Fimasartan
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Identification
- Summary
Fimasartan is an angiotensin II receptor antagonist (ARB) used to treat hypertension and heart failure.
- Generic Name
- Fimasartan
- DrugBank Accession Number
- DB09279
- Background
Fimasartan is an angiotensin II receptor antagonist (ARB) drug employed in the treatment of both hypertension and heart failure. It has been found to be safe when administered with hydrochlorothiazide (a diuretic) in clinical trials. Fimasartan was initially approved September 9th, 2010 in South Korea and is marketed under the brand name Kanarb by Boryung Pharmaceuticals.
- Type
- Small Molecule
- Groups
- Investigational
- Structure
- Weight
- Average: 501.65
Monoisotopic: 501.23107982 - Chemical Formula
- C27H31N7OS
- Synonyms
- Fimasartan
Pharmacology
- Indication
Used for the treatment of hypertension and heart failure 1.
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Indication Type Indication Combined Product Details Approval Level Age Group Patient Characteristics Dose Form Treatment of Hypertension,essential •••••••••••• ••••••• •••• •••••• - Contraindications & Blackbox Warnings
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- Pharmacodynamics
Fimasartan is a selective angiotensin receptor 1 (AR1) inhibitor 1. It acts to lower blood pressure by inhibiting vasoconstriction
- Mechanism of action
Angiotensin II activates AR1 leading to vasoconstriction and increased noradrenaline release which further increases vasoconstriction via action at α1-adrenergic receptors 1,2. It also stimulates secretion of aldosterone which acts to increase sodium and water reabsorption in the renal tubules 2. Fimasartan bind to and antagonizes AR1 preventing vasoconstriction and reducing aldosterone secretion to increase natriuresis leading to a reduction in blood volume. Together these effects produce an anti-hypertensive effect.
Target Actions Organism AType-1 angiotensin II receptor antagonistHumans - Absorption
Tmax is 0.5-1.3 h 1.
- Volume of distribution
Not Available
- Protein binding
Not Available
- Metabolism
- Not Available
- Route of elimination
Most is eliminated unchangd in bile with less than 3% in the urine 1.
- Half-life
The half life of elimination is 7-10 h 1.
- Clearance
Not Available
- Adverse Effects
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- Toxicity
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 Integrate drug-drug
interactions in your softwareAbaloparatide The risk or severity of adverse effects can be increased when Abaloparatide is combined with Fimasartan. Abemaciclib Abemaciclib may decrease the excretion rate of Fimasartan which could result in a higher serum level. Acebutolol The risk or severity of adverse effects can be increased when Acebutolol is combined with Fimasartan. Aceclofenac The risk or severity of renal failure, hyperkalemia, and hypertension can be increased when Fimasartan is combined with Aceclofenac. Acemetacin The risk or severity of renal failure, hyperkalemia, and hypertension can be increased when Fimasartan is combined with Acemetacin. - Food Interactions
- Not Available
Products
- Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.
- Product Ingredients
Ingredient UNII CAS InChI Key Fimasartan potassium anhydrous T2ICP7GBBN 1402813-38-0 OCKQGXSJNJCCDO-UHFFFAOYSA-N Fimasartan potassium trihydrate 4516BN0T4B 1020110-23-9 IJEKJHQBGZFMMI-UHFFFAOYSA-N - International/Other Brands
- Kanarb (Boryung Pharmaceuticals)
Categories
- ATC Codes
- C09DA10 — Fimasartan 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
- C09CA — Angiotensin II receptor blockers (ARBs), plain
- C09C — ANGIOTENSIN II RECEPTOR BLOCKERS (ARBs), PLAIN
- 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
- Drug Categories
- Agents Acting on the Renin-Angiotensin System
- Agents causing hyperkalemia
- Angiotensin II receptor blockers (ARBs) and calcium channel blockers
- Angiotensin II receptor blockers (ARBs) and diuretics
- Angiotensin II receptor blockers (ARBs), plain
- Angiotensin Receptor Antagonists
- BCRP/ABCG2 Substrates
- Benzene Derivatives
- Hypotensive Agents
- Lipid Modifying Agents
- OATP1B1/SLCO1B1 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 / Pyrimidones / Hydropyrimidines / Thioamides / Heteroaromatic compounds / Lactams / Thiocarboxylic acid amides / Azacyclic compounds / Thiocarbonyl compounds / Organopnictogen compounds show 4 more
- Substituents
- Aromatic heteromonocyclic compound / Azacycle / Azole / Biphenyl / Heteroaromatic compound / Hydrocarbon derivative / Hydropyrimidine / Lactam / Organic nitrogen compound / Organic oxide show 13 more
- Molecular Framework
- Aromatic heteromonocyclic compounds
- External Descriptors
- Not Available
- Affected organisms
- Humans and other mammals
Chemical Identifiers
- UNII
- P58222188P
- CAS number
- 247257-48-3
- InChI Key
- AMEROGPZOLAFBN-UHFFFAOYSA-N
- InChI
- InChI=1S/C27H31N7OS/c1-5-6-11-24-28-18(2)23(16-25(36)33(3)4)27(35)34(24)17-19-12-14-20(15-13-19)21-9-7-8-10-22(21)26-29-31-32-30-26/h7-10,12-15H,5-6,11,16-17H2,1-4H3,(H,29,30,31,32)
- IUPAC Name
- 2-(2-butyl-4-methyl-6-oxo-1-{[2'-(1H-1,2,3,4-tetrazol-5-yl)-[1,1'-biphenyl]-4-yl]methyl}-1,6-dihydropyrimidin-5-yl)-N,N-dimethylethanethioamide
- SMILES
- CCCCC1=NC(C)=C(CC(=S)N(C)C)C(=O)N1CC1=CC=C(C=C1)C1=C(C=CC=C1)C1=NN=NN1
References
- General References
- Kim JH, Lee JH, Paik SH, Kim JH, Chi YH: Fimasartan, a novel angiotensin II receptor antagonist. Arch Pharm Res. 2012 Jul;35(7):1123-6. doi: 10.1007/s12272-012-0700-z. [Article]
- Rang, H. P. and Dale, M. M. (2012). Rang and Dale's Pharmacology (7th ed.). Edinburgh: Elsevier/Churchill Livingstone. [ISBN:978-0-7020-3471-8]
- External Links
- PubChem Compound
- 9870652
- PubChem Substance
- 310265172
- ChemSpider
- 8046343
- BindingDB
- 50364573
- ChEBI
- 136044
- ChEMBL
- CHEMBL1951143
- ZINC
- ZINC000003842872
- Wikipedia
- Fimasartan
Clinical Trials
- Clinical Trials
Clinical Trial & Rare Diseases Add-on Data Package
Explore 4,000+ rare diseases, orphan drugs & condition pairs, clinical trial why stopped data, & more. Preview package Phase Status Purpose Conditions Count Start Date Why Stopped 100+ additional columns Unlock 175K+ rows when you subscribe.View sample dataNot Available Completed Not Available Hypertension 1 somestatus stop reason just information to hide Not Available Completed Not Available Hypertension and Dyslipidemia 1 somestatus stop reason just information to hide Not Available Completed Not Available Hypertension / Left Ventricular Hypertrophy 1 somestatus stop reason just information to hide Not Available Completed Treatment Diabetes Mellitus / Hypertension 1 somestatus stop reason just information to hide 4 Completed Treatment Hypertension 2 somestatus stop reason just information to hide
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
Form Route Strength Tablet Oral 66.010 mg Tablet Oral Tablet Oral 60.000 mg Tablet, film coated Oral 60 mg Tablet Oral 120 mg Tablet Oral 60 mg Tablet, film coated Oral 120.00 mg Tablet, film coated Oral 60.00 mg Tablet, film coated Oral 120 mg Tablet, coated Oral 60 mg - Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
- Not Available
- Predicted Properties
Property Value Source Water Solubility 0.00469 mg/mL ALOGPS logP 4.09 ALOGPS logP 4.21 Chemaxon logS -5 ALOGPS pKa (Strongest Acidic) 4.23 Chemaxon pKa (Strongest Basic) 1.34 Chemaxon Physiological Charge -1 Chemaxon Hydrogen Acceptor Count 5 Chemaxon Hydrogen Donor Count 1 Chemaxon Polar Surface Area 90.37 Å2 Chemaxon Rotatable Bond Count 9 Chemaxon Refractivity 161.24 m3·mol-1 Chemaxon Polarizability 54.86 Å3 Chemaxon Number of Rings 4 Chemaxon Bioavailability 1 Chemaxon Rule of Five No 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
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 246.9687507 predictedDarkChem Lite v0.1.0 [M-H]- 209.97954 predictedDeepCCS 1.0 (2019) [M+H]+ 248.4845507 predictedDarkChem Lite v0.1.0 [M+H]+ 212.3751 predictedDeepCCS 1.0 (2019) [M+Na]+ 247.0883507 predictedDarkChem Lite v0.1.0 [M+Na]+ 218.28764 predictedDeepCCS 1.0 (2019)
Targets
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Antagonist
- General Function
- Receptor for angiotensin II, a vasoconstricting peptide, which acts as a key regulator of blood pressure and sodium retention by the kidney (PubMed:15611106, PubMed:1567413, PubMed:25913193, PubMed:26420482, PubMed:30639100, PubMed:32079768, PubMed:8987975). The activated receptor in turn couples to G-alpha proteins G(q) (GNAQ, GNA11, GNA14 or GNA15) and thus activates phospholipase C and increases the cytosolic Ca(2+) concentrations, which in turn triggers cellular responses such as stimulation of protein kinase C (PubMed:15611106)
- Specific Function
- angiotensin type I receptor activity
- Gene Name
- AGTR1
- Uniprot ID
- P30556
- Uniprot Name
- Type-1 angiotensin II receptor
- Molecular Weight
- 41060.53 Da
References
- Kim JH, Lee JH, Paik SH, Kim JH, Chi YH: Fimasartan, a novel angiotensin II receptor antagonist. Arch Pharm Res. 2012 Jul;35(7):1123-6. doi: 10.1007/s12272-012-0700-z. [Article]
Transporters
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- Mediates the Na(+)-independent uptake of organic anions (PubMed:10358072, PubMed:15159445, PubMed:17412826). Shows broad substrate specificity, can transport both organic anions such as bile acid taurocholate (cholyltaurine) and conjugated steroids (dehydroepiandrosterone 3-sulfate, 17-beta-glucuronosyl estradiol, and estrone 3-sulfate), as well as eicosanoids (prostaglandin E2, thromboxane B2, leukotriene C4, and leukotriene E4), and thyroid hormones (T4/L-thyroxine, and T3/3,3',5'-triiodo-L-thyronine) (PubMed:10358072, PubMed:10601278, PubMed:10873595, PubMed:11159893, PubMed:12196548, PubMed:12568656, PubMed:15159445, PubMed:15970799, PubMed:16627748, PubMed:17412826, PubMed:19129463, PubMed:26979622). Can take up bilirubin glucuronides from plasma into the liver, contributing to the detoxification-enhancing liver-blood shuttling loop (PubMed:22232210). Involved in the clearance of endogenous and exogenous substrates from the liver (PubMed:10358072, PubMed:10601278). Transports coproporphyrin I and III, by-products of heme synthesis, and may be involved in their hepatic disposition (PubMed:26383540). May contribute to regulate the transport of organic compounds in testes across the blood-testis-barrier (Probable). Can transport HMG-CoA reductase inhibitors (also known as statins), such as pravastatin and pitavastatin, a clinically important class of hypolipidemic drugs (PubMed:10601278, PubMed:15159445, PubMed:15970799). May play an important role in plasma and tissue distribution of the structurally diverse chemotherapeutic drug methotrexate (PubMed:23243220). May also transport antihypertension agents, such as the angiotensin-converting enzyme (ACE) inhibitor prodrug enalapril, and the highly selective angiotensin II AT1-receptor antagonist valsartan, in the liver (PubMed:16624871, PubMed:16627748). Shows a pH-sensitive substrate specificity towards prostaglandin E2 and T4 which may be ascribed to the protonation state of the binding site and leads to a stimulation of substrate transport in an acidic microenvironment (PubMed:19129463). Hydrogencarbonate/HCO3(-) acts as the probable counteranion that exchanges for organic anions (PubMed:19129463)
- Specific Function
- bile acid transmembrane transporter activity
- Gene Name
- SLCO1B1
- Uniprot ID
- Q9Y6L6
- Uniprot Name
- Solute carrier organic anion transporter family member 1B1
- Molecular Weight
- 76447.99 Da
References
- Choi Y, Lee S, Jang IJ, Yu KS: Pharmacokinetic interaction between fimasartan and atorvastatin in healthy male volunteers. Drug Des Devel Ther. 2018 Jul 24;12:2301-2309. doi: 10.2147/DDDT.S165171. eCollection 2018. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- Broad substrate specificity ATP-dependent transporter of the ATP-binding cassette (ABC) family that actively extrudes a wide variety of physiological compounds, dietary toxins and xenobiotics from cells (PubMed:11306452, PubMed:12958161, PubMed:19506252, PubMed:20705604, PubMed:28554189, PubMed:30405239, PubMed:31003562). Involved in porphyrin homeostasis, mediating the export of protoporphyrin IX (PPIX) from both mitochondria to cytosol and cytosol to extracellular space, it also functions in the cellular export of heme (PubMed:20705604, PubMed:23189181). Also mediates the efflux of sphingosine-1-P from cells (PubMed:20110355). Acts as a urate exporter functioning in both renal and extrarenal urate excretion (PubMed:19506252, PubMed:20368174, PubMed:22132962, PubMed:31003562, PubMed:36749388). In kidney, it also functions as a physiological exporter of the uremic toxin indoxyl sulfate (By similarity). Also involved in the excretion of steroids like estrone 3-sulfate/E1S, 3beta-sulfooxy-androst-5-en-17-one/DHEAS, and other sulfate conjugates (PubMed:12682043, PubMed:28554189, PubMed:30405239). Mediates the secretion of the riboflavin and biotin vitamins into milk (By similarity). Extrudes pheophorbide a, a phototoxic porphyrin catabolite of chlorophyll, reducing its bioavailability (By similarity). Plays an important role in the exclusion of xenobiotics from the brain (Probable). It confers to cells a resistance to multiple drugs and other xenobiotics including mitoxantrone, pheophorbide, camptothecin, methotrexate, azidothymidine, and the anthracyclines daunorubicin and doxorubicin, through the control of their efflux (PubMed:11306452, PubMed:12477054, PubMed:15670731, PubMed:18056989, PubMed:31254042). In placenta, it limits the penetration of drugs from the maternal plasma into the fetus (By similarity). May play a role in early stem cell self-renewal by blocking differentiation (By similarity)
- Specific Function
- ABC-type xenobiotic transporter activity
- Gene Name
- ABCG2
- Uniprot ID
- Q9UNQ0
- Uniprot Name
- Broad substrate specificity ATP-binding cassette transporter ABCG2
- Molecular Weight
- 72313.47 Da
References
- Choi Y, Lee S, Jang IJ, Yu KS: Pharmacokinetic interaction between fimasartan and atorvastatin in healthy male volunteers. Drug Des Devel Ther. 2018 Jul 24;12:2301-2309. doi: 10.2147/DDDT.S165171. eCollection 2018. [Article]
Drug created at October 29, 2015 15:04 / Updated at October 29, 2024 14:22