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Details

Stereochemistry ACHIRAL
Molecular Formula C23H24N2O4S
Molecular Weight 424.5146
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of EPROSARTAN

SMILES

CCCCc1ncc(/C(/[H])=C(\Cc2cccs2)/C(=O)O)n1Cc3ccc(cc3)C(=O)O

InChI

InChIKey=OROAFUQRIXKEMV-LDADJPATSA-N
InChI=1S/C23H24N2O4S/c1-2-3-6-21-24-14-19(12-18(23(28)29)13-20-5-4-11-30-20)25(21)15-16-7-9-17(10-8-16)22(26)27/h4-5,7-12,14H,2-3,6,13,15H2,1H3,(H,26,27)(H,28,29)/b18-12+

HIDE SMILES / InChI

Description
Curator's Comment:: Description was created based on several sources, including https://www.drugs.com/pro/eprosartan.html

Eprosartan is an angiotensin II receptor antagonist used for the treatment of high blood pressure. It acts on the renin-angiotensin system in two ways to decrease total peripheral resistance. First, it blocks the binding of angiotensin II to AT1 receptors in vascular smooth muscle, causing vascular dilatation. Second, it inhibits sympathetic norepinephrine production, further reducing blood pressure. Eprosartan is indicated for the management of hypertension alone or in combination with other classes of antihypertensive agents. Also used as a first-line agent in the treatment of diabetic nephropathy, as well as a second-line agent in the treatment of congestive heart failure (only in those intolerant of ACE inhibitors).

CNS Activity

Curator's Comment:: Eprosartan readily crosses the blood-brain barrier in vivo and selectively inhibits binding to AT1 receptors in specific brain nuclei.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
1.5 nM [IC50]
60.0 µM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
TEVETEN

Approved Use

TEVETEN® is indicated for the treatment of hypertension.

Launch Date

1.00448639E12
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
1273 ng/mL
400 mg single, oral
dose: 400 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
EPROSARTAN plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
439 ng/mL
100 mg single, oral
dose: 100 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
EPROSARTAN plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
702 ng/mL
200 mg single, oral
dose: 200 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
EPROSARTAN plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
1857 ng/mL
800 mg single, oral
dose: 800 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
EPROSARTAN plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
2246 ng/mL
20 mg single, intravenous
dose: 20 mg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
EPROSARTAN plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
1205 ng/mL
300 mg single, oral
dose: 300 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
EPROSARTAN plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FED
1612 ng/mL
300 mg single, oral
dose: 300 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
EPROSARTAN plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
4887 ng × h/L
400 mg single, oral
dose: 400 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
EPROSARTAN plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
1400 ng × h/mL
100 mg single, oral
dose: 100 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
EPROSARTAN plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
2620 ng × h/mL
200 mg single, oral
dose: 200 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
EPROSARTAN plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
7855 ng × h/mL
800 mg single, oral
dose: 800 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
EPROSARTAN plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
2671 ng × h/mL
20 mg single, intravenous
dose: 20 mg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
EPROSARTAN plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
4950 ng × h/mL
300 mg single, oral
dose: 300 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
EPROSARTAN plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FED
5750 ng × h/mL
300 mg single, oral
dose: 300 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
EPROSARTAN plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
2.07 h
20 mg single, intravenous
dose: 20 mg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
EPROSARTAN plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
7.25 h
300 mg single, oral
dose: 300 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
EPROSARTAN plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FED
4.52 h
300 mg single, oral
dose: 300 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
EPROSARTAN plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
20 h
600 mg 1 times / day multiple, oral
dose: 600 mg
route of administration: Oral
experiment type: MULTIPLE
co-administered:
EPROSARTAN plasma
Homo sapiens
population: UNKNOWN
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
Funbound

Funbound

ValueDoseCo-administeredAnalytePopulation
2%
600 mg 1 times / day multiple, oral
dose: 600 mg
route of administration: Oral
experiment type: MULTIPLE
co-administered:
EPROSARTAN plasma
Homo sapiens
population: UNKNOWN
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
Doses

Doses

DosePopulationAdverse events​
800 mg single, oral
Highest studied dose
Dose: 800 mg
Route: oral
Route: single
Dose: 800 mg
Sources: Page: p.38
healthy, 20-43
n = 23
Health Status: healthy
Age Group: 20-43
Sex: M
Population Size: 23
Sources: Page: p.38
Other AEs: Headache, Earache...
Other AEs:
Headache (17.4%)
Earache (4.3%)
Sources: Page: p.38
12000 mg single, oral
Overdose
Dose: 12000 mg
Route: oral
Route: single
Dose: 12000 mg
Sources:
unknown
n = 1
Health Status: unknown
Population Size: 1
Sources:
Other AEs: Circulatory collapse...
Other AEs:
Circulatory collapse
Sources:
AEs

AEs

AESignificanceDosePopulation
Headache 17.4%
800 mg single, oral
Highest studied dose
Dose: 800 mg
Route: oral
Route: single
Dose: 800 mg
Sources: Page: p.38
healthy, 20-43
n = 23
Health Status: healthy
Age Group: 20-43
Sex: M
Population Size: 23
Sources: Page: p.38
Earache 4.3%
800 mg single, oral
Highest studied dose
Dose: 800 mg
Route: oral
Route: single
Dose: 800 mg
Sources: Page: p.38
healthy, 20-43
n = 23
Health Status: healthy
Age Group: 20-43
Sex: M
Population Size: 23
Sources: Page: p.38
Circulatory collapse
12000 mg single, oral
Overdose
Dose: 12000 mg
Route: oral
Route: single
Dose: 12000 mg
Sources:
unknown
n = 1
Health Status: unknown
Population Size: 1
Sources:
Overview

Overview

Drug as perpetrator​Drug as victimTox targets

Tox targets

TargetModalityActivityMetaboliteClinical evidence
PubMed

PubMed

TitleDatePubMed
Characterization of [3H]SK&F 108566 as a radioligand for angiotensin type-1 receptor.
1993
Eprosartan versus enalapril in elderly patients with hypertension: a double-blind, randomized trial.
2001
The clinical profile of the angiotensin II receptor blocker eprosartan.
2002 Jun
Moxonidine normalizes sympathetic hyperactivity in patients with eprosartan-treated chronic renal failure.
2004 Nov
Prediction of genotoxicity of chemical compounds by statistical learning methods.
2005 Jun
Effects of eprosartan on serum metabolic parameters in patients with essential hypertension.
2007
Introduction: The pharmacological profile of eprosartan--implications for cerebrovascular and cardiovascular risk reduction.
2007 Nov
Clinical profile of eprosartan: a different angiotensin II receptor blocker.
2008 Oct
Patents

Patents

Sample Use Guides

Usual Adult Dose for Hypertension Initial dose: 600 mg orally once a day as monotherapy assuming euvolemia Maintenance dose: 400 to 800 mg orally per day in 1 or 2 divided doses
Route of Administration: Oral
Eprosartan (1 uM) inhibited the tail amplitude of HERG currents elicited on repolarization after pulses to +60 mV from 239 +/- 78 to 179 +/- 72 pA.
Name Type Language
EPROSARTAN
HSDB   INN   MI   USAN   VANDF   WHO-DD  
USAN   INN  
Official Name English
SK&F-108566
Code English
EPROSARTAN [MI]
Common Name English
EPROSARTAN [USAN]
Common Name English
EPROSARTAN [WHO-DD]
Common Name English
2-THIOPHENEPROPANOIC ACID, .ALPHA.-((2-BUTYL-1-((4-CARBOXYPHENYL)METHYL)-LH-IMIDAZOL-5-YL)METHYLENE)-, (E)-
Common Name English
EPROSARTAN [INN]
Common Name English
EPROSARTAN [VANDF]
Common Name English
EPROSARTAN [HSDB]
Common Name English
SK&F 108566
Code English
(E)-2-BUTYL-1-(P-CARBOXYBENZYL)-.ALPHA.-2-THENYLIMIDAZOLE-5-ACRYLIC ACID
Common Name English
Classification Tree Code System Code
NDF-RT N0000175561
Created by admin on Sat Jun 26 06:25:22 UTC 2021 , Edited by admin on Sat Jun 26 06:25:22 UTC 2021
NCI_THESAURUS C66930
Created by admin on Sat Jun 26 06:25:22 UTC 2021 , Edited by admin on Sat Jun 26 06:25:22 UTC 2021
WHO-VATC QC09DA02
Created by admin on Sat Jun 26 06:25:22 UTC 2021 , Edited by admin on Sat Jun 26 06:25:22 UTC 2021
WHO-VATC QC09CA02
Created by admin on Sat Jun 26 06:25:22 UTC 2021 , Edited by admin on Sat Jun 26 06:25:22 UTC 2021
LIVERTOX 360
Created by admin on Sat Jun 26 06:25:22 UTC 2021 , Edited by admin on Sat Jun 26 06:25:22 UTC 2021
WHO-ATC C09DA02
Created by admin on Sat Jun 26 06:25:22 UTC 2021 , Edited by admin on Sat Jun 26 06:25:22 UTC 2021
WHO-ATC C09CA02
Created by admin on Sat Jun 26 06:25:22 UTC 2021 , Edited by admin on Sat Jun 26 06:25:22 UTC 2021
NDF-RT N0000000070
Created by admin on Sat Jun 26 06:25:22 UTC 2021 , Edited by admin on Sat Jun 26 06:25:22 UTC 2021
Code System Code Type Description
MESH
C068373
Created by admin on Sat Jun 26 06:25:22 UTC 2021 , Edited by admin on Sat Jun 26 06:25:22 UTC 2021
PRIMARY
INN
7223
Created by admin on Sat Jun 26 06:25:22 UTC 2021 , Edited by admin on Sat Jun 26 06:25:22 UTC 2021
PRIMARY
NCI_THESAURUS
C61749
Created by admin on Sat Jun 26 06:25:22 UTC 2021 , Edited by admin on Sat Jun 26 06:25:22 UTC 2021
PRIMARY
WIKIPEDIA
EPROSARTAN
Created by admin on Sat Jun 26 06:25:22 UTC 2021 , Edited by admin on Sat Jun 26 06:25:22 UTC 2021
PRIMARY
ChEMBL
CHEMBL813
Created by admin on Sat Jun 26 06:25:22 UTC 2021 , Edited by admin on Sat Jun 26 06:25:22 UTC 2021
PRIMARY
EVMPD
SUB06586MIG
Created by admin on Sat Jun 26 06:25:22 UTC 2021 , Edited by admin on Sat Jun 26 06:25:22 UTC 2021
PRIMARY
HSDB
7521
Created by admin on Sat Jun 26 06:25:22 UTC 2021 , Edited by admin on Sat Jun 26 06:25:22 UTC 2021
PRIMARY
RXCUI
83515
Created by admin on Sat Jun 26 06:25:22 UTC 2021 , Edited by admin on Sat Jun 26 06:25:22 UTC 2021
PRIMARY RxNorm
IUPHAR
588
Created by admin on Sat Jun 26 06:25:22 UTC 2021 , Edited by admin on Sat Jun 26 06:25:22 UTC 2021
PRIMARY
DRUG BANK
DB00876
Created by admin on Sat Jun 26 06:25:22 UTC 2021 , Edited by admin on Sat Jun 26 06:25:22 UTC 2021
PRIMARY
DRUG CENTRAL
1037
Created by admin on Sat Jun 26 06:25:22 UTC 2021 , Edited by admin on Sat Jun 26 06:25:22 UTC 2021
PRIMARY
LACTMED
Eprosartan
Created by admin on Sat Jun 26 06:25:22 UTC 2021 , Edited by admin on Sat Jun 26 06:25:22 UTC 2021
PRIMARY
PUBCHEM
5281037
Created by admin on Sat Jun 26 06:25:22 UTC 2021 , Edited by admin on Sat Jun 26 06:25:22 UTC 2021
PRIMARY
FDA UNII
2KH13Z0S0Y
Created by admin on Sat Jun 26 06:25:22 UTC 2021 , Edited by admin on Sat Jun 26 06:25:22 UTC 2021
PRIMARY
CAS
133040-01-4
Created by admin on Sat Jun 26 06:25:22 UTC 2021 , Edited by admin on Sat Jun 26 06:25:22 UTC 2021
PRIMARY
EPA CompTox
133040-01-4
Created by admin on Sat Jun 26 06:25:22 UTC 2021 , Edited by admin on Sat Jun 26 06:25:22 UTC 2021
PRIMARY
MERCK INDEX
M4961
Created by admin on Sat Jun 26 06:25:22 UTC 2021 , Edited by admin on Sat Jun 26 06:25:22 UTC 2021
PRIMARY Merck Index