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
Defined Stereocenters 1 / 1
E/Z Centers 0
Optical Activity UNSPECIFIED

Description

LCZ696 contains equal molar amounts of valsartan and sacubitril (1:1 ratio). Sacubitril is a prodrug that is rapidly metabolized by enzymatic cleavage of the ethyl ester group into the biologically active neprilysin inhibitor, LBQ 657. Valsartan, a blocker of the angiotensin II type-1 receptor, is biologically active in its original form. FDA has approved ENTRESTO, previously known as LCZ696, for the treatment of heart failure with reduced ejection fraction.

CNS Activity

Originator

Approval Year

PubMed

PubMed

TitleDatePubMed
Pharmacological profile of valsartan: a potent, orally active, nonpeptide antagonist of the angiotensin II AT1-receptor subtype.
1993 Oct
Angiotensin II receptor blockade with single doses of valsartan in healthy, normotensive subjects.
1994
Binding of valsartan to mammalian angiotensin AT1 receptors.
1995 Nov 10
Remodelling of resistance arteries in genetically hypertensive rats by treatment with valsartan, an angiotensin II receptor antagonist.
1996 Jun-Jul
Development and validation of chiral high-performance liquid chromatographic methods for the quantitation of valsartan and of the tosylate of valinebenzyl ester.
1996 Nov 8
Valsartan, a new angiotensin II antagonist for the treatment of essential hypertension: a comparative study of the efficacy and safety against amlodipine.
1996 Sep
Enantiomeric LC separation of valsartan on amylose based stationary phase.
2009 Aug
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 Apr
Determination of the R-enantiomer of valsartan in pharmaceutical formulation by capillary electrophoresis.
2015
LCZ696 : a new paradigm for the treatment of heart failure?
2015 Feb
Sacubitril/valsartan (LCZ696) for the treatment of heart failure.
2016
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 Apr
Pharmacodynamic and Pharmacokinetic Profiles of Sacubitril/Valsartan (LCZ696) in Patients with Heart Failure and Reduced Ejection Fraction.
2016 Aug
LCZ696 (Valsartan/Sacubitril)--A Possible New Treatment for Hypertension and Heart Failure.
2016 Jan
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 Mar
Patents
Substance Class Chemical
Created
by admin
on Mon Oct 21 21:20:44 UTC 2019
Edited
by admin
on Mon Oct 21 21:20:44 UTC 2019
Record UNII
80M03YXJ7I
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
VALSARTAN
EMA EPAR   EP   HSDB   INN   JAN   MART.   MI   ORANGE BOOK   USAN   USP   USP-RS   VANDF   WHO-DD  
INN   USAN  
Official Name English
VALSARTAN COMPONENT OF COPALIA
Brand Name English
COPALIA COMPONENT VALSARTAN
Brand Name English
VALSARTAN COMPONENT OF VALTURNA
Common 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
VALSARTAN COMPONENT OF EXFORGE HCT
Common Name English
BYVALSON COMPONENT OF VALSARTAN
Common Name English
IMPRIDA-HCT COMPONENT VALSARTAN
Brand Name English
CGP 48933
Code English
DIOVAN HCT COMPONENT VALSARTAN
Common Name English
VALSARTAN [EMA EPAR]
Common Name English
VALSARTAN [MI]
Common Name English
VALTURNA COMPONENT VALSARTAN
Brand Name English
VALSARTAN [USAN]
Common Name English
VALSARTAN [ORANGE BOOK]
Common Name English
VALSARTAN COMPONENT OF DAFIRO
Brand Name English
VALSARTAN [MART.]
Common Name English
VALSARTAN COMPONENT OF IMMPRIDA
Brand Name English
VALSARTAN COMPONENT OF DIOVAN HCT
Common Name English
EXFORGE COMPONENT VALSARTAN
Brand Name English
VALSARTAN COMPONENT OF EXFORGE
Brand Name English
DIOVAN
Brand Name English
VALSARTAN [EP]
Common Name English
DAFIRO COMPONENT VALSARTAN
Brand Name English
VALSARTAN [HSDB]
Common Name English
VALSARTAN COMPONENT OF ENTRESTO
Brand 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
VALSARTAN [WHO-DD]
Common Name English
VALSARTAN COMPONENT OF DAFIRO-HCT
Brand Name English
VALSARTAN COMPONENT OF COPALIA-HCT
Brand Name English
VALSARTAN COMPONENT OF BYVALSON
Common Name English
ENTRESTO COMPONENT VALSARTAN
Brand Name English
PREXXARTAN
Brand Name English
IMPRIDA COMPONENT VALSARTAN
Brand Name English
VALSARTAN [INN]
Common Name English
VALSARTAN COMPONENT OF IMPRIDA-HCT
Brand Name English
VALSARTAN [USP]
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 Oct 21 21:20:44 UTC 2019 , Edited by admin on Mon Oct 21 21:20:44 UTC 2019
EMA ASSESSMENT REPORTS IMPRADA-HCT (WITHDRAWN: HYPERTENSION)
Created by admin on Mon Oct 21 21:20:44 UTC 2019 , Edited by admin on Mon Oct 21 21:20:44 UTC 2019
WHO-ATC C10BX10
Created by admin on Mon Oct 21 21:20:44 UTC 2019 , Edited by admin on Mon Oct 21 21:20:44 UTC 2019
EMA ASSESSMENT REPORTS EXFORGE (AUTHORIZED: HYPERTENSION)
Created by admin on Mon Oct 21 21:20:44 UTC 2019 , Edited by admin on Mon Oct 21 21:20:44 UTC 2019
WHO-VATC QC09CA03
Created by admin on Mon Oct 21 21:20:44 UTC 2019 , Edited by admin on Mon Oct 21 21:20:44 UTC 2019
NDF-RT N0000175561
Created by admin on Mon Oct 21 21:20:44 UTC 2019 , Edited by admin on Mon Oct 21 21:20:44 UTC 2019
WHO-ATC C09DX02
Created by admin on Mon Oct 21 21:20:44 UTC 2019 , Edited by admin on Mon Oct 21 21:20:44 UTC 2019
EMA ASSESSMENT REPORTS COPALIA (AUTHORIZED: HYPERTENSION)
Created by admin on Mon Oct 21 21:20:44 UTC 2019 , Edited by admin on Mon Oct 21 21:20:44 UTC 2019
WHO-ATC C09DX01
Created by admin on Mon Oct 21 21:20:44 UTC 2019 , Edited by admin on Mon Oct 21 21:20:44 UTC 2019
WHO-VATC QC09DA03
Created by admin on Mon Oct 21 21:20:44 UTC 2019 , Edited by admin on Mon Oct 21 21:20:44 UTC 2019
EMA ASSESSMENT REPORTS EXFORGE-HCT (AUTHORIZED: HYPERTENSION)
Created by admin on Mon Oct 21 21:20:44 UTC 2019 , Edited by admin on Mon Oct 21 21:20:44 UTC 2019
NCI_THESAURUS C66930
Created by admin on Mon Oct 21 21:20:44 UTC 2019 , Edited by admin on Mon Oct 21 21:20:44 UTC 2019
WHO-ATC C09DB08
Created by admin on Mon Oct 21 21:20:44 UTC 2019 , Edited by admin on Mon Oct 21 21:20:44 UTC 2019
EMA ASSESSMENT REPORTS DARFIRO-HCT (AUTHORIZED: HYPERTENSION)
Created by admin on Mon Oct 21 21:20:44 UTC 2019 , Edited by admin on Mon Oct 21 21:20:44 UTC 2019
LIVERTOX 1019
Created by admin on Mon Oct 21 21:20:44 UTC 2019 , Edited by admin on Mon Oct 21 21:20:44 UTC 2019
EMA ASSESSMENT REPORTS COPALIA-HCT (AUTHORIZED: HYPERTENSION)
Created by admin on Mon Oct 21 21:20:44 UTC 2019 , Edited by admin on Mon Oct 21 21:20:44 UTC 2019
WHO-ATC C09DA03
Created by admin on Mon Oct 21 21:20:44 UTC 2019 , Edited by admin on Mon Oct 21 21:20:44 UTC 2019
NDF-RT N0000000070
Created by admin on Mon Oct 21 21:20:44 UTC 2019 , Edited by admin on Mon Oct 21 21:20:44 UTC 2019
EMA ASSESSMENT REPORTS DAFIRO (AUTHORIZED: HYPERTENSION)
Created by admin on Mon Oct 21 21:20:44 UTC 2019 , Edited by admin on Mon Oct 21 21:20:44 UTC 2019
FDA ORPHAN DRUG 494115
Created by admin on Mon Oct 21 21:20:44 UTC 2019 , Edited by admin on Mon Oct 21 21:20:44 UTC 2019
WHO-VATC QC09DX01
Created by admin on Mon Oct 21 21:20:44 UTC 2019 , Edited by admin on Mon Oct 21 21:20:44 UTC 2019
EMA ASSESSMENT REPORTS IMPRIDA (AUTHORIZED: HYPERTENSION)
Created by admin on Mon Oct 21 21:20:44 UTC 2019 , Edited by admin on Mon Oct 21 21:20:44 UTC 2019
WHO-ATC C09DX05
Created by admin on Mon Oct 21 21:20:44 UTC 2019 , Edited by admin on Mon Oct 21 21:20:44 UTC 2019
WHO-ATC C09DX04
Created by admin on Mon Oct 21 21:20:44 UTC 2019 , Edited by admin on Mon Oct 21 21:20:44 UTC 2019
WHO-VATC QC09DX02
Created by admin on Mon Oct 21 21:20:44 UTC 2019 , Edited by admin on Mon Oct 21 21:20:44 UTC 2019
WHO-ATC C09DB01
Created by admin on Mon Oct 21 21:20:44 UTC 2019 , Edited by admin on Mon Oct 21 21:20:44 UTC 2019
WHO-VATC QC09DB01
Created by admin on Mon Oct 21 21:20:44 UTC 2019 , Edited by admin on Mon Oct 21 21:20:44 UTC 2019
Code System Code Type Description
INN
7016
Created by admin on Mon Oct 21 21:20:44 UTC 2019 , Edited by admin on Mon Oct 21 21:20:44 UTC 2019
PRIMARY
RXCUI
69749
Created by admin on Mon Oct 21 21:20:44 UTC 2019 , Edited by admin on Mon Oct 21 21:20:44 UTC 2019
PRIMARY RxNorm
CAS
137862-53-4
Created by admin on Mon Oct 21 21:20:44 UTC 2019 , Edited by admin on Mon Oct 21 21:20:44 UTC 2019
PRIMARY
LactMed
137862-53-4
Created by admin on Mon Oct 21 21:20:44 UTC 2019 , Edited by admin on Mon Oct 21 21:20:44 UTC 2019
PRIMARY
IUPHAR
3937
Created by admin on Mon Oct 21 21:20:44 UTC 2019 , Edited by admin on Mon Oct 21 21:20:44 UTC 2019
PRIMARY
ChEMBL
CHEMBL1069
Created by admin on Mon Oct 21 21:20:44 UTC 2019 , Edited by admin on Mon Oct 21 21:20:44 UTC 2019
PRIMARY
MESH
C081489
Created by admin on Mon Oct 21 21:20:44 UTC 2019 , Edited by admin on Mon Oct 21 21:20:44 UTC 2019
PRIMARY
WIKIPEDIA
VALSARTAN
Created by admin on Mon Oct 21 21:20:44 UTC 2019 , Edited by admin on Mon Oct 21 21:20:44 UTC 2019
PRIMARY
HSDB
137862-53-4
Created by admin on Mon Oct 21 21:20:44 UTC 2019 , Edited by admin on Mon Oct 21 21:20:44 UTC 2019
PRIMARY
EPA CompTox
137862-53-4
Created by admin on Mon Oct 21 21:20:44 UTC 2019 , Edited by admin on Mon Oct 21 21:20:44 UTC 2019
PRIMARY
DRUG BANK
DB00177
Created by admin on Mon Oct 21 21:20:44 UTC 2019 , Edited by admin on Mon Oct 21 21:20:44 UTC 2019
PRIMARY
NCI_THESAURUS
C47781
Created by admin on Mon Oct 21 21:20:44 UTC 2019 , Edited by admin on Mon Oct 21 21:20:44 UTC 2019
PRIMARY
MERCK INDEX
M11372
Created by admin on Mon Oct 21 21:20:44 UTC 2019 , Edited by admin on Mon Oct 21 21:20:44 UTC 2019
PRIMARY Merck Index
PUBCHEM
60846
Created by admin on Mon Oct 21 21:20:44 UTC 2019 , Edited by admin on Mon Oct 21 21:20:44 UTC 2019
PRIMARY
EVMPD
SUB00017MIG
Created by admin on Mon Oct 21 21:20:44 UTC 2019 , Edited by admin on Mon Oct 21 21:20:44 UTC 2019
PRIMARY
Related Record Type Details
TRANSPORTER -> INHIBITOR
TRANSPORTER -> INHIBITOR
TRANSPORTER -> INHIBITOR
TRANSPORTER -> INHIBITOR
TARGET -> INHIBITOR
SALT/SOLVATE -> PARENT
BINDER->LIGAND
BINDING
TRANSPORTER -> INHIBITOR
BASIS OF STRENGTH->SUBSTANCE
ASSAY (HPLC)
USP
TRANSPORTER -> INHIBITOR
BASIS OF STRENGTH->SUBSTANCE
ASSAY (TITRATION)
EP
Related Record Type Details
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
Related Record Type Details
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
IMPURITY -> PARENT
IMPURITY -> PARENT
IMPURITY -> PARENT
Probable human carcinogen.
IMPURITY -> PARENT
UNSPECIFIED
EP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
IMPURITY -> PARENT
Priority toxic pollutant.
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
IMPURITY -> PARENT
NDMA is an organic chemical that is in a family of potent carcinogens.
Related Record Type Details
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