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Identification
NameLosartan
Accession NumberDB00678  (APRD00052)
TypeSmall Molecule
GroupsApproved
Description

Losartan is an angiotensin-receptor blocker (ARB) that may be used alone or with other agents to treat hypertension. Losartan and its longer acting metabolite, E-3174, lower blood pressure by antagonizing the renin-angiotensin-aldosterone system (RAAS); they compete with angiotensin II for binding to the type-1 angiotensin II receptor (AT1) subtype and prevents the blood pressure increasing effects of angiotensin II. Unlike angiotensin-converting enzyme (ACE) inhibitors, ARBs do not have the adverse effect of dry cough. Losartan may be used to treat hypertension, isolated systolic hypertension, left ventricular hypertrophy and diabetic nephropathy. It may also be used as an alternative agent for the treatment of systolic dysfunction, myocardial infarction, coronary artery disease, and heart failure.

Structure
Thumb
Synonyms
SynonymLanguageCode
(2-Butyl-4-chloro-1-{[2'-(1H-tetrazol-5-yl)biphenyl-4-yl]methyl}-1H-imidazol-5-yl)methanolNot AvailableNot Available
2-N-Butyl-4-chloro-5-hydroxymethyl-1-[(2'-(1H-tetrazol-5-yl)biphenyl-4-yl)methyl]imidazoleNot AvailableNot Available
DuP 89Not AvailableNot Available
LosartanNot AvailableNot Available
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Hyzaartablet, film coated12.5; 50 mg/1; mgoralMerck Sharp & Dohme Corp.1995-04-28Not AvailableUs
Hyzaartablet, film coated12.5; 100 mg/1; mgoralMerck Sharp & Dohme Corp.1995-04-28Not AvailableUs
Hyzaartablet, film coated25; 100 mg/1; mgoralMerck Sharp & Dohme Corp.1995-04-28Not AvailableUs
Cozaartablet, film coated25 mgoralMerck Sharp & Dohme Corp.1995-04-14Not AvailableUs
Cozaartablet, film coated50 mgoralMerck Sharp & Dohme Corp.1995-04-14Not AvailableUs
Cozaartablet, film coated100 mgoralMerck Sharp & Dohme Corp.1995-04-14Not AvailableUs
Losartan Potassiumtablet, film coated25 mgoralSandoz Inc.1995-04-14Not AvailableUs
Losartan Potassiumtablet, film coated50 mgoralSandoz Inc.1995-04-14Not AvailableUs
Losartan Potassiumtablet, film coated100 mgoralSandoz Inc.1995-04-14Not AvailableUs
Hyzaartablet, film coated25; 100 mg/1; mgoralRebel Distributors Corp1995-04-28Not AvailableUs
Hyzaartablet, film coated12.5; 50 mg/1; mgoralAphena Pharma Solutions Tennessee, Llc1995-04-28Not AvailableUs
Cozaartablet25 mgoralREMEDYREPACK INC.2011-04-07Not AvailableUs
Cozaartablet, film coated100 mgoralREMEDYREPACK INC.2011-04-22Not AvailableUs
Cozaartablet, film coated25 mgoralREMEDYREPACK INC.2011-05-19Not AvailableUs
Cozaartablet, film coated100 mgoralPhysicians Total Care, Inc.2003-08-06Not AvailableUs
Cozaartablet, film coated50 mgoralPhysicians Total Care, Inc.1996-04-01Not AvailableUs
Hyzaartablet, film coated25; 100 mg/1; mgoralPhysicians Total Care, Inc.2004-04-09Not AvailableUs
Cozaartablet, film coated25 mgoralPhysicians Total Care, Inc.2004-06-02Not AvailableUs
Cozaartablet, film coated25 mgoralCardinal Health1995-04-14Not AvailableUs
Cozaartablet, film coated50 mgoralCardinal Health1995-04-14Not AvailableUs
Cozaartablet, film coated100 mgoralPd Rx Pharmaceuticals, Inc.1995-04-14Not AvailableUs
Hyzaartablet, film coated25; 100 mg/1; mgoralPd Rx Pharmaceuticals, Inc.1995-04-28Not AvailableUs
Cozaartablet, film coated50 mgoralbryant ranch prepack1995-04-14Not AvailableUs
Cozaartablet, film coated100 mgoralbryant ranch prepack1995-04-14Not AvailableUs
Hyzaartablet, film coated12.5; 50 mg/1; mgoralbryant ranch prepack1995-04-28Not AvailableUs
Cozaartablet100 mgoralMerck Canada IncNot AvailableNot AvailableCanada
Cozaartablet25 mgoralMerck Canada IncNot AvailableNot AvailableCanada
Cozaartablet50 mgoralMerck Canada IncNot AvailableNot AvailableCanada
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Losartan Potassiumtablet25 mgoralRoxane Laboratories, Inc.2010-10-06Not AvailableUs
Losartan Potassiumtablet50 mgoralRoxane Laboratories, Inc.2010-10-06Not AvailableUs
Losartan Potassiumtablet100 mgoralRoxane Laboratories, Inc.2010-10-06Not AvailableUs
Losartan Potassiumtablet, film coated25 mgoralTeva Pharmaceuticals USA Inc2010-04-06Not AvailableUs
Losartan Potassiumtablet, film coated50 mgoralTeva Pharmaceuticals USA Inc2010-04-06Not AvailableUs
Losartan Potassiumtablet, film coated100 mgoralTeva Pharmaceuticals USA Inc2010-04-06Not AvailableUs
Losartan Potassiumtablet, film coated25 mgoralMylan Pharmaceuticals Inc.2012-12-06Not AvailableUs
Losartan Potassiumtablet, film coated50 mgoralMylan Pharmaceuticals Inc.2012-12-06Not AvailableUs
Losartan Potassiumtablet, film coated100 mgoralMylan Pharmaceuticals Inc.2012-12-06Not AvailableUs
Losartan Potassiumtablet, film coated25 mgoralWatson Laboratories, Inc.2011-02-22Not AvailableUs
Losartan Potassiumtablet, film coated50 mgoralWatson Laboratories, Inc.2011-02-22Not AvailableUs
Losartan Potassiumtablet, film coated100 mgoralWatson Laboratories, Inc.2011-02-22Not AvailableUs
Losartan Potassiumtablet, film coated25 mgoralQualitest Pharmaceuticals2012-01-04Not AvailableUs
Losartan Potassiumtablet, film coated50 mgoralQualitest Pharmaceuticals2012-01-04Not AvailableUs
Losartan Potassiumtablet, film coated100 mgoralQualitest Pharmaceuticals2012-01-04Not AvailableUs
Losartan Potassiumtablet, film coated100 mgoralNcs Health Care Of Ky, Inc Dba Vangard Labs2010-04-06Not AvailableUs
Losartan Potassiumtablet, film coated50 mgoralNcs Health Care Of Ky, Inc Dba Vangard Labs2010-04-06Not AvailableUs
Losartan Potassiumtablet, film coated25 mgoralNcs Health Care Of Ky, Inc Dba Vangard Labs2010-04-06Not AvailableUs
Losartan Potassiumtablet, film coated25 mgoralSandoz Inc2010-10-06Not AvailableUs
Losartan Potassiumtablet, film coated50 mgoralSandoz Inc2010-10-06Not AvailableUs
Losartan Potassiumtablet, film coated100 mgoralSandoz Inc2010-10-06Not AvailableUs
Losartan Potassiumtablet100 mgoralMajor Pharmaceuticals2014-06-09Not AvailableUs
Losartan Potassiumtablet50 mgoralMajor Pharmaceuticals2014-06-09Not AvailableUs
Losartan Potassiumtablet25 mgoralMajor Pharmaceuticals2014-06-09Not AvailableUs
Losartan Potassiumtablet25 mgoralTorrent Pharmaceuticals Limited2010-10-06Not AvailableUs
Losartan Potassiumtablet100 mgoralTorrent Pharmaceuticals Limited2010-10-06Not AvailableUs
Losartan Potassiumtablet50 mgoralTorrent Pharmaceuticals Limited2010-10-06Not AvailableUs
Losartan Potassiumtablet, film coated25 mgoralPACK Pharmaceuticals, LLC2011-06-01Not AvailableUs
Losartan Potassiumtablet, film coated50 mgoralPACK Pharmaceuticals, LLC2014-07-30Not AvailableUs
Losartan Potassiumtablet, film coated100 mgoralPACK Pharmaceuticals, LLC2014-07-30Not AvailableUs
Losartan Potassiumtablet100 mgoralSTAT Rx USA LLC2010-10-06Not AvailableUs
Losartan Potassiumtablet, film coated25 mgoralNorth Star Rx Llc2010-10-03Not AvailableUs
Losartan Potassiumtablet, film coated50 mgoralNorth Star Rx Llc2010-10-03Not AvailableUs
Losartan Potassiumtablet, film coated100 mgoralNorth Star Rx Llc2010-10-03Not AvailableUs
Losartan Potassiumtablet, film coated25 mgoralMacleods Pharmaceuticals Limited2012-05-10Not AvailableUs
Losartan Potassiumtablet, film coated50 mgoralMacleods Pharmaceuticals Limited2012-06-01Not AvailableUs
Losartan Potassiumtablet, film coated100 mgoralMacleods Pharmaceuticals Limited2012-06-01Not AvailableUs
Losartan Potassiumtablet100 mgoralLake Erie Medical DBA Quality Care Products LLC2010-10-06Not AvailableUs
Losartan Potassiumtablet50 mgoralLake Erie Medical DBA Quality Care Products LLC2010-10-06Not AvailableUs
Losartan Potassiumtablet25 mgoralLake Erie Medical DBA Quality Care Products LLC2010-10-06Not AvailableUs
Losartan Potassiumtablet, film coated25 mgoralMicro Labs Limited2012-12-06Not AvailableUs
Losartan Potassiumtablet, film coated50 mgoralMicro Labs Limited2012-12-06Not AvailableUs
Losartan Potassiumtablet, film coated100 mgoralMicro Labs Limited2012-12-06Not AvailableUs
Losartan Potassiumtablet, film coated25 mgoralPd Rx Pharmaceuticals, Inc.2010-10-06Not AvailableUs
Losartan Potassiumtablet, film coated50 mgoralPd Rx Pharmaceuticals, Inc.2010-10-06Not AvailableUs
Losartan Potassiumtablet, film coated100 mgoralPd Rx Pharmaceuticals, Inc.2010-10-06Not AvailableUs
Losartan Potassiumtablet25 mgoralREMEDYREPACK INC.2011-07-15Not AvailableUs
Losartan Potassiumtablet25 mgoralREMEDYREPACK INC.2011-12-07Not AvailableUs
Losartan Potassiumtablet50 mgoralREMEDYREPACK INC.2013-03-08Not AvailableUs
Losartan Potassiumtablet25 mgoralAv Pak2014-03-27Not AvailableUs
Losartan Potassiumtablet50 mgoralAv Pak2014-03-27Not AvailableUs
Losartan Potassiumtablet100 mgoralAv Pak2014-03-27Not AvailableUs
Losartan Potassiumtablet25 mgoralUnit Dose Services2010-10-06Not AvailableUs
Losartan Potassiumtablet50 mgoralUnit Dose Services2010-10-06Not AvailableUs
Losartan Potassiumtablet100 mgoralUnit Dose Services2010-10-06Not AvailableUs
Losartan Potassiumtablet50 mgoralREMEDYREPACK INC.2013-02-26Not AvailableUs
Losartan Potassiumtablet50 mgoralREMEDYREPACK INC.2014-12-16Not AvailableUs
Losartan Potassiumtablet, film coated100 mgoralREMEDYREPACK INC.2012-12-27Not AvailableUs
Losartan Potassiumtablet100 mgoralREMEDYREPACK INC.2013-05-14Not AvailableUs
Losartan Potassiumtablet50 mgoralREMEDYREPACK INC.2013-05-30Not AvailableUs
Losartan Potassiumtablet50 mgoralREMEDYREPACK INC.2013-05-15Not AvailableUs
Losartan Potassiumtablet25 mgoralREMEDYREPACK INC.2014-04-09Not AvailableUs
Losartan Potassiumtablet, film coated50 mgoralState of Florida DOH Central Pharmacy2014-01-01Not AvailableUs
Losartan Potassiumtablet, film coated25 mgoralState of Florida DOH Central Pharmacy2014-01-01Not AvailableUs
Losartan Potassiumtablet100 mgoralState of Florida DOH Central Pharmacy2013-01-01Not AvailableUs
Losartan Potassiumtablet50 mgoralState of Florida DOH Central Pharmacy2014-01-01Not AvailableUs
Losartan Potassiumtablet, film coated50 mgoralPhysicians Total Care, Inc.2010-04-13Not AvailableUs
Losartan Potassiumtablet, film coated100 mgoralPhysicians Total Care, Inc.2010-04-13Not AvailableUs
Losartan Potassiumtablet, film coated25 mgoralPhysicians Total Care, Inc.2010-04-27Not AvailableUs
Losartan Potassiumtablet, film coated50 mgoralCardinal Health2011-08-12Not AvailableUs
Losartan Potassiumtablet100 mgoralClinical Solutions Wholesale2010-10-06Not AvailableUs
Losartan Potassiumtablet50 mgoralClinical Solutions Wholesale2010-10-06Not AvailableUs
Losartan Potassiumtablet, film coated100 mgoralClinical Solutions Wholesale2010-04-06Not AvailableUs
Losartan Potassiumtablet, film coated25 mgoralGolden State Medical Supply, Inc.2011-02-22Not AvailableUs
Losartan Potassiumtablet, film coated50 mgoralGolden State Medical Supply, Inc.2011-02-22Not AvailableUs
Losartan Potassiumtablet, film coated100 mgoralGolden State Medical Supply, Inc.2011-02-22Not AvailableUs
Losartan Potassiumtablet, film coated25 mgoralApotex Corp2010-10-03Not AvailableUs
Losartan Potassiumtablet, film coated50 mgoralApotex Corp2010-10-03Not AvailableUs
Losartan Potassiumtablet, film coated100 mgoralApotex Corp2010-10-03Not AvailableUs
Losartan Potassiumtablet50 mgoralSt Marys Medical Park Pharmacy2013-07-11Not AvailableUs
Losartan Potassiumtablet100 mgoralSt Marys Medical Park Pharmacy2013-07-11Not AvailableUs
Losartan Potassiumtablet25 mgoralSt Marys Medical Park Pharmacy2014-04-21Not AvailableUs
Losartan Potassiumtablet, film coated25 mgoralEndo Pharmaceuticals Inc. DBA Endo Generic Products2010-11-12Not AvailableUs
Losartan Potassiumtablet, film coated50 mgoralEndo Pharmaceuticals Inc. DBA Endo Generic Products2010-11-12Not AvailableUs
Losartan Potassiumtablet, film coated100 mgoralEndo Pharmaceuticals Inc. DBA Endo Generic Products2010-11-12Not AvailableUs
Losartan Potassiumtablet100 mgoralDIRECT RX2014-01-01Not AvailableUs
Losartan Potassiumtablet, film coated25 mgoralbryant ranch prepack2010-10-03Not AvailableUs
Losartan Potassiumtablet, film coated25 mgoralMc Kesson Packaging Services A Business Unit Of Mc Kesson Corporation2010-10-03Not AvailableUs
Losartan Potassiumtablet, film coated50 mgoralMc Kesson Packaging Services A Business Unit Of Mc Kesson Corporation2010-10-03Not AvailableUs
Losartan Potassiumtablet, film coated100 mgoralMc Kesson Packaging Services A Business Unit Of Mc Kesson Corporation2010-10-03Not AvailableUs
Losartan Potassiumtablet, film coated50 mgoralReady Meds2012-01-04Not AvailableUs
Losartan Potassiumtablet, film coated100 mgoralReady Meds2012-01-04Not AvailableUs
Losartan Potassiumtablet, film coated25 mgoralCadila Healthcare Limited2010-10-04Not AvailableUs
Losartan Potassiumtablet, film coated50 mgoralCadila Healthcare Limited2010-10-04Not AvailableUs
Losartan Potassiumtablet, film coated100 mgoralCadila Healthcare Limited2010-10-04Not AvailableUs
Losartan Potassiumtablet, film coated25 mgoralAurobindo Pharma Limited2010-10-06Not AvailableUs
Losartan Potassiumtablet, film coated50 mgoralAurobindo Pharma Limited2010-10-06Not AvailableUs
Losartan Potassiumtablet, film coated100 mgoralAurobindo Pharma Limited2010-10-06Not AvailableUs
Losartan Potassiumtablet, film coated50 mgoralMed Vantx, Inc.2010-10-03Not AvailableUs
Losartan Potassiumtablet, film coated50 mgoralMed Vantx, Inc.2010-12-28Not AvailableUs
Losartan Potassiumtablet, film coated50 mgoralDispensing Solutions, Inc.2010-12-28Not AvailableUs
Losartan Potassiumtablet, film coated25 mgoralDispensing Solutions, Inc.2010-12-28Not AvailableUs
Losartan Potassiumtablet25 mgoralCarilion Materials Management2010-10-06Not AvailableUs
Losartan Potassiumtablet, film coated50 mgoralCarilion Materials Management2010-04-06Not AvailableUs
Losartan Potassiumtablet25 mgoralLupin Pharmaceuticals, Inc.2010-10-06Not AvailableUs
Losartan Potassiumtablet50 mgoralLupin Pharmaceuticals, Inc.2010-10-06Not AvailableUs
Losartan Potassiumtablet100 mgoralLupin Pharmaceuticals, Inc.2010-10-06Not AvailableUs
Losartan Potassiumtablet25 mgoralLegacy Pharmaceutical Packaging2010-10-06Not AvailableUs
Losartan Potassiumtablet, film coated25 mgoralLegacy Pharmaceutical Packaging2010-04-06Not AvailableUs
Losartan Potassiumtablet50 mgoralLegacy Pharmaceutical Packaging2011-02-21Not AvailableUs
Losartan Potassiumtablet, film coated50 mgoralLegacy Pharmaceutical Packaging2010-04-06Not AvailableUs
Losartan Potassiumtablet100 mgoralLegacy Pharmaceutical Packaging2010-10-06Not AvailableUs
Losartan Potassiumtablet, film coated100 mgoralLegacy Pharmaceutical Packaging2010-04-06Not AvailableUs
Losartan Potassiumtablet, film coated50 mgoralLegacy Pharmaceutical Packaging2010-10-03Not AvailableUs
Losartan Potassiumtablet50 mgoralLegacy Pharmaceutical Packaging2010-10-06Not AvailableUs
Losartan Potassiumtablet50 mgoralPreferred Pharmaceuticals, Inc.2013-06-06Not AvailableUs
Losartan Potassiumtablet, film coated50 mgoralPreferred Pharmaceuticals, Inc.2011-03-21Not AvailableUs
Losartan Potassiumtablet, film coated50 mgoralPreferred Pharmaceuticals, Inc.2013-01-25Not AvailableUs
Losartan Potassiumtablet50 mgoralLife Line Home Care Services, Inc.2010-10-06Not AvailableUs
Losartan Potassiumtablet, film coated50 mgoralMc Kesson Contract Packaging2013-04-10Not AvailableUs
Losartan Potassiumtablet, film coated25 mgoralVirtus Pharmaceuticals LLC2014-03-25Not AvailableUs
Losartan Potassiumtablet, film coated50 mgoralVirtus Pharmaceuticals LLC2014-03-25Not AvailableUs
Losartan Potassiumtablet, film coated100 mgoralVirtus Pharmaceuticals LLC2014-03-25Not AvailableUs
Losartantablet25.0 mgoralSivem Pharmaceuticals UlcNot AvailableNot AvailableCanada
Losartantablet50.0 mgoralSivem Pharmaceuticals UlcNot AvailableNot AvailableCanada
Losartantablet100.0 mgoralSivem Pharmaceuticals UlcNot AvailableNot AvailableCanada
Losartantablet25 mgoralSanis Health IncNot AvailableNot AvailableCanada
Losartantablet50 mgoralSanis Health IncNot AvailableNot AvailableCanada
Losartantablet100 mgoralSanis Health IncNot AvailableNot AvailableCanada
Losartantablet25 mgoralPro Doc LimiteeNot AvailableNot AvailableCanada
Losartantablet50 mgoralPro Doc LimiteeNot AvailableNot AvailableCanada
Losartantablet100 mgoralPro Doc LimiteeNot AvailableNot AvailableCanada
Over the Counter ProductsNot Available
International Brands
NameCompany
LortaanNot Available
Brand mixtures
Brand NameIngredients
AnzaplusLosartan + Hydrochlorothiazide
HyzaarLosartan + Hydrochlorothiazide
Salts
Name/CASStructureProperties
Losartan Potassium
Thumb
  • InChI Key: OXCMYAYHXIHQOA-UHFFFAOYSA-N
  • Monoisotopic Mass: 460.118068924
  • Average Mass: 461.001
DBSALT000112
Categories
CAS number114798-26-4
WeightAverage: 422.911
Monoisotopic: 422.162187095
Chemical FormulaC22H23ClN6O
InChI KeyPSIFNNKUMBGKDQ-UHFFFAOYSA-N
InChI
InChI=1S/C22H23ClN6O/c1-2-3-8-20-24-21(23)19(14-30)29(20)13-15-9-11-16(12-10-15)17-6-4-5-7-18(17)22-25-27-28-26-22/h4-7,9-12,30H,2-3,8,13-14H2,1H3,(H,25,26,27,28)
IUPAC Name
[2-butyl-4-chloro-1-({4-[2-(2H-1,2,3,4-tetrazol-5-yl)phenyl]phenyl}methyl)-1H-imidazol-5-yl]methanol
SMILES
CCCCC1=NC(Cl)=C(CO)N1CC1=CC=C(C=C1)C1=CC=CC=C1C1=NNN=N1
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as biphenyltetrazoles and derivatives. These are organic compounds containing a biphenyl attached to a tetrazole. A carbon atom of the biphenyl moiety is boned to a carbon or the nitrogen atom of the tetrazole moiety.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassAzoles
Sub ClassTetrazoles
Direct ParentBiphenyltetrazoles and derivatives
Alternative Parents
Substituents
  • Biphenyltetrazole
  • Biphenyl
  • 1,2,4,5-tetrasubstituted imidazole
  • Phenylmethylamine
  • Benzenoid
  • N-substituted imidazole
  • Monocyclic benzene moiety
  • Aryl halide
  • Aryl chloride
  • Heteroaromatic compound
  • Imidazole
  • Azacycle
  • Hydrocarbon derivative
  • Aromatic alcohol
  • Primary alcohol
  • Organooxygen compound
  • Organonitrogen compound
  • Organochloride
  • Organohalogen compound
  • Alcohol
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Pharmacology
IndicationMay be used as a first line agent to treat uncomplicated hypertension, isolated systolic hypertension and left ventricular hypertrophy. May be used as a first line agent to delay progression of diabetic nephropathy. Losartan may be also used as a second line agent in the treatment of congestive heart failure, systolic dysfunction, myocardial infarction and coronary artery disease in those intolerant of ACE inhibitors.
PharmacodynamicsLosartan is the first of a class of antihypertensive agents called angiotensin II receptor blockers (ARBs). Losartan and its longer acting active metabolite, E-3174, are specific and selective type-1 angiotensin II receptor (AT1) antagonists which block the blood pressure increasing effects angiotensin II via the renin-angiotensin-aldosterone system (RAAS). RAAS is a homeostatic mechanism for regulating hemodynamics, water and electrolyte balance. During sympathetic stimulation or when renal blood pressure or blood flow is reduced, renin is released from granular cells of the juxtaglomerular apparatus in the kidneys. Renin cleaves circulating angiotensinogen to angiotensin I, which is cleaved by angiotensin converting enzyme (ACE) to angiotensin II. Angiotensin II increases blood pressure by increasing total peripheral resistance, increasing sodium and water reabsorption in the kidneys via aldosterone secretion, and altering cardiovascular structure. Angiotensin II binds to two receptors: AT1 and type-2 angiotensin II receptor (AT2). AT1 is a G-protein coupled receptor (GPCR) that mediates the vasoconstrictive and aldosterone-secreting effects of angiotensin II. Studies performed in recent years suggest that AT2 antagonizes AT1-mediated effects and directly affects long-term blood pressure control by inducing vasorelaxation and increasing urinary sodium excretion. Angiotensin receptor blockers (ARBs) are non-peptide competitive inhibitors of AT1. ARBs block the ability of angiotensin II to stimulate pressor and cell proliferative effects. Unlike ACE inhibitors, ARBs do not affect bradykinin-induced vasodilation. The overall effect of ARBs is a decrease in blood pressure.
Mechanism of actionLosartan competitively inhibits the binding of angiotensin II to AT1 in many tissues including vascular smooth muscle and the adrenal glands. Losartan is metabolized to its active metabolite, E-3174, which is 10 to 40 times more potent than losartan and acts as a non-competitive AT1 antagonist. Inhibition of angiotensin II binding to AT1 inhibits its AT1-mediated vasoconstrictive and aldosterone-secreting effects and results in decreased vascular resistance and blood pressure. Losartan is 1,000 times more selective for AT1 than AT2. Inhibition of aldosterone secretion may increase sodium and water excretion while decreasing potassium excretion. Losartan is effective for reducing blood pressure and may be used to treat essential hypertension, left ventricular hypertrophy and diabetic nephropathy.
AbsorptionLosartan is well absorbed and undergoes substantial first-pass metabolism; the systemic bioavailability of losartan is approximately 33%. Mean peak concentrations of losartan and its active metabolite are reached in 1 hour and in 3-4 hours, respectively. While maximum plasma concentrations of losartan and its active metabolite are approximately equal, the AUC of the metabolite is about 4 times as great as that of losartan. When given with a meal, absorption is slows down and Cmax decreases.
Volume of distribution
  • 34 L [losartan, healthy subjects]
  • 12 L [active metabolite, healthy subjects]
Protein binding99.7% protein bound, primarily to albumin
Metabolism

Hepatic. Losartan is metabolized to a 5-carboxylic acid derivative (E-3174) via an aldehyde intermediate (E-3179) primarily by cytochrome P450 (CYP) 2C9 and CYP3A4. E-3174 is an active metabolite with 10- to 40-fold higher potency than its parent compound, losartan. Approxiamtely 14% of losartan is converted to E-3174; however, the AUC of E-3174 was found to be 4- to 8-fold higher than losartan and E-3174 is considered the main contributor to the pharmacologic effects of this medication.

SubstrateEnzymesProduct
Losartan
E-3179Details
Losartan
Losartan N2-glucuronideDetails
E-3179
E-3174Details
Route of eliminationFollowing oral administration of losartan, 35% of the dose is recovered in the urine and about 60% in the feces. Following an intravenous dose, 45% is recovered in the urine and 50% in the feces.
Half lifeThe terminal t1/2 of losartan is 2 hours. The active metabolite has a half-life of 6-9 hours.
Clearance
  • Total plasma clearance = 600 mL/min [losartan]
  • Total plasma clearance = 50 mL/min [active metabolite]
  • Renal clearance = 75 mL/min [losartan]
  • Renal clearance = 25 mL/min [active metabolite]
ToxicityHypotension and tachycardia; Bradycardia could occur from parasympathetic (vagal) stimulation, LD50= 1000 mg/kg (orally in rat)
Affected organisms
  • Humans and other mammals
Pathways
PathwayCategorySMPDB ID
Losartan Action PathwayDrug actionSMP00162
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+1.0
Blood Brain Barrier-0.7812
Caco-2 permeable-0.8957
P-glycoprotein substrateSubstrate0.6993
P-glycoprotein inhibitor INon-inhibitor0.8782
P-glycoprotein inhibitor IIInhibitor0.5309
Renal organic cation transporterNon-inhibitor0.5689
CYP450 2C9 substrateNon-substrate0.6839
CYP450 2D6 substrateNon-substrate0.9115
CYP450 3A4 substrateNon-substrate0.6226
CYP450 1A2 substrateInhibitor0.5514
CYP450 2C9 substrateNon-inhibitor0.5423
CYP450 2D6 substrateNon-inhibitor0.8102
CYP450 2C19 substrateInhibitor0.6288
CYP450 3A4 substrateInhibitor0.796
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.7049
Ames testNon AMES toxic0.5382
CarcinogenicityNon-carcinogens0.6595
BiodegradationNot ready biodegradable1.0
Rat acute toxicity2.6055 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Strong inhibitor0.5781
hERG inhibition (predictor II)Inhibitor0.8084
Pharmacoeconomics
Manufacturers
  • Merck research laboratories div merck co inc
  • Teva pharmaceuticals usa inc
  • Merck & Co., Inc.
Packagers
Dosage forms
FormRouteStrength
Tabletoral100 mg
Tabletoral100.0 mg
Tabletoral25 mg
Tabletoral25.0 mg
Tabletoral50 mg
Tabletoral50.0 mg
Tablet, film coatedoral100 mg
Tablet, film coatedoral12.5; 100 mg/1; mg
Tablet, film coatedoral12.5; 50 mg/1; mg
Tablet, film coatedoral25 mg
Tablet, film coatedoral25; 100 mg/1; mg
Tablet, film coatedoral50 mg
Prices
Unit descriptionCostUnit
Losartan Potassium 90 50 mg tablet Bottle211.78USD bottle
Losartan Potassium-HCTZ 30 50-12.5 mg tablet Bottle78.05USD bottle
Hyzaar 100-25 mg tablet3.91USD tablet
Hyzaar 100-12.5 mg tablet3.87USD tablet
Hyzaar 100-12.5 tablet3.61USD tablet
Hyzaar 100-25 tablet3.61USD tablet
Losartan Potassium-HCTZ 100-12.5 mg tablet3.54USD tablet
Losartan Potassium-HCTZ 100-25 mg tablet3.54USD tablet
Cozaar 100 mg tablet3.41USD tablet
Losartan potassium 100 mg tablet3.14USD tablet
Hyzaar 50-12.5 mg tablet2.97USD tablet
Hyzaar 50-12.5 tablet2.65USD tablet
Cozaar 50 mg tablet2.5USD tablet
Losartan potassium 50 mg tablet2.26USD tablet
Cozaar 25 mg tablet1.92USD tablet
Losartan potassium 25 mg tablet1.72USD tablet
Cozaar 100 mg Tablet1.31USD tablet
Cozaar 25 mg Tablet1.31USD tablet
Cozaar 50 mg Tablet1.31USD tablet
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
CountryPatent NumberApprovedExpires (estimated)
Canada13340921995-01-242012-01-24
Canada20855842003-02-112011-06-07
United States52100791993-11-112010-11-11
United States56080751992-03-042009-03-04
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point184 °CPhysProp
water solubility0.82 mg/LNot Available
logP6.1Not Available
pKa5.5MERCK INDEX (1996); approx.
Predicted Properties
PropertyValueSource
Water Solubility0.0047 mg/mLALOGPS
logP4.5ALOGPS
logP5.08ChemAxon
logS-5ALOGPS
pKa (Strongest Acidic)7.4ChemAxon
pKa (Strongest Basic)4.12ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area92.51 Å2ChemAxon
Rotatable Bond Count8ChemAxon
Refractivity131.85 m3·mol-1ChemAxon
Polarizability44.86 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
SpectraNot Available
References
Synthesis Reference

Gordon C. Campbell, Jr., Anil M. Dwivedi, Dorothy A. Levorse, James A. McCauley, Krishnaswamy S. Raghavan, “Polymorphs of losartan and the process for the preparation of form II of losartan.” U.S. Patent US5608075, issued May, 1994.

US5608075
General Reference
  1. Dahlof B, Devereux RB, Kjeldsen SE, Julius S, Beevers G, de Faire U, Fyhrquist F, Ibsen H, Kristiansson K, Lederballe-Pedersen O, Lindholm LH, Nieminen MS, Omvik P, Oparil S, Wedel H: Cardiovascular morbidity and mortality in the Losartan Intervention For Endpoint reduction in hypertension study (LIFE): a randomised trial against atenolol. Lancet. 2002 Mar 23;359(9311):995-1003. Pubmed
  2. Guo ZX, Qiu MC: [Losartan downregulates the expression of transforming growth factor beta type I and type II receptors in kidney of diabetic rat] Zhonghua Nei Ke Za Zhi. 2003 Jun;42(6):403-8. Pubmed
  3. Habashi JP, Judge DP, Holm TM, Cohn RD, Loeys BL, Cooper TK, Myers L, Klein EC, Liu G, Calvi C, Podowski M, Neptune ER, Halushka MK, Bedja D, Gabrielson K, Rifkin DB, Carta L, Ramirez F, Huso DL, Dietz HC: Losartan, an AT1 antagonist, prevents aortic aneurysm in a mouse model of Marfan syndrome. Science. 2006 Apr 7;312(5770):117-21. Pubmed
  4. Bader, M. (2004). Renin-angiotensin-aldosterone system. In S. Offermanns, & W. Rosenthal (Eds.). Encyclopedic reference of molecular pharmacology (pp. 810-814). Berlin, Germany: Springer.
  5. Sica, D.A., Gehr, T.W.B., & Ghosh, S. (2005). Clinical pharmacokinetics of losartan. Clinical Pharmacokinetics, 44(8), 797-814. PMID: 16029066
  6. Stanfield, C.L., & Germann, W.J. (2008). Principles of human physiology (3 rd ed.). San Francisco, CA: Pearson Education, Inc.
  7. FDA label
External Links
ATC CodesC09CA01
AHFS Codes
  • 24:32.08
PDB EntriesNot Available
FDA labelDownload (212 KB)
MSDSDownload (19 KB)
Interactions
Drug Interactions
Drug
AmilorideIncreased risk of hyperkalemia
DrospirenoneIncreased risk of hyperkalemia
IndomethacinIndomethacin decreases the effect of losartan
Insulin LisproConcomitant therapy with angiotensin II receptor blockers may increase the blood-glucose-lowering effect of insulin lispro and thus the chance of hypoglycemia should be monitored closely.
LithiumLosartan increases serum levels of lithium
PotassiumIncreased risk of hyperkalemia
QuinupristinThis combination presents an increased risk of toxicity
RifampicinRifampin decreases the effect of losartan
SpironolactoneIncreased risk of hyperkalemia
TobramycinIncreased risk of nephrotoxicity
TolbutamideTolbutamide, a strong CYP2C9 inhibitor, may decrease the metabolism and clearance of Losartan. Consider alternate therapy or monitor for changes in Losartan therapeutic and adverse effects if Tolbutamide is initiated, discontinued or dose changed.
TrandolaprilThe angiotensin II receptor blocker, Losartan, may increase the adverse effects of Trandolapril.
TreprostinilAdditive hypotensive effect. Monitor antihypertensive therapy during concomitant use.
TretinoinThe moderate CYP2C8 inhibitor, Losartan, may decrease the metabolism and clearance of oral Tretinoin. Monitor for changes in Tretinoin effectiveness and adverse/toxic effects if Losartan is initiated, discontinued to dose changed.
TriamtereneIncreased risk of hyperkalemia
Food Interactions
  • Take without regard to meals. Take at same time each day. Food delays absorption, but does not affect the extent of absorption.

Targets

1. Type-1 angiotensin II receptor

Kind: protein

Organism: Human

Pharmacological action: yes

Actions: antagonist

Components

Name UniProt ID Details
Type-1 angiotensin II receptor P30556 Details

References:

  1. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. Pubmed
  2. Sardo MA, Castaldo M, Cinquegrani M, Bonaiuto M, Fontana L, Campo S, Campo GM, Altavilla D, Saitta A: Effects of AT1 receptor antagonist losartan on sICAM-1 and TNF-alpha levels in uncomplicated hypertensive patients. Angiology. 2004 Mar-Apr;55(2):195-203. Pubmed
  3. Dickstein K, Timmermans P, Segal R: Losartan: a selective angiotensin II type 1 (AT1) receptor antagonist for the treatment of heart failure. Expert Opin Investig Drugs. 1998 Nov;7(11):1897-914. Pubmed
  4. Anand-Srivastava MB, Palaparti A: Angiotensin-II-induced enhanced expression of Gi proteins is attenuated by losartan in A10 vascular smooth muscle cells: role of AT1 receptors. Can J Physiol Pharmacol. 2003 Feb;81(2):150-8. Pubmed
  5. Rocha I, Bras-Rosario L, Amparo-Barros M, Silva-Carvalho L: Angiotensin AT1 receptor antagonist losartan and the defence reaction in the anaesthetised rat. Effect on the carotid chemoreflex. Exp Physiol. 2003 May;88(3):309-14. Pubmed
  6. Guan J, Cheng DY, Chen XJ, Zhang Y, Wang H, Su QL: [The effects of losartan on pulmonary arterial collagen and AT1 in chronic hypoxic rats] Sichuan Da Xue Xue Bao Yi Xue Ban. 2004 Nov;35(6):774-7. Pubmed

Enzymes

1. Cytochrome P450 2C9

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: substrate inhibitor

Components

Name UniProt ID Details
Cytochrome P450 2C9 P11712 Details

References:

  1. Song JC, White CM: Pharmacologic, pharmacokinetic, and therapeutic differences among angiotensin II receptor antagonists. Pharmacotherapy. 2000 Feb;20(2):130-9. Pubmed
  2. Sica DA, Gehr TW, Ghosh S: Clinical pharmacokinetics of losartan. Clin Pharmacokinet. 2005;44(8):797-814. Pubmed
  3. Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. Pubmed
  4. Flockhart DA. Drug Interactions: Cytochrome P450 Drug Interaction Table. Indiana University School of Medicine (2007). Accessed May 28, 2010.
  5. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. Epub 2009 Nov 24. Pubmed
  6. Yasar U, Forslund-Bergengren C, Tybring G, Dorado P, Llerena A, Sjoqvist F, Eliasson E, Dahl ML: Pharmacokinetics of losartan and its metabolite E-3174 in relation to the CYP2C9 genotype. Clin Pharmacol Ther. 2002 Jan;71(1):89-98. Pubmed

2. Cytochrome P450 3A4

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: substrate inhibitor

Components

Name UniProt ID Details
Cytochrome P450 3A4 P08684 Details

References:

  1. Song JC, White CM: Pharmacologic, pharmacokinetic, and therapeutic differences among angiotensin II receptor antagonists. Pharmacotherapy. 2000 Feb;20(2):130-9. Pubmed
  2. Sica DA, Gehr TW, Ghosh S: Clinical pharmacokinetics of losartan. Clin Pharmacokinet. 2005;44(8):797-814. Pubmed
  3. Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. Pubmed
  4. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. Epub 2009 Nov 24. Pubmed

3. Cytochrome P450 3A5

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: substrate

Components

Name UniProt ID Details
Cytochrome P450 3A5 P20815 Details

References:

  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. Epub 2009 Nov 24. Pubmed

4. Cytochrome P450 2C8

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: substrate inhibitor

Components

Name UniProt ID Details
Cytochrome P450 2C8 P10632 Details

References:

  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. Epub 2009 Nov 24. Pubmed

5. Cytochrome P450 2C19

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: inhibitor

Components

Name UniProt ID Details
Cytochrome P450 2C19 P33261 Details

References:

  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. Epub 2009 Nov 24. Pubmed

6. Cytochrome P450 1A2

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: inhibitor

Components

Name UniProt ID Details
Cytochrome P450 1A2 P05177 Details

References:

  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. Epub 2009 Nov 24. Pubmed

7. UDP-glucuronosyltransferase 1-1

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: substrate

Components

Name UniProt ID Details
UDP-glucuronosyltransferase 1-1 P22309 Details

References:

  1. Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. Pubmed

8. UDP-glucuronosyltransferase 1-3

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: substrate

Components

Name UniProt ID Details
UDP-glucuronosyltransferase 1-3 P35503 Details

References:

  1. Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. Pubmed

9. UDP-glucuronosyltransferase 1-10

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: substrate

Components

Name UniProt ID Details
UDP-glucuronosyltransferase 1-10 Q9HAW8 Details

References:

  1. Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. Pubmed

10. UDP-glucuronosyltransferase 2B7

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: substrate

Components

Name UniProt ID Details
UDP-glucuronosyltransferase 2B7 P16662 Details

References:

  1. Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. Pubmed

11. UDP-glucuronosyltransferase 2B17

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: substrate

Components

Name UniProt ID Details
UDP-glucuronosyltransferase 2B17 O75795 Details

References:

  1. Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. Pubmed

Carriers

1. Serum albumin

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: substrate

Components

Name UniProt ID Details
Serum albumin P02768 Details

References:

  1. FDA label

Transporters

1. Multidrug resistance protein 1

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: substrate inhibitor

Components

Name UniProt ID Details
Multidrug resistance protein 1 P08183 Details

References:

  1. Takara K, Kakumoto M, Tanigawara Y, Funakoshi J, Sakaeda T, Okumura K: Interaction of digoxin with antihypertensive drugs via MDR1. Life Sci. 2002 Feb 15;70(13):1491-500. Pubmed
  2. Borgnia MJ, Eytan GD, Assaraf YG: Competition of hydrophobic peptides, cytotoxic drugs, and chemosensitizers on a common P-glycoprotein pharmacophore as revealed by its ATPase activity. J Biol Chem. 1996 Feb 9;271(6):3163-71. Pubmed
  3. Soldner A, Benet LZ, Mutschler E, Christians U: Active transport of the angiotensin-II antagonist losartan and its main metabolite EXP 3174 across MDCK-MDR1 and caco-2 cell monolayers. Br J Pharmacol. 2000 Mar;129(6):1235-43. Pubmed

2. Solute carrier family 22 member 6

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: inhibitor

Components

Name UniProt ID Details
Solute carrier family 22 member 6 Q4U2R8 Details

References:

  1. Race JE, Grassl SM, Williams WJ, Holtzman EJ: Molecular cloning and characterization of two novel human renal organic anion transporters (hOAT1 and hOAT3). Biochem Biophys Res Commun. 1999 Feb 16;255(2):508-14. Pubmed

3. Solute carrier family 22 member 12

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: inhibitor

Components

Name UniProt ID Details
Solute carrier family 22 member 12 Q96S37 Details

References:

  1. Lipkowitz MS: Regulation of uric acid excretion by the kidney. Curr Rheumatol Rep. 2012 Apr;14(2):179-88. doi: 10.1007/s11926-012-0240-z. Pubmed
  2. Burnier M, Roch-Ramel F, Brunner HR: Renal effects of angiotensin II receptor blockade in normotensive subjects. Kidney Int. 1996 Jun;49(6):1787-90. Pubmed

4. Solute carrier family 2, facilitated glucose transporter member 9

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: inhibitor

Components

Name UniProt ID Details
Solute carrier family 2, facilitated glucose transporter member 9 Q9NRM0 Details

References:

  1. Lipkowitz MS: Regulation of uric acid excretion by the kidney. Curr Rheumatol Rep. 2012 Apr;14(2):179-88. doi: 10.1007/s11926-012-0240-z. Pubmed
  2. Burnier M, Roch-Ramel F, Brunner HR: Renal effects of angiotensin II receptor blockade in normotensive subjects. Kidney Int. 1996 Jun;49(6):1787-90. Pubmed

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Drug created on June 13, 2005 07:24 / Updated on September 16, 2013 17:11