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IdentificationPharmacologyInteractionsReferencesTrialsEconomicsPropertiesSpectraTaxonomyFimasartan
Identification
- Name
- Fimasartan
- Accession Number
- DB09279
- Type
- Small Molecule
- Groups
- Investigational
- Description
Fimasartan is a non-peptide angiotensin II receptor antagonist (ARB) used for the treatment of hypertension and heart failure. Concurrent administration of fimasartan with diuretic hydrochlorothiazide has shown to be safe in clinical trials. Fimasartan was approved for use in South Korea in September 9th, 2010 and is available under the brand name Kanarb through Boryung Pharmaceuticals, who are presently seeking worldwide partnership.
- Structure
Structure for Fimasartan (DB09279)
- 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 antagonistHuman - 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
Drug Interaction 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. Acetylsalicylic acid The risk or severity of renal failure, hyperkalemia, and hypertension can be increased when Fimasartan is combined with Acetylsalicylic acid. 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. Aldesleukin The risk or severity of adverse effects can be increased when Aldesleukin is combined with Fimasartan. Aliskiren The risk or severity of hyperkalemia can be increased when Aliskiren is combined with Fimasartan. Alminoprofen The risk or severity of renal failure, hyperkalemia, and hypertension can be increased when Fimasartan is combined with Alminoprofen. Alprenolol The risk or severity of hyperkalemia can be increased when Alprenolol is combined with Fimasartan. - 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
- C09CA10 — Fimasartan
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
- 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
- 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]
Drug created on October 29, 2015 09:04 / Updated on November 02, 2018 08:49