2-(6-methoxynaphthalen-2-yl)propanoic acid

• ChemBase ID: 667
• Molecular Formular: C14H14O3
• Molecular Mass: 230.25916
• Monoisotopic Mass: 230.09429431
• SMILES: O(c1cc2c(cc(C(C)C(=O)O)cc2)cc1)C
• Canonical SMILES: COc1ccc2c(c1)ccc(c2)C(C(=O)O)C
• InChI: InChI=1S/C14H14O3/c1-9(14(15)16)10-3-4-12-8-13(17-2)6-5-11(12)7-10/h3-9H,1-2H3,(H,15,16)
• InChIKey: CMWTZPSULFXXJA-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-(6-methoxynaphthalen-2-yl)propanoic acid
• IUPAC Traditional name: naprosyn
• Brand Name: Aleve; Anaprox; Bonyl; DL Naproxen; DL-Naproxen; Diocodal; Dysmenalgit; Ec-naprosyn; Equiproxen; Floginax; Laraflex; Laser; Mnpa; Naixan; Naprelan; Napren; Naprium; Naprius; Naprosine; Naprosyn; Naprosyne; Naproxen Sodium; Naprux; Naxen; Naxyn; Niaxan; Nycopren; Panoxen; Pranoxen; Prexan; Proxen; Proxine; Reuxen; Veradol; Xenar
• Synonyms: (RS)-Naproxen; (+/-)-2-(6-Methoxy-2-naphthalenyl)propionic Acid; (+/-)-2-(6-Methoxy-2-naphthyl)propionic Acid; (+/-)-6-Methoxy-α-methyl-2-naphthaleneacetic Acid; (+/-)-Naproxen; 2-(6-Methoxy-2-naphthyl)propanoic Acid; dl-Naproxen; rac-Naproxen; (RS)-Naproxen-d3; (+/-)-2-(6-Methoxy-2-naphthalenyl)propionic Acid-d3; (+/-)-2-(6-Methoxy-2-naphthyl)propionic Acid-d3; (+/-)-6-Methoxy-α-(methyl-d3)-2-naphthaleneacetic Acid; (+/-)-Naproxen-d3; 2-(6-Methoxy-2-naphthyl)propanoic Acid-d3; dl-Naproxen-d3; rac Naproxen-d3; Naproxen; 2-(6-Methoxynaphthalen-2-yl)propanoic acid; (+)-2-(6-methoxy-2-naphthyl)-propionic acid; S(+)-6-methoxy-α-methyl-2-naphthaleneacetic acid); [S(+)-2-(6-Methoxy-2-naphthyl)propionic acid]

Database IDs

• CAS Number: 23981-80-8; 22204-53-1
• EC Number: 244-838-7
• MDL Number: MFCD00439456
• PubChem SID: 160964130
• PubChem CID: 1302

CALCULATED PROPERTIES

JChem

• Acid pKa: 4.1903534
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): 1.6579665
• LogD (pH = 7.4): -0.054211214
• Log P: 2.985786
• Molar Refractivity: 64.8535 cm^3
• Polarizability: 26.3861 Å^3
• Polar Surface Area: 46.53 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 3.29
• LOG S: -3.65
• Solubility (Water): 5.11e-02 g/l

PROPERTIES

Physical Property

• Solubility: 15.9 mg/L; Chloroform; Methanol
• Apperance: Off-White Solid; White Solid
• Melting Point: 154-154°C; 156-157°C; 157-158°C
• Hydrophobicity(logP): 2.8

Safety Information

• Storage Condition: -20°C Freezer; Refrigerator; Room Temperature (15-30°C)
• RTECS: UF5275000
• European Hazard Symbols: Harmful (Xn)
• Risk Statements: R:22-36/37/38
• Safety Statements: S:25-26-36/37/39

Product Information

• Purity: 95+%; 97%

DETAILS

MP Biomedicals - 02190247

Pharmacological agent that reportedly may show activity through ability to inhibit prostaglandin biosynthesis.

DrugBank - DB00788

• Drug Groups: approved
• Description: An anti-inflammatory agent with analgesic and antipyretic properties. Both the acid and its sodium salt are used in the treatment of rheumatoid arthritis and other rheumatic or musculoskeletal disorders, dysmenorrhea, and acute gout. [PubChem]
• Indication: For the treatment of rheumatoid arthritis, osteoarthritis, ankylosing spondylitis, tendinitis, bursitis, and acute gout. Also for the relief of mild to moderate pain and the treatment of primary dysmenorrhea.
• Pharmacology: Naproxen is a member of the arylacetic acid group of nonsteroidal anti-inflammatory drugs (NSAIDs). Naproxen has analgesic and antipyretic properties. As with other NSAIDs, its mode of action is not fully understood; however, its ability to inhibit prostaglandin synthesis may be involved in the anti-inflammatory effect.
• Toxicity: ORAL (LD₅₀): Acute: 248 mg/kg [Rat]. 360 mg/kg [Mouse]. Symptoms of overdose include drowsiness, heartburn, indigestion, nausea, and vomiting.
• Affected Organisms: Humans and other mammals
• Biotransformation: Naproxen is extensively metabolized to 6-0-desmethyl naproxen and both parent and metabolites do not induce metabolizing enzymes.
• Absorption: Naproxen itself is rapidly and completely absorbed from the GI tract with an in vivo bioavailability of 95%. Although naproxen itself is well absorbed, the sodium salt form is more rapidly absorbed resulting in higher peak plasma levels for a given dose. Food causes a slight decrease in the rate absorption.
• Half Life: The observed terminal elimination half-life is approximately 15 hours.
• Protein Binding: At therapeutic levels naproxen is greater than 99% albumin-bound.
• References: Kearney PM, Baigent C, Godwin J, Halls H, Emberson JR, Patrono C: Do selective cyclo-oxygenase-2 inhibitors and traditional non-steroidal anti-inflammatory drugs increase the risk of atherothrombosis? Meta-analysis of randomised trials. BMJ. 2006 Jun 3;332(7553):1302-8. [Pubmed] ; Zhang J, Ding EL, Song Y: Adverse effects of cyclooxygenase 2 inhibitors on renal and arrhythmia events: meta-analysis of randomized trials. JAMA. 2006 Oct 4;296(13):1619-32. Epub 2006 Sep 12. [Pubmed]
• External Links: Wikipedia; RxList; PDRhealth; Drugs.com

Toronto Research Chemicals - N377527

Labelled Naproxen. An anti-inflammatory, analgesic, antipyretic. A non-steroidal anti-inflammatory.

Toronto Research Chemicals - N377526

An anti-inflammatory, analgesic, antipyretic. A non-steroidal anti-inflammatory.

REFERENCES

• Tomlinson, et al., Biochem. Biophys. Res. Commun. , 46 : 552 (1972).
• Kearney PM, Baigent C, Godwin J, Halls H, Emberson JR, Patrono C: Do selective cyclo-oxygenase-2 inhibitors and traditional non-steroidal anti-inflammatory drugs increase the risk of atherothrombosis? Meta-analysis of randomised trials. BMJ. 2006 Jun 3;332(7553):1302-8. Pubmed
• Zhang J, Ding EL, Song Y: Adverse effects of cyclooxygenase 2 inhibitors on renal and arrhythmia events: meta-analysis of randomized trials. JAMA. 2006 Oct 4;296(13):1619-32. Epub 2006 Sep 12. Pubmed
• Harrison, I.T., et al.: J. Med. Chem., 13, 203 (1970)
• Harrison, I.T., et al.: J. Med. Chem., 13, 203 (1970)