Fimasartan

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
Thumb
Weight
Average: 501.65
Monoisotopic: 501.23107982
Chemical Formula
C27H31N7OS
Synonyms
  • Fimasartan

Pharmacology

Indication

Used for the treatment of hypertension and heart failure 1.

Pharmacology
Accelerate your drug discovery research with the industry’s only fully connected ADMET dataset, ideal for:
Machine Learning
Data Science
Drug Discovery
Accelerate your drug discovery research with our fully connected ADMET dataset
Learn more
Associated Conditions
Contraindications & Blackbox Warnings
Contraindications
Contraindications & Blackbox Warnings
With our commercial data, access important information on dangerous risks, contraindications, and adverse effects.
Learn more
Our Blackbox Warnings cover Risks, Contraindications, and Adverse Effects
Learn more
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.

TargetActionsOrganism
AType-1 angiotensin II receptor
antagonist
Humans
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
Medicalerrors
Reduce medical errors
and improve treatment outcomes with our comprehensive & structured data on drug adverse effects.
Learn more
Reduce medical errors & improve treatment outcomes with our adverse effects data
Learn more
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.
DrugInteraction
AbemaciclibAbemaciclib may decrease the excretion rate of Fimasartan which could result in a higher serum level.
AcebutololThe risk or severity of hyperkalemia can be increased when Acebutolol is combined with Fimasartan.
AceclofenacThe risk or severity of renal failure, hyperkalemia, and hypertension can be increased when Fimasartan is combined with Aceclofenac.
AcemetacinThe risk or severity of renal failure, hyperkalemia, and hypertension can be increased when Fimasartan is combined with Acemetacin.
AcetylcysteineThe excretion of Fimasartan can be decreased when combined with Acetylcysteine.
Acetylsalicylic acidThe risk or severity of renal failure, hyperkalemia, and hypertension can be increased when Fimasartan is combined with Acetylsalicylic acid.
AfatinibAfatinib may decrease the excretion rate of Fimasartan which could result in a higher serum level.
AlclofenacThe risk or severity of renal failure, hyperkalemia, and hypertension can be increased when Fimasartan is combined with Alclofenac.
AldesleukinThe risk or severity of adverse effects can be increased when Aldesleukin is combined with Fimasartan.
AlectinibAlectinib may decrease the excretion rate of Fimasartan which could result in a higher serum level.
Interactions
Improve patient outcomes
Build effective decision support tools with the industry’s most comprehensive drug-drug interaction checker.
Learn more
Food Interactions
Not Available

Products

Products
Comprehensive & structured drug product info
From application numbers to product codes, connect different identifiers through our commercial datasets.
Learn more
Easily connect various identifiers back to our datasets
Learn more
Product Ingredients
IngredientUNIICASInChI Key
Fimasartan potassium anhydrousT2ICP7GBBN1402813-38-0OCKQGXSJNJCCDO-UHFFFAOYSA-N
Fimasartan potassium trihydrate4516BN0T4B1020110-23-9IJEKJHQBGZFMMI-UHFFFAOYSA-N
International/Other Brands
Kanarb (Boryung Pharmaceuticals)

Categories

ATC Codes
C09DA10 — Fimasartan and diureticsC09CA10 — FimasartanC09DB09 — Fimasartan and amlodipineC10BX16 — Rosuvastatin and fimasartan
Drug Categories
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
  1. 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]
  2. 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]
PubChem Compound
9870652
PubChem Substance
310265172
ChemSpider
8046343
BindingDB
50364573
ChEBI
136044
ChEMBL
CHEMBL1951143
ZINC
ZINC000003842872
Wikipedia
Fimasartan

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
4CompletedTreatmentEssential,Hypertension / Hypertension,Essential1
4CompletedTreatmentHigh Blood Pressure (Hypertension)2
4TerminatedTreatmentCoronary Artery Disease (CAD)1
4Unknown StatusTreatmentBlood Pressures / Stroke, Ischemic1
4Unknown StatusTreatmentCritical Stenosis of Aortic Valve1
4Unknown StatusTreatmentHigh Blood Pressure (Hypertension)1
4Unknown StatusTreatmentHypertension Arterial1
3Active Not RecruitingTreatmentChronic Kidney Disease (CKD)1
3CompletedTreatmentDyslipidemia / Hypertension,Essential1
3CompletedTreatmentEssential Hypertension, Dyslipidemia2

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
FormRouteStrength
Tablet, film coatedOral
Tablet, film coatedOral120 mg
Tablet, coatedOral60 mg
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.00469 mg/mLALOGPS
logP4.09ALOGPS
logP4.21ChemAxon
logS-5ALOGPS
pKa (Strongest Acidic)4.23ChemAxon
pKa (Strongest Basic)1.34ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area90.37 Å2ChemAxon
Rotatable Bond Count9ChemAxon
Refractivity161.24 m3·mol-1ChemAxon
Polarizability54.86 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted ADMET Features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Targets

Drugtargets
Accelerate your drug discovery research
with our fully connected ADMET & drug target dataset.
Learn more
Accelerate your drug discovery research with our ADMET & drug target dataset
Learn more
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
  1. 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
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
  1. 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
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
  1. 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 on October 29, 2015 15:04 / Updated on June 13, 2021 14:15