EPROSARTAN MESYLATE DIHYDRATE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C23H24N2O4S.CH4O3S.2H2O
Molecular Weight	556.649
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	1
Charge	0

SHOW SMILES / InChI

Structure of EPROSARTAN MESYLATE DIHYDRATE

Structure Search

SMILES

O.O.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=HIUNDVRJXJGSGV-KMDBKMSFSA-N

InChI=1S/C23H24N2O4S.CH4O3S.2H2O/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);2*1H2/b18-12+;;;

HIDE SMILES / InChI

Molecular Formula	H2O
Molecular Weight	18.0153
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

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

Description
Sources: http://www.drugbank.ca/drugs/DB00876
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

Originator

Approval Year

Targets

Primary Target	Pharmacology	Potency
Type-1 angiotensin II receptor 41 Target ID: CHEMBL227 Sources: http://www.drugbank.ca/drugs/DB00876	Antagonist 2849
Angiotensin II receptor (AT-1) type-1 3 Target ID: CHEMBL2094250 Sources: https://www.ncbi.nlm.nih.gov/pubmed/8576904	Antagonist 2849	1.5 nM [IC50]
urate transport 3 Target ID: GO:0015747 Sources: https://www.ncbi.nlm.nih.gov/pubmed/8558420	Inhibitor 8504	60.0 µM [IC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Hypertension 575 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2011/020738s026lbl.pdf	Primary		Approved 8583	TEVETEN Approved Use TEVETEN® is indicated for the treatment of hypertension. Launch Date 2001

C_max

Value	Dose	Analyte	Population
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
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
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
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
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
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

AUC

Value	Dose	Analyte	Population
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
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
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
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
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
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

T_1/2

Value	Dose	Analyte	Population
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
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
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
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

F_unbound

Value	Dose	Co-administered	Analyte	Population
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

Dose	Population	Adverse 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	healthy, 20-43 Health Status: healthy Age Group: 20-43 Sex: M Sources: https://pubmed.ncbi.nlm.nih.gov/9597557	Other AEs: Headache, Earache... Other AEs: Headache (17.4%) Earache (4.3%) Sources: https://pubmed.ncbi.nlm.nih.gov/9597557
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 Health Status: unknown 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

AE	Significance	Dose	Population
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	healthy, 20-43 Health Status: healthy Age Group: 20-43 Sex: M Sources: https://pubmed.ncbi.nlm.nih.gov/9597557
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	healthy, 20-43 Health Status: healthy Age Group: 20-43 Sex: M Sources: https://pubmed.ncbi.nlm.nih.gov/9597557
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 Health Status: unknown Sources: https://www.medicines.org.uk/emc/product/712/smpc#gref

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
inhibitor 2252	inhibitor 2438	inhibitor 2507	inhibitor 2217

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP1A 70 CYP2A6 879 CYP2C19 2057 CYP2E 4 CYP3A 227 CYP1A2 2153 CYP2E1 1060 Kv4.3 16 Kv1.5 27	UGT 219 CYP 303 OATP1B1 503 MRP2 252

Drug as perpetrator

Target	Modality	Activity
CYP1A 122	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2014/020738s029lbl.pdf#page=4 Page: 4.0	no
CYP1A2 2333	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/10877007/	no
CYP2A6 911	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2014/020738s029lbl.pdf#page=4 Page: 4.0	no
CYP2C19 2141	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2014/020738s029lbl.pdf#page=4 Page: 4.0	no
CYP2C9 2497	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/10877007/	no
CYP2D6 2546	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2014/020738s029lbl.pdf#page=4 Page: 4.0	no
CYP2E 13	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2014/020738s029lbl.pdf#page=4 Page: 4.0	no
CYP2E1 1146	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/10877007/	no
CYP3A 317	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2014/020738s029lbl.pdf#page=4 Page: 4.0	no
CYP3A4 2633	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/10877007/	no
Kv1.5 42	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/11259627/	yes
Kv4.3 16	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/11259627/	yes

Drug as victim

Target	Modality	Activity
CYP 303	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2014/020738s029lbl.pdf#page=4 Page: 4.0	no
MRP2 252	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/24911086/	yes
OATP1B1 503	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/24911086/	yes
UGT 219	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2014/020738s029lbl.pdf#page=2 Page: 2.0	yes

Tox targets

Target	Modality	Activity	Metabolite	Clinical evidence
hERG 2263	inhibitor 2237 Sources: https://pubmed.ncbi.nlm.nih.gov/11259627/

Sourcing

Vendor/Aggregator	ID	URL
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

Title	Date	PubMed
Clinical profile of eprosartan: a different angiotensin II receptor blocker.	2008-10	18855637
Introduction: The pharmacological profile of eprosartan--implications for cerebrovascular and cardiovascular risk reduction.	2007-11	18093407
Effects of eprosartan on serum metabolic parameters in patients with essential hypertension.	2007	18949087
Prediction of genotoxicity of chemical compounds by statistical learning methods.	2005-06	15962942
Moxonidine normalizes sympathetic hyperactivity in patients with eprosartan-treated chronic renal failure.	2004-11	15504943
Eprosartan for the treatment of hypertension.	2003-01	12517247
Clinical profile of eprosartan.	2002-12	12766389
The clinical profile of the angiotensin II receptor blocker eprosartan.	2002-06	12184062
Eprosartan versus enalapril in elderly patients with hypertension: a double-blind, randomized trial.	2001	11800061
Efficacy and safety of eprosartan in severe hypertension. Eprosartan Multinational Study Group.	1999	10451039
Characterization of [3H]SK&F 108566 as a radioligand for angiotensin type-1 receptor.	1993	8463997
Pharmacological characterization of the nonpeptide angiotensin II receptor antagonist, SK&F 108566.	1992-01	1309870

Patents

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 `Mon Mar 31 22:41:28 GMT 2025` Edited by `admin` on `Mon Mar 31 22:41:28 GMT 2025`
Record UNII	9G2HB74868
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

2-THIOPHENEPROPANOIC ACID, .ALPHA.-((2-BUTYL-1-((4-CARBOXYPHENYL)METHYL)-1H-IMIDAZOL-5-YL)METHYLENE)-, (.ALPHA.E)-, MONOMETHANESULFONATE, DIHYDRATE

Preferred Name

English

EPROSARTAN MESYLATE DIHYDRATE

Common Name

English

2-THIOPHENEPROPANOIC ACID, .ALPHA.-((2-BUTYL-1-((4-CARBOXYPHENYL)METHYL)-1H-IMIDAZOL-5-YL)METHYLENE)-, (E)-, MONOMETHANESULFONATE, DIHYDRATE

Systematic Name

English

Code System Code Type Description

EVMPD

SUB127293