Candesartan
This drug entry is a stub and has not been fully annotated. It is scheduled to be annotated soon.
Identification
- Name
- Candesartan
- Accession Number
- DB13919
- Description
Candesartan is an angiotensin-receptor blocker (ARB) that may be used alone or with other agents to treat hypertension. It is available as a prodrug in the form of candesartan cilexetil.
- Type
- Small Molecule
- Groups
- Experimental
- Structure
Structure for Candesartan (DB13919)
- Weight
- Average: 440.454
Monoisotopic: 440.159688536 - Chemical Formula
- C24H20N6O3
- Synonyms
- 2-ethoxy-1-(p-(o-1H-tetrazol-5-ylphenyl)benzyl)-7-benzimidazolecarboxylic acid
- External IDs
- CV-11974
Pharmacology
- Indication
- Not Available
- Associated Conditions
- Contraindications & Blackbox Warnings
Learn about our commercial Contraindications & Blackbox Warnings data.
Learn More- Pharmacodynamics
- Not Available
- Mechanism of action
Target Actions Organism AType-1 angiotensin II receptor antagonistHumans - Absorption
- Not Available
- Volume of distribution
- Not Available
- Protein binding
- Not Available
- Metabolism
- Not Available
- Route of elimination
- Not Available
- Half-life
- Not Available
- Clearance
- Not Available
- Adverse Effects
Learn about our commercial Adverse Effects data.
Learn More- Toxicity
- Not Available
- Affected organisms
- Not Available
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs
- Not Available
Interactions
- Drug Interactions
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Drug Interaction Unlock Additional DataAbatacept The metabolism of Candesartan can be increased when combined with Abatacept. Abiraterone The metabolism of Candesartan can be decreased when combined with Abiraterone. Acebutolol The risk or severity of hyperkalemia can be increased when Acebutolol is combined with Candesartan. Aceclofenac The risk or severity of renal failure, hyperkalemia, and hypertension can be increased when Candesartan is combined with Aceclofenac. Acemetacin The risk or severity of renal failure, hyperkalemia, and hypertension can be increased when Candesartan is combined with Acemetacin. Acenocoumarol The metabolism of Acenocoumarol can be decreased when combined with Candesartan. Acetohexamide The metabolism of Acetohexamide can be decreased when combined with Candesartan. Acetyl sulfisoxazole The metabolism of Candesartan can be decreased when combined with Acetyl sulfisoxazole. Acetylsalicylic acid The risk or severity of renal failure, hyperkalemia, and hypertension can be increased when Candesartan is combined with Acetylsalicylic acid. Adalimumab The metabolism of Candesartan can be increased when combined with Adalimumab. Additional Data Available- Extended DescriptionExtended Description
Extended description of the mechanism of action and particular properties of each drug interaction.
Learn more - Severity
- Evidence Level
- ActionAction
An effect category for each drug interaction. Know how this interaction affects the subject drug.
Learn more
- Food Interactions
- Not Available
Products
Categories
- ATC Codes
- C09DA06 — Candesartan and diuretics
- C09DA — Angiotensin II receptor blockers (ARBs) and diuretics
- C09D — ANGIOTENSIN II RECEPTOR BLOCKERS (ARBs), COMBINATIONS
- C09 — AGENTS ACTING ON THE RENIN-ANGIOTENSIN SYSTEM
- C — CARDIOVASCULAR SYSTEM
- C09DB — Angiotensin II receptor blockers (ARBs) and calcium channel blockers
- C09D — ANGIOTENSIN II RECEPTOR BLOCKERS (ARBs), COMBINATIONS
- C09 — AGENTS ACTING ON THE RENIN-ANGIOTENSIN SYSTEM
- C — CARDIOVASCULAR SYSTEM
- C09DX — Angiotensin II receptor blockers (ARBs), other combinations
- C09D — ANGIOTENSIN II RECEPTOR BLOCKERS (ARBs), COMBINATIONS
- C09 — AGENTS ACTING ON THE RENIN-ANGIOTENSIN SYSTEM
- C — CARDIOVASCULAR SYSTEM
- Drug Categories
- Agents Acting on the Renin-Angiotensin System
- Agents causing hyperkalemia
- Angiotensin 2 Receptor Blocker
- Angiotensin II receptor blockers (ARBs) and calcium channel blockers
- Angiotensin II receptor blockers (ARBs) and diuretics
- Angiotensin II receptor blockers (ARBs), plain
- Angiotensin II Type 2 Receptor Blockers
- Angiotensin Receptor Antagonists
- Antihypertensive Agents
- Cardiovascular Agents
- Cytochrome P-450 CYP2C8 Inhibitors
- Cytochrome P-450 CYP2C8 Inhibitors (strength unknown)
- Cytochrome P-450 CYP2C8 Inhibitors (weak)
- Cytochrome P-450 CYP2C9 Inhibitors
- Cytochrome P-450 CYP2C9 Inhibitors (weak)
- Cytochrome P-450 CYP2C9 Substrates
- Cytochrome P-450 Enzyme Inhibitors
- Cytochrome P-450 Substrates
- Heterocyclic Compounds, Fused-Ring
- OATP1B1/SLCO1B1 Inhibitors
- P-glycoprotein inhibitors
- UGT1A3 substrates
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as biphenyls and derivatives. These are organic compounds containing to benzene rings linked together by a C-C bond.
- Kingdom
- Organic compounds
- Super Class
- Benzenoids
- Class
- Benzene and substituted derivatives
- Sub Class
- Biphenyls and derivatives
- Direct Parent
- Biphenyls and derivatives
- Alternative Parents
- Phenyltetrazoles and derivatives / Benzimidazoles / Alkyl aryl ethers / N-substituted imidazoles / Vinylogous amides / Heteroaromatic compounds / Monocarboxylic acids and derivatives / Carboxylic acids / Azacyclic compounds / Organopnictogen compounds show 3 more
- Substituents
- Alkyl aryl ether / Aromatic heteropolycyclic compound / Azacycle / Azole / Benzimidazole / Biphenyl / Carboxylic acid / Carboxylic acid derivative / Ether / Heteroaromatic compound show 14 more
- Molecular Framework
- Aromatic heteropolycyclic compounds
- External Descriptors
- biphenylyltetrazole, benzimidazolecarboxylic acid (CHEBI:3347)
Chemical Identifiers
- UNII
- S8Q36MD2XX
- CAS number
- 139481-59-7
- InChI Key
- 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-{[2'-(1H-1,2,3,4-tetrazol-5-yl)-[1,1'-biphenyl]-4-yl]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=NN=NN1
References
- General References
- FDA Approved Drug Products: Atacand (candesartan cilexetil) oral tablets [Link]
- External Links
- Human Metabolome Database
- HMDB0014934
- KEGG Drug
- D00522
- PubChem Compound
- 2541
- PubChem Substance
- 347829334
- ChemSpider
- 2445
- BindingDB
- 50240609
- 214354
- ChEBI
- 3347
- ChEMBL
- CHEMBL1016
- ZINC
- ZINC000003782818
- PharmGKB
- PA448765
- Wikipedia
- Candesartan
Clinical Trials
- Clinical Trials
Phase Status Purpose Conditions Count 4 Completed Prevention Cardiovascular Heart Disease / Stroke 1 4 Completed Prevention High Blood Pressure (Hypertension) 1 4 Completed Treatment Angiotensin Converting Enzyme / Angiotensin Receptor Blockers / Cardiopulmonary Bypass / Coronary Artery Disease (CAD) / Fibrinolysis / Inflammatory Reaction 1 4 Completed Treatment BMI >30 kg/m2 / High Blood Pressure (Hypertension) 1 4 Completed Treatment Cardiovascular Heart Disease / Chronic Kidney Disease (CKD) / Hypertension,Essential / Stroke 1 4 Completed Treatment High Blood Pressure (Hypertension) 2 4 Completed Treatment High Blood Pressure (Hypertension) / Left Ventricular Hypertrophy 1 4 Recruiting Treatment Heart Diseases / Type 2 Diabetes Mellitus 1 4 Recruiting Treatment Novel Coronavirus Infectious Disease (COVID-19) 1 4 Suspended Prevention High Blood Pressure (Hypertension) / Novel Coronavirus Infectious Disease (COVID-19) 1
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
Form Route Strength Tablet 16 MG Tablet 8 MG Tablet 32 MG Tablet Oral 2 MG Tablet 4 MG Tablet Oral 32 MG Tablet Oral 8 MG Tablet Tablet Oral 4 MG Tablet Oral 16 MG/12.5MG Tablet Oral 8 MG/12.5MG Tablet 16 mg/1 Tablet 8 mg/1 Tablet Oral 16 mg - Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
- Not Available
- Predicted Properties
Property Value Source Water Solubility 0.00745 mg/mL ALOGPS logP 3.44 ALOGPS logP 4.68 ChemAxon logS -4.8 ALOGPS pKa (Strongest Acidic) 3.44 ChemAxon pKa (Strongest Basic) 1.5 ChemAxon Physiological Charge -2 ChemAxon Hydrogen Acceptor Count 7 ChemAxon Hydrogen Donor Count 2 ChemAxon Polar Surface Area 118.81 Å2 ChemAxon Rotatable Bond Count 7 ChemAxon Refractivity 134.92 m3·mol-1 ChemAxon Polarizability 45.29 Å3 ChemAxon Number of Rings 5 ChemAxon Bioavailability 1 ChemAxon Rule of Five Yes ChemAxon Ghose Filter No ChemAxon Veber's Rule No ChemAxon MDDR-like Rule Yes ChemAxon - Predicted ADMET Features
- Not Available
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Targets
- Kind
- Protein
- Organism
- Humans
- 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
- Uniprot Name
- Type-1 angiotensin II receptor
- Molecular Weight
- 41060.53 Da
References
- Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352]
- 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]
- 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]
- 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]
- 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]
- 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]
- 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]
- 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]
- 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]
- 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]
- 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
- Humans
- 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 un...
- Gene Name
- CYP2C8
- Uniprot ID
- P10632
- Uniprot Name
- Cytochrome P450 2C8
- Molecular Weight
- 55824.275 Da
References
- 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]
- Backman JT, Filppula AM, Niemi M, Neuvonen PJ: Role of Cytochrome P450 2C8 in Drug Metabolism and Interactions. Pharmacol Rev. 2016 Jan;68(1):168-241. doi: 10.1124/pr.115.011411. [PubMed:26721703]
- Kind
- Protein
- Organism
- Humans
- 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 un...
- Gene Name
- CYP2C9
- Uniprot ID
- P11712
- Uniprot Name
- Cytochrome P450 2C9
- Molecular Weight
- 55627.365 Da
References
- McClellan KJ, Goa KL: Candesartan cilexetil. A review of its use in essential hypertension. Drugs. 1998 Nov;56(5):847-69. [PubMed:9829158]
- 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]
- Rendic S: Summary of information on human CYP enzymes: human P450 metabolism data. Drug Metab Rev. 2002 Feb-May;34(1-2):83-448. [PubMed:11996015]
- Taavitsainen P, Kiukaanniemi K, Pelkonen O: In vitro inhibition screening of human hepatic P450 enzymes by five angiotensin-II receptor antagonists. Eur J Clin Pharmacol. 2000 May;56(2):135-40. [PubMed:10877007]
- Kind
- Protein
- Organism
- Humans
- 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 reg...
- Gene Name
- UGT1A3
- Uniprot ID
- P35503
- Uniprot Name
- UDP-glucuronosyltransferase 1-3
- Molecular Weight
- 60337.835 Da
References
- 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
- Humans
- 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 gas...
- Gene Name
- PTGS1
- Uniprot ID
- P23219
- Uniprot Name
- Prostaglandin G/H synthase 1
- Molecular Weight
- 68685.82 Da
References
- 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
- Humans
- 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
- Uniprot Name
- Multidrug resistance protein 1
- Molecular Weight
- 141477.255 Da
References
- 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]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Sodium-independent organic anion transmembrane transporter activity
- Specific Function
- Mediates the Na(+)-independent uptake of organic anions such as pravastatin, taurocholate, methotrexate, dehydroepiandrosterone sulfate, 17-beta-glucuronosyl estradiol, estrone sulfate, prostagland...
- Gene Name
- SLCO1B1
- Uniprot ID
- Q9Y6L6
- Uniprot Name
- Solute carrier organic anion transporter family member 1B1
- Molecular Weight
- 76447.99 Da
References
- Karlgren M, Ahlin G, Bergstrom CA, Svensson R, Palm J, Artursson P: In vitro and in silico strategies to identify OATP1B1 inhibitors and predict clinical drug-drug interactions. Pharm Res. 2012 Feb;29(2):411-26. doi: 10.1007/s11095-011-0564-9. Epub 2011 Aug 23. [PubMed:21861202]
Drug created on October 22, 2017 11:19 / Updated on August 01, 2020 07:41
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