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Identification
NameMilrinone
Accession NumberDB00235  (APRD00010)
TypeSmall Molecule
GroupsApproved
DescriptionA positive inotropic cardiotonic agent with vasodilator properties. It inhibits cAMP phosphodiesterase activity in myocardium and vascular smooth muscle. Milrinone is a derivative of amrinone and has 20-30 times the ionotropic potency of amrinone. [PubChem]
Structure
Thumb
Synonyms
1,6-Dihydro-2-methyl-6-oxo(3,4'-bipyridine)-5-carbonitrile
Milrinona
Milrinone
Milrinonum
External Identifiers Not Available
Approved Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Milrinone Injectionsolution1 mgintravenousTeva Canada Limited2003-05-252015-07-22Canada
Milrinone Lactate Injectionsolution1.0 mgintravenousSandoz Canada Incorporated2003-06-25Not applicableCanada
Milrinone Lactate Injectionsolution1.0 mgintravenousFresenius Kabi Canada Ltd2003-07-03Not applicableCanada
Milrinone Lactate Injectionsolution1 mgintravenousSterimax IncNot applicableNot applicableCanada
Milrinone Lactate Injectionsolution1 mgintravenousMylan Pharmaceuticals UlcNot applicableNot applicableCanada
Primacor Injection 1mg/mlsolution1 mgintravenousSanofi Synthelabo Canada Inc1995-12-312005-08-01Canada
Approved Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Apo-milrinone Injectablesolution1.0 mgintravenousApotex Inc2005-07-292013-08-02Canada
Milrinone Lactateinjection1 mg/mLintravenousWest Ward Pharmaceutical Corp.2002-05-28Not applicableUs
Milrinone Lactateinjection, solution50 mg/50mLintravenousWest ward Pharmaceutical Corp2010-12-03Not applicableUs
Milrinone Lactateinjection1 mg/mLintravenousWest Ward Pharmaceutical Corp.2002-05-28Not applicableUs
Milrinone Lactateinjection, solution20 mg/20mLintravenousWest ward Pharmaceutical Corp2010-12-03Not applicableUs
Milrinone Lactateinjection, solution1 mg/mLintravenousHospira, Inc.2014-09-03Not applicableUs
Milrinone Lactateinjection, solution1 mg/mLintravenousFresenius Kabi USA, LLC2002-08-01Not applicableUs
Milrinone Lactateinjection, solution10 mg/10mLintravenousWest ward Pharmaceutical Corp2010-12-03Not applicableUs
Milrinone Lactateinjection, solution200 ug/mLintravenousHospira, Inc.2002-05-28Not applicableUs
Milrinone Lactate In Dextroseinjection, solution200 ug/mLintravenousWest Ward Pharmaceuticals Corp2010-01-21Not applicableUs
Milrinone Lactate In Dextroseinjection, solution.2 mg/mLintravenousBaxter Healthcare Corporation2002-05-28Not applicableUs
Milrinone Lactate In Dextroseinjection, solution200 ug/mLintravenousWest Ward Pharmaceuticals Corp2010-01-21Not applicableUs
Milrinone Lactate In Dextroseinjection, solution.2 mg/mLintravenousBaxter Healthcare Corporation2002-05-28Not applicableUs
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International Brands
NameCompany
CorotropNot Available
CorotropeNot Available
MilrilaNot Available
PrimacorNot Available
Brand mixturesNot Available
Salts
Name/CASStructureProperties
Milrinone Lactate
ThumbNot applicableDBSALT000891
Categories
UNIIJU9YAX04C7
CAS number78415-72-2
WeightAverage: 211.2194
Monoisotopic: 211.074561925
Chemical FormulaC12H9N3O
InChI KeyInChIKey=PZRHRDRVRGEVNW-UHFFFAOYSA-N
InChI
InChI=1S/C12H9N3O/c1-8-11(9-2-4-14-5-3-9)6-10(7-13)12(16)15-8/h2-6H,1H3,(H,15,16)
IUPAC Name
6-methyl-2-oxo-5-(pyridin-4-yl)-1,2-dihydropyridine-3-carbonitrile
SMILES
CC1=C(C=C(C#N)C(=O)N1)C1=CC=NC=C1
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as bipyridines and oligopyridines. These are organic compounds containing two pyridine rings linked to each other.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassPyridines and derivatives
Sub ClassBipyridines and oligopyridines
Direct ParentBipyridines and oligopyridines
Alternative Parents
Substituents
  • Bipyridine
  • 3-pyridinecarbonitrile
  • Methylpyridine
  • Pyridinone
  • Dihydropyridine
  • Hydropyridine
  • Heteroaromatic compound
  • Lactam
  • Azacycle
  • Nitrile
  • Carbonitrile
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Pharmacology
IndicationIndicated for the treatment of congestive heart failure.
PharmacodynamicsMilrinone, a synthetic dimethylxanthine derivative structurally related to theophylline and caffeine, is used in the treatment of peripheral vascular diseases and in the management of cerebrovascular insufficiency, sickle cell disease, and diabetic neuropathy.
Mechanism of actionMilrinone inhibits erythrocyte phosphodiesterase, resulting in an increase in erythrocyte cAMP activity. Subsequently, the erythrocyte membrane becomes more resistant to deformity. Along with erythrocyte activity, Milrinone also decreases blood viscosity by reducing plasma fibrinogen concentrations and increasing fibrinolytic activity.
Related Articles
AbsorptionMilrinone is rapidly and almost completely absorbed after oral administration. Bioavailability is 92% (in healthy volunteers).
Volume of distribution
  • 0.38 liters/kg [intravenous injections of 12.5 mcg/kg to 125 mcg/kg to congestive heart failure patients]
  • 0.45 liters/kg [intravenous infusions of 0.20 mcg/kg/min to 0.70 mcg/kg/min to congestive heart failure patients]
Protein binding70 to 80%
Metabolism

There are five metabolites but the O-glucuronide represents the major pathway of biotransformation.

Route of eliminationThe primary route of excretion of milrinone in man is via the urine.
Half life2.3 hours
Clearance
  • 0.13 L/kg/hr [congestive heart failure patients, following IV injections of 12.5 mcg/kg to 125 mcg/kg]
  • 0.14 L/kg/hr [congestive heart failure patients, following infusions of 0.2 mcg/kg/min to 0.7 mcg/kg/min]
ToxicityLD50 = 0.3 mg/L in rats
Affected organisms
  • Humans and other mammals
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+1.0
Blood Brain Barrier+0.9807
Caco-2 permeable+0.6889
P-glycoprotein substrateNon-substrate0.8041
P-glycoprotein inhibitor INon-inhibitor0.7835
P-glycoprotein inhibitor IINon-inhibitor0.9799
Renal organic cation transporterNon-inhibitor0.8614
CYP450 2C9 substrateNon-substrate0.7016
CYP450 2D6 substrateNon-substrate0.8411
CYP450 3A4 substrateNon-substrate0.5641
CYP450 1A2 substrateInhibitor0.5399
CYP450 2C9 inhibitorNon-inhibitor0.9071
CYP450 2D6 inhibitorNon-inhibitor0.9816
CYP450 2C19 inhibitorNon-inhibitor0.9025
CYP450 3A4 inhibitorNon-inhibitor0.8827
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.7866
Ames testNon AMES toxic0.7822
CarcinogenicityNon-carcinogens0.9351
BiodegradationNot ready biodegradable0.993
Rat acute toxicity2.5820 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.991
hERG inhibition (predictor II)Non-inhibitor0.8941
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Pharmacoeconomics
Manufacturers
  • App pharmaceuticals llc
  • Baxter healthcare corp anesthesia and critical care
  • Baxter healthcare corp anesthesia critical care
  • Bedford laboratories div ben venue laboratories inc
  • Bioniche pharma usa llc
  • Claris lifesciences ltd
  • Gland pharma ltd
  • Hospira inc
  • International medicated systems ltd
  • B braun medical inc
  • Baxter healthcare corp
  • Bedford laboratories
  • Hikma farmaceutica (portugal) sa
  • Sanofi aventis us llc
Packagers
Dosage forms
FormRouteStrength
Injectionintravenous1 mg/mL
Injection, solutionintravenous1 mg/mL
Injection, solutionintravenous10 mg/10mL
Injection, solutionintravenous20 mg/20mL
Injection, solutionintravenous200 ug/mL
Injection, solutionintravenous50 mg/50mL
Injection, solutionintravenous.2 mg/mL
Solutionintravenous1.0 mg
Solutionintravenous1 mg
Prices
Unit descriptionCostUnit
Primacor 0.2 mg/ml-d5w 100 ml1.6USD ml
Milrinone-d5w 20 mg/100 ml1.45USD ml
Milrinone lact 20 mg/20 ml vial1.44USD ml
Milrinone lact 10 mg/10 ml vial1.31USD ml
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
PatentsNot Available
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point>300 °CPhysProp
water solubilitySlightly solubleNot Available
logP0.4Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.209 mg/mLALOGPS
logP1.04ALOGPS
logP0.33ChemAxon
logS-3ALOGPS
pKa (Strongest Acidic)7.54ChemAxon
pKa (Strongest Basic)4.82ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area65.78 Å2ChemAxon
Rotatable Bond Count1ChemAxon
Refractivity61.14 m3·mol-1ChemAxon
Polarizability21.46 Å3ChemAxon
Number of Rings2ChemAxon
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
References
Synthesis ReferenceNot Available
General ReferencesNot Available
External Links
ATC CodesC01CE02
AHFS Codes
  • 24:04.08
PDB EntriesNot Available
FDA labelDownload (491 KB)
MSDSDownload (34.8 KB)
Interactions
Drug Interactions
Drug
AbciximabMilrinone may increase the anticoagulant activities of Abciximab.
AbciximabAbciximab may increase the antiplatelet activities of Milrinone.
AcenocoumarolMilrinone may increase the anticoagulant activities of Acenocoumarol.
Acetylsalicylic acidThe risk or severity of adverse effects can be increased when Milrinone is combined with Acetylsalicylic acid.
Acetylsalicylic acidAcetylsalicylic acid may increase the antiplatelet activities of Milrinone.
AlprostadilMilrinone may increase the antiplatelet activities of Alprostadil.
AlteplaseMilrinone may increase the anticoagulant activities of Alteplase.
ALX-0081Milrinone may increase the anticoagulant activities of ALX-0081.
Aminosalicylic AcidThe risk or severity of adverse effects can be increased when Milrinone is combined with Aminosalicylic Acid.
AnagrelideMilrinone may increase the anticoagulant activities of Anagrelide.
AnagrelideAnagrelide may increase the antiplatelet activities of Milrinone.
AncrodMilrinone may increase the anticoagulant activities of Ancrod.
AnistreplaseMilrinone may increase the anticoagulant activities of Anistreplase.
Antithrombin III humanMilrinone may increase the anticoagulant activities of Antithrombin III human.
ApixabanMilrinone may increase the anticoagulant activities of Apixaban.
ArdeparinMilrinone may increase the anticoagulant activities of Ardeparin.
ArgatrobanMilrinone may increase the anticoagulant activities of Argatroban.
ArgatrobanArgatroban may increase the antiplatelet activities of Milrinone.
AstaxanthinMilrinone may increase the anticoagulant activities of Astaxanthin.
AzelastineMilrinone may increase the antiplatelet activities of Azelastine.
BatroxobinMilrinone may increase the anticoagulant activities of Batroxobin.
BecaplerminMilrinone may increase the anticoagulant activities of Becaplermin.
BemiparinMilrinone may increase the anticoagulant activities of Bemiparin.
BeraprostMilrinone may increase the anticoagulant activities of Beraprost.
BeraprostBeraprost may increase the antiplatelet activities of Milrinone.
BivalirudinMilrinone may increase the anticoagulant activities of Bivalirudin.
CangrelorMilrinone may increase the anticoagulant activities of Cangrelor.
CangrelorCangrelor may increase the antiplatelet activities of Milrinone.
CertoparinMilrinone may increase the anticoagulant activities of Certoparin.
CilostazolMilrinone may increase the anticoagulant activities of Cilostazol.
CilostazolCilostazol may increase the antiplatelet activities of Milrinone.
Citric AcidMilrinone may increase the anticoagulant activities of Citric Acid.
ClopidogrelMilrinone may increase the anticoagulant activities of Clopidogrel.
ClopidogrelClopidogrel may increase the antiplatelet activities of Milrinone.
CollagenaseThe risk or severity of adverse effects can be increased when Milrinone is combined with Collagenase.
Dabigatran etexilateMilrinone may increase the anticoagulant activities of Dabigatran etexilate.
DalteparinMilrinone may increase the anticoagulant activities of Dalteparin.
DanaparoidMilrinone may increase the anticoagulant activities of Danaparoid.
DasatinibDasatinib may increase the anticoagulant activities of Milrinone.
DefibrotideMilrinone may increase the anticoagulant activities of Defibrotide.
DefibrotideDefibrotide may increase the antiplatelet activities of Milrinone.
Deoxycholic AcidThe risk or severity of adverse effects can be increased when Milrinone is combined with Deoxycholic Acid.
DesirudinMilrinone may increase the anticoagulant activities of Desirudin.
DesmoteplaseMilrinone may increase the anticoagulant activities of Desmoteplase.
DextranMilrinone may increase the anticoagulant activities of Dextran.
Dextran 40Milrinone may increase the anticoagulant activities of Dextran 40.
Dextran 70Milrinone may increase the anticoagulant activities of Dextran 70.
Dextran 75Milrinone may increase the anticoagulant activities of Dextran 75.
DicoumarolMilrinone may increase the anticoagulant activities of Dicoumarol.
DiflunisalThe risk or severity of adverse effects can be increased when Milrinone is combined with Diflunisal.
DipyridamoleMilrinone may increase the anticoagulant activities of Dipyridamole.
DipyridamoleDipyridamole may increase the antiplatelet activities of Milrinone.
DitazoleMilrinone may increase the anticoagulant activities of Ditazole.
Drotrecogin alfaMilrinone may increase the anticoagulant activities of Drotrecogin alfa.
Edetic AcidMilrinone may increase the anticoagulant activities of Edetic Acid.
EdoxabanMilrinone may increase the anticoagulant activities of Edoxaban.
EnoxaparinMilrinone may increase the anticoagulant activities of Enoxaparin.
EpinastineMilrinone may increase the antiplatelet activities of Epinastine.
EpoprostenolMilrinone may increase the anticoagulant activities of Epoprostenol.
EpoprostenolEpoprostenol may increase the antiplatelet activities of Milrinone.
EptifibatideMilrinone may increase the anticoagulant activities of Eptifibatide.
EptifibatideEptifibatide may increase the antiplatelet activities of Milrinone.
Ethyl biscoumacetateMilrinone may increase the anticoagulant activities of Ethyl biscoumacetate.
FibrinolysinMilrinone may increase the anticoagulant activities of Fibrinolysin.
Fondaparinux sodiumMilrinone may increase the anticoagulant activities of Fondaparinux sodium.
GlucosamineGlucosamine may increase the antiplatelet activities of Milrinone.
HeparinMilrinone may increase the anticoagulant activities of Heparin.
HirulogMilrinone may increase the anticoagulant activities of Hirulog.
Ibritumomab tiuxetanThe risk or severity of adverse effects can be increased when Milrinone is combined with Ibritumomab tiuxetan.
IbrutinibThe risk or severity of adverse effects can be increased when Ibrutinib is combined with Milrinone.
IbudilastMilrinone may increase the antiplatelet activities of Ibudilast.
Icosapent ethylMilrinone may increase the antiplatelet activities of Icosapent ethyl.
IfenprodilMilrinone may increase the antiplatelet activities of Ifenprodil.
IloprostMilrinone may increase the anticoagulant activities of Iloprost.
IloprostIloprost may increase the antiplatelet activities of Milrinone.
LepirudinMilrinone may increase the anticoagulant activities of Lepirudin.
LimaprostLimaprost may increase the antiplatelet activities of Milrinone.
MesalazineThe risk or severity of adverse effects can be increased when Milrinone is combined with Mesalazine.
NadroparinMilrinone may increase the anticoagulant activities of Nadroparin.
NCX 4016Milrinone may increase the anticoagulant activities of NCX 4016.
NCX 4016NCX 4016 may increase the antiplatelet activities of Milrinone.
NimesulideMilrinone may increase the antiplatelet activities of Nimesulide.
ObinutuzumabThe risk or severity of adverse effects can be increased when Milrinone is combined with Obinutuzumab.
Omega-3 fatty acidsOmega-3 fatty acids may increase the antiplatelet activities of Milrinone.
OtamixabanMilrinone may increase the anticoagulant activities of Otamixaban.
ParnaparinMilrinone may increase the anticoagulant activities of Parnaparin.
Pentosan PolysulfateThe risk or severity of adverse effects can be increased when Pentosan Polysulfate is combined with Milrinone.
Pentosan PolysulfateMilrinone may increase the anticoagulant activities of Pentosan Polysulfate.
PentoxifyllinePentoxifylline may increase the antiplatelet activities of Milrinone.
PhenindioneMilrinone may increase the anticoagulant activities of Phenindione.
PhenprocoumonMilrinone may increase the anticoagulant activities of Phenprocoumon.
PlasminMilrinone may increase the anticoagulant activities of Plasmin.
PrasugrelMilrinone may increase the anticoagulant activities of Prasugrel.
PrasugrelPrasugrel may increase the antiplatelet activities of Milrinone.
Protein CMilrinone may increase the anticoagulant activities of Protein C.
ProtocatechualdehydeMilrinone may increase the anticoagulant activities of Protocatechualdehyde.
ResveratrolMilrinone may increase the antiplatelet activities of Resveratrol.
ReteplaseMilrinone may increase the anticoagulant activities of Reteplase.
ReviparinMilrinone may increase the anticoagulant activities of Reviparin.
RidogrelMilrinone may increase the antiplatelet activities of Ridogrel.
RiociguatMilrinone may increase the hypotensive activities of Riociguat.
RivaroxabanMilrinone may increase the anticoagulant activities of Rivaroxaban.
RosiglitazoneMilrinone may increase the anticoagulant activities of Rosiglitazone.
Salicylic acidThe risk or severity of adverse effects can be increased when Milrinone is combined with Salicylic acid.
SCH-530348Milrinone may increase the antiplatelet activities of SCH-530348.
SelexipagMilrinone may increase the anticoagulant activities of Selexipag.
SevofluraneMilrinone may increase the antiplatelet activities of Sevoflurane.
SRT501Milrinone may increase the antiplatelet activities of SRT501.
StreptokinaseMilrinone may increase the anticoagulant activities of Streptokinase.
SulodexideMilrinone may increase the anticoagulant activities of Sulodexide.
TenecteplaseMilrinone may increase the anticoagulant activities of Tenecteplase.
TesmilifeneMilrinone may increase the antiplatelet activities of Tesmilifene.
TicagrelorMilrinone may increase the anticoagulant activities of Ticagrelor.
TiclopidineMilrinone may increase the anticoagulant activities of Ticlopidine.
TiclopidineTiclopidine may increase the antiplatelet activities of Milrinone.
TinzaparinMilrinone may increase the anticoagulant activities of Tinzaparin.
TipranavirTipranavir may increase the antiplatelet activities of Milrinone.
TirofibanMilrinone may increase the anticoagulant activities of Tirofiban.
TirofibanTirofiban may increase the antiplatelet activities of Milrinone.
TositumomabThe risk or severity of adverse effects can be increased when Milrinone is combined with Tositumomab.
TranilastMilrinone may increase the antiplatelet activities of Tranilast.
TrapidilMilrinone may increase the antiplatelet activities of Trapidil.
TreprostinilMilrinone may increase the anticoagulant activities of Treprostinil.
TreprostinilTreprostinil may increase the antiplatelet activities of Milrinone.
TriflusalMilrinone may increase the anticoagulant activities of Triflusal.
TriflusalTriflusal may increase the antiplatelet activities of Milrinone.
UrokinaseMilrinone may increase the anticoagulant activities of Urokinase.
Vitamin EVitamin E may increase the antiplatelet activities of Milrinone.
VorapaxarMilrinone may increase the anticoagulant activities of Vorapaxar.
VorapaxarVorapaxar may increase the antiplatelet activities of Milrinone.
WarfarinMilrinone may increase the anticoagulant activities of Warfarin.
XimelagatranMilrinone may increase the anticoagulant activities of Ximelagatran.
Food InteractionsNot Available

Targets

Kind
Protein
Organism
Human
Pharmacological action
yes
Actions
inhibitor
General Function:
Metal ion binding
Specific Function:
Cyclic nucleotide phosphodiesterase with a dual-specificity for the second messengers cAMP and cGMP, which are key regulators of many important physiological processes.
Gene Name:
PDE3A
Uniprot ID:
Q14432
Molecular Weight:
124978.06 Da
References
  1. Cone J, Wang S, Tandon N, Fong M, Sun B, Sakurai K, Yoshitake M, Kambayashi J, Liu Y: Comparison of the effects of cilostazol and milrinone on intracellular cAMP levels and cellular function in platelets and cardiac cells. J Cardiovasc Pharmacol. 1999 Oct;34(4):497-504. [PubMed:10511123 ]
  2. Kuthe A, Magert H, Uckert S, Forssmann WG, Stief CG, Jonas U: Gene expression of the phosphodiesterases 3A and 5A in human corpus cavernosum penis. Eur Urol. 2000 Jul;38(1):108-14. [PubMed:10859452 ]
  3. Lefievre L, de Lamirande E, Gagnon C: Presence of cyclic nucleotide phosphodiesterases PDE1A, existing as a stable complex with calmodulin, and PDE3A in human spermatozoa. Biol Reprod. 2002 Aug;67(2):423-30. [PubMed:12135876 ]
  4. Zhang W, Ke H, Colman RW: Identification of interaction sites of cyclic nucleotide phosphodiesterase type 3A with milrinone and cilostazol using molecular modeling and site-directed mutagenesis. Mol Pharmacol. 2002 Sep;62(3):514-20. [PubMed:12181427 ]
  5. Shakur Y, Fong M, Hensley J, Cone J, Movsesian MA, Kambayashi J, Yoshitake M, Liu Y: Comparison of the effects of cilostazol and milrinone on cAMP-PDE activity, intracellular cAMP and calcium in the heart. Cardiovasc Drugs Ther. 2002 Sep;16(5):417-27. [PubMed:12652111 ]
  6. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
Comments
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Drug created on June 13, 2005 07:24 / Updated on August 17, 2016 12:23