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

• ChemBase ID: 5922
• Molecular Formular: C14H14O3
• Molecular Mass: 230.25916
• Monoisotopic Mass: 230.09429431
• SMILES: c1(OC)ccc2c(c1)ccc([C@H](C)C(=O)O)c2
• Canonical SMILES: COc1ccc2c(c1)ccc(c2)[C@@H](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)/t9-/m0/s1
• InChIKey: CMWTZPSULFXXJA-VIFPVBQESA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-2-(6-methoxynaphthalen-2-yl)propanoic acid
• IUPAC Traditional name: naproxen
• Brand Name: Aleve
• Synonyms: (S)-6-Methoxy-α-methyl-2-naphthaleneacetic Acid; po-Naproxen; Aproxen; Bonyl; CG 3117; Diocodal; Dysmenalgit; Equiproxen; Floginax; Laraflex; Laser; MNPA; Naixan; Napren; Naprium; Naprius; Naprosyn; Naprosyne; Naprux; Naxen; Nycopren; Panoxen; Prexan; Proxen; Proxine; RS 3540; Reuxen; Veradol; Xenar; Xenar-CR; d-2-(6-Methoxy-2-naphthyl)propionic Acid; d-Naproxen; (+)-6-Methoxy-alpha-methyl-2-naphthaleneacetic acid; (S)-(+)-2-(6-Methoxy-2-naphthyl)propionic acid; (S)-(+)-2-(6-Methoxy-2-naphthyl)propionic acid; Naproxen; (S)-(+)-6-Methoxy-α-methyl-2-naphthaleneacetic acid; (S)-(+)-6-Methoxy-α-methyl-2-naphthaleneacetic acid; (S)-2-(6-Methoxynaphthalen-2-yl)propanoic acid; (S)-naproxen; Naproxen; Naproxen; (2S)-2-(6-methoxynaphthalen-2-yl)propanoic acid; (S)-(+)-2-(6-甲氧基-2-萘基)丙酸; 萘普生; (S)-(+)-6-甲氧基-α-甲基-2-萘乙酸; (S)-(+)-6-甲氧基-α-甲基-2-萘乙酸; (S)-(+)-2-(6-甲氧基-2-萘基)丙酸; 萘普生; 氧萘丙酸

Database IDs

• CAS Number: 22204-53-1
• EC Number: 244-838-7
• MDL Number: MFCD00010500
• Beilstein Number: 3591067; 3591068
• Merck Index: 146417
• PubChem SID: 24857178; 99444769; 24883816; 160969347; 24870224; 24897861
• PubChem CID: 156391
• CHEBI ID: 7476
• ATC CODE: M01AE02; M02AA12; G02CC02
• CHEMBL: 154
• Chemspider ID: 137720
• DailyMed ID: 43871
• DrugBank ID: DB00788
• KEGG ID: D00118
• Unique Ingredient Identifier: 57Y76R9ATQ
• Wikipedia Title: Naproxen
• Medline Plus: a681029

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: Methanol; Chloroform; Dichloromethane; Ether; Ethyl Acetate; THF.
• Apperance: Off-White Solid
• Melting Point: 152-154 °C(lit.); 154-156°C; 155-157°C
• Optical Rotation: [α]20/D +66±2°, c = 1% in chloroform; [α]25/D +66°, c = 1 in chloroform; +66 (c=1 in chloroform)

Safety Information

• Storage Condition: -20°C Freezer
• Storage Warning: IRRITANT
• RTECS: UF5275000
• European Hazard Symbols: X; Harmful (Xn)
• UN Number: 2811; UN2811
• German water hazard class: 3
• Hazard Class: 6.1
• Packing Group: 3; III
• Risk Statements: 22; 22-36/37/38
• Safety Statements: 26-36/37; 36/37
• TSCA Listed: false; 否
• GHS Pictograms: GHS06
• GHS Signal Word: Danger
• GHS Hazard statements: H301; H301-H315-H319-H335
• GHS Precautionary statements: P261-P301+P310-P305+P351+P338-P302+P352-P405-P501A; P301 + P310
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Faceshields, Gloves
• RID/ADR: UN 2811 6.1/PG 3

Pharmacology Properties

• Admin Routes: Oral
• Bioavailability: 95% (oral)
• Excretion: Renal
• Half Life: 12–24 hours
• Metabolism: Hepatic (to 6-desmethylnaproxen)
• Protein Bound: 99%
• Legal Status: OTC (US); OTC(Ca); P (UK); S2 (Australia)
• Pregnancy Category: C (Australia); C (US)
• US Licence: naproxen
• Gene Information: human ... MAPK14(1432), PTGS1(5742), PTGS2(5743)rat ... Alox5(25290), Ptgs1(24693)

Product Information

• Purity: 95+%; 97%; 98%; 98% (T); 99%
• Grade: purum; VETRANAL™, analytical standard
• Suitability: meets USP testing specifications; suitable for 1694 per US EPA
• Pharmacopeia Traceability: traceable to BP 435; traceable to PhEur N0250000; traceable to USP 1457301
• Linear Formula: CH3OC10H6CH(CH3)CO2H
• Classification: Genuine Natural Compounds

DETAILS

DrugBank - DB08298

Drug information: experimental

Toronto Research Chemicals - N377520

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

Sigma Aldrich - 36405

Biochem/physiol Actions
Non-selective cyclooxygenase (COX-1 and COX-2) inhibitor.

Sigma Aldrich - 46482

Biochem/physiol Actions
Non-selective cyclooxygenase (COX-1 and COX-2) inhibitor.
Legal Information
VETRANAL is a trademark of Sigma-Aldrich Co. LLC

Sigma Aldrich - N8280

Biochem/physiol Actions
非选择性环加氧酶(COX-1 和 COX-2)抑制剂。

Sigma Aldrich - 65126

Biochem/physiol Actions
Non-selective cyclooxygenase (COX-1 and COX-2) inhibitor.
Other Notes
Naproxen is a cyclooxygenase inhibitor; it is used as anti-inflammatory agent; Reagent for the chiral derivatization of amino acids for GC separation 1,2

Sigma Aldrich - 284785

Biochem/physiol Actions
Non-selective cyclooxygenase (COX-1 and COX-2) inhibitor.
Packaging
5, 25 g in poly bottle

REFERENCES

• Harrison, I.T., et al.: J. Med. Chem., 13, 203 (1970)