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

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	MOL RATIO 1 MOL RATIO (average)

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	1 / 1
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description

Valsartan (DIOVAN®) is a tetrazole derivative, and specific angiotensin II type 1 (AT1) receptor blocker that is indicated for the treatment of hypertension, to lower blood pressure. Angiotensin II is formed from angiotensin I in a reaction catalyzed by angiotensin-converting enzyme. Angiotensin II is the principal pressor agent of the renin-angiotensin system, with effects that include vasoconstriction, stimulation of synthesis and release of aldosterone, cardiac stimulation, and renal reabsorption of sodium. Valsartan (DIOVAN®) blocks the vasoconstrictor and aldosterone-secreting effects of angiotensin II by selectively blocking the binding of angiotensin II to the AT1 receptor in many tissues, such as vascular smooth muscle and the adrenal gland. Its action is therefore independent of the pathways for angiotensin II synthesis.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Potency
Type-1 angiotensin II receptor 40	Antagonist 2,778	2.38 nM [Ki]
Neprilysin 29	Inhibitor 8,297	2.3 nM [IC50]
Type-1 angiotensin II receptor 40	Blocker 537	2.43 nM [IC50]

Conditions

Condition	Modality	Highest Phase	Product
Unknown 2,578
Chronic heart failure with reduced ejection fraction 4	Primary	Approved 8,429	ENTRESTO
Hypertension 567	Primary	Approved 8,429	DIOVAN
Heart failure 103	Primary	Approved 8,429	DIOVAN
Myocardial infarction 121	Palliative	Approved 8,429	DIOVAN

C_max

Value	Dose	Analyte	Population
2808 ng/mL	80 mg single, oral	VALSARTAN plasma	Homo sapiens
5756 ng/mL	80 mg single, oral	VALSARTAN plasma	Homo sapiens
2.141 μg/mL	160 mg single, oral	VALSARTAN plasma	Homo sapiens

AUC

Value	Dose	Analyte	Population
20650 ng × h/mL	80 mg single, oral	VALSARTAN plasma	Homo sapiens
34310 ng × h/mL	80 mg single, oral	VALSARTAN plasma	Homo sapiens
22.56 μg × h/mL	160 mg single, oral	VALSARTAN plasma	Homo sapiens

T_1/2

Value	Dose	Analyte	Population
8.45 h	80 mg single, oral	VALSARTAN plasma	Homo sapiens
8 h	80 mg single, oral	VALSARTAN plasma	Homo sapiens
9.55 h	160 mg single, oral	VALSARTAN plasma	Homo sapiens

Doses

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Dose	Population	Adverse events
2.24 mg single, oral Overdose	unknown, 25 years n = 1	Other AEs: Muscle cramps...
640 mg 1 times / day steady, oral Highest studied dose	unhealthy, 57.5 years n = 131	Disc. AE: Hyperkalemia... Other AEs: Dizziness, Headache...
320 mg 1 times / day steady, oral Recommended	pregnant	Disc. AE: Disorder fetal...
320 mg 1 times / day steady, oral Recommended	unhealthy n = 2316	Disc. AE: Headache, Dizziness...
320 mg 1 times / day steady, oral Recommended	unhealthy n = 2506	Disc. AE: Creatinine increased, Potassium increased...

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AEs

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AE	Significance	Dose	Population
Muscle cramps	1 patient	2.24 mg single, oral Overdose	unknown, 25 years n = 1
Hyperkalemia	1 patient Disc. AE	640 mg 1 times / day steady, oral Highest studied dose	unhealthy, 57.5 years n = 131
Nausea	4.2%	640 mg 1 times / day steady, oral Highest studied dose	unhealthy, 57.5 years n = 131
Peripheral edema	4.2%	640 mg 1 times / day steady, oral Highest studied dose	unhealthy, 57.5 years n = 131
Diarrhea	5%	640 mg 1 times / day steady, oral Highest studied dose	unhealthy, 57.5 years n = 131

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Sourcing

Sourcing

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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

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PubMed

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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
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	24446062
LCZ696 : a new paradigm for the treatment of heart failure?	2015 Feb	25597387

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Patents

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

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
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

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Classification Tree

Code System

Code

Angiotensin II antagonists, plain

WHO-ATC

C09CA03

VASCULAR DISEASES

EMA ASSESSMENT REPORTS

IMPRADA-HCT (WITHDRAWN: HYPERTENSION)

HMG CoA reductase inhibitors, other combinations

WHO-ATC

C10BX10

VASCULAR DISEASES

EMA ASSESSMENT REPORTS

EXFORGE (AUTHORIZED: HYPERTENSION)

Designated/Withdrawn

FDA ORPHAN DRUG

494115

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Code System

Code

Type

Description

NSC

758927

PRIMARY

DAILYMED

80M03YXJ7I

PRIMARY

INN

7016

PRIMARY

RXCUI

69749

PRIMARY

RxNorm

CAS

137862-53-4

PRIMARY

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Related Record

Type

Details


					XYD5147M6H

PEPT-1

TRANSPORTER -> INHIBITOR


					I81U7H57XI

OAT-1

TRANSPORTER -> INHIBITOR


					056QD38ZSG

TYPE-1 ANGIOTENSIN II RECEPTOR

TARGET -> INHIBITOR


					WB8FT61183

SACUBITRIL VALSARTAN SODIUM HYDRATE

SALT/SOLVATE -> PARENT


					6D53G0FD0Z

PLASMA PROTEIN FRACTION (HUMAN)

BINDER->LIGAND

Interaction Type:

BINDING

Amount:

95 % (average)

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Related Record

Type

Details


					N891C54AXX

VALERYL-4-HYDROXYVALSARTAN

METABOLITE INACTIVE -> PARENT


					N891C54AXX

VALERYL-4-HYDROXYVALSARTAN

METABOLITE INACTIVE -> PARENT

Comments:

Valsartan was metabolized to a small extent only. The only notable metabolite in plasma, urine and faecs

Interaction Type:

MAJOR

Qualification:

FECAL; PLASMA; URINE

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Related Record

Type

Details


					2P0MPU907C

VALSARTAN BENZYL ESTER

IMPURITY -> PARENT

Interaction Type:

CHROMATOGRAPHIC PURITY (HPLC/UV)

Qualification:

USP

Amount:

RELATIONSHIP_AMOUNT [<0.2] WEIGHT PERCENT (limits)


					3IQ78TTX1A

N-NITROSODIETHYLAMINE

IMPURITY -> PARENT

Comments:

Probable human carcinogen.

Amount:

Other
Value is based on drug's maximum daily dose of 320 mg/day dose as reflected on the drug label.


					13EG6HX8ND

METHYL N-((2'-CYANO(1,1'-BIPHENYL)-4-YL)METHYL)-L-VALINATE

IMPURITY -> PARENT

Amount:


					2P0MPU907C

VALSARTAN BENZYL ESTER

IMPURITY -> PARENT

Comments:

UNSPECIFIED

Qualification:

EP


					IDC67444MI

VALSARTAN, D-

IMPURITY -> PARENT

Interaction Type:

CHROMATOGRAPHIC PURITY (HPLC/UV)

Qualification:

EP

Amount:

RELATIONSHIP_AMOUNT [<1] PERCENT PEAK AREA (limits)

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Related Record

Type

Details


					80M03YXJ7I

VALSARTAN

ACTIVE MOIETY

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Name	Property Type	Amount	Parameters
Volume of Distribution	PHARMACOKINETIC	0.24 Liters/Kilogram (average)

Route of Elimination	PHARMACOKINETIC	MOLE PERCENT OF AMOUNT EXCRETED 83 % (average) FECAL, MAINLY AS UNCHANGED DRUG	ROUTE OF ADMINISTRATION: ORAL

MAXIMUM TOLERATED DOSE	TOXICITY	320 mg/day (average)

PROTEIN BINDING	PHARMACOKINETIC	95 % (average) ALBUMIN

Route of Elimination	PHARMACOKINETIC	MOLE PERCENT OF AMOUNT EXCRETED 13 % (average) RENAL, MAINLY AS UNCHANGED DRUG	ROUTE OF ADMINISTRATION: ORAL

RENAL CLEARANCE	PHARMACOKINETIC	0.62 L/hr (average) ROUTE OF ADMINISTRATION: IV

Biological Half-life	PHARMACOKINETIC	6 hours (average)

SMILES

InChI

CNS Activity

Originator

Approval Year

Targets

Conditions

Cmax

AUC

T1/2

Doses

AEs

Sourcing

PubMed

Patents

Sample Use Guides

C_max

T_1/2