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

Details

Stereochemistry ABSOLUTE
Molecular Formula C24H29N5O3
Molecular Weight 435.5188
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of VALSARTAN

SMILES

CCCCC(=O)N(CC1=CC=C(C=C1)C2=CC=CC=C2C3=NN=NN3)[C@@H](C(C)C)C(O)=O

InChI

InChIKey=ACWBQPMHZXGDFX-QFIPXVFZSA-N
InChI=1S/C24H29N5O3/c1-4-5-10-21(30)29(22(16(2)3)24(31)32)15-17-11-13-18(14-12-17)19-8-6-7-9-20(19)23-25-27-28-26-23/h6-9,11-14,16,22H,4-5,10,15H2,1-3H3,(H,31,32)(H,25,26,27,28)/t22-/m0/s1

HIDE SMILES / InChI

Molecular Formula C24H29N5O3
Molecular Weight 435.5188
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 1 / 1
E/Z Centers 0
Optical Activity UNSPECIFIED

Description

There is no information in the literature about pharmacological and biological application of definite isomer of valsatran, R – form (also known as VALSARTAN, D- or CGP-49309). However there were found, that in the tablets of valsartan, which are used to treat high blood pressure and to heart failure, the R-enantiomer was an impurity.

CNS Activity

Curator's Comment: LBQ657 (an LCZ696 metabolite) achieves CSF concentrations sufficient to inhibit neprilysin, but LCZ696 did not cause changes in CSF levels of aggregable Abeta isoforms (1-42 and 1-40) compared with placebo

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
ENTRESTO

Approved Use

ENTRESTO is a combination of sacubitril, a neprilysin inhibitor, and valsartan, an angiotensin II receptor blocker, indicated to reduce the risk of cardiovascular death and hospitalization for heart failure in patients with chronic heart failure (NYHA Class II-IV) and reduced ejection fraction. ENTRESTO is usually administered in conjunction with other heart failure therapies, in place of an ACE inhibitor or other ARB.

Launch Date

2015
Primary
DIOVAN

Approved Use

Diovan is an angiotensin II receptor blocker (ARB) indicated for: Treatment of hypertension, to lower blood pressure. Lowering blood pressure reduces the risk of fatal and nonfatal cardiovascular events, primarily strokes and myocardial infarctions (1.1) Treatment of heart failure (NYHA class II-IV); Diovan significantly reduced hospitalization for heart failure (1.2) Reduction of cardiovascular mortality in clinically stable patients with left ventricular failure or left ventricular dysfunction following myocardial infarction (1.3)

Launch Date

2011
Primary
DIOVAN

Approved Use

Diovan is an angiotensin II receptor blocker (ARB) indicated for: Treatment of hypertension, to lower blood pressure. Lowering blood pressure reduces the risk of fatal and nonfatal cardiovascular events, primarily strokes and myocardial infarctions (1.1) Treatment of heart failure (NYHA class II-IV); Diovan significantly reduced hospitalization for heart failure (1.2) Reduction of cardiovascular mortality in clinically stable patients with left ventricular failure or left ventricular dysfunction following myocardial infarction (1.3)

Launch Date

2011
Palliative
DIOVAN

Approved Use

Diovan is an angiotensin II receptor blocker (ARB) indicated for: Treatment of hypertension, to lower blood pressure. Lowering blood pressure reduces the risk of fatal and nonfatal cardiovascular events, primarily strokes and myocardial infarctions (1.1) Treatment of heart failure (NYHA class II-IV); Diovan significantly reduced hospitalization for heart failure (1.2) Reduction of cardiovascular mortality in clinically stable patients with left ventricular failure or left ventricular dysfunction following myocardial infarction (1.3)

Launch Date

2011
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
2.141 μg/mL
160 mg single, oral
dose: 160 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
VALSARTAN plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
2808 ng/mL
80 mg single, oral
dose: 80 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
VALSARTAN plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
5756 ng/mL
80 mg single, oral
dose: 80 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
VALSARTAN plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
22.56 μg × h/mL
160 mg single, oral
dose: 160 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
VALSARTAN plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
20650 ng × h/mL
80 mg single, oral
dose: 80 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
VALSARTAN plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
34310 ng × h/mL
80 mg single, oral
dose: 80 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
VALSARTAN plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
9.55 h
160 mg single, oral
dose: 160 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
VALSARTAN plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
8.45 h
80 mg single, oral
dose: 80 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
VALSARTAN plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
8 h
80 mg single, oral
dose: 80 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
VALSARTAN plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
PubMed

PubMed

TitleDatePubMed
Pharmacodynamic and Pharmacokinetic Profiles of Sacubitril/Valsartan (LCZ696) in Patients with Heart Failure and Reduced Ejection Fraction.
2016-08
LCZ696, an angiotensin receptor-neprilysin inhibitor, improves cardiac function with the attenuation of fibrosis in heart failure with reduced ejection fraction in streptozotocin-induced diabetic mice.
2016-04
Influence of Ejection Fraction on Outcomes and Efficacy of Sacubitril/Valsartan (LCZ696) in Heart Failure with Reduced Ejection Fraction: The Prospective Comparison of ARNI with ACEI to Determine Impact on Global Mortality and Morbidity in Heart Failure (PARADIGM-HF) Trial.
2016-03
LCZ696 (Valsartan/Sacubitril)--A Possible New Treatment for Hypertension and Heart Failure.
2016-01
Sacubitril/valsartan (LCZ696) for the treatment of heart failure.
2016
LCZ696 : a new paradigm for the treatment of heart failure?
2015-02
Determination of the R-enantiomer of valsartan in pharmaceutical formulation by capillary electrophoresis.
2015
Efficacy and safety of LCZ696, a first-in-class angiotensin receptor neprilysin inhibitor, in Asian patients with hypertension: a randomized, double-blind, placebo-controlled study.
2014-04
Enantiomeric LC separation of valsartan on amylose based stationary phase.
2009-08
Development and validation of chiral high-performance liquid chromatographic methods for the quantitation of valsartan and of the tosylate of valinebenzyl ester.
1996-11-08
Valsartan, a new angiotensin II antagonist for the treatment of essential hypertension: a comparative study of the efficacy and safety against amlodipine.
1996-09
Remodelling of resistance arteries in genetically hypertensive rats by treatment with valsartan, an angiotensin II receptor antagonist.
1996-06-01
Binding of valsartan to mammalian angiotensin AT1 receptors.
1995-11-10
Angiotensin II receptor blockade with single doses of valsartan in healthy, normotensive subjects.
1994
Pharmacological profile of valsartan: a potent, orally active, nonpeptide antagonist of the angiotensin II AT1-receptor subtype.
1993-10
Patents

Sample Use Guides

The recommended starting dose of ENTRESTO, previously known as LCZ696, is 49/51 mg (sacubitril/valsartan) twice-daily. Double the dose of ENTRESTO after 2 to 4 weeks to the target maintenance dose of 97/103 mg (sacubitril/valsartan) twice-daily, as tolerated by the patient.
Route of Administration: Oral
In Vitro Use Guide
Sources: Von Lueder TG, Wang B, Kompa A, Huang L, Webb R, Jordan P, Krum H. ARNi, combined neprilysin and angiotensin receptor inhibition augments anti-fibrotic and anti-hypertrophic effects in vitro. Eur.Heart J. 2012;33:P5834.
Curator's Comment: ...
30 nM to 1 uM valsartan (LCZ696 component) in the presence of 10 uM LBQ657 (Sacubitril (LCZ696 component) metabolite) demonstrate anti-fibrotic and anti-hypertrophic effects on rat cardiac fibroblasts and cardiomyocytes, respectively, cultured with 100 nM angiotensin II
Substance Class Chemical
Created
by admin
on Mon Mar 31 18:29:58 GMT 2025
Edited
by admin
on Mon Mar 31 18:29:58 GMT 2025
Record UNII
80M03YXJ7I
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
DIOVAN HCT COMPONENT VALSARTAN
Preferred Name English
VALSARTAN
EMA EPAR   EP   HSDB   INN   JAN   MART.   MI   ORANGE BOOK   USAN   USP   USP-RS   VANDF   WHO-DD  
INN   USAN  
Official Name English
COPALIA COMPONENT VALSARTAN
Brand Name English
L-VALINE, N-(1-OXOPENTYL)-N-((2'-(1H-TETRAZOL-5-YL)(1,1'-BIPHENYL)-4-YL)METHYL)-
Systematic Name English
VALSARTAN [VANDF]
Common Name English
IMPRIDA-HCT COMPONENT VALSARTAN
Brand Name English
NSC-758927
Code English
CGP 48933
Code English
VALSARTAN [EMA EPAR]
Common Name English
VALSARTAN [MI]
Common Name English
VALSARTAN [USP MONOGRAPH]
Common Name English
VALTURNA COMPONENT VALSARTAN
Brand Name English
VALSARTAN [USAN]
Common Name English
VALSARTAN [ORANGE BOOK]
Common Name English
VALSARTAN [EP IMPURITY]
Common Name English
VALSARTAN [MART.]
Common Name English
Valsartan [WHO-DD]
Common Name English
EXFORGE COMPONENT VALSARTAN
Brand Name English
DIOVAN
Brand Name English
DAFIRO COMPONENT VALSARTAN
Brand Name English
VALSARTAN [HSDB]
Common Name English
AGSAV301 COMPONENT VALSARTAN
Common Name English
COPALIA-HCT COMPONENT VALSARTAN
Brand Name English
EXFORGE HCT COMPONENT VALSARTAN
Common Name English
VALSARTAN [USP-RS]
Common Name English
VALSARTAN [JAN]
Common Name English
ENTRESTO COMPONENT VALSARTAN
Brand Name English
VALSARTAN [EP MONOGRAPH]
Common Name English
PREXXARTAN
Brand Name English
IMPRIDA COMPONENT VALSARTAN
Brand Name English
valsartan [INN]
Common Name English
DAFIRO-HCT COMPONENT VALSARTAN
Brand Name English
N-(P-(O-1H-TETRAZOL-5-YLPHENYL)BENZYL)-N-VALERYL-L-VALINE
Common Name English
CGP-48933
Code English
Classification Tree Code System Code
WHO-ATC C09CA03
Created by admin on Mon Mar 31 18:29:58 GMT 2025 , Edited by admin on Mon Mar 31 18:29:58 GMT 2025
EMA ASSESSMENT REPORTS IMPRADA-HCT (WITHDRAWN: HYPERTENSION)
Created by admin on Mon Mar 31 18:29:58 GMT 2025 , Edited by admin on Mon Mar 31 18:29:58 GMT 2025
WHO-ATC C10BX10
Created by admin on Mon Mar 31 18:29:58 GMT 2025 , Edited by admin on Mon Mar 31 18:29:58 GMT 2025
EMA ASSESSMENT REPORTS EXFORGE (AUTHORIZED: HYPERTENSION)
Created by admin on Mon Mar 31 18:29:58 GMT 2025 , Edited by admin on Mon Mar 31 18:29:58 GMT 2025
FDA ORPHAN DRUG 494115
Created by admin on Mon Mar 31 18:29:58 GMT 2025 , Edited by admin on Mon Mar 31 18:29:58 GMT 2025
WHO-VATC QC09CA03
Created by admin on Mon Mar 31 18:29:58 GMT 2025 , Edited by admin on Mon Mar 31 18:29:58 GMT 2025
NDF-RT N0000175561
Created by admin on Mon Mar 31 18:29:58 GMT 2025 , Edited by admin on Mon Mar 31 18:29:58 GMT 2025
WHO-ATC C09DX02
Created by admin on Mon Mar 31 18:29:58 GMT 2025 , Edited by admin on Mon Mar 31 18:29:58 GMT 2025
EMA ASSESSMENT REPORTS COPALIA (AUTHORIZED: HYPERTENSION)
Created by admin on Mon Mar 31 18:29:58 GMT 2025 , Edited by admin on Mon Mar 31 18:29:58 GMT 2025
WHO-ATC C09DX01
Created by admin on Mon Mar 31 18:29:58 GMT 2025 , Edited by admin on Mon Mar 31 18:29:58 GMT 2025
WHO-VATC QC09DA03
Created by admin on Mon Mar 31 18:29:58 GMT 2025 , Edited by admin on Mon Mar 31 18:29:58 GMT 2025
EMA ASSESSMENT REPORTS EXFORGE-HCT (AUTHORIZED: HYPERTENSION)
Created by admin on Mon Mar 31 18:29:58 GMT 2025 , Edited by admin on Mon Mar 31 18:29:58 GMT 2025
NCI_THESAURUS C66930
Created by admin on Mon Mar 31 18:29:58 GMT 2025 , Edited by admin on Mon Mar 31 18:29:58 GMT 2025
WHO-ATC C09DB08
Created by admin on Mon Mar 31 18:29:58 GMT 2025 , Edited by admin on Mon Mar 31 18:29:58 GMT 2025
EMA ASSESSMENT REPORTS DARFIRO-HCT (AUTHORIZED: HYPERTENSION)
Created by admin on Mon Mar 31 18:29:58 GMT 2025 , Edited by admin on Mon Mar 31 18:29:58 GMT 2025
LIVERTOX NBK547944
Created by admin on Mon Mar 31 18:29:58 GMT 2025 , Edited by admin on Mon Mar 31 18:29:58 GMT 2025
EMA ASSESSMENT REPORTS COPALIA-HCT (AUTHORIZED: HYPERTENSION)
Created by admin on Mon Mar 31 18:29:58 GMT 2025 , Edited by admin on Mon Mar 31 18:29:58 GMT 2025
WHO-ATC C09DA03
Created by admin on Mon Mar 31 18:29:58 GMT 2025 , Edited by admin on Mon Mar 31 18:29:58 GMT 2025
NDF-RT N0000000070
Created by admin on Mon Mar 31 18:29:58 GMT 2025 , Edited by admin on Mon Mar 31 18:29:58 GMT 2025
EMA ASSESSMENT REPORTS DAFIRO (AUTHORIZED: HYPERTENSION)
Created by admin on Mon Mar 31 18:29:58 GMT 2025 , Edited by admin on Mon Mar 31 18:29:58 GMT 2025
WHO-VATC QC09DX01
Created by admin on Mon Mar 31 18:29:58 GMT 2025 , Edited by admin on Mon Mar 31 18:29:58 GMT 2025
EMA ASSESSMENT REPORTS IMPRIDA (AUTHORIZED: HYPERTENSION)
Created by admin on Mon Mar 31 18:29:58 GMT 2025 , Edited by admin on Mon Mar 31 18:29:58 GMT 2025
WHO-ATC C09DX05
Created by admin on Mon Mar 31 18:29:58 GMT 2025 , Edited by admin on Mon Mar 31 18:29:58 GMT 2025
WHO-ATC C09DX04
Created by admin on Mon Mar 31 18:29:58 GMT 2025 , Edited by admin on Mon Mar 31 18:29:58 GMT 2025
WHO-VATC QC09DX02
Created by admin on Mon Mar 31 18:29:58 GMT 2025 , Edited by admin on Mon Mar 31 18:29:58 GMT 2025
WHO-ATC C09DB01
Created by admin on Mon Mar 31 18:29:58 GMT 2025 , Edited by admin on Mon Mar 31 18:29:58 GMT 2025
WHO-VATC QC09DB01
Created by admin on Mon Mar 31 18:29:58 GMT 2025 , Edited by admin on Mon Mar 31 18:29:58 GMT 2025
Code System Code Type Description
NSC
758927
Created by admin on Mon Mar 31 18:29:58 GMT 2025 , Edited by admin on Mon Mar 31 18:29:58 GMT 2025
PRIMARY
DAILYMED
80M03YXJ7I
Created by admin on Mon Mar 31 18:29:58 GMT 2025 , Edited by admin on Mon Mar 31 18:29:58 GMT 2025
PRIMARY
INN
7016
Created by admin on Mon Mar 31 18:29:58 GMT 2025 , Edited by admin on Mon Mar 31 18:29:58 GMT 2025
PRIMARY
RXCUI
69749
Created by admin on Mon Mar 31 18:29:58 GMT 2025 , Edited by admin on Mon Mar 31 18:29:58 GMT 2025
PRIMARY RxNorm
CAS
137862-53-4
Created by admin on Mon Mar 31 18:29:58 GMT 2025 , Edited by admin on Mon Mar 31 18:29:58 GMT 2025
PRIMARY
IUPHAR
3937
Created by admin on Mon Mar 31 18:29:58 GMT 2025 , Edited by admin on Mon Mar 31 18:29:58 GMT 2025
PRIMARY
ChEMBL
CHEMBL1069
Created by admin on Mon Mar 31 18:29:58 GMT 2025 , Edited by admin on Mon Mar 31 18:29:58 GMT 2025
PRIMARY
FDA UNII
80M03YXJ7I
Created by admin on Mon Mar 31 18:29:58 GMT 2025 , Edited by admin on Mon Mar 31 18:29:58 GMT 2025
PRIMARY
MESH
C081489
Created by admin on Mon Mar 31 18:29:58 GMT 2025 , Edited by admin on Mon Mar 31 18:29:58 GMT 2025
PRIMARY
WIKIPEDIA
VALSARTAN
Created by admin on Mon Mar 31 18:29:58 GMT 2025 , Edited by admin on Mon Mar 31 18:29:58 GMT 2025
PRIMARY
SMS_ID
100000088000
Created by admin on Mon Mar 31 18:29:58 GMT 2025 , Edited by admin on Mon Mar 31 18:29:58 GMT 2025
PRIMARY
RS_ITEM_NUM
1708762
Created by admin on Mon Mar 31 18:29:58 GMT 2025 , Edited by admin on Mon Mar 31 18:29:58 GMT 2025
PRIMARY
HSDB
7519
Created by admin on Mon Mar 31 18:29:58 GMT 2025 , Edited by admin on Mon Mar 31 18:29:58 GMT 2025
PRIMARY
EPA CompTox
DTXSID6023735
Created by admin on Mon Mar 31 18:29:58 GMT 2025 , Edited by admin on Mon Mar 31 18:29:58 GMT 2025
PRIMARY
DRUG BANK
DB00177
Created by admin on Mon Mar 31 18:29:58 GMT 2025 , Edited by admin on Mon Mar 31 18:29:58 GMT 2025
PRIMARY
NCI_THESAURUS
C47781
Created by admin on Mon Mar 31 18:29:58 GMT 2025 , Edited by admin on Mon Mar 31 18:29:58 GMT 2025
PRIMARY
LACTMED
Valsartan
Created by admin on Mon Mar 31 18:29:58 GMT 2025 , Edited by admin on Mon Mar 31 18:29:58 GMT 2025
PRIMARY
DRUG CENTRAL
2806
Created by admin on Mon Mar 31 18:29:58 GMT 2025 , Edited by admin on Mon Mar 31 18:29:58 GMT 2025
PRIMARY
CHEBI
9927
Created by admin on Mon Mar 31 18:29:58 GMT 2025 , Edited by admin on Mon Mar 31 18:29:58 GMT 2025
PRIMARY
USAN
HH-50
Created by admin on Mon Mar 31 18:29:58 GMT 2025 , Edited by admin on Mon Mar 31 18:29:58 GMT 2025
PRIMARY
MERCK INDEX
m11372
Created by admin on Mon Mar 31 18:29:58 GMT 2025 , Edited by admin on Mon Mar 31 18:29:58 GMT 2025
PRIMARY Merck Index
PUBCHEM
60846
Created by admin on Mon Mar 31 18:29:58 GMT 2025 , Edited by admin on Mon Mar 31 18:29:58 GMT 2025
PRIMARY
EVMPD
SUB00017MIG
Created by admin on Mon Mar 31 18:29:58 GMT 2025 , Edited by admin on Mon Mar 31 18:29:58 GMT 2025
PRIMARY
Related Record Type Details
TRANSPORTER -> INHIBITOR
TRANSPORTER -> INHIBITOR
TRANSPORTER -> INHIBITOR
TARGET -> INHIBITOR
SALT/SOLVATE -> PARENT
BINDER->LIGAND
BINDING
BASIS OF STRENGTH->SUBSTANCE
ASSAY (HPLC)
USP
BASIS OF STRENGTH->SUBSTANCE
ASSAY (TITRATION)
EP
TRANSPORTER -> INHIBITOR
SALT/SOLVATE -> PARENT
TRANSPORTER -> INHIBITOR
TRANSPORTER -> INHIBITOR
SALT/SOLVATE -> PARENT
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METABOLITE INACTIVE -> PARENT
METABOLITE INACTIVE -> PARENT
Valsartan was metabolized to a small extent only. The only notable metabolite in plasma, urine and faecs
MAJOR
FECAL; PLASMA; URINE
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EP
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IMPURITY -> PARENT
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ACTIVE MOIETY
Name Property Type Amount Referenced Substance Defining Parameters References
Volume of Distribution PHARMACOKINETIC
Route of Elimination PHARMACOKINETIC ROUTE OF ADMINISTRATION: ORAL

MAXIMUM TOLERATED DOSE TOXICITY
PROTEIN BINDING PHARMACOKINETIC
Route of Elimination PHARMACOKINETIC ROUTE OF ADMINISTRATION: ORAL

RENAL CLEARANCE PHARMACOKINETIC
Biological Half-life PHARMACOKINETIC