Identification
- Name
- Fimasartan
- Accession Number
- DB09279
- Type
- Small Molecule
- Groups
- Investigational
- Description
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.
- Structure
- Synonyms
- Not Available
- Product Ingredients
Ingredient UNII CAS InChI Key Fimasartan potassium trihydrate 4516BN0T4B 1020110-23-9 IJEKJHQBGZFMMI-UHFFFAOYSA-N - International/Other Brands
- Kanarb (Boryung Pharmaceuticals)
- Categories
- UNII
- P58222188P
- CAS number
- 247257-48-3
- Weight
- Average: 501.65
Monoisotopic: 501.23107982 - Chemical Formula
- C27H31N7OS
- 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
Pharmacology
- Indication
Used for the treatment of hypertension and heart failure 1.
- 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
- Toxicity
- Not Available
- Affected organisms
- Humans and other mammals
- 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 Data7,8-Dichloro-1,2,3,4-tetrahydroisoquinoline 7,8-Dichloro-1,2,3,4-tetrahydroisoquinoline may increase the orthostatic hypotensive activities of Fimasartan. Abemaciclib Abemaciclib may decrease the excretion rate of Fimasartan which could result in a higher serum level. Acebutolol The risk or severity of hyperkalemia 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. Acetylcysteine The excretion of Fimasartan can be decreased when combined with Acetylcysteine. Acetylsalicylic acid The risk or severity of renal failure, hyperkalemia, and hypertension can be increased when Fimasartan is combined with Acetylsalicylic acid. Afatinib Afatinib may decrease the excretion rate of Fimasartan which could result in a higher serum level. Agmatine The risk or severity of hyperkalemia can be increased when Agmatine is combined with Fimasartan. Alclofenac The risk or severity of renal failure, hyperkalemia, and hypertension can be increased when Fimasartan is combined with Alclofenac. 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
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. [PubMed:22864732]
- 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
- Wikipedia
- Fimasartan
- 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
Clinical Trials
- Clinical Trials
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage forms
- Not Available
- 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
Spectrum Spectrum Type Splash Key Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS Not Available
Taxonomy
- 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
- Biphenyl / Phenyltetrazole / Pyrimidone / Hydropyrimidine / Pyrimidine / Azole / Heteroaromatic compound / Tetrazole / Thioamide / Lactam show 13 more
- Molecular Framework
- Aromatic heteromonocyclic compounds
- External Descriptors
- Not Available
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
- 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. [PubMed:22864732]
Transporters
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- 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
- 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. [PubMed:30087555]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- Xenobiotic-transporting atpase activity
- Specific Function
- High-capacity urate exporter functioning in both renal and extrarenal urate excretion. Plays a role in porphyrin homeostasis as it is able to mediates the export of protoporhyrin IX (PPIX) both fro...
- Gene Name
- ABCG2
- Uniprot ID
- Q9UNQ0
- Uniprot Name
- ATP-binding cassette sub-family G member 2
- 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. [PubMed:30087555]
Drug created on October 29, 2015 09:04 / Updated on December 02, 2019 08:41