EPROSARTAN

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 Search

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

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 40 Target ID: CHEMBL227 Sources: http://www.drugbank.ca/drugs/DB00876	Antagonist 2778
Angiotensin II receptor (AT-1) type-1 3 Target ID: CHEMBL2094250 Sources: https://www.ncbi.nlm.nih.gov/pubmed/8576904	Antagonist 2778	1.5 nM [IC50]
urate transport 3 Target ID: GO:0015747 Sources: https://www.ncbi.nlm.nih.gov/pubmed/8558420	Inhibitor 8297	60.0 µM [IC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Hypertension 567 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2011/020738s026lbl.pdf	Primary		Approved 8429	TEVETEN Approved Use TEVETEN® is indicated for the treatment of hypertension. Launch Date 1.00448639E12

C_max

Value	Dose	Analyte	Population
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

Value	Dose	Analyte	Population
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

T_1/2

Value	Dose	Analyte	Population
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

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 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

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 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

CYP3A4	CYP2C9	CYP2D6	hERG
inhibitor 1587	inhibitor 1767	inhibitor 1852	inhibitor 1612

OverviewOther

Other Inhibitor	Other Substrate	Other 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

Target	Modality	Activity
CYP1A 121	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2014/020738s029lbl.pdf#page=4 Page: 4.0	no
CYP1A2 1692	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/10877007/	no
CYP2A6 739	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2014/020738s029lbl.pdf#page=4 Page: 4.0	no
CYP2C19 1553	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2014/020738s029lbl.pdf#page=4 Page: 4.0	no
CYP2C9 1819	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/10877007/	no
CYP2D6 1891	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2014/020738s029lbl.pdf#page=4 Page: 4.0	no
CYP2E 13	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2014/020738s029lbl.pdf#page=4 Page: 4.0	no
CYP2E1 970	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/10877007/	no
CYP3A 298	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2014/020738s029lbl.pdf#page=4 Page: 4.0	no
CYP3A4 1925	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/10877007/	no
Kv1.5 41	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/11259627/	yes
Kv4.3 16	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/11259627/	yes

Drug as victim

Target	Modality	Activity
CYP 270	substrate 3367 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2014/020738s029lbl.pdf#page=4 Page: 4.0	no
MRP2 205	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/24911086/	yes
OATP1B1 406	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/24911086/	yes
UGT 192	substrate 3367 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 1647	inhibitor 1626 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
Pharmacological characterization of the nonpeptide angiotensin II receptor antagonist, SK&F 108566.	1992 Jan	1309870
Characterization of [3H]SK&F 108566 as a radioligand for angiotensin type-1 receptor.	1993	8463997
Clinical profile of eprosartan.	2002 Dec	12766389
The clinical profile of the angiotensin II receptor blocker eprosartan.	2002 Jun	12184062
Eprosartan for the treatment of hypertension.	2003 Jan	12517247
Moxonidine normalizes sympathetic hyperactivity in patients with eprosartan-treated chronic renal failure.	2004 Nov	15504943
Prediction of genotoxicity of chemical compounds by statistical learning methods.	2005 Jun	15962942
Effects of eprosartan on serum metabolic parameters in patients with essential hypertension.	2007	18949087
Introduction: The pharmacological profile of eprosartan--implications for cerebrovascular and cardiovascular risk reduction.	2007 Nov	18093407
Clinical profile of eprosartan: a different angiotensin II receptor blocker.	2008 Oct	18855637

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.

Name

Type

Language

EPROSARTAN

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