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22204-53-1

22204-53-1 Structure

22204-53-1 Structure
IdentificationMore
[Name]

Naproxen
[CAS]

22204-53-1
[Synonyms]

D-2-(6-METHOXY-2-NAPHTHYL)PROPIONIC ACID
D-NAPROXEN
(+)-NAPROXEN
NAPROXEN
NAPROXENE
(S)-(+)-2-(6-METHOXY-2-NAPHTHYL)PROPIONIC ACID
(S)-(+)-(6-METHOXY-2-NAPHTHYL)PROPIONIC ACID
(+)-(S)-6-METHOXY-ALPHA-METHYL-2-NAPHTHALENEACETIC ACID
(S)-(+)-6-METHOXY-ALPHA-METHYL-2-NAPHTHALENEACETIC ACID
(S)-6-METHOXY-ALPHA-METHYL-2-NAPHTHALENEACETIC ACID
S(+)-6-METHOXY-ALPHA-METHYLNAPHTHALENE-2-ACETIC ACID
(S)-6-METHOXY-A-METHYL-2-NAPHTHALENEACETIC ACID
(S)-(+)-NAPROXEN
(S)-NAPROXEN
()-2-(methoxy-2-naphthyl)-propionicacid
()-2-(methoxy-2-naphthyl)-propionsaeure
()-propionicaci
(+)-2-(Methoxy-2-naphthyl)-propionic acid
(+)-2-(methoxy-2-naphthyl)-propionicacid
(+)-2-(Methoxy-2-naphthyl)-propionsaeure
[EINECS(EC#)]

244-838-7
[Molecular Formula]

C14H14O3
[MDL Number]

MFCD00010500
[Molecular Weight]

230.26
[MOL File]

22204-53-1.mol
Chemical PropertiesBack Directory
[Appearance]

white to light yellow crystal powde
[Melting point ]

152-154 °C (lit.)
[mp ]

152-154 °C(lit.)
[Boiling point ]

332.25°C (rough estimate)
[alpha ]

D +66° (in chloroform)
[density ]

1.1450 (rough estimate)
[refractive index ]

67.5 ° (C=1, CHCl3)
[Fp ]

9℃
[storage temp. ]

2-8°C
[solubility ]

Practically insoluble in water, soluble in ethanol (96 per cent) and in methanol.
[pka]

pKa 4.28± 0.02(H2O,t =25,I=0.01) (Uncertain)
[form ]

powder
[optical activity]

[α]25/D +66°, c = 1 in chloroform
[Water Solubility ]

Insoluble in water.
[Usage]

An anti-inflammatory, analgesic, antipyretic. A non-steroidal anti-inflammatory
[Merck ]

14,6417
[BRN ]

3591067
[CAS DataBase Reference]

22204-53-1(CAS DataBase Reference)
[NIST Chemistry Reference]

Naproxen(22204-53-1)
[EPA Substance Registry System]

2-Naphthaleneacetic acid, 6-methoxy-.alpha.-methyl-, (.alpha.S)- (22204-53-1)
Safety DataBack Directory
[Hazard Codes ]

Xn
[Risk Statements ]

R22:Harmful if swallowed.
[Safety Statements ]

S36/37:Wear suitable protective clothing and gloves .
[RIDADR ]

UN 2811 6.1/PG 3
[WGK Germany ]

3
[RTECS ]

UF5275000
[HazardClass ]

6.1(b)
[PackingGroup ]

III
[HS Code ]

29189900
[Hazardous Substances Data]

22204-53-1(Hazardous Substances Data)
[Toxicity]

LD50 in mice (mg/kg): 435 i.v.; 1234 orally; in rats (mg/kg): 575 i.p.; 534 orally (Roszkowski)
Raw materials And Preparation ProductsBack Directory
【Raw materials】

Methanol-->Toluene-->Hydrogen-->2-Naphthol-->2-Acetyl-6-methoxynaphthalene-->Cadmium chloride-->Magnesium-->Sodium hydroxide-->2-Bromo-6-methoxynaphthalene-->Ethyl 2-bromopropionate-->ZANAMIVIR HYDRATE-->(R)-(+)-4-Isopropyl-2-oxazolidinone
【Preparation Products】

Naproxen sodium-->(S)-(+)-Naproxen chloride
Material Safety Data Sheet(MSDS)Back Directory
[msds information]

(+)-2-(6-Methoxy-2-naphthyl)-propionic acid(22204-53-1).msds
Hazard InformationBack Directory
[Description]

Naproxen is synthesized from 2-methoxynaphthalene and the (+)-isomer obtained by resolution with cinchonidine (61). It was introduced in the United States in 1976 and, as a generic drug, has consistently been among the more popular NSAIDs. It is marketed as the S-(+)-enantiomer, but interestingly, the sodium salt of the (–)-isomer also is on the market as Anaprox. As an inhibitor of prostaglandin biosynthesis, it is 12 times more potent than aspirin, 10 times more potent than phenylbutazone, three to four times more potent than ibuprofen, and four times times more potent than fenoprofen, but it is approximately 300 times less potent than indomethacin.
[Originator]

Naprosyn,Syntex,UK,1973
[Indications]

Naproxen (Naprosyn) also has pharmacological properties and clinical uses similar to those of ibuprofen. It exhibits approximately equal selectivity for COX-1 and COX-2 and is better tolerated than certain NSAIDs, such as indomethacin. Adverse reactions related to the GI tract occur in about 14% of all patients, and severe GI bleeding has been reported. CNS complaints (headache, dizziness, drowsiness), dermatological effects (pruritus, skin eruptions, echinoses), tinnitus, edema, and dyspnea also occur.
[Definition]

ChEBI: A methoxynaphthalene that is 2-methoxynaphthalene substituted by a carboxy ethyl group at position 6. Naproxen is a non-steroidal anti-inflammatory drug commonly used for the reduction of pain, fever, inflammation and stiffness caused by conditions such a osteoarthritis, kidney stones, rheumatoid arthritis, psoriatic arthritis, gout, ankylosing spondylitis, menstrual cramps, tendinitis, bursitis, and for the treatment of primary dysmenorrhea. It works by inhibiting both the COX-1 and COX-2 enzymes.
[Manufacturing Process]

According to US Patent 3,658,858, a solution of 24 grams of 2-bromo-6- methoxynaphthalene in 300 ml of tetrahydrofuran is slowly added to 2.5 grams of magnesium turnings and 100 ml of tetrahydrofuran at reflux temperature. After the addition is complete, 20 grams of cadium chloride is added, and the resultant mixture is refluxed for 10 minutes to yield a solution of di-(6-methoxy-2-naphthyl)cadmium (which can be separated by conventional chromatography, although separation is unnecessary).
A solution of 18 grams of ethyl 2-bromopropionate in 20 ml of tetrahydrofuran is then added to the cooled reaction mixture. After 24 hours at 20°C, the product is hydrolyzed by adding 200 ml of 5 weight percent methanolic sodium hydroxide followed by heating to reflux for 1 hour. The reaction mixture is then diluted with excess 1 N sulfuric acid and extracted with ether. The ether phase is separated, evaporated to dryness and the residue is recrystallized from acetone-hexane to yield 2-(6-methoxy-2- naphthyl)propionic acid.
[Brand name]

Naprosyn (Roche).
[Therapeutic Function]

Antiinflammatory
[Synthesis Reference(s)]

Tetrahedron, 49, p. 8433, 1993 DOI: 10.1016/S0040-4020(01)81926-8
[General Description]

Naproxen (Naprosyn, Anaprox), marketed as the (S)-enantiomer,is well absorbed after oral administration, givingpeak plasma levels in 2 to 4 hours and a half-life of 13 hours.Naproxen is highly protein bound and displaces most protein-bound drugs. It is recommended for use in RA, OA, acute gouty inflammation, and in primary dysmenorrhea. Itshows good analgesic activity (i.e., 400 mg is comparable to75–150 mg of oral meperidine and superior to 65 mg ofpropoxyphene and 325 mg of aspirin plus 30 mg of codeine).It is also available OTC as 200-mg tablets (Aleve).
[Pharmacokinetics]

Naproxen is almost completely absorbed following oral administration. Peak plasma levels are achieved within 2 to 4 hours following administration. Like most of the acidic NSAIDs (pKa = 4.2), it is highly bound (99.6%) to plasma proteins. Approximately 70% of an administered dose is eliminated as either unchanged drug (60%) or as conjugates of unchanged drug (10%). The remainder is converted to the 6-O-desmethyl metabolite by both CYP3A4 and CYP1A2 and, further, to the glucuronide conjugate of the demethylated metabolite. The 6-O-desmethyl metabolite lacks anti-inflammatory activity. Like most of the arylalkanoic acids, the most common side effect associated with the use of naproxen is irritation to the GI tract. The most common other adverse reactions are associated with CNS disturbances (e.g., nausea and dizziness).
[Clinical Use]

Naproxen is indicated for the treatment of rheumatoid arthritis, osteoarthritis, juvenile arthritis, ankylosing spondylitis, tendinitis, bursitis, acute gout, and primary dysmenorrhea and for the relief of mild to moderate pain.
[Chemical Synthesis]

Naproxene, 2-(6-methoxy-2-naphthyl)-propionic acid (3.2.15) can be synthesized by the methods of synthesis described for ibuprofen as well as by the methods of fenoprofen (3.2.21) and ketoprofen (3.2.27) synthesis that will be described below from 2-acetyl or 2-chloromethyl-6-methoxynaphthaline [99–101].
[Veterinary Drugs and Treatments]

The manufacturer lists the following indications: “…for the relief of inflammation and associated pain and lameness exhibited with myositis and other soft tissue diseases of the musculoskeletal system of the horse.” (Package Insert; Equiproxen?—Syntex). It has also been used as an antiinflammatory/analgesic in dogs for the treatment of osteoarthritis and other musculoskeletal inflammatory diseases (see adverse reactions below).
Questions And AnswerBack Directory
[Non-steroidal anti-inflammatory drugs]

Naproxen is a non-steroidal anti-inflammatory drug ,it is a PG synthase inhibitor, which can inhibit prostaglandin synthetase, it has significant analgesic and antipyretic effects, oral absorption is rapid and complete, 2 to 4 hours after a dose ,plasma concentration reaches the peak, in the blood , more than 99% is bound to plasma proteins, t1/2 is 13 to 14 hours, about 95% is discharged from the urine with the prototype and metabolites.it is clinically used For the treatment of rheumatic and rheumatoid arthritis , osteoarthritis, ankylosing spondylitis, gout, arthritis, tenosynovitis.it can also be used to alleviate pain caused by musculoskeletal sprains, contusions,damages and dysmenorrhea . But it should be noted that like other non-steroidal anti-inflammatory drugs, the same serious gastrointestinal adverse reactions could occur at any time while taking naproxen during treatment, so the active gastroduodenal ulcer patients are hanged, other gastrointestinal tract disease patients should take this drug under close medical supervision.
The above information is edited by the Chemicalbook of Tian Ye.
[Chemical Properties]

White crystal or crystalline powder. Melting point 155.3 ℃. Soluble in acetone, soluble in methanol, ethanol, acetic acid, insoluble in benzene, practically insoluble in water. In case of light,it is color-graded, odorless, tasteless.
[Uses]

It is a non-steroidal anti-inflammatory drug for the relief of fever and inflammation and pain associated with arthritis or other symptoms , it has anti-inflammatory, antipyretic and analgesic effects. Naproxen plays a role by inhibiting the cyclooxygenase, which generates prostaglandin and is one kind of enzymes related to inflammatory mediators . It is recommended to take the drug during meals to reduce stomach irritation.
[Used in Particular Diseases]

Acute Gouty Arthritis:
Dosage and Frequency: 500 mg twice daily for 3 days, then 250–500 mg daily for 4–7 days
[production method]

by methylation, acetylation With 2-naphthol , 6-methoxy-2-acetonaphthone is produced, then it is condensed with acid ester, then generate the product through isomerization, hydrolysis, oxidation, and split and other reactions.
[Category]

Toxic substances
[Toxicity grading]

Highly toxic
[Acute toxicity]

Oral-rat LD50 248 mg/kg; Oral-Mouse LD50: 360 mg/kg
[Flammability and hazard characteristics]

Combustible; combustion produces toxic and acrid smoke.
[Storage Characteristics]

Ventilated, low-temperature ,dry storeroom, it should be stored and transported from food raw materials separately.
[Extinguishing agent]

Water, dry powder, foam,sand
Spectrum DetailBack Directory
[Spectrum Detail]

Naproxen(22204-53-1) 13C NMR
Naproxen(22204-53-1) MS
Naproxen(22204-53-1) 1H NMR
Naproxen(22204-53-1) IR2
Naproxen(22204-53-1) IR1
Well-known Reagent Company Product InformationBack Directory
[Acros Organics]

(S)-Naproxen, 97%(22204-53-1)
[Alfa Aesar]

(S)-(+)-2-(6-Methoxy-2-naphthyl)propionic acid, 99%(22204-53-1)
[Sigma Aldrich]

22204-53-1(sigmaaldrich)
[TCI AMERICA]

(S)-(+)-2-(6-Methoxy-2-naphthyl)propionic Acid,>99.0%(GC)(T)(22204-53-1)
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