Fimasartan

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

3D

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MOLSDF3D-SDFPDBSMILESInChI

Similar Structures

Structure for Fimasartan (DB09279)

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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

• Agents Acting on the Renin-Angiotensin System
• Agents causing hyperkalemia
• Angiotensin II receptor blockers (ARBs) and diuretics
• Angiotensin II receptor blockers (ARBs), plain
• Angiotensin Receptor Antagonists
• BCRP/ABCG2 Substrates
• Benzene Derivatives
• Hypotensive Agents
• OATP1B1/SLCO1B1 Substrates

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

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.

• All Drugs
• Approved
• Vet approved
• Nutraceutical
• Illicit
• Withdrawn
• Investigational
• Experimental

Drug	Interaction
Unlock Additional Data
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.
Alclofenac	The risk or severity of renal failure, hyperkalemia, and hypertension can be increased when Fimasartan is combined with Alclofenac.

Additional Data Available

Extended Description
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
Evidence Level
A rating for the strength of the evidence supporting each drug interaction.
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Action
Action
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Food Interactions

Not Available

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. [PubMed:22864732]
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]

External Links

PubChem Compound

9870652

PubChem Substance

310265172

ChemSpider

8046343

BindingDB

50364573

ChEBI

136044

ChEMBL

CHEMBL1951143

ZINC

ZINC000003842872

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

C09CA10 — Fimasartan

• 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

Clinical Trials

Clinical Trials

Phase	Status	Purpose	Conditions	Count
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 kidney function	1
1	Completed	Other	Diabetes / High Blood Pressure (Hypertension)	1
1	Completed	Other	High Blood Pressure (Hypertension)	3
1	Completed	Treatment	Drug Drug Interaction (DDI)	1
1	Completed	Treatment	High Blood Pressure (Hypertension) / Hyperlipidemias	2
1	Completed	Treatment	Hypertension, Hyperlipidemia	2
1	Completed	Treatment	Hypertension,Essential	1
2	Completed	Treatment	High Blood Pressure (Hypertension)	3
2	Completed	Treatment	Hypertension,Essential	3
3	Active Not Recruiting	Treatment	Chronic Kidney Disease (CKD)	1
3	Completed	Treatment	Arterial Hypertension	1
3	Completed	Treatment	Dyslipidemia / Hypertension,Essential	1
3	Completed	Treatment	Essential Hypertension, Dyslipidemia	2
3	Completed	Treatment	High Blood Pressure (Hypertension)	3
3	Completed	Treatment	Hypertension,Essential	3
3	Completed	Treatment	The Elderly (≥ 70 Years) With Essential Hypertension	1
3	Recruiting	Treatment	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 / Hypertension,Essential	1
4	Completed	Treatment	High Blood Pressure (Hypertension)	2
4	Not Yet Recruiting	Treatment	Arterial Hypertension	1
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 / 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 compoundsOrganooxygen compounds / Organonitrogen compounds / Organic oxides / Hydrocarbon derivatives

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Substituents

Biphenyl / Phenyltetrazole / Pyrimidone / Hydropyrimidine / Pyrimidine / Azole / Heteroaromatic compound / Tetrazole / Thioamide / LactamAzacycle / Organoheterocyclic compound / Thiocarboxylic acid amide / Hydrocarbon derivative / Organosulfur compound / Organooxygen compound / Organonitrogen compound / Organic oxide / Organopnictogen compound / Organic nitrogen compound / Organic oxygen compound / Thiocarbonyl group / Aromatic heteromonocyclic compound

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Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

Not Available

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Drug created on October 29, 2015 09:04 / Updated on June 12, 2020 10:52