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Naproxen

Non-steroidal anti-inflammatory drugs Chemical Properties Uses Used in Particular Diseases production method Category Toxicity grading Acute toxicity Flammability and hazard characteristics Storage Characteristics Extinguishing agent
Naproxen
Naproxen structure
CAS No.
22204-53-1
Chemical Name:
Naproxen
Synonyms
axer;Bonyl;Xenar;Naxen;Naxyn;cg3117;Prexan;Proxen;Reuxen;Naixan
CBNumber:
CB8274937
Molecular Formula:
C14H14O3
Formula Weight:
230.26
MOL File:
22204-53-1.mol

Naproxen Properties

Melting point:
152-154 °C (lit.)
alpha 
D +66° (in chloroform)
Boiling point:
332.25°C (rough estimate)
Density 
1.1450 (rough estimate)
refractive index 
67.5 ° (C=1, CHCl3)
Flash point:
9℃
storage temp. 
2-8°C
solubility 
Practically insoluble in water, soluble in ethanol (96 per cent) and in methanol.
form 
powder
pka
pKa 4.28± 0.02(H2O,t =25,I=0.01) (Uncertain)
optical activity
[α]25/D +66°, c = 1 in chloroform
Water Solubility 
Insoluble in water.
Merck 
14,6417
BRN 
3591067
CAS DataBase Reference
22204-53-1(CAS DataBase Reference)
EWG's Food Scores
1
FDA UNII
57Y76R9ATQ
NCI Dictionary of Cancer Terms
Naprosyn; naproxen
NCI Drug Dictionary
Naprosyn
NIST Chemistry Reference
Naproxen(22204-53-1)
EPA Substance Registry System
2-Naphthaleneacetic acid, 6-methoxy-.alpha.-methyl-, (.alpha.S)- (22204-53-1)
SAFETY
  • Risk and Safety Statements
Symbol(GHS) 
GHS02,GHS06,GHS07,GHS08
Signal word  Danger
Hazard statements  H225-H301+H311+H331-H370-H301-H315-H319-H361-H335
Precautionary statements  P261-P280a-P301+P310a-P305+P351+P338-P501a-P210-P260-P280-P301+P310-P311-P201-P202-P264-P270-P301+P310+P330-P302+P352+P332+P313+P362+P364-P305+P351+P338+P337+P313-P308+P313-P405-P501
Hazard Codes  Xn,T,F
Risk Statements  22-39/23/24/25-23/24/25-11-36/37/38
Safety Statements  36/37-45-16-7-26
RIDADR  UN 2811 6.1/PG 3
WGK Germany  3
RTECS  UF5275000
HazardClass  6.1(b)
PackingGroup  III
HS Code  29189900
Toxicity LD50 in mice (mg/kg): 435 i.v.; 1234 orally; in rats (mg/kg): 575 i.p.; 534 orally (Roszkowski)

Naproxen price More Price(18)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich N-042 Naproxen solution 1.0?mg/mL in methanol, ampule of 1?mL, certified reference material, Cerilliant? 22204-53-1 1 mL $28.8 2021-03-22 Buy
Sigma-Aldrich 284785 (S)-(+)-6-Methoxy-α-methyl-2-naphthaleneacetic acid 98% 22204-53-1 5g $41.6 2021-03-22 Buy
Sigma-Aldrich N0250000 Naproxen European Pharmacopoeia (EP) Reference Standard 22204-53-1 $190 2021-03-22 Buy
Sigma-Aldrich 1457301 Naproxen United States Pharmacopeia (USP) Reference Standard 22204-53-1 200mg $366 2021-03-22 Buy
TCI Chemical M1021 (S)-(+)-2-(6-Methoxy-2-naphthyl)propionic Acid >99.0%(GC)(T) 22204-53-1 25g $23 2021-03-22 Buy

Naproxen Chemical Properties,Uses,Production

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

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.

Chemical Properties

white to light yellow crystal powde

Originator

Naprosyn,Syntex,UK,1973

Uses

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

Uses

Being analogous to other drugs of this series, naproxene exhibits analgesic, fever-reducing, and long-lasting anti-inflammatory action. It causes reduction and removal of painful symptoms including joint pain, stiffness, and swelling in the joints. It is used in the same indications as ibuprofen.

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.

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.

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).

Naproxen Preparation Products And Raw materials

Raw materials

Preparation Products


Naproxen Suppliers

Global( 463)Suppliers
Supplier Tel Fax Email Country ProdList Advantage
Beijing Cooperate Pharmaceutical Co.,Ltd
010-60279497
010-60279497 sales01@cooperate-pharm.com CHINA 1817 55
Shanghai Bojing Chemical Co.,Ltd.
+86-21-37122233
+86-21-37127788 Candy@bj-chem.com CHINA 497 55
Henan Tianfu Chemical Co.,Ltd.
0371-55170693
0371-55170693 info@tianfuchem.com CHINA 22607 55
Guangzhou PI PI Biotech Inc
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020-81716319 sales@pipitech.com;87478684@qq.com China 3245 55
Hefei TNJ Chemical Industry Co.,Ltd.
86-0551-65418684 18949823763
86-0551-65418684 info@tnjchem.com China 3001 55
Hebei Minshang Biotechnology Co., Ltd
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+8619933070948
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+86 18953170293
+86 0531-67809011 sales@sdzschem.com CHINA 2858 58

View Lastest Price from Naproxen manufacturers

Image Release date Product Price Min. Order Purity Supply Ability Manufacturer
2021-10-27 Naproxen
22204-53-1
US $0.00 / KG 100g 98%+ 100kg WUHAN CIRCLE POWDER TECHNOLOGY CO.,LTD
2021-10-14 Naproxen
22204-53-1
US $96.00 / KG 25KG 99.99% 20 tons Hebei Dongdu Import and Export Co. LTD
2021-10-08 Naproxen
22204-53-1
US $100.00 / KG 1g 99% 10tons WUHAN CIRCLE POWDER TECHNOLOGY CO.,LTD

Naproxen Spectrum


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