Valsartan

Base Information

• Chemical Name: Valsartan
• CAS No.: 137862-53-4
• Molecular Formula: C24H29N5O3
• Molecular Weight: 435.526
• Hs Code.: 29339900
• European Community (EC) Number: 604-045-2,695-249-0
• NSC Number: 758927
• UNII: 80M03YXJ7I
• DSSTox Substance ID: DTXSID6023735
• Nikkaji Number: J550.722G
• Wikipedia: Valsartan
• Wikidata: Q155472
• NCI Thesaurus Code: C47781
• RXCUI: 69749
• Pharos Ligand ID: YFG7PFZLBM2W
• Metabolomics Workbench ID: 42585
• ChEMBL ID: CHEMBL1069
• Mol file: 137862-53-4.mol

Synonyms:48933, CGP;CGP 48933;Diovan;Kalpress;Miten;N-valeryl-N-((2'-(1H-tetrazol-5-yl)biphenyl-4-yl)methyl)valine;Nisis;Provas;Tareg;Vals;valsartan

Chemical Property of Valsartan

Chemical Property:

• Appearance/Colour: white crystalline powder
• Vapor Pressure: 1.06E-19mmHg at 25°C
• Melting Point: 116-117 °C
• Refractive Index: 1.586
• Boiling Point: 684.9 °C at 760 mmHg
• PKA: 3.56±0.10(Predicted)
• Flash Point: 368 °C
• PSA: 112.07000
• Density: 1.212 g/cm³
• LogP: 4.16170
• Storage Temp.: -20°C Freezer, Under inert atmosphere
• Solubility.: DMSO: ≥20mg/mL
• Water Solubility.: 84.99mg/L(25 oC)
• XLogP3: 4.4
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 10
• Exact Mass: 435.22703980
• Heavy Atom Count: 32
• Complexity: 608

Purity/Quality:

99.9% ^*data from raw suppliers

Valsartan ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-37/39

MSDS Files:

SDS file from LookChem

Useful:

• Drug Classes: Angiotensin II Receptor Antagonists
• Canonical SMILES: CCCCC(=O)N(CC1=CC=C(C=C1)C2=CC=CC=C2C3=NNN=N3)C(C(C)C)C(=O)O
• Isomeric SMILES: CCCCC(=O)N(CC1=CC=C(C=C1)C2=CC=CC=C2C3=NNN=N3)[C@@H](C(C)C)C(=O)O
• Recent ClinicalTrials: A Study to Evaluate the Effect of Sodium Zirconium Cyclosilicate on Chronic Kidney Disease (CKD) Progression in Participants With CKD and Hyperkalaemia or at Risk of Hyperkalaemia
• Recent EU Clinical Trials: Empower the Heart of Patients with Terminal Cancer using Cardiac Medicines Trial
• Recent NIPH Clinical Trials: A Study to Evaluate the Effect of Sodium Zirconium Cyclosilicate on Chronic Kidney Disease (CKD) Progression in Participants With CKD and Hyperkalaemia or at Risk of Hyperkalaemia
• Pharmacological Action: Valsartan is an orally active Angiotensin II receptor type 1 antagonist. It reduces blood pressure and is primarily used in the treatment of hypertension.; Valsartan is available both as a standalone medication and in combination with other antihypertensive drugs.; It is a lipophilic drug with a moderate onset of action compared to other drugs in the same category.
• Combination Drugs and New Class: Sacubitril/valsartan represents a new class of drugs known as angiotensin receptor neprilysin inhibitors.; Valsartan is available in combination with other antihypertensive drugs to enhance its therapeutic effects.
• Market and Generic Industries: Developed by Novartis, Valsartan has a wide market presence in both developed and developing countries. Due to its effectiveness and market demand, Valsartan is a significant target for the generic drug industry.
• Comparison with Other Antihypertensive Agents: Valsartan is among the most frequently prescribed antihypertensive agents. It inhibits the binding of angiotensin II to its AT1 receptor, thereby regulating blood pressure.
• Treatment of Specific Conditions: Valsartan is considered a first-line treatment for hypertensive patients with sleep apnea. It has shown significant reductions in blood pressure, especially when used in combination with continuous positive airway pressure (CPAP) treatment for obstructive sleep apnea (OSA).
• Clinical Trials and Research: Clinical trials, such as the NAVIGATOR trial, have investigated Valsartan's potential to protect individuals with impaired fasting glucose (IFG) and/or impaired glucose tolerance (IGT) against type 2 diabetes and cardiovascular disease. Valsartan has demonstrated benefits in increasing insulin sensitivity and reducing the onset of type 2 diabetes.
• Safety and Tolerability: Valsartan is safe and well-tolerated, with reported side effects including headaches and dose-dependent dizziness.; Monitoring of renal function and serum potassium is recommended in at-risk patients.

Technology Process of Valsartan

There total 121 articles about Valsartan which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 99.9%

(S)-N-(1-carboxy-2-methyl-prop-1-yl)-N-pentarloyl-N-[2'-(1H-tetrazol-5-yl)biphenyl-4-yl-methyl]amine barium salt → N-pentanoyl-N-[[2'-(1H-tetrazol-5-yl)-[1,1'-biphenyl]-4-yl]-methyl]-(L)-valine (137862-53-4,137862-87-4)

Guidance literature:

With hydrogenchloride; water; pH=2 - 2.5;

Reference yield: 95.0%

N-[[2'-(1-triphenylmethyltetrazol-5yl)biphenyl-4-yl]methyl]-N-valeryl-L-valine methyl ester (781664-81-1) → N-pentanoyl-N-[[2'-(1H-tetrazol-5-yl)-[1,1'-biphenyl]-4-yl]-methyl]-(L)-valine (137862-53-4,137862-87-4)

Guidance literature:

N-[[2'-(1-triphenylmethyltetrazol-5yl)biphenyl-4-yl]methyl]-N-valeryl-L-valine methyl ester; With methanol; potassium hydroxide; for 4h; Heating / reflux;

With water; for 5h; Heating / reflux;

Reference yield: 92.0%

(2S)-3-methyl-2-{N-[2'-(1H-tetrazol-5-yl)-biphenyl-4-ylmethyl]-N'-(thiophene-2-carbonyl)-amino}-butanoic acid (1033772-60-9) → N-pentanoyl-N-[[2'-(1H-tetrazol-5-yl)-[1,1'-biphenyl]-4-yl]-methyl]-(L)-valine (137862-53-4,137862-87-4)

Guidance literature:

With sodium azide; dichloro[(-)-sparteine-N,N']copper(II); In ethyl acetate; at 70 - 80 ℃; for 4h; Concentration; Reagent/catalyst; Large scale;

upstream raw materials:

(S)-4-isopropyl-3-pentanoyl-2-[2'-(2-trityl-2H-tetrazol-5-yl)-biphenyl-4-yl]oxazolidin-5-one

(S)-2-[(4-bromo-benzyl)-pentanoyl-amino]-3-methyl-butyric acid

(2-(2H-tetrazol-5-yl)phenyl)boronic acid

C₂₄H₂₇N₅O₃

Downstream raw materials:

valsartan:β-cyclodextrin

(S)-methyl 2-((S)-2-(N-((2'-(1H-tetrazol-5-yl)biphenyl-4-yl)methyl)pentanamido)-3-methylbutanamido)-3-phenylpropanoate

(S)-2-((S)-2-(N-((2'-(1H-tetrazol-5-yl)biphenyl-4-yl)methyl)pentanamido)-3-methylbutanamido)-3-phenylpropanoic acid

trisodium [3-((1S,3R)-1-biphenyl-4-yl-methyl-3-ethoxycarbonyl-1-butylcarbamoyl)propionate-(S)-3’-methyl-2’-(pentanoyl{2”-(tetrazol-5-ylate)biphenyl-4’-yl-methyl}amino)butyrate] hemipentahydrate

Refernces

• 1、 Aalla, Sampath,Gilla, Goverdhan,Bojja, Yakambram,Anumula, Raghupathi Reddy,Vummenthala, Prabhakar Reddy,Padi, Pratap Reddy. "An efficient and telescopic process for valsartan, an angiotensin II Receptor Blocker". . p. 682 - 686. Retrieved 2012.
• 2、 Ghosh, Samir,Kumar, A. Sanjeev,Mehta, G. N.. "A short and efficient synthesis of valsartan via a Negishi reaction". . . Retrieved 2010.
• 3、 -. "A PROCESS FOR THE PREPARATION OF HIGHLY PURE VALSARTAN". Page/Page column 11-16. . Retrieved 2021/06/11.
• 4、 Carpentier, Florian,Felpin, Fran?ois-Xavier,Zammattio, Fran?oise,Le Grognec, Erwan. "Synthesis of 5-Substituted 1 H-Tetrazoles from Nitriles by Continuous Flow: Application to the Synthesis of Valsartan". . p. 752 - 761. Retrieved 2020/03/13.