Indications and Usage Mechanisms of Action Pharmacokinetics Clinical Research
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Valsartan

Indications and Usage Mechanisms of Action Pharmacokinetics Clinical Research
Product Name
Valsartan
CAS No.
137862-53-4
Chemical Name
Valsartan
Synonyms
DIOVAN;Nisis;Valsratan;Varsartan;Tareg;CGP-48933;VALSARTAN;Valsatarn;Valsartane;L-Valsartan
CBNumber
CB6182539
Molecular Formula
C24H29N5O3
Formula Weight
435.52
MOL File
137862-53-4.mol
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Valsartan Property

Melting point:
116-117°C
Boiling point:
684.9±65.0 °C(Predicted)
Density 
1.212±0.06 g/cm3(Predicted)
vapor pressure 
0-0Pa at 20-25℃
storage temp. 
2-8°C
solubility 
DMSO: ≥20mg/mL
form 
powder
pka
3.56±0.10(Predicted)
color 
white to tan
optical activity
[α]/D -55 to -70°, c = 1 in methanol
Water Solubility 
84.99mg/L(25 ºC)
Merck 
14,9916
BCS Class
2
Stability:
Hygroscopic
InChIKey
ACWBQPMHZXGDFX-QFIPXVFZSA-N
LogP
1.2-2.8 at 25℃ and pH2.5-7
Surface tension
59.6-68.1mN/m at 10-100mg/L and 20℃
Dissociation constant
3.76-4.38 at 25℃
CAS DataBase Reference
137862-53-4(CAS DataBase Reference)
EPA Substance Registry System
L-Valine, N-(1-oxopentyl)-N-[[2'-(2H-tetrazol-5-yl)[1,1'-biphenyl]-4-yl]methyl]- (137862-53-4)
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Safety

Hazard Codes 
Xi
Risk Statements 
36/37/38
Safety Statements 
26-37/39
WGK Germany 
3
RTECS 
YV9455000
HS Code 
29339900
Hazardous Substances Data
137862-53-4(Hazardous Substances Data)
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Warning
Hazard statements

H336May cause drowsiness or dizziness

Precautionary statements

P201Obtain special instructions before use.

P308+P313IF exposed or concerned: Get medical advice/attention.

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
PHR1315
Product name
Valsartan
Purity
Pharmaceutical Secondary Standard; Certified Reference Material
Packaging
1g
Price
$97.5
Updated
2024/03/01
Sigma-Aldrich
Product number
1708762
Product name
Valsartan
Purity
United States Pharmacopeia (USP) Reference Standard
Packaging
350mg
Price
$436
Updated
2024/03/01
TCI Chemical
Product number
V0112
Product name
Valsartan
Purity
>98.0%(HPLC)(T)
Packaging
1g
Price
$56
Updated
2024/03/01
TCI Chemical
Product number
V0112
Product name
Valsartan
Purity
>98.0%(HPLC)(T)
Packaging
5g
Price
$184
Updated
2024/03/01
Cayman Chemical
Product number
14178
Product name
Valsartan
Purity
≥98%
Packaging
10mg
Price
$44
Updated
2024/03/01
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Valsartan Chemical Properties,Usage,Production

Indications and Usage

Valsartan (137862-53-4) is a type of specific angiotensin I (AT1) receptor antagonist and a clinical non-dermal AT1 receptor antagonist following losartan that has important effects in adjusting bodily blood pressure and maintaining electrolyte-body fluid balance. Valsartan’s antihypertensive effects are stronger than those of enalapril and is suitable for treating hypertension, mild to moderate primary hypertension, and especially secondary hypertension caused by renal damage. It can significantly reduce proteinuria for hypertension patients with diabetes or normal liver functions, and it can promote uric acid and urinary sodium to protect the kidney. Valsartan is also suitable for reducing the cardiovascular mortality for high risk patients (left ventricular failure or dysfunction) after experiencing a heart attack.

Mechanisms of Action

Valsartan (137862-53-4) selectively affects the AT1 receptor subtype and prevents AT1 from binding with AT1 receptors (its selective AT1 receptor antagonizing effect is about 20000 times greater than its effects on AT2 receptors), thus inhibiting vasoconstriction and aldosterone release, producing an antihypertensive effect, but it cannot inhibit the release of aldosterone caused by potassium ions (K+). Valsartan does not affect angiotensin-converting enzymes (ACE) or renin and its receptors, and it does not inhibit ion channels related to blood pressure regulation and sodium balance. Valsartan does not inhibit ACE and does not affect bodily bradykinin levels, thus causing less coughing side effects than ACE inhibitors. Valsartan does not affect heart rate when lowering blood pressure. Sudden ceasing in Valsartan use will not cause rebound hypertension or other side effects. Valsartan does not affect hypertension patients’ overall cholesterol, triglyceride, blood glucose, or uric acid levels.

Pharmacokinetics

For most patients, a single oral dose will have antihypertensive effects that occur within 2 hours, peak at 4-6 hours, and continue for over 24 hours. 2-4 weeks of treatment will result in maximum hypertensive curative effects, which will last throughout long-term treatment. It can be used with thiazide diuretics to further strengthen antihypertensive effects.

Clinical Research

A clinical trial showed that Valsartan has very noticeable effects on mild to moderate hypertension. A daily dose of ≥80 mg can effectively control systolic and diastolic blood pressure while not affecting blood pressure’s circadian rhythm; a daily 160mg dose has more noticeable effects than a daily 100mg dose of losartan. Moderate hypertension patients with intact renal functions have a good tolerance towards Valsartan, Valsartan’s curative effects are significantly superior to those of ACE inhibitors, and there are minimal adverse reactions. Effective in treating severe hypertension when combined with other antihypertensive drugs.

Description

Diovan(Valsartan) was launched in Germany and the UK as an angiotensin Ⅱ antagonist for use as an antihypertensive agent. Biphenylbromomethyl nitrite serves as the starting material for a three step synthesis of the compound, in which the (S)- enantiomer is more active than the (R)-enantiomer. Valsartan is a nonpeptide drug which is a highly specific antagonist of the AT1 receptor and is potent and orally active. This receptor is responsible for angiotensin Ⅱ cardiovascular effects (aldosterone and catecholamine secretion, vascular constriction, positive inotropic response and renal effects). Unlike losartan, it is not a prodrug and a single daily dose is comparible in activity to the ACE drug enalapril. It also did not exhibit the coughing side effect observed with ACE inhibitors. Diovan(Valsartan) is slowly metabolized (long lasting) with its main metabolite being significantly less active. There was no evidence of rebound hypertension when drug treatment was terminated and was as effective as the dihydropyridine Ca antagonist anlodipine.

Chemical Properties

White Crystalline Powder

Originator

Norvartis (Switzerland)

Uses

Valsartan is used as a first-line drug for the treatment of uncomplicated hypertension, isolated systolic hypertension, and left ventricular hypertrophy. Valsartan is a clinically widely used antihypertensive agent with the advantages of low side effects and good tolerability, and can also be used for the treatment of hypertension in patients with diabetes and renal disease.

Definition

ChEBI: A monocarboxylic acid amide consisting of L-valine in which the amino hydrogens have been replaced by a pentanoyl and a [2'-(1H-tetrazol-5-yl)biphenyl]-4-yl]methyl group. It exhibits antihypertensive activity.

brand name

Diovan (Novartis).

Therapeutic Function

Antihypertensive

General Description

Valsartan, N-(1-oxopentyl)-N-[[2'-(1H-tetrazol-5-yl)[1,1'-biphenyl]-4-yl]methyl]-L-valine (Diovan), likelosartan, possesses the acidic tetrazole system, which mostlikely plays a role, similar to that of the acidic groups of angiotensinII, in binding to the angiotensin II receptor. In addition,the biphenyl system that serves to separate the tetrazolefrom the aliphatic nitrogen is still present. In addition, there isa carboxylic acid side chain in the valine moiety that alsoserves to bind to the angiotensin II receptor.

Biochem/physiol Actions

Valsartan is an Angiotensin II type 1 (AT1) receptor antagonist and anti-hypertensive. Valsartan renders protection against heart attack and stroke resulting from abrupt increase in blood pressure. Valsartan reduces myocardial-infarction-related complications in heart attack survivors.

Synthesis

An aqueous solution (120 ml) of potassium hydroxide (0.568 mol, 31.8 g) is added in succession with 2-[(4-bromo-benzyl)-pentanoyl-amino]-3-methyl-butyric acid (0.811 mol, 30.0 g), tetrahydrofuran (120 ml), triphenylphosphine (0.0121 mol, 3.2 g) and palladium acetate (0.00405 mol, 0.91 g). The reaction mixture is refluxed and added with 2-(2H-tetrazol-5-yl)-benzene-boronic acid (0.142 mol, 27.0 g) in portions in about 6 h. After completion of the addition, the mixture is left to react for 2h, then cooled to room temperature and the phases are separated. The organic phase is diluted with water (120 ml) and tetrahydrofuran is distilled off under reduced pressure. The remaining aqueous solution is acidified to pH 6.5 and washed with isopropyl acetate (60 ml). The aqueous phase is acidified to pH 2 and diluted with isopropyl acetate (60 ml), the diphasic solution is filtered to remove phenyltetrazol. Phases are separated and the organic phase is concentrated under reduced pressure, to obtain a thick oil that is crystallized from isopropyl acetate (90 ml) and heptane (150 ml). The resulting product is filtered, washed twice with a 1:1 isopropyl acetate/heptane mixture (30 ml), and dried in static dryer at 45°C to obtain 28.2 g of Valsartan.

Drug interactions

Potentially hazardous interactions with other drugs
Anaesthetics: enhanced hypotensive effect.
Analgesics: antagonism of hypotensive effect and increased risk of renal impairment with NSAIDs; hyperkalaemia with ketorolac and other NSAIDs.
Antihypertensives: increased risk of hyperkalaemia, hypotension and renal impairment with ACE-Is and aliskiren.
Ciclosporin: increased risk of hyperkalaemia and nephrotoxicity.
Diuretics: enhanced hypotensive effect; hyperkalaemia with potassium-sparing diuretics.
ESAs: increased risk of hyperkalaemia; antagonism of hypotensive effect.
Lithium: reduced excretion (possibility of enhanced lithium toxicity).
Potassium salts: increased risk of hyperkalaemia.
Tacrolimus: increased risk of hyperkalaemia and nephrotoxicity.

Metabolism

Valsartan is not highly metabolised as only about 20% of dose is recovered as metabolites. A hydroxy metabolite has been identified in plasma at low concentrations (less than 10% of the valsartan AUC). This metabolite is pharmacologically inactive.
Valsartan is mainly eliminated by biliary excretion in faeces (about 83% of dose) and renally in urine (about 13% of dose), mainly as unchanged drug.

storage

Store at RT

References

1) Criscione?et al. (1993),?Pharmacological profile of valsartan: a potent, orally active, nonpeptide antagonist of the angiotensin II AT1-receptor subtype; Br. J. Pharmacol.,?110?761 2) Wexler?et al. (1996), Nonpeptide angiotensin II receptor antagonists: the next generation in antihypertensive therapy; J. Med. Chem.,?39?625 3) Iwashita?et al. (2013),?Valsartan restores inflammatory response by macrophages in adipose and hepatic tissues of LPS-infused mice; Adipocyte,?2?28

Valsartan Preparation Products And Raw materials

Raw materials

Preparation Products

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Valsartan Suppliers

Guangzhou Dreampharm Biotechnology Co., Ltd.
Tel
17825480238
Fax
QQ 3008233717
Email
3008233717@qq.com
Country
China
ProdList
9844
Advantage
12
Shenzhen SUNGENING Bio-Medical Co., Ltd.
Tel
0755-28967200 13631290199
Fax
0755-28967200
Email
wxf@sungening.com
Country
China
ProdList
9506
Advantage
60
Jiangxi ravel Biotechnology Co.,Ltd
Tel
400-880-2824 18107960669
Fax
18140514863
Email
bd@ruiweier.cn
Country
China
ProdList
995
Advantage
58
Hubei Xingcheng Biotechnology Co., Ltd
Tel
19171210221
Fax
QQ:3505191060
Email
3371991952@qq.com
Country
China
ProdList
960
Advantage
58
J & K SCIENTIFIC LTD.
Tel
010-82848833 400-666-7788
Fax
86-10-82849933
Email
jkinfo@jkchemical.com
Country
China
ProdList
96815
Advantage
76
Meryer (Shanghai) Chemical Technology Co., Ltd.
Tel
4006608290; 18621169109
Fax
86-21-61259102
Email
market03@meryer.com
Country
China
ProdList
40241
Advantage
62
INTATRADE GmbH
Tel
+49 3493/605464
Fax
+49 3493/605470
Email
sales@intatrade.de
Country
Germany
ProdList
3576
Advantage
66
3B Pharmachem (Wuhan) International Co.,Ltd.
Tel
821-50328103-801 18930552037
Fax
86-21-50328109
Email
3bsc@sina.com
Country
China
ProdList
15848
Advantage
69
TCI (Shanghai) Development Co., Ltd.
Tel
021-67121386
Fax
021-67121385
Email
Sales-CN@TCIchemicals.com
Country
China
ProdList
24539
Advantage
81
ShangHai DEMO Chemical Co.,Ltd
Tel
400-021-7337 2355568890
Fax
0086-21-50182339
Email
sales@demochem.com
Country
China
ProdList
2572
Advantage
57
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View Lastest Price from Valsartan manufacturers

Hebei Dangtong Import and export Co LTD
Product
Valsartan 137862-53-4
Price
US $50.00-40.00/kg
Min. Order
1kg
Purity
99%
Supply Ability
20Tons
Release date
2023-10-09
Jinan Jianfeng Chemical Co., Ltd
Product
Valsartan 137862-53-4
Price
US $1.00/g
Min. Order
1g
Purity
99
Supply Ability
2000
Release date
2021-10-21
Sinoway Industrial co., ltd.
Product
Valsartan 137862-53-4
Price
US $240.00-120.00/Kg/Bag
Min. Order
1Kg/Bag
Purity
EP / USP / JP
Supply Ability
20 tons
Release date
2023-12-01

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