZG, Chu XP, Simon RP: Ca2+ -permeable acid-sensing ion channels and ischemic brain injury. J Membr Biol. 2006 Jan;209(1):59-68. Epub 2006 Apr 17. [PubMed:16685601 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
inhibitor
General Function:
Solute:proton antiporter activity
Specific Function:
Involved in pH regulation to eliminate acids generated by active metabolism or to counter adverse environmental conditions. Major proton extruding system driven by the inward sodium ion chemical gradient. Plays an important role in signal transduction.
Gene Name:
SLC9A1
Uniprot ID:
P19634
Molecular Weight:
90762.13 Da
References
  1. Lee MG, Ahn W, Choi JY, Luo X, Seo JT, Schultheis PJ, Shull GE, Kim KH, Muallem S: Na(+)-dependent transporters mediate HCO(3)(-) salvage across the luminal membrane of the main pancreatic duct. J Clin Invest. 2000 Jun;105(11):1651-8. [PubMed:10841524 ]
  2. Konstantinou-Tegou A, Kaloyianni M, Bourikas D, Koliakos G: The effect of leptin on Na(+)-H(+) antiport (NHE 1) activity of obese and normal subjects erythrocytes. Mol Cell Endocrinol. 2001 Oct 25;183(1-2):11-8. [PubMed:11604219 ]
  3. Serrani RE, Mujica G, Gioia IA, Corchs JL: Neonatal red blood cells: amiloride-insensitive Na+-H+ transport isoform would express Na+-Li+ exchange. Acta Physiol Pharmacol Bulg. 2000;25(3-4):71-4. [PubMed:11688549 ]
  4. Cuthbert AW, Supuran CT, MacVinish LJ: Bicarbonate-dependent chloride secretion in Calu-3 epithelia in response to 7,8-benzoquinoline. J Physiol. 2003 Aug 15;551(Pt 1):79-92. Epub 2003 Jul 18. [PubMed:12872009 ]
  5. Furukawa O, Bi LC, Guth PH, Engel E, Hirokawa M, Kaunitz JD: NHE3 inhibition activates duodenal bicarbonate secretion in the rat. Am J Physiol Gastrointest Liver Physiol. 2004 Jan;286(1):G102-9. Epub 2003 Jul 24. [PubMed:12881227 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
inhibitor
General Function:
Serine-type endopeptidase activity
Specific Function:
Specifically cleaves the zymogen plasminogen to form the active enzyme plasmin.
Gene Name:
PLAU
Uniprot ID:
P00749
Molecular Weight:
48507.09 Da
References
  1. Vakili J, Standker L, Detheux M, Vassart G, Forssmann WG, Parmentier M: Urokinase plasminogen activator and plasmin efficiently convert hemofiltrate CC chemokine 1 into its active. J Immunol. 2001 Sep 15;167(6):3406-13. [PubMed:11544332 ]
  2. Jankun J, Skrzypczak-Jankun E: Binding site of amiloride to urokinase plasminogen activator depends on species. Int J Mol Med. 2001 Oct;8(4):365-71. [PubMed:11562773 ]
  3. Luikart S, Masri M, Wahl D, Hinkel T, Beck JM, Gyetko MR, Gupta P, Oegema T: Urokinase is required for the formation of mactinin, an alpha-actinin fragment that promotes monocyte/macrophage maturation. Biochim Biophys Acta. 2002 Aug 19;1591(1-3):99-107. [PubMed:12183060 ]
  4. Chen YX, O'Brien ER: Ethyl isopropyl amiloride inhibits smooth muscle cell proliferation and migration by inducing apoptosis and antagonizing urokinase plasminogen activator activity. Can J Physiol Pharmacol. 2003 Jul;81(7):730-9. [PubMed:12897821 ]
  5. Cejkova J, Cejka C, Zvarova J: Effects of inhibition of urokinase-type plasminogen activator (u-PA) by amiloride in the cornea and tear fluid of eyes irradiated with UVB. Acta Histochem. 2005;107(1):77-86. Epub 2005 Mar 4. [PubMed:15866288 ]
  6. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]

Enzymes

Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
inhibitor
General Function:
Zinc ion binding
Specific Function:
Catalyzes the degradation of compounds such as putrescine, histamine, spermine, and spermidine, substances involved in allergic and immune responses, cell proliferation, tissue differentiation, tumor formation, and possibly apoptosis. Placental DAO is thought to play a role in the regulation of the female reproductive function.
Gene Name:
AOC1
Uniprot ID:
P19801
Molecular Weight:
85377.1 Da
References
  1. Padiglia A, Medda R, Lorrai A, Murgia B, Pedersen JZ, Finazzi Agro A, Floris G: Interaction of Pig Kidney and Lentil Seedling Copper-Containing Amine Oxidases with Guanidinium Compounds. J Enzyme Inhib. 1999 Nov;15(1):91-100. [PubMed:10938536 ]
  2. Padiglia A, Medda R, Lorrai A, Murgia B, Pedersen JZ, Agro AF, Floris G: Interaction of pig kidney and lentil seedling copper-containing amine oxidases with guanidinium compounds. J Enzyme Inhib. 2000;15(1):91-100. [PubMed:10850957 ]
Kind
Protein
Organism
Pig
Pharmacological action
unknown
Actions
inhibitor
General Function:
Zinc ion binding
Specific Function:
Catalyzes the degradation of compounds such as putrescine, histamine, spermine, and spermidine, substances involved in allergic and immune responses, cell proliferation, tissue differentiation, tumor formation, and possibly apoptosis.
Gene Name:
AOC1
Uniprot ID:
Q9TRC7
Molecular Weight:
85474.24 Da
References
  1. Padiglia A, Medda R, Lorrai A, Murgia B, Pedersen JZ, Finazzi Agro A, Floris G: Interaction of Pig Kidney and Lentil Seedling Copper-Containing Amine Oxidases with Guanidinium Compounds. J Enzyme Inhib. 1999 Nov;15(1):91-100. [PubMed:10938536 ]
  2. Padiglia A, Medda R, Lorrai A, Murgia B, Pedersen JZ, Agro AF, Floris G: Interaction of pig kidney and lentil seedling copper-containing amine oxidases with guanidinium compounds. J Enzyme Inhib. 2000;15(1):91-100. [PubMed:10850957 ]

Transporters

Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
inhibitor
General Function:
Quaternary ammonium group transmembrane transporter activity
Specific Function:
Mediates tubular uptake of organic compounds from circulation. Mediates the influx of agmatine, dopamine, noradrenaline (norepinephrine), serotonin, choline, famotidine, ranitidine, histamin, creatinine, amantadine, memantine, acriflavine, 4-[4-(dimethylamino)-styryl]-N-methylpyridinium ASP, amiloride, metformin, N-1-methylnicotinamide (NMN), tetraethylammonium (TEA), 1-methyl-4-phenylpyridiniu...
Gene Name:
SLC22A2
Uniprot ID:
O15244
Molecular Weight:
62579.99 Da
References
  1. Urakami Y, Okuda M, Masuda S, Akazawa M, Saito H, Inui K: Distinct characteristics of organic cation transporters, OCT1 and OCT2, in the basolateral membrane of renal tubules. Pharm Res. 2001 Nov;18(11):1528-34. [PubMed:11758759 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
inhibitor
General Function:
Secondary active organic cation transmembrane transporter activity
Specific Function:
Translocates a broad array of organic cations with various structures and molecular weights including the model compounds 1-methyl-4-phenylpyridinium (MPP), tetraethylammonium (TEA), N-1-methylnicotinamide (NMN), 4-(4-(dimethylamino)styryl)-N-methylpyridinium (ASP), the endogenous compounds choline, guanidine, histamine, epinephrine, adrenaline, noradrenaline and dopamine, and the drugs quinine...
Gene Name:
SLC22A1
Uniprot ID:
O15245
Molecular Weight:
61153.345 Da
References
  1. Urakami Y, Okuda M, Masuda S, Akazawa M, Saito H, Inui K: Distinct characteristics of organic cation transporters, OCT1 and OCT2, in the basolateral membrane of renal tubules. Pharm Res. 2001 Nov;18(11):1528-34. [PubMed:11758759 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
inhibitor
General Function:
Symporter activity
Specific Function:
Sodium-ion dependent, low affinity carnitine transporter. Probably transports one sodium ion with one molecule of carnitine. Also transports organic cations such as tetraethylammonium (TEA) without the involvement of sodium. Relative uptake activity ratio of carnitine to TEA is 1.78. A key substrate of this transporter seems to be ergothioneine (ET).
Gene Name:
SLC22A4
Uniprot ID:
Q9H015
Molecular Weight:
62154.48 Da
References
  1. Wu X, George RL, Huang W, Wang H, Conway SJ, Leibach FH, Ganapathy V: Structural and functional characteristics and tissue distribution pattern of rat OCTN1, an organic cation transporter, cloned from placenta. Biochim Biophys Acta. 2000 Jun 1;1466(1-2):315-27. [PubMed:10825452 ]
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Drug created on June 13, 2005 07:24 / Updated on August 17, 2016 12:23