VALSARTAN

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 Search

SMILES

CCCCC(=O)N(CC1=CC=C(C=C1)C2=C(C=CC=C2)C3=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
Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2017/021283s50lbl.pdfhttps://www.pharma.us.novartis.com/sites/www.pharma.us.novartis.com/files/entresto.pdfhttps://www.ncbi.nlm.nih.gov/pubmed/25052956
Curator's Comment: Description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/19934029 https://www.ncbi.nlm.nih.gov/pubmed/26082640 http://www.accessdata.fda.gov/drugsatfda_docs/nda/2015/207620Orig1s000PharmR.pdf

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

Originator

Approval Year

Targets

Primary Target	Pharmacology	Potency
Type-1 angiotensin II receptor 39 Target ID: CHEMBL227 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/nda/2015/207620Orig1s000PharmR.pdf	Antagonist 2737	2.38 nM [Ki]
Neprilysin 28 Target ID: CHEMBL1944 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/nda/2015/207620Orig1s000PharmR.pdf	Inhibitor 8146	2.3 nM [IC50]
Type-1 angiotensin II receptor 39 Target ID: CHEMBL227 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2017/021283s50lbl.pdf	Blocker 530	2.43 nM [IC50]

Conditions

Condition	Modality	Highest Phase	Product
Unknown 2554
Chronic heart failure with reduced ejection fraction 4 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2015/207620Orig1s000lbl.pdf	Primary	Approved 8307	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 1.43614083E12
Hypertension 546 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2017/021283s50lbl.pdf	Primary	Approved 8307	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 1.31086077E12
Heart failure 87 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2017/021283s50lbl.pdf	Primary	Approved 8307	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 1.31086077E12
Myocardial infarction 103 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2017/021283s50lbl.pdf	Palliative	Approved 8307	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 1.31086077E12

C_max

Value	Dose	Analyte	Population
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
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

AUC

Value	Dose	Analyte	Population
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
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

T_1/2

Value	Dose	Analyte	Population
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
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

Doses

Dose	Population	Adverse events
2.24 mg single, oral Overdose Dose: 2.24 mg Route: oral Route: single Dose: 2.24 mg Sources: https://pubmed.ncbi.nlm.nih.gov/15222725	unknown, 25 years n = 1 Health Status: unknown Age Group: 25 years Sex: F Population Size: 1 Sources: https://pubmed.ncbi.nlm.nih.gov/15222725	Other AEs: Muscle cramps... Other AEs: Muscle cramps (1 patient) Sources: https://pubmed.ncbi.nlm.nih.gov/15222725
640 mg 1 times / day steady, oral Highest studied dose Dose: 640 mg, 1 times / day Route: oral Route: steady Dose: 640 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/17762658	unhealthy, 57.5 years n = 131 Health Status: unhealthy Age Group: 57.5 years Sex: M+F Population Size: 131 Sources: https://pubmed.ncbi.nlm.nih.gov/17762658	Disc. AE: Hyperkalemia... Other AEs: Dizziness, Headache... AEs leading to discontinuation/dose reduction: Hyperkalemia (1 patient) Other AEs: Dizziness (8.3%) Headache (9.2%) Back pain (5.8%) Upper respiratory tract infection (5.8%) Nasopharyngitis (5%) Diarrhea (5%) Hypoglycemia (5%) Peripheral edema (4.2%) Nausea (4.2%) Sources: https://pubmed.ncbi.nlm.nih.gov/17762658
320 mg 1 times / day steady, oral Recommended Dose: 320 mg, 1 times / day Route: oral Route: steady Dose: 320 mg, 1 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/020665s039lbl.pdf https://pubmed.ncbi.nlm.nih.gov/15329835	pregnant Health Status: pregnant Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/020665s039lbl.pdf https://pubmed.ncbi.nlm.nih.gov/15329835	Disc. AE: Disorder fetal... AEs leading to discontinuation/dose reduction: Disorder fetal Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/020665s039lbl.pdf https://pubmed.ncbi.nlm.nih.gov/15329835
320 mg 1 times / day steady, oral Recommended Dose: 320 mg, 1 times / day Route: oral Route: steady Dose: 320 mg, 1 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/020665s039lbl.pdf	unhealthy n = 2316 Health Status: unhealthy Condition: hypertension Population Size: 2316 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/020665s039lbl.pdf	Disc. AE: Headache, Dizziness... AEs leading to discontinuation/dose reduction: Headache (2.3%) Dizziness (2.3%) Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/020665s039lbl.pdf
320 mg 1 times / day steady, oral Recommended Dose: 320 mg, 1 times / day Route: oral Route: steady Dose: 320 mg, 1 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/020665s039lbl.pdf	unhealthy n = 2506 Health Status: unhealthy Condition: Heart Failure Population Size: 2506 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/020665s039lbl.pdf	Disc. AE: Creatinine increased, Potassium increased... AEs leading to discontinuation/dose reduction: Creatinine increased (0.5%) Potassium increased (0.5%) Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/020665s039lbl.pdf

AEs

Sourcing

Vendor/Aggregator	ID	URL
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
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
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

PubMed

Title	Date	PubMed

Remodelling of resistance arteries in genetically hypertensive rats by treatment with valsartan, an angiotensin II receptor antagonist.	1996 Jun-Jul	8800589
Valsartan, a new angiotensin II antagonist for the treatment of essential hypertension: a comparative study of the efficacy and safety against amlodipine.	1996 Sep	8841157

Patents

Sample Use Guides

In Vivo Use Guide

The recommended starting dose of DIOVAN® is 80 mg or 160 mg once daily when used as monotherapy in patients who are not volume-depleted. Patients requiring greater reductions may be started at the higher dose. DIOVAN® may be used over a dose range of 80 mg to 320 mg daily, administered once a day.

Route of Administration: Other

In Vitro Use Guide

Valsartan competed with [125I]-angiotensin II (AII) at its specific binding sites in rat aortic smooth muscle cell membranes (AT1-receptor subtype) with a Ki of 2.38 nM, but was about 30,000 times less active in human myometrial membranes (AT2-receptor subtype). In rabbit aortic rings incubated for 5 min with valsartan, at concentrations of 2, 20 and 200 nM, the concentration-response curve of AII was displaced to the right and the maximum response was reduced by 33%, 36% and 40%, respectively. Prolongation of the incubation time with valsartan to 1 h or 3 h, further reduced the maximum response by 48% or 59% (after 20 nM) and by 59% or 60% (after 200 nM), respectively. After 3 h incubation an apparent pKb value of 9.26 was calculated. Contractions induced by noradrenaline, 5-hydroxytryptamine, or potassium chloride were not affected by valsartan.

Substance Class	Chemical Created by `admin` on `Fri Dec 16 20:21:52 UTC 2022` Edited by `admin` on `Fri Dec 16 20:21:52 UTC 2022`
Record UNII	80M03YXJ7I
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

VALSARTAN

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

NSC-758927

Code

English

CGP 48933

Code

English

DIOVAN HCT COMPONENT VALSARTAN

Common Name

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 COMPONENT OF IMMPRIDA

Brand Name

English

VALSARTAN COMPONENT OF DIOVAN HCT

Common Name

English

Valsartan [WHO-DD]

Common Name

English

EXFORGE COMPONENT VALSARTAN

Brand Name

English

VALSARTAN COMPONENT OF EXFORGE

Brand Name

English

DIOVAN

Brand Name

English

DAFIRO COMPONENT VALSARTAN

Brand Name

English

VALSARTAN [HSDB]

Common Name

English

VALSARTAN COMPONENT OF ENTRESTO

Brand 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

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

VALSARTAN [EP MONOGRAPH]

Common 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

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