You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on DrugBank.
Identification
NameCandesartan
Accession NumberDB00796  (APRD00420)
TypeSmall Molecule
GroupsApproved
Description

Candesartan is an angiotensin-receptor blocker (ARB) that may be used alone or with other agents to treat hypertension. It is administered orally as the prodrug, candesartan cilexetil, which is rapidly converted to its active metabolite, candesartan, during absorption in the gastrointestinal tract. Candesartan lowers blood pressure by antagonizing the renin-angiotensin-aldosterone system (RAAS); it competes 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. Candesartan 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 heart failure, systolic dysfunction, myocardial infarction and coronary artery disease.

Structure
Thumb
Synonyms
2-Ethoxy-1-(P-(O-1H-tetrazol-5-ylphenyl)benzyl)-7-benzimidazolecarboxylic acid
2-Ethoxy-1-{[2'-(1H-tetrazol-5-yl)biphenyl-4-yl]methyl}-1H-benzimidazole-7-carboxylic acid
2-Ethoxy-1-{[2'-(1H-tetrazol-5-yl)biphenyl-4ethyl]}-1H-benzimidazole-7-carboxylic acid
Blopress
Candesartan cilexetil
CV-11974
External Identifiers Not Available
Approved Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Ach-candesartantablet32 mgoralAccord Healthcare Inc2012-02-16Not applicableCanada
Ach-candesartantablet16 mgoralAccord Healthcare Inc2012-02-16Not applicableCanada
Ach-candesartantablet8 mgoralAccord Healthcare Inc2012-02-16Not applicableCanada
Ach-candesartantablet4 mgoralAccord Healthcare Inc2012-02-16Not applicableCanada
Act Candesartantablet32 mgoralActavis Pharma Company2011-11-30Not applicableCanada
Act Candesartantablet16 mgoralActavis Pharma Company2011-12-15Not applicableCanada
Act Candesartantablet8 mgoralActavis Pharma Company2011-11-30Not applicableCanada
Act Candesartantablet4 mgoralActavis Pharma Company2011-11-30Not applicableCanada
Atacandtablet4 mgoralAstrazeneca Canada Inc2005-06-28Not applicableCanada
Atacandtablet16 mg/1oralPhysicians Total Care, Inc.2000-11-21Not applicableUs
Atacandtablet4 mg/1oralAstra Zeneca Lp1998-09-14Not applicableUs
Atacandtablet8 mg/1oralCarilion Materials Management1998-09-14Not applicableUs
Atacandtablet4 mg/1oralCarilion Materials Management1998-09-14Not applicableUs
Atacandtablet4 mg/1oralbryant ranch prepack1998-09-14Not applicableUs
Atacandtablet16 mg/1oralbryant ranch prepack1998-09-14Not applicableUs
Atacandtablet32 mg/1oralAstra Zeneca Lp1998-09-14Not applicableUs
Atacandtablet32 mgoralAstrazeneca Canada Inc2008-07-17Not applicableCanada
Atacandtablet16 mg/1oralAstra Zeneca Lp1998-09-14Not applicableUs
Atacandtablet16 mg/1oralCardinal Health2009-11-11Not applicableUs
Atacandtablet8 mg/1oralAstra Zeneca Lp1998-09-14Not applicableUs
Atacand Tab 16 mgtablet16 mgoralAstrazeneca Canada Inc1998-12-07Not applicableCanada
Atacand Tab 8mgtablet8 mgoralAstrazeneca Canada Inc1998-12-07Not applicableCanada
Auro-candesartantablet32 mgoralAuro Pharma Inc2015-12-02Not applicableCanada
Auro-candesartantablet16 mgoralAuro Pharma Inc2015-12-02Not applicableCanada
Auro-candesartantablet8 mgoralAuro Pharma Inc2015-12-02Not applicableCanada
Auro-candesartantablet4 mgoralAuro Pharma Inc2015-12-02Not applicableCanada
Candesartantablet16 mgoralRanbaxy Pharmaceuticals Canada Inc.Not applicableNot applicableCanada
Candesartantablet4 mgoralSanis Health Inc2012-07-20Not applicableCanada
Candesartantablet32 mgoralActavis Pharma CompanyNot applicableNot applicableCanada
Candesartantablet32 mgoralRanbaxy Pharmaceuticals Canada Inc.Not applicableNot applicableCanada
Candesartantablet16 mgoralSivem Pharmaceuticals Ulc2012-07-11Not applicableCanada
Candesartantablet8 mgoralRanbaxy Pharmaceuticals Canada Inc.Not applicableNot applicableCanada
Candesartantablet16 mgoralActavis Pharma CompanyNot applicableNot applicableCanada
Candesartantablet32 mgoralPro Doc Limitee2014-06-05Not applicableCanada
Candesartantablet8 mgoralSivem Pharmaceuticals Ulc2012-07-11Not applicableCanada
Candesartantablet4 mgoralRanbaxy Pharmaceuticals Canada Inc.Not applicableNot applicableCanada
Candesartantablet4 mgoralActavis Pharma CompanyNot applicableNot applicableCanada
Candesartantablet16 mgoralPro Doc Limitee2012-02-02Not applicableCanada
Candesartantablet4 mgoralSivem Pharmaceuticals Ulc2012-07-11Not applicableCanada
Candesartantablet8 mgoralActavis Pharma CompanyNot applicableNot applicableCanada
Candesartantablet8 mgoralPro Doc Limitee2012-02-02Not applicableCanada
Candesartantablet32 mgoralSanis Health Inc2015-01-12Not applicableCanada
Candesartantablet16 mgoralSanis Health Inc2012-07-20Not applicableCanada
Candesartantablet8 mgoralSanis Health Inc2012-07-20Not applicableCanada
Candesartan Cilexetiltablet32 mg/1oralPar Pharmaceutical Inc.2013-05-21Not applicableUs
Candesartan Cilexetiltablet16 mg/1oralPar Pharmaceutical Inc.2013-05-21Not applicableUs
Candesartan Cilexetiltablet8 mg/1oralPar Pharmaceutical Inc.2013-05-21Not applicableUs
Candesartan Cilexetiltablet4 mg/1oralPar Pharmaceutical Inc.2013-05-21Not applicableUs
Candesartan Cilexetiltablet32 mg/1oralAmerican Health Packaging2015-09-01Not applicableUs
Candesartan Cilexetiltablet8 mg/1oralAmerican Health Packaging2015-09-01Not applicableUs
Candesartan Cilexetiltablet32 mgoralAlembic Pharmaceuticals LimitedNot applicableNot applicableCanada
Candesartan Cilexetiltablet8 mgoralAlembic Pharmaceuticals LimitedNot applicableNot applicableCanada
Candesartan Cilexetiltablet16 mgoralAlembic Pharmaceuticals LimitedNot applicableNot applicableCanada
Candesartan Cilexetiltablet4 mgoralAlembic Pharmaceuticals LimitedNot applicableNot applicableCanada
Dom-candesartantablet8 mgoralDominion Pharmacal2013-10-16Not applicableCanada
Dom-candesartantablet32 mgoralDominion PharmacalNot applicableNot applicableCanada
Dom-candesartantablet16 mgoralDominion PharmacalNot applicableNot applicableCanada
Dom-candesartantablet4 mgoralDominion PharmacalNot applicableNot applicableCanada
Ipg-candesartantablet16 mgoralInternational Pharmaceutical Generics LtdNot applicableNot applicableCanada
Ipg-candesartantablet32 mgoralInternational Pharmaceutical Generics LtdNot applicableNot applicableCanada
Ipg-candesartantablet8 mgoralInternational Pharmaceutical Generics LtdNot applicableNot applicableCanada
Ipg-candesartantablet4 mgoralInternational Pharmaceutical Generics LtdNot applicableNot applicableCanada
Jamp-candesartantablet32 mgoralJamp Pharma Corporation2012-06-11Not applicableCanada
Jamp-candesartantablet16 mgoralJamp Pharma Corporation2012-06-11Not applicableCanada
Jamp-candesartantablet8 mgoralJamp Pharma Corporation2012-06-11Not applicableCanada
Jamp-candesartantablet4 mgoralJamp Pharma Corporation2012-06-29Not applicableCanada
Mylan-candesartantablet8 mgoralMylan Pharmaceuticals Ulc2012-02-09Not applicableCanada
Mylan-candesartantablet16 mgoralMylan Pharmaceuticals Ulc2012-02-09Not applicableCanada
Mylan-candesartantablet4 mgoralMylan Pharmaceuticals Ulc2012-02-09Not applicableCanada
Mylan-candesartantablet32 mgoralMylan Pharmaceuticals Ulc2012-02-09Not applicableCanada
Ntp-candesartantablet32 mgoralTeva Canada LimitedNot applicableNot applicableCanada
Ntp-candesartantablet16 mgoralTeva Canada LimitedNot applicableNot applicableCanada
Ntp-candesartantablet8 mgoralTeva Canada LimitedNot applicableNot applicableCanada
PMS-candesartantablet32 mgoralPharmascience Inc2012-08-06Not applicableCanada
PMS-candesartantablet16 mgoralPharmascience Inc2012-08-06Not applicableCanada
PMS-candesartantablet8 mgoralPharmascience Inc2012-08-06Not applicableCanada
PMS-candesartantablet4 mgoralPharmascience Inc2012-08-06Not applicableCanada
Q-candesartantablet32 mgoralQd Pharmaceuticals UlcNot applicableNot applicableCanada
Q-candesartantablet16 mgoralQd Pharmaceuticals UlcNot applicableNot applicableCanada
Q-candesartantablet8 mgoralQd Pharmaceuticals UlcNot applicableNot applicableCanada
Q-candesartantablet4 mgoralQd Pharmaceuticals UlcNot applicableNot applicableCanada
Ran-candesartantablet16 mgoralRanbaxy Pharmaceuticals Canada Inc.2013-01-17Not applicableCanada
Ran-candesartantablet8 mgoralRanbaxy Pharmaceuticals Canada Inc.2013-01-17Not applicableCanada
Ran-candesartantablet4 mgoralRanbaxy Pharmaceuticals Canada Inc.2013-01-17Not applicableCanada
Ran-candesartantablet32 mgoralRanbaxy Pharmaceuticals Canada Inc.2013-01-17Not applicableCanada
Riva-candesartantablet4 mgoralLaboratoire Riva Inc2014-12-03Not applicableCanada
Riva-candesartantablet32 mgoralLaboratoire Riva Inc2014-12-03Not applicableCanada
Riva-candesartantablet16 mgoralLaboratoire Riva Inc2014-12-03Not applicableCanada
Riva-candesartantablet8 mgoralLaboratoire Riva Inc2014-12-03Not applicableCanada
Sandoz Candesartantablet32 mgoralSandoz Canada Incorporated2012-11-23Not applicableCanada
Sandoz Candesartantablet16 mgoralSandoz Canada Incorporated2011-04-26Not applicableCanada
Sandoz Candesartantablet8 mgoralSandoz Canada Incorporated2011-04-26Not applicableCanada
Sandoz Candesartantablet4 mgoralSandoz Canada Incorporated2011-04-26Not applicableCanada
Sandoz Candesartantablet32 mgoralSandoz Canada Incorporated2014-03-19Not applicableCanada
Septa-candesartantablet32 mgoralSepta Pharmaceuticals IncNot applicableNot applicableCanada
Septa-candesartantablet16 mgoralSepta Pharmaceuticals IncNot applicableNot applicableCanada
Teva-candesartantablet32 mgoralTeva Canada Limited2012-06-01Not applicableCanada
Teva-candesartantablet16 mgoralTeva Canada Limited2012-06-01Not applicableCanada
Teva-candesartantablet8 mgoralTeva Canada Limited2012-06-01Not applicableCanada
Zinda-candesartantablet32 mgoralZinda Pharma LimitedNot applicableNot applicableCanada
Zinda-candesartantablet16 mgoralZinda Pharma LimitedNot applicableNot applicableCanada
Approved Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Apo-candesartantablet32 mgoralApotex Inc2013-07-16Not applicableCanada
Apo-candesartantablet16 mgoralApotex Inc2011-04-26Not applicableCanada
Apo-candesartantablet8 mgoralApotex Inc2011-04-26Not applicableCanada
Apo-candesartantablet4 mgoralApotex Inc2011-04-26Not applicableCanada
Candesartan Cilexetiltablet16 mg/1oralAmerican Health Packaging2015-09-01Not applicableUs
Candesartan Cilexetiltablet4 mg/1oralSandoz Inc2013-05-21Not applicableUs
Candesartan Cilexetiltablet32 mg/1oralApotex Corp2014-01-13Not applicableUs
Candesartan Cilexetiltablet16 mg/1oralApotex Corp2014-01-13Not applicableUs
Candesartan Cilexetiltablet8 mg/1oralApotex Corp2014-01-13Not applicableUs
Candesartan Cilexetiltablet4 mg/1oralApotex Corp2014-01-13Not applicableUs
Candesartan Cilexetiltablet32 mg/1oralSandoz Inc2013-05-21Not applicableUs
Candesartan Cilexetiltablet16 mg/1oralSandoz Inc2013-05-21Not applicableUs
Candesartan Cilexetiltablet16 mg/1oralCarilion Materials Management2013-05-21Not applicableUs
Candesartan Cilexetiltablet8 mg/1oralSandoz Inc2013-05-21Not applicableUs
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International Brands
NameCompany
AmiasEureco (Netherlands), Takeda (United Kingdom)
BlopressTakeda
Brand mixtures
NameLabellerIngredients
Act Candesartan/hctActavis Pharma Company
Apo-candesartan/hctzApotex Inc
Atacand HctAstra Zeneca Lp
Atacand PlusAstrazeneca Canada Inc
Auro-candesartan HctAuro Pharma Inc
Candesartan Cilexetil and HydrochlorothiazideMylan Pharmaceuticals Inc.
Candesartan Cilexetil and Hydrochlorothiazide TabletsAlembic Pharmaceuticals Limited
Candesartan Cilexetil-hydrochlorothiazidePar Pharmaceutical Inc.
Candesartan HctSivem Pharmaceuticals Ulc
Candesartan-hctzPro Doc Limitee
Candesartan/hctzSanis Health Inc
Ipg-candesartan + HctInternational Pharmaceutical Generics Ltd
Mylan-candesartan HctzMylan Pharmaceuticals Ulc
PMS-candesartan HctzPharmascience Inc
Sandoz Candesartan PlusSandoz Canada Incorporated
Septa-candesartan HctzSepta Pharmaceuticals Inc
Teva-candesartan/hctzTeva Canada Limited
Zinda-candesartan/hydrochlorothiazideZinda Pharma Limited
SaltsNot Available
Categories
UNIIS8Q36MD2XX
CAS number139481-59-7
WeightAverage: 440.454
Monoisotopic: 440.159688536
Chemical FormulaC24H20N6O3
InChI KeyInChIKey=HTQMVQVXFRQIKW-UHFFFAOYSA-N
InChI
InChI=1S/C24H20N6O3/c1-2-33-24-25-20-9-5-8-19(23(31)32)21(20)30(24)14-15-10-12-16(13-11-15)17-6-3-4-7-18(17)22-26-28-29-27-22/h3-13H,2,14H2,1H3,(H,31,32)(H,26,27,28,29)
IUPAC Name
2-ethoxy-1-({4-[2-(2H-1,2,3,4-tetrazol-5-yl)phenyl]phenyl}methyl)-1H-1,3-benzodiazole-7-carboxylic acid
SMILES
CCOC1=NC2=CC=CC(C(O)=O)=C2N1CC1=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
  • Benzimidazole
  • Phenylmethylamine
  • Benzoyl
  • Alkyl aryl ether
  • Benzenoid
  • N-substituted imidazole
  • Monocyclic benzene moiety
  • Heteroaromatic compound
  • Vinylogous amide
  • Imidazole
  • Azacycle
  • Monocarboxylic acid or derivatives
  • Ether
  • Carboxylic acid
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic 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. Candesartan 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.
PharmacodynamicsCandesartan cilexetil is an ARB prodrug that is rapidly converted to candesartan, its active metabolite, during absorption from the gastrointestinal tract. Candesartan confers blood pressure lowering effects by antagonizing the hypertensive effects of angiotensin II via the 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: type-1 angiotensin II receptor (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 actionCandesartan selectively blocks the binding of angiotensin II to AT1 in many tissues including vascular smooth muscle and the adrenal glands. This inhibits the AT1-mediated vasoconstrictive and aldosterone-secreting effects of angiotensin II and results in an overall decrease in blood pressure. Candesartan is greater than 10,000 times more selective for AT1 than AT2. Inhibition of aldosterone secretion may increase sodium and water excretion while decreasing potassium excretion.
Related Articles
AbsorptionFollowing administration of the candesartan cilexetil prodrug, the absolute bioavailability of candesartan was estimated to be 15%. Food with a high fat content has no affect on the bioavailability of candesartan from candesartan cilexetil.
Volume of distribution
  • 0.13 L/kg
Protein bindingCandesartan is highly bound to plasma proteins (>99%) and does not penetrate red blood cells.
Metabolism

The prodrug candesartan cilexetil undergoes rapid and complete ester hydrolysis in the intestinal wall to form the active drug, candesartan. Elimination of candesartan is primarily as unchanged drug in the urine and, by the biliary route, in the feces. Minor hepatic metabolism of candesartan (<20%)occurs by O-deethylation via cytochrome P450 2C9 to form an inactive metabolite. Candesartan undergoes N-glucuronidation in the tetrazole ring by uridine diphosphate glucuronosyltransferase 1A3 (UGT1A3). O-glucuronidation may also occur. 75% of candesartan is excreted as unchanged drug in urine and feces.

SubstrateEnzymesProduct
Candesartan
O-Deethylated candesartanDetails
Candesartan
Candesartan N2-glucuronideDetails
Candesartan
Candesartan O-glucuronideDetails
Route of eliminationWhen candesartan is administered orally, about 26% of the dose is excreted unchanged in urine. Candesartan is mainly excreted unchanged in urine and feces (via bile).
Half lifeApproximately 9 hours.
Clearance
  • 0.37 mL/min/kg
ToxicityNo lethality was observed in acute toxicity studies in mice, rats and dogs given single oral doses of up to 2000 mg/kg of candesartan cilexetil or in rats given single oral doses of up to 2000 mg/kg of candesartan cilexetil in combination with 1000 mg/kg of hydrochlorothiazide. In mice given single oral doses of the primary metabolite, candesartan, the minimum lethal dose was greater than 1000 mg/kg but less than 2000 mg/kg.
Affected organisms
  • Humans and other mammals
Pathways
PathwayCategorySMPDB ID
Candesartan Action PathwayDrug actionSMP00158
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+1.0
Blood Brain Barrier+0.8717
Caco-2 permeable-0.6208
P-glycoprotein substrateSubstrate0.5186
P-glycoprotein inhibitor INon-inhibitor0.848
P-glycoprotein inhibitor IINon-inhibitor0.9115
Renal organic cation transporterNon-inhibitor0.8266
CYP450 2C9 substrateNon-substrate0.7397
CYP450 2D6 substrateNon-substrate0.9116
CYP450 3A4 substrateNon-substrate0.6504
CYP450 1A2 substrateInhibitor0.5594
CYP450 2C9 inhibitorInhibitor0.5195
CYP450 2D6 inhibitorNon-inhibitor0.889
CYP450 2C19 inhibitorInhibitor0.5151
CYP450 3A4 inhibitorInhibitor0.7392
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.7895
Ames testAMES toxic0.556
CarcinogenicityNon-carcinogens0.7561
BiodegradationNot ready biodegradable0.9972
Rat acute toxicity2.5515 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.794
hERG inhibition (predictor II)Non-inhibitor0.5837
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Pharmacoeconomics
Manufacturers
  • Astrazeneca pharmaceuticals lp
Packagers
Dosage forms
FormRouteStrength
Tabletoral16 mg/1
Tabletoral32 mg/1
Tabletoral32 mg
Tabletoral4 mg/1
Tabletoral4 mg
Tabletoral8 mg/1
Tabletoral
Tabletoral16 mg
Tabletoral8 mg
Prices
Unit descriptionCostUnit
Atacand 30 4 mg tablet Bottle75.98USD bottle
Atacand 30 8 mg tablet Bottle74.96USD bottle
Atacand hct 32-25 mg tablet3.64USD tablet
Atacand hct 32-12.5 mg tablet3.43USD tablet
Atacand 32 mg tablet3.36USD tablet
Atacand hct 16-12.5 mg tablet3.36USD tablet
Atacand 16 mg tablet2.49USD tablet
Atacand 4 mg tablet2.44USD tablet
Atacand 8 mg tablet2.44USD tablet
Atacand 16 mg Tablet1.28USD tablet
Atacand 32 mg Tablet1.28USD tablet
Atacand 8 mg Tablet1.28USD tablet
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)
CA2040955 No1998-02-032011-04-22Canada
CA2083305 No2003-12-092012-11-19Canada
US5534534 No1994-01-092014-01-09Us
US5705517 No1994-04-182011-04-18Us
Properties
StateSolid
Experimental Properties
PropertyValueSource
logP6.1Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.00771 mg/mLALOGPS
logP4.02ALOGPS
logP5.05ChemAxon
logS-4.8ALOGPS
pKa (Strongest Acidic)2.97ChemAxon
pKa (Strongest Basic)1.71ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area118.81 Å2ChemAxon
Rotatable Bond Count7ChemAxon
Refractivity134.92 m3·mol-1ChemAxon
Polarizability45.35 Å3ChemAxon
Number of Rings5ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
SpectraNot Available
References
Synthesis Reference

Marina Etinger, Boris Fedotev, Ben-Zion Dolitzky, “Preparation of candesartan cilexetil.” U.S. Patent US20050131037, issued June 16, 2005.

US20050131037
General References
  1. Pfeffer MA, Swedberg K, Granger CB, Held P, McMurray JJ, Michelson EL, Olofsson B, Ostergren J, Yusuf S, Pocock S: Effects of candesartan on mortality and morbidity in patients with chronic heart failure: the CHARM-Overall programme. Lancet. 2003 Sep 6;362(9386):759-66. [PubMed:13678868 ]
  2. Mendis B, Page SR: Candesartan: widening indications for this angiotensin II receptor blocker? Expert Opin Pharmacother. 2009 Aug;10(12):1995-2007. doi: 10.1517/14656560903092197. [PubMed:19563275 ]
  3. Baguet JP, Barone-Rochette G, Neuder Y: Candesartan cilexetil in the treatment of chronic heart failure. Vasc Health Risk Manag. 2009;5(1):257-64. Epub 2009 Apr 8. [PubMed:19436650 ]
  4. Stanfield, Cindy L.;Germann, William J. (2009). Principles of Human Physiology (3rd ed.). Benjamin-Cummings Publishing Company. [ISBN:978-0321556660 ]
  5. Bader, M. (2004). Renin-angiotensin-aldosterone system. In Encyclopedic reference of molecular pharmacology (pp. 810-814). Berlin: Springer. [ISBN:9783540298328 ]
External Links
ATC CodesC09CA06C09DA06C09DB07
AHFS Codes
  • 24:32.08
PDB EntriesNot Available
FDA labelDownload (49.4 KB)
MSDSNot Available
Interactions
Drug Interactions
Drug
AldesleukinThe risk or severity of adverse effects can be increased when Aldesleukin is combined with Candesartan.
AlfuzosinAlfuzosin may increase the hypotensive activities of Candesartan.
AliskirenAliskiren may increase the hyperkalemic activities of Candesartan.
AmifostineCandesartan may increase the hypotensive activities of Amifostine.
AmodiaquineThe serum concentration of Amodiaquine can be increased when it is combined with Candesartan.
ArdeparinArdeparin may increase the hyperkalemic activities of Candesartan.
BrimonidineBrimonidine may increase the antihypertensive activities of Candesartan.
ButabarbitalButabarbital may increase the hypotensive activities of Candesartan.
ButethalButethal may increase the hypotensive activities of Candesartan.
CanagliflozinCanagliflozin may increase the hyperkalemic activities of Candesartan.
CiprofloxacinCandesartan may increase the arrhythmogenic activities of Ciprofloxacin.
CyclosporineCandesartan may increase the hyperkalemic activities of Cyclosporine.
DapoxetineDapoxetine may increase the orthostatic hypotensive activities of Candesartan.
DiazoxideDiazoxide may increase the hypotensive activities of Candesartan.
DrospirenoneCandesartan may increase the hyperkalemic activities of Drospirenone.
DuloxetineCandesartan may increase the orthostatic hypotensive activities of Duloxetine.
EplerenoneEplerenone may increase the hyperkalemic activities of Candesartan.
HeparinHeparin may increase the hyperkalemic activities of Candesartan.
HeptabarbitalHeptabarbital may increase the hypotensive activities of Candesartan.
HexobarbitalHexobarbital may increase the hypotensive activities of Candesartan.
InfliximabThe risk or severity of adverse effects can be increased when Candesartan is combined with Infliximab.
LevodopaCandesartan may increase the orthostatic hypotensive activities of Levodopa.
LithiumThe serum concentration of Lithium can be increased when it is combined with Candesartan.
MethohexitalMethohexital may increase the hypotensive activities of Candesartan.
MethylphenidateMethylphenidate may decrease the antihypertensive activities of Candesartan.
MolsidomineMolsidomine may increase the hypotensive activities of Candesartan.
MoxonidineMoxonidine may increase the hypotensive activities of Candesartan.
NicorandilNicorandil may increase the hypotensive activities of Candesartan.
ObinutuzumabCandesartan may increase the hypotensive activities of Obinutuzumab.
PentobarbitalPentobarbital may increase the hypotensive activities of Candesartan.
PentoxifyllinePentoxifylline may increase the hypotensive activities of Candesartan.
PerindoprilThe risk or severity of adverse effects can be increased when Candesartan is combined with Perindopril.
PhenelzinePhenelzine may increase the orthostatic hypotensive activities of Candesartan.
PrimidonePrimidone may increase the hypotensive activities of Candesartan.
QuinineQuinine may increase the hypotensive activities of Candesartan.
RisperidoneCandesartan may increase the hypotensive activities of Risperidone.
RituximabCandesartan may increase the hypotensive activities of Rituximab.
SecobarbitalSecobarbital may increase the hypotensive activities of Candesartan.
TadalafilTadalafil may increase the antihypertensive activities of Candesartan.
TolvaptanTolvaptan may increase the hyperkalemic activities of Candesartan.
TranylcypromineTranylcypromine may increase the orthostatic hypotensive activities of Candesartan.
TreprostinilTreprostinil may increase the hypotensive activities of Candesartan.
TriamtereneCandesartan may increase the hyperkalemic activities of Triamterene.
TrimethoprimTrimethoprim may increase the hyperkalemic activities of Candesartan.
ValsartanThe risk or severity of adverse effects can be increased when Valsartan is combined with Candesartan.
VardenafilVardenafil may increase the antihypertensive activities of Candesartan.
YohimbineYohimbine may decrease the antihypertensive activities of Candesartan.
Food Interactions
  • Administer on a regular basis, at about the same time each day.
  • Take without regard to meals.

Targets

Kind
Protein
Organism
Human
Pharmacological action
yes
Actions
antagonist
General Function:
Protein heterodimerization activity
Specific Function:
Receptor for angiotensin II. Mediates its action by association with G proteins that activate a phosphatidylinositol-calcium second messenger system.
Gene Name:
AGTR1
Uniprot ID:
P30556
Molecular Weight:
41060.53 Da
References
  1. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
  2. Cervenka L, Navar LG: Renal responses of the nonclipped kidney of two-kidney/one-clip Goldblatt hypertensive rats to type 1 angiotensin II receptor blockade with candesartan. J Am Soc Nephrol. 1999 Jan;10 Suppl 11:S197-201. [PubMed:9892163 ]
  3. Malmqvist K, Kahan T, Dahl M: Angiotensin II type 1 (AT1) receptor blockade in hypertensive women: benefits of candesartan cilexetil versus enalapril or hydrochlorothiazide. Am J Hypertens. 2000 May;13(5 Pt 1):504-11. [PubMed:10826401 ]
  4. Wada T, Inada Y, Ojima M, Sanada T, Shibouta Y, Nishikawa K: Comparison of the antihypertensive effects of the new angiotensin II (AT1) receptor antagonist candesartan cilexetil (TCV-116) and the angiotensin converting enzyme inhibitor enalapril in rats. Hypertens Res. 1996 Jun;19(2):75-81. [PubMed:10968199 ]
  5. Engelhorn T, Doerfler A, Heusch G, Schulz R: Reduction of cerebral infarct size by the AT1-receptor blocker candesartan, the HMG-CoA reductase inhibitor rosuvastatin and their combination. An experimental study in rats. Neurosci Lett. 2006 Oct 2;406(1-2):92-6. Epub 2006 Aug 9. [PubMed:16901636 ]
  6. Caballero-George C, Vanderheyden PM, Solis PN, Gupta MP, Pieters L, Vauquelin G, Vlietinck A: In vitro effect of sanguinarine alkaloid on binding of [3H]candesartan to the human angiotensin AT1 receptor. Eur J Pharmacol. 2003 Jan 5;458(3):257-62. [PubMed:12504781 ]
  7. McInnes GT, O'Kane KP, Istad H, Keinanen-Kiukaanniemi S, Van Mierlo HF: Comparison of the AT1-receptor blocker, candesartan cilexetil, and the ACE inhibitor, lisinopril, in fixed combination with low dose hydrochlorothiazide in hypertensive patients. J Hum Hypertens. 2000 Apr;14(4):263-9. [PubMed:10805052 ]
  8. Vauquelin G, Fierens F, Van Liefde I: Long-lasting angiotensin type 1 receptor binding and protection by candesartan: comparison with other biphenyl-tetrazole sartans. J Hypertens Suppl. 2006 Mar;24(1):S23-30. [PubMed:16601569 ]
  9. Mendis B, Page SR: Candesartan: widening indications for this angiotensin II receptor blocker? Expert Opin Pharmacother. 2009 Aug;10(12):1995-2007. doi: 10.1517/14656560903092197. [PubMed:19563275 ]
  10. Meredith PA: Candesartan cilexetil--a review of effects on cardiovascular complications in hypertension and chronic heart failure. Curr Med Res Opin. 2007 Jul;23(7):1693-705. [PubMed:17588300 ]
  11. Baguet JP, Barone-Rochette G, Neuder Y: Candesartan cilexetil in the treatment of chronic heart failure. Vasc Health Risk Manag. 2009;5(1):257-64. Epub 2009 Apr 8. [PubMed:19436650 ]

Enzymes

Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrateinhibitor
General Function:
Steroid hydroxylase activity
Specific Function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. This enzyme contributes to the wide pharmacokinetics variability of the metabolism of drugs such as S-warfarin, diclofenac, phenyto...
Gene Name:
CYP2C9
Uniprot ID:
P11712
Molecular Weight:
55627.365 Da
References
  1. McClellan KJ, Goa KL: Candesartan cilexetil. A review of its use in essential hypertension. Drugs. 1998 Nov;56(5):847-69. [PubMed:9829158 ]
  2. 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:19515014 ]
  3. 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. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
inhibitor
General Function:
Steroid hydroxylase activity
Specific Function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. In the epoxidation of arachidonic acid it generates only 14,15- and 11,12-cis-epoxyeicosatrienoic acids. It is the principal enzyme...
Gene Name:
CYP2C8
Uniprot ID:
P10632
Molecular Weight:
55824.275 Da
References
  1. Walsky RL, Gaman EA, Obach RS: Examination of 209 drugs for inhibition of cytochrome P450 2C8. J Clin Pharmacol. 2005 Jan;45(1):68-78. [PubMed:15601807 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrate
General Function:
Retinoic acid binding
Specific Function:
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. Isoform 2 lacks transferase activity but acts as a negative regulator of isoform 1.
Gene Name:
UGT1A3
Uniprot ID:
P35503
Molecular Weight:
60337.835 Da
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:19515014 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrate
General Function:
Prostaglandin-endoperoxide synthase activity
Specific Function:
Converts arachidonate to prostaglandin H2 (PGH2), a committed step in prostanoid synthesis. Involved in the constitutive production of prostanoids in particular in the stomach and platelets. In gastric epithelial cells, it is a key step in the generation of prostaglandins, such as prostaglandin E2 (PGE2), which plays an important role in cytoprotection. In platelets, it is involved in the gener...
Gene Name:
PTGS1
Uniprot ID:
P23219
Molecular Weight:
68685.82 Da
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:19515014 ]

Transporters

Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
inhibitor
General Function:
Xenobiotic-transporting atpase activity
Specific Function:
Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells.
Gene Name:
ABCB1
Uniprot ID:
P08183
Molecular Weight:
141477.255 Da
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:11895100 ]
Comments
comments powered by Disqus
Drug created on June 13, 2005 07:24 / Updated on April 21, 2016 12:13