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

Similar Structures

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	antagonist	Humans

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Additional Data Available

Adverse Effects

Comprehensive structured data on known drug adverse effects with statistical prevalence. MedDRA and ICD10 ids are provided for adverse effect conditions and symptoms.

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Additional Data Available

Contraindications

Structured data covering drug contraindications. Each contraindication describes a scenario in which the drug is not to be used. Includes restrictions on co-administration, contraindicated populations, and more.

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Additional Data Available

Blackbox Warnings

Structured data representing warnings from the black box section of drug labels. These warnings cover important and dangerous risks, contraindications, or adverse effects.

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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
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1-(3-Mercapto-2-Methyl-Propionyl)-Pyrrolidine-2-Carboxylic Acid	The risk or severity of adverse effects can be increased when Fimasartan is combined with 1-(3-Mercapto-2-Methyl-Propionyl)-Pyrrolidine-2-Carboxylic Acid.
7,8-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.

Additional Data Available

Extended Description

Extended description of the mechanism of action and particular properties of each drug interaction.

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Severity

A severity rating for each drug interaction, from minor to major.

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Evidence Level

A rating for the strength of the evidence supporting each drug interaction.

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Action

Evidence Level

An effect category for each drug interaction. Know how this interaction affects the subject drug.

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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

C09CA10 — Fimasartan

Clinical Trials

Clinical Trials

Phase	Status	Purpose	Conditions	Count
1	Active Not Recruiting	Other	Diabetes Mellitus (DM) / High Blood Pressure (Hypertension)	1
1	Completed	Not Available	Healthy Volunteers	2
1	Completed	Not Available	Hepatic Impairment / Hypertension,Essential	1
1	Completed	Not Available	High Blood Pressure (Hypertension)	5
1	Completed	Not Available	Hypertension,Essential	8
1	Completed	Not Available	Impaired Renal Function	1
1	Completed	Other	High Blood Pressure (Hypertension)	2
1	Completed	Treatment	High Blood Pressure (Hypertension) / Hyperlipidemias	2
1	Completed	Treatment	Hypertension, Hyperlipidemia	1
1	Completed	Treatment	Hypertension,Essential	1
2	Completed	Treatment	High Blood Pressure (Hypertension)	3
2	Completed	Treatment	Hypertension,Essential	2
3	Active Not Recruiting	Treatment	Essential Hypertension, Dyslipidemia	1
3	Completed	Treatment	Arterial Hypertension	1
3	Completed	Treatment	Essential Hypertension, Dyslipidemia	1
3	Completed	Treatment	High Blood Pressure (Hypertension)	3
3	Completed	Treatment	Hypertension,Essential	3
3	Recruiting	Treatment	Chronic Kidney Disease (CKD)	1
3	Recruiting	Treatment	Dyslipidemias / Hypertension,Essential	1
4	Active Not Recruiting	Treatment	Blood Pressures / Stroke, Ischemic	1
4	Active Not Recruiting	Treatment	High Blood Pressure (Hypertension)	1
4	Completed	Treatment	Essential,Hypertension	1
4	Completed	Treatment	High Blood Pressure (Hypertension)	2
4	Terminated	Treatment	Coronary Artery Disease	1
4	Unknown Status	Treatment	Critical Stenosis of Aortic Valve	1
Not Available	Active Not Recruiting	Not Available	High Blood Pressure (Hypertension)	1
Not Available	Completed	Treatment	Diabetes Mellitus (DM) / High Blood Pressure (Hypertension)	1

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

Details1. Type-1 angiotensin II receptor

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

Details1. Solute carrier organic anion transporter family member 1B1

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]

Details2. ATP-binding cassette sub-family G member 2

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 May 09, 2019 00:15

Fimasartan

Identification

Structure for Fimasartan (DB09279)

Pharmacology

Interactions

References

Clinical Trials

Pharmacoeconomics

Properties

Spectra

Taxonomy

Targets

References

Transporters

References

References