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Details

Stereochemistry ABSOLUTE
Molecular Formula C24H28N5O3.Na
Molecular Weight 457.5006
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of VALSARTAN MONOSODIUM

SMILES

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

InChI

InChIKey=KVPFCQWDTYOLIK-FTBISJDPSA-M
InChI=1S/C24H29N5O3.Na/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);/q;+1/p-1/t22-;/m0./s1

HIDE SMILES / InChI
Molecular Formula C24H28N5O3
Molecular Weight 434.5108
Charge -1
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 1 / 1
E/Z Centers 0
Optical Activity UNSPECIFIED
Molecular Formula Na
Molecular Weight 22.98976928
Charge 1
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description
Curator's Comment: description was created based on several sources, including https://www.ncbi.nlm.nih.gov/mesh/2009869

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

CNS Active
4002
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

Originator

Approval Year

1996
224
Targets

Targets

Primary TargetPharmacologyConditionPotency
Antagonist
2849
 2.38 nM [Ki]
Inhibitor
8504
 2.3 nM [IC50]
Blocker
555
 2.43 nM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Approved
8583
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
Approved
8583
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
Approved
8583
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
Approved
8583
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
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/21617777
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
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/27128457
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
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/27128457
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
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/21617777
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
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/27128457
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
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/27128457
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
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/21617777
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
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/27128457
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
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/27128457
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
Sourcing

Sourcing

Vendor/AggregatorIDURL
ChEBI
CHEBI:9927
https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:9927
ChemicalBook
CB14657818
https://www.chemicalbook.com/ChemicalProductProperty_EN_CB14657818
ChemicalBook
CB23133442
https://www.chemicalbook.com/ChemicalProductProperty_EN_CB23133442
ChemicalBook
CB34813436
https://www.chemicalbook.com/ChemicalProductProperty_EN_CB34813436
ChemicalBook
CB3952405
https://www.chemicalbook.com/ChemicalProductProperty_EN_CB3952405
ChemicalBook
CB6182539
https://www.chemicalbook.com/ChemicalProductProperty_EN_CB6182539
eMolecules
1989469
https://www.emolecules.com/cgi-bin/more?vid=1989469
eMolecules
2724803
https://www.emolecules.com/cgi-bin/more?vid=2724803
eMolecules
32278148
https://www.emolecules.com/cgi-bin/more?vid=32278148
eMolecules
33507560
https://www.emolecules.com/cgi-bin/more?vid=33507560
MolPort
MolPort-002-507-854
https://www.molport.com/shop/molecule-link/MolPort-002-507-854
MolPort
MolPort-003-666-608
https://www.molport.com/shop/molecule-link/MolPort-003-666-608
Selleck Chemicals
Valsartan(Diovan)
http://www.selleckchem.com/products/Valsartan(Diovan).html
ZINC
ZINC000003875259
http://zinc15.docking.org/substances/ZINC000003875259
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

Patents

US20050010053
4
US5399578
4
US5965592
4
US6294197
4
US8475839
4
WO/2016/151525A1
4
null
9

Sample Use Guides

In Vivo Use Guide
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 Wed Apr 02 12:47:04 GMT 2025
Edited
by admin
on Wed Apr 02 12:47:04 GMT 2025
Record UNII
D6XN347U2D
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
VALSARTAN SODIUM SALT
Preferred Name English
VALSARTAN MONOSODIUM
Common Name English
L-VALINE, N-(1-OXOPENTYL)-N-((2'-(2H-TETRAZOL-5-YL)(1,1'-BIPHENYL)-4-YL)METHYL)-, SODIUM SALT (1:1)
Systematic Name English
Code System Code Type Description
PUBCHEM
23682221
Created by admin on Wed Apr 02 12:47:04 GMT 2025 , Edited by admin on Wed Apr 02 12:47:04 GMT 2025
PRIMARY
CAS
1178578-85-2
Created by admin on Wed Apr 02 12:47:04 GMT 2025 , Edited by admin on Wed Apr 02 12:47:04 GMT 2025
NON-SPECIFIC STOICHIOMETRY
CAS
391231-02-0
Created by admin on Wed Apr 02 12:47:04 GMT 2025 , Edited by admin on Wed Apr 02 12:47:04 GMT 2025
PRIMARY
FDA UNII
D6XN347U2D
Created by admin on Wed Apr 02 12:47:04 GMT 2025 , Edited by admin on Wed Apr 02 12:47:04 GMT 2025
PRIMARY
Related Record Type Details
Structure of VALSARTAN
PARENT -> SALT/SOLVATE
Related Record Type Details
Structure of VALSARTAN
ACTIVE MOIETY
NIH
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