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

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+;;;

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Description

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	Antagonist 2,849
Angiotensin II receptor (AT-1) type-1 3	Antagonist 2,849	1.5 nM [IC50]
urate transport 3	Inhibitor 8,504	60.0 µM [IC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Hypertension 575	Primary		Approved 8,583	TEVETEN

C_max

Value	Dose	Analyte	Population
439 ng/mL	100 mg single, oral	EPROSARTAN plasma	Homo sapiens
702 ng/mL	200 mg single, oral	EPROSARTAN plasma	Homo sapiens
1273 ng/mL	400 mg single, oral	EPROSARTAN plasma	Homo sapiens
1857 ng/mL	800 mg single, oral	EPROSARTAN plasma	Homo sapiens
1612 ng/mL	300 mg single, oral	EPROSARTAN plasma	Homo sapiens
1205 ng/mL	300 mg single, oral	EPROSARTAN plasma	Homo sapiens
2246 ng/mL	20 mg single, intravenous	EPROSARTAN plasma	Homo sapiens

AUC

Value	Dose	Analyte	Population
1400 ng × h/mL	100 mg single, oral	EPROSARTAN plasma	Homo sapiens
2620 ng × h/mL	200 mg single, oral	EPROSARTAN plasma	Homo sapiens
4887 ng × h/L	400 mg single, oral	EPROSARTAN plasma	Homo sapiens
7855 ng × h/mL	800 mg single, oral	EPROSARTAN plasma	Homo sapiens
5750 ng × h/mL	300 mg single, oral	EPROSARTAN plasma	Homo sapiens
4950 ng × h/mL	300 mg single, oral	EPROSARTAN plasma	Homo sapiens
2671 ng × h/mL	20 mg single, intravenous	EPROSARTAN plasma	Homo sapiens

T_1/2

Value	Dose	Analyte	Population
4.52 h	300 mg single, oral	EPROSARTAN plasma	Homo sapiens
7.25 h	300 mg single, oral	EPROSARTAN plasma	Homo sapiens
2.07 h	20 mg single, intravenous	EPROSARTAN plasma	Homo sapiens
20 h	600 mg 1 times / day multiple, oral	EPROSARTAN plasma	Homo sapiens

F_unbound

Value	Dose	Co-administered	Analyte	Population
2%	600 mg 1 times / day multiple, oral		EPROSARTAN plasma	Homo sapiens

Doses

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Dose	Population	Adverse events
800 mg single, oral Highest studied dose	healthy, 20-43	Other AEs: Headache, Earache...
12000 mg single, oral Overdose	unknown	Other AEs: Circulatory collapse...

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AEs

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AE	Significance	Dose	Population
Headache	17.4%	800 mg single, oral Highest studied dose	healthy, 20-43
Earache	4.3%	800 mg single, oral Highest studied dose	healthy, 20-43
Circulatory collapse		12000 mg single, oral Overdose	unknown

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Overview

CYP3A4	CYP2C9	CYP2D6	hERG
inhibitor 2,252	inhibitor 2,438	inhibitor 2,507	inhibitor 2,217

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP1A 70 CYP2A6 879 CYP2C19 2,057 CYP2E 4 CYP3A 227 CYP1A2 2,153 CYP2E1 1,060 Kv4.3 16 Kv1.5 27	UGT 219 CYP 303 OATP1B1 503 MRP2 252

Drug as perpetrator

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Target	Modality	Activity
CYP1A 122	inhibitor 4,027	no
CYP1A2 2,333	inhibitor 4,027	no
CYP2A6 911	inhibitor 4,027	no
CYP2C19 2,141	inhibitor 4,027	no
CYP2C9 2,497	inhibitor 4,027	no

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Drug as victim

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Target	Modality	Activity
CYP 303	substrate 4,014	no
MRP2 252	substrate 4,014	yes
OATP1B1 503	substrate 4,014	yes
UGT 219	substrate 4,014	yes

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Tox targets

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Target	Modality	Activity	Metabolite	Clinical evidence
hERG 2,263	inhibitor 2,237

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Sourcing

Sourcing

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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

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PubMed

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Title	Date	PubMed
Characterization of [3H]SK&F 108566 as a radioligand for angiotensin type-1 receptor.	1993	8463997
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
Introduction: The pharmacological profile of eprosartan--implications for cerebrovascular and cardiovascular risk reduction.	2007 Nov	18093407

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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.

Show entries

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

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Code System

Code

Type

Description

EVMPD

SUB127293

PRIMARY

SMS_ID

100000153337

PRIMARY

CAS

197855-71-3

PRIMARY

FDA UNII

9G2HB74868

PRIMARY

PUBCHEM

9872439

PRIMARY

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ACTIVE MOIETY


					2KH13Z0S0Y

EPROSARTAN

SUBSTANCE RECORD


					9G2HB74868

EPROSARTAN MESYLATE DIHYDRATE

SMILES

InChI

CNS Activity

Originator

Approval Year

Targets

Conditions

Cmax

AUC

T1/2

Funbound

Doses

AEs

Overview

OverviewOther

Drug as perpetrator​

Drug as victim

Tox targets

Sourcing

PubMed

Patents

Sample Use Guides

C_max

T_1/2

F_unbound

Drug as perpetrator