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Details

Stereochemistry ACHIRAL
Molecular Formula C23H24N2O4S
Molecular Weight 424.513
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of EPROSARTAN

SMILES

CCCCC1=NC=C(\C=C(/CC2=CC=CS2)C(O)=O)N1CC3=CC=C(C=C3)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
Molecular Formula C23H24N2O4S
Molecular Weight 424.513
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 1
Optical Activity NONE

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

CNS Penetrant
2554
Curator's Comment: Eprosartan readily crosses the blood-brain barrier in vivo and selectively inhibits binding to AT1 receptors in specific brain nuclei.

Originator

Approval Year

1997
172
Targets

Targets

Primary TargetPharmacologyConditionPotency
Antagonist
2778
Antagonist
2778
 1.5 nM [IC50]
Inhibitor
8297
 60.0 µM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Approved
8429
TEVETEN

Approved Use

TEVETEN® is indicated for the treatment of hypertension.

Launch Date

2001
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
1273 ng/mL
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/9597557/
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
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/9597557/
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
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/9597557/
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
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/9597557/
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
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/9737815/
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
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/9737815/
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
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/9737815/
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
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/9597557/
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
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/9597557/
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
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/9597557/
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
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/9597557/
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
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/9737815/
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
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/9737815/
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
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/9737815/
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
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/9737815/
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
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/9737815/
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
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/9737815/
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
DRUG LABEL
https://www.accessdata.fda.gov/drugsatfda_docs/label/2014/020738s029lbl.pdf
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%
DRUG LABEL
https://www.accessdata.fda.gov/drugsatfda_docs/label/2014/020738s029lbl.pdf
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:
https://pubmed.ncbi.nlm.nih.gov/9597557
Page: p.38
healthy, 20-43
n = 23
Health Status: healthy
Age Group: 20-43
Sex: M
Population Size: 23
Sources:
https://pubmed.ncbi.nlm.nih.gov/9597557
Page: p.38
Other AEs: Headache, Earache...
Other AEs:
Headache (17.4%)
Earache (4.3%)
Sources:
https://pubmed.ncbi.nlm.nih.gov/9597557
Page: p.38
12000 mg single, oral
Overdose
Dose: 12000 mg
Route: oral
Route: single
Dose: 12000 mg
Sources:
https://www.medicines.org.uk/emc/product/712/smpc#gref
unknown
n = 1
Health Status: unknown
Population Size: 1
Sources:
https://www.medicines.org.uk/emc/product/712/smpc#gref
Other AEs: Circulatory collapse...
Other AEs:
Circulatory collapse
Sources:
https://www.medicines.org.uk/emc/product/712/smpc#gref
AEs

AEs

AESignificanceDosePopulation
Headache 17.4%
800 mg single, oral
Highest studied dose
Dose: 800 mg
Route: oral
Route: single
Dose: 800 mg
Sources:
https://pubmed.ncbi.nlm.nih.gov/9597557
Page: p.38
healthy, 20-43
n = 23
Health Status: healthy
Age Group: 20-43
Sex: M
Population Size: 23
Sources:
https://pubmed.ncbi.nlm.nih.gov/9597557
Page: p.38
Earache 4.3%
800 mg single, oral
Highest studied dose
Dose: 800 mg
Route: oral
Route: single
Dose: 800 mg
Sources:
https://pubmed.ncbi.nlm.nih.gov/9597557
Page: p.38
healthy, 20-43
n = 23
Health Status: healthy
Age Group: 20-43
Sex: M
Population Size: 23
Sources:
https://pubmed.ncbi.nlm.nih.gov/9597557
Page: p.38
Circulatory collapse
12000 mg single, oral
Overdose
Dose: 12000 mg
Route: oral
Route: single
Dose: 12000 mg
Sources:
https://www.medicines.org.uk/emc/product/712/smpc#gref
unknown
n = 1
Health Status: unknown
Population Size: 1
Sources:
https://www.medicines.org.uk/emc/product/712/smpc#gref
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG
inhibitor
1587
inhibitor
1767
inhibitor
1852
inhibitor
1612

OverviewOther

Other InhibitorOther SubstrateOther Inducer
CYP1A
72

CYP2A6
707

CYP2C19
1478

CYP2E
4

CYP3A
214

CYP1A2
1524

CYP2E1
882

Kv4.3
16

Kv1.5
26
UGT
192

CYP
270

OATP1B1
406

MRP2
205
Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
CYP1A
121
 no
CYP1A2
1692
 no
CYP2A6
739
 no
CYP2C19
1553
 no
CYP2C9
1819
 no
CYP2D6
1891
 no
CYP2E
13
 no
CYP2E1
970
 no
CYP3A
298
 no
CYP3A4
1925
 no
Kv1.5
41
 yes
Kv4.3
16
 yes
Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
CYP
270
 no
MRP2
205
 yes
OATP1B1
406
 yes
UGT
192
 yes
Tox targets

Tox targets

TargetModalityActivityMetaboliteClinical evidence
hERG
1647
Sourcing

Sourcing

Vendor/AggregatorIDURL
ChEBI
CHEBI:4814
https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:4814
ChemicalBook
CB0135346
https://www.chemicalbook.com/ChemicalProductProperty_EN_CB0135346
ZINC
ZINC000029319828
http://zinc15.docking.org/substances/ZINC000029319828
PubMed

PubMed

TitleDatePubMed
Pharmacological characterization of the nonpeptide angiotensin II receptor antagonist, SK&F 108566.
1992 Jan
Characterization of [3H]SK&F 108566 as a radioligand for angiotensin type-1 receptor.
1993
Clinical profile of eprosartan.
2002 Dec
The clinical profile of the angiotensin II receptor blocker eprosartan.
2002 Jun
Eprosartan for the treatment of hypertension.
2003 Jan
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

JP2005516940A
28

Sample Use Guides

In Vivo Use Guide
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
In Vitro Use Guide
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.
Substance Class Chemical
Created
by admin
on Fri Dec 15 16:37:23 GMT 2023
Edited
by admin
on Fri Dec 15 16:37:23 GMT 2023
Record UNII
2KH13Z0S0Y
Record Status Validated (UNII)
Record Version
  • Download
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
2-THIOPHENEPROPANOIC ACID, .ALPHA.-((2-BUTYL-1-((4-CARBOXYPHENYL)METHYL)-LH-IMIDAZOL-5-YL)METHYLENE)-, (E)-
Common Name English
Eprosartan [WHO-DD]
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 Fri Dec 15 16:37:23 GMT 2023 , Edited by admin on Fri Dec 15 16:37:23 GMT 2023
NCI_THESAURUS C66930
Created by admin on Fri Dec 15 16:37:23 GMT 2023 , Edited by admin on Fri Dec 15 16:37:23 GMT 2023
WHO-VATC QC09DA02
Created by admin on Fri Dec 15 16:37:23 GMT 2023 , Edited by admin on Fri Dec 15 16:37:23 GMT 2023
WHO-VATC QC09CA02
Created by admin on Fri Dec 15 16:37:23 GMT 2023 , Edited by admin on Fri Dec 15 16:37:23 GMT 2023
LIVERTOX NBK548507
Created by admin on Fri Dec 15 16:37:23 GMT 2023 , Edited by admin on Fri Dec 15 16:37:23 GMT 2023
WHO-ATC C09DA02
Created by admin on Fri Dec 15 16:37:23 GMT 2023 , Edited by admin on Fri Dec 15 16:37:23 GMT 2023
WHO-ATC C09CA02
Created by admin on Fri Dec 15 16:37:23 GMT 2023 , Edited by admin on Fri Dec 15 16:37:23 GMT 2023
NDF-RT N0000000070
Created by admin on Fri Dec 15 16:37:23 GMT 2023 , Edited by admin on Fri Dec 15 16:37:23 GMT 2023
Code System Code Type Description
MESH
C068373
Created by admin on Fri Dec 15 16:37:23 GMT 2023 , Edited by admin on Fri Dec 15 16:37:23 GMT 2023
PRIMARY
INN
7223
Created by admin on Fri Dec 15 16:37:23 GMT 2023 , Edited by admin on Fri Dec 15 16:37:23 GMT 2023
PRIMARY
NCI_THESAURUS
C61749
Created by admin on Fri Dec 15 16:37:23 GMT 2023 , Edited by admin on Fri Dec 15 16:37:23 GMT 2023
PRIMARY
WIKIPEDIA
EPROSARTAN
Created by admin on Fri Dec 15 16:37:23 GMT 2023 , Edited by admin on Fri Dec 15 16:37:23 GMT 2023
PRIMARY
ChEMBL
CHEMBL813
Created by admin on Fri Dec 15 16:37:23 GMT 2023 , Edited by admin on Fri Dec 15 16:37:23 GMT 2023
PRIMARY
EVMPD
SUB06586MIG
Created by admin on Fri Dec 15 16:37:23 GMT 2023 , Edited by admin on Fri Dec 15 16:37:23 GMT 2023
PRIMARY
USAN
FF-70
Created by admin on Fri Dec 15 16:37:23 GMT 2023 , Edited by admin on Fri Dec 15 16:37:23 GMT 2023
PRIMARY
HSDB
7521
Created by admin on Fri Dec 15 16:37:23 GMT 2023 , Edited by admin on Fri Dec 15 16:37:23 GMT 2023
PRIMARY
RXCUI
83515
Created by admin on Fri Dec 15 16:37:23 GMT 2023 , Edited by admin on Fri Dec 15 16:37:23 GMT 2023
PRIMARY RxNorm
IUPHAR
588
Created by admin on Fri Dec 15 16:37:23 GMT 2023 , Edited by admin on Fri Dec 15 16:37:23 GMT 2023
PRIMARY
DRUG BANK
DB00876
Created by admin on Fri Dec 15 16:37:23 GMT 2023 , Edited by admin on Fri Dec 15 16:37:23 GMT 2023
PRIMARY
CHEBI
4814
Created by admin on Fri Dec 15 16:37:23 GMT 2023 , Edited by admin on Fri Dec 15 16:37:23 GMT 2023
PRIMARY
DRUG CENTRAL
1037
Created by admin on Fri Dec 15 16:37:23 GMT 2023 , Edited by admin on Fri Dec 15 16:37:23 GMT 2023
PRIMARY
SMS_ID
100000084574
Created by admin on Fri Dec 15 16:37:23 GMT 2023 , Edited by admin on Fri Dec 15 16:37:23 GMT 2023
PRIMARY
LACTMED
Eprosartan
Created by admin on Fri Dec 15 16:37:23 GMT 2023 , Edited by admin on Fri Dec 15 16:37:23 GMT 2023
PRIMARY
PUBCHEM
5281037
Created by admin on Fri Dec 15 16:37:23 GMT 2023 , Edited by admin on Fri Dec 15 16:37:23 GMT 2023
PRIMARY
FDA UNII
2KH13Z0S0Y
Created by admin on Fri Dec 15 16:37:23 GMT 2023 , Edited by admin on Fri Dec 15 16:37:23 GMT 2023
PRIMARY
CAS
133040-01-4
Created by admin on Fri Dec 15 16:37:23 GMT 2023 , Edited by admin on Fri Dec 15 16:37:23 GMT 2023
PRIMARY
DAILYMED
2KH13Z0S0Y
Created by admin on Fri Dec 15 16:37:23 GMT 2023 , Edited by admin on Fri Dec 15 16:37:23 GMT 2023
PRIMARY
EPA CompTox
DTXSID0022989
Created by admin on Fri Dec 15 16:37:23 GMT 2023 , Edited by admin on Fri Dec 15 16:37:23 GMT 2023
PRIMARY
MERCK INDEX
m4961
Created by admin on Fri Dec 15 16:37:23 GMT 2023 , Edited by admin on Fri Dec 15 16:37:23 GMT 2023
PRIMARY Merck Index
Related Record Type Details
PLASMA PROTEIN FRACTION (HUMAN)
BINDER->LIGAND
BINDING
Structure of EPROSARTAN MESYLATE
SALT/SOLVATE -> PARENT
TYPE-1 ANGIOTENSIN II RECEPTOR
TARGET -> INHIBITOR
Related Record Type Details
Structure of BENZYL(METHYL)NITROSAMINE
IMPURITY -> PARENT
Priority toxic pollutant.
Structure of N-NITROSODIETHYLAMINE
IMPURITY -> PARENT
Probable human carcinogen.
Structure of N-NITROSODIMETHYLAMINE
IMPURITY GENOTOXIC->PARENT
NDMA is an organic chemical that is in a family of potent carcinogens.
Related Record Type Details
Structure of EPROSARTAN
ACTIVE MOIETY
Name Property Type Amount Referenced Substance Defining Parameters References
Biological Half-life PHARMACOKINETIC
Volume of Distribution PHARMACOKINETIC
NIH
NCATS
PRIVACY ACT
ACCESSIBILITY
DISCLAIMER
HHS VULNERABILITY DISCLOSURE
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