Naproxen

Base Information

• Chemical Name: Naproxen
• CAS No.: 22204-53-1
• Molecular Formula: C14H14O3
• Molecular Weight: 230.263
• Hs Code.: DERIVATION
• European Community (EC) Number: 244-838-7
• NSC Number: 757239,750183
• UNII: 57Y76R9ATQ
• DSSTox Substance ID: DTXSID4040686
• Wikipedia: Naproxen
• Wikidata: Q1215575
• NCI Thesaurus Code: C680
• RXCUI: 7258
• Pharos Ligand ID: 6CXLZU39MTX9
• Metabolomics Workbench ID: 37931
• ChEMBL ID: CHEMBL154
• Mol file: 22204-53-1.mol

Synonyms:Aleve;Anaprox;Methoxypropiocin;Naprosin;Naprosyn;Naproxen;Naproxen Sodium;Naproxenate, Sodium;Proxen;Sodium Naproxenate;Sodium, Naproxen;Synflex

Chemical Property of Naproxen

Chemical Property:

• Appearance/Colour: White or almost white crystalline powder
• Vapor Pressure: 3.01E-07mmHg at 25°C
• Melting Point: 152-154 °C(lit.)
• Refractive Index: 67.5 ° (C=1, CHCl3)
• Boiling Point: 403.888 °C at 760 mmHg
• PKA: pKa 4.28± 0.02(H2O,t =25,I=0.01) (Uncertain)
• Flash Point: 154.529 °C
• PSA: 46.53000
• Density: 1.197 g/cm³
• LogP: 3.03650
• Storage Temp.: -20°C Freezer
• Solubility.: Practically insoluble in water, soluble in ethanol (96 per cent) and in methanol.
• Water Solubility.: Insoluble in water.
• XLogP3: 3.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 230.094294304
• Heavy Atom Count: 17
• Complexity: 277

Purity/Quality:

99% ^*data from raw suppliers

(S)-Naproxen ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn,T,F
• Statements: 22-39/23/24/25-23/24/25-11-36/37/38
• Safety Statements: 36/37-45-16-7-26

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Drug Classes: Nonsteroidal Antiinflammatory Drugs
• Canonical SMILES: CC(C1=CC2=C(C=C1)C=C(C=C2)OC)C(=O)O
• Isomeric SMILES: C[C@@H](C1=CC2=C(C=C1)C=C(C=C2)OC)C(=O)O
• Recent ClinicalTrials: Duloxetine for LBP
• Recent EU Clinical Trials: Efficacy of Addition of Naproxen in the Treatment of critically ill Patients Hospitalized for COVID-19 Infection / Enacovid Study
• Recent NIPH Clinical Trials: Effect of etdolac on gastric acid and mucous secretion –comparison with naproxen-
• General Description: Naproxen is a nonsteroidal anti-inflammatory drug (NSAID) commonly used for its analgesic and anti-inflammatory properties. Recent research has focused on developing prodrugs of naproxen to improve its pharmacokinetic profile and reduce gastrointestinal (GI) toxicity while retaining its therapeutic efficacy. These prodrugs, synthesized through modifications such as conjugation with glucose and amino acids, have demonstrated comparable anti-inflammatory and analgesic effects with significantly lower GI irritation, making them promising candidates for safer oral administration.

Technology Process of Naproxen

There total 243 articles about Naproxen 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: 98.0%

Naprelan (26159-34-2) → (2S)-2-(6-methoxy(2-naphthyl))propanoic acid (22204-53-1)

Guidance literature:

With hydrogenchloride; In methanol; at 20 ℃;

DOI:10.3390/molecules24071237

Reference yield: 97.9%

(R)-praziquanammonium (S)-2-(6-methoxy-naphthalen-2-yl)-propionate → (2S)-2-(6-methoxy(2-naphthyl))propanoic acid (22204-53-1) + (R)-(-)-1,2,3,6,7,11b-hexahydro-4H-pyrazino[2,1-a]isoquinolin-4-one (55375-92-3,55375-90-1)

Guidance literature:

With hydrogenchloride; In water; at 20 ℃; for 0.5h; pH=1;

Reference yield: 96.0%

S-2-(6-methoxy-2-naphthyl)propionaldehyde (32305-59-2) + 2-pentene (109-68-2) → (2S)-2-(6-methoxy(2-naphthyl))propanoic acid (22204-53-1)

Guidance literature:

With sodium dihydrogenphosphate; sodium chlorite; In water; at 20 ℃; for 1h;

upstream raw materials:

carbon monoxide

2-methoxy-6-vinylnapthalene

methyl 2-(6-methoxy-2-naphthyl)propionate

(R,S) naproxen ethyl ester

Downstream raw materials:

(S)-6-methoxy-α-methyl-2-naphthaleneacetic acid ethyl ester

(S)-2-<<(S)-2-(6-Methoxy-2-naphthyl)propionylamino>methyl>-3-phenylpropionsaeure-methylester

(S)-naproxenoyl chloride

(+)-naproxen acid chloride

Refernces

Synthesis and evaluation of novel prodrugs of naproxen

10.1007/s00044-010-9364-8

This research presents the synthesis and evaluation of novel prodrugs of naproxen, a nonsteroidal anti-inflammatory drug (NSAID), aimed at enhancing its pharmaceutical and pharmacokinetic properties while reducing gastrointestinal (GI) toxicity. The study involved the reaction of naproxen with thionyl chloride to form an acid chloride, which was then reacted with glucose to produce glucosyl naproxen. This was followed by acetylation and reaction with various amino acids to yield the prodrugs. The synthesized prodrugs were evaluated for analgesic and anti-inflammatory activities and assessed for GI toxicity. The results indicated that the prodrugs maintained the therapeutic activities of naproxen while significantly reducing GI irritation. Key chemicals used in the synthesis process included naproxen, thionyl chloride, glucose, pyridine, acetic anhydride, and different amino acids such as glycine, valine, alanine, cysteine, and others. The synthesized compounds were characterized using IR, NMR, and MS spectral methods. The study concluded that these novel prodrugs could be potentially useful naproxen derivatives for oral administration due to their stability in aqueous solutions, retention of analgesic and anti-inflammatory activity, and notably reduced GI irritation.