U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ACHIRAL
Molecular Formula C23H24N2O4S.CH4O3S
Molecular Weight 520.618
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of EPROSARTAN MESYLATE

SMILES

CS(O)(=O)=O.CCCCC1=NC=C(\C=C(/CC2=CC=CS2)C(O)=O)N1CC3=CC=C(C=C3)C(O)=O

InChI

InChIKey=DJSLTDBPKHORNY-XMMWENQYSA-N
InChI=1S/C23H24N2O4S.CH4O3S/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;1-5(2,3)4/h4-5,7-12,14H,2-3,6,13,15H2,1H3,(H,26,27)(H,28,29);1H3,(H,2,3,4)/b18-12+;

HIDE SMILES / InChI

Molecular Formula CH4O3S
Molecular Weight 96.106
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

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

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
Clinical profile of eprosartan.
2002 Dec
Eprosartan for the treatment of hypertension.
2003 Jan
Prediction of genotoxicity of chemical compounds by statistical learning methods.
2005 Jun
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.
Substance Class Chemical
Created
by admin
on Fri Dec 15 15:53:56 UTC 2023
Edited
by admin
on Fri Dec 15 15:53:56 UTC 2023
Record UNII
8N2L1NX8S3
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
EPROSARTAN MESYLATE
ORANGE BOOK   USAN   USP-RS   VANDF  
USAN  
Official Name English
EPROSARTAN MESYLATE [VANDF]
Common Name English
EPROSARTAN MESYLATE COMPONENT OF TEVETEN HCT
Common Name English
EPROSARTAN MESILATE
MART.   WHO-DD  
Common Name English
2-THIOPHENEPROPANOIC ACID, .ALPHA.-((2-BUTYL-1-((4-CARBOXYPHENYL)METHYL)-1H-IMIDAZOL-5-YL)METHYLENE)-, (E)-, MONOMETHANESULPHONATE
Common Name English
SK&F-108566-J
Code English
EPROSARTAN MESYLATE [ORANGE BOOK]
Common Name English
EPROSARTAN MONOMETHANESULFONATE [MI]
Common Name English
(E)-2-BUTYL-1-(P-CARBOXYBENZYL)-.ALPHA.-2-THENYLIMIDAZOLE-5-ACRYLIC ACID, MONOMETHANESULPHONATE
Common Name English
EPROSARTAN MESYLATE [USAN]
Common Name English
EPROSARTAN MESILATE [MART.]
Common Name English
EPROSARTAN MESYLATE [USP MONOGRAPH]
Common Name English
SK&F 108566-J
Code English
EPROSARTAN MESYLATE [USP-RS]
Common Name English
Eprosartan mesilate [WHO-DD]
Common Name English
EPROSARTAN MONOMETHANESULFONATE
MI  
Common Name English
TEVETEN HCT COMPONENT EPROSARTAN MESYLATE
Common Name English
TEVETEN
Brand Name English
2-THIOPHENEPROPANOIC ACID, .ALPHA.-((2-BUTYL-1-((4-CARBOXYPHENYL)METHYL)-1H-IMIDAZOL-5-YL)METHYLENE)-, (E)-, MONOMETHANESULFONATE
Common Name English
(E)-2-BUTYL-1-(P-CARBOXYBENZYL)-.ALPHA.-2-THENYLIMIDAZOLE-5-ACRYLIC ACID, MONOMETHANESULFONATE
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C66930
Created by admin on Fri Dec 15 15:53:56 UTC 2023 , Edited by admin on Fri Dec 15 15:53:56 UTC 2023
Code System Code Type Description
PUBCHEM
5282474
Created by admin on Fri Dec 15 15:53:56 UTC 2023 , Edited by admin on Fri Dec 15 15:53:56 UTC 2023
PRIMARY
RS_ITEM_NUM
1238217
Created by admin on Fri Dec 15 15:53:56 UTC 2023 , Edited by admin on Fri Dec 15 15:53:56 UTC 2023
PRIMARY
NCI_THESAURUS
C47515
Created by admin on Fri Dec 15 15:53:56 UTC 2023 , Edited by admin on Fri Dec 15 15:53:56 UTC 2023
PRIMARY
FDA UNII
8N2L1NX8S3
Created by admin on Fri Dec 15 15:53:56 UTC 2023 , Edited by admin on Fri Dec 15 15:53:56 UTC 2023
PRIMARY
EPA CompTox
DTXSID7044217
Created by admin on Fri Dec 15 15:53:56 UTC 2023 , Edited by admin on Fri Dec 15 15:53:56 UTC 2023
PRIMARY
DAILYMED
8N2L1NX8S3
Created by admin on Fri Dec 15 15:53:56 UTC 2023 , Edited by admin on Fri Dec 15 15:53:56 UTC 2023
PRIMARY
CAS
144143-96-4
Created by admin on Fri Dec 15 15:53:56 UTC 2023 , Edited by admin on Fri Dec 15 15:53:56 UTC 2023
PRIMARY
MERCK INDEX
m4961
Created by admin on Fri Dec 15 15:53:56 UTC 2023 , Edited by admin on Fri Dec 15 15:53:56 UTC 2023
PRIMARY Merck Index
USAN
FF-70 SALT
Created by admin on Fri Dec 15 15:53:56 UTC 2023 , Edited by admin on Fri Dec 15 15:53:56 UTC 2023
PRIMARY
DRUG BANK
DBSALT000927
Created by admin on Fri Dec 15 15:53:56 UTC 2023 , Edited by admin on Fri Dec 15 15:53:56 UTC 2023
PRIMARY
EVMPD
SUB01920MIG
Created by admin on Fri Dec 15 15:53:56 UTC 2023 , Edited by admin on Fri Dec 15 15:53:56 UTC 2023
PRIMARY
CHEBI
48409
Created by admin on Fri Dec 15 15:53:56 UTC 2023 , Edited by admin on Fri Dec 15 15:53:56 UTC 2023
PRIMARY
ChEMBL
CHEMBL813
Created by admin on Fri Dec 15 15:53:56 UTC 2023 , Edited by admin on Fri Dec 15 15:53:56 UTC 2023
PRIMARY
RXCUI
236878
Created by admin on Fri Dec 15 15:53:56 UTC 2023 , Edited by admin on Fri Dec 15 15:53:56 UTC 2023
PRIMARY RxNorm
SMS_ID
100000091306
Created by admin on Fri Dec 15 15:53:56 UTC 2023 , Edited by admin on Fri Dec 15 15:53:56 UTC 2023
PRIMARY
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