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Naproxen Produkt Beschreibung

Naproxen Struktur
22204-53-1
CAS-Nr.
22204-53-1
Bezeichnung:
Naproxen
Englisch Name:
Naproxen
Synonyma:
axer;Bonyl;Xenar;Naxen;Naxyn;cg3117;Prexan;Proxen;Reuxen;Naixan
CBNumber:
CB8274937
Summenformel:
C14H14O3
Molgewicht:
230.26
MOL-Datei:
22204-53-1.mol

Naproxen Eigenschaften

Schmelzpunkt:
152-154 °C (lit.)
alpha 
D +66° (in chloroform)
Siedepunkt:
332.25°C (rough estimate)
Dichte
1.1450 (rough estimate)
Brechungsindex
67.5 ° (C=1, CHCl3)
Flammpunkt:
9℃
storage temp. 
2-8°C
Löslichkeit
Practically insoluble in water, soluble in ethanol (96 per cent) and in methanol.
Aggregatzustand
powder
pka
pKa 4.28± 0.02(H2O,t =25,I=0.01) (Uncertain)
Optische Aktivität
[α]25/D +66°, c = 1 in chloroform
Wasserlöslichkeit
Insoluble in water.
Merck 
14,6417
BRN 
3591067
CAS Datenbank
22204-53-1(CAS DataBase Reference)
NIST chemische Informationen
Naproxen(22204-53-1)
EPA chemische Informationen
2-Naphthaleneacetic acid, 6-methoxy-.alpha.-methyl-, (.alpha.S)- (22204-53-1)
Sicherheit
  • Risiko- und Sicherheitserklärung
  • Gefahreninformationscode (GHS)
Kennzeichnung gefährlicher Xn,T,F
R-Sätze: 22-39/23/24/25-23/24/25-11-36/37/38
S-Sätze: 36/37-45-16-7-26
RIDADR  UN 2811 6.1/PG 3
WGK Germany  3
RTECS-Nr. UF5275000
HazardClass  6.1(b)
PackingGroup  III
HS Code  29189900
Giftige Stoffe Daten 22204-53-1(Hazardous Substances Data)
Toxizität LD50 in mice (mg/kg): 435 i.v.; 1234 orally; in rats (mg/kg): 575 i.p.; 534 orally (Roszkowski)
Bildanzeige (GHS)
Alarmwort Achtung
Gefahrenhinweise
Code Gefahrenhinweise Gefahrenklasse Abteilung Alarmwort Symbol P-Code
H225 Flüssigkeit und Dampf leicht entzündbar. Entzündbare Flüssigkeiten Kategorie 2 Achtung P210,P233, P240, P241, P242, P243,P280, P303+ P361+P353, P370+P378,P403+P235, P501
H301 Giftig bei Verschlucken. Akute Toxizität oral Kategorie 3 Achtung P264, P270, P301+P310, P321, P330,P405, P501
H315 Verursacht Hautreizungen. Hautreizung Kategorie 2 Warnung P264, P280, P302+P352, P321,P332+P313, P362
H319 Verursacht schwere Augenreizung. Schwere Augenreizung Kategorie 2 Warnung P264, P280, P305+P351+P338,P337+P313P
H335 Kann die Atemwege reizen. Spezifische Zielorgan-Toxizität (einmalige Exposition) Kategorie 3 (Atemwegsreizung) Warnung
H361 Kann vermutlich die Fruchtbarkeit beeinträchtigen oder das Kind im Mutterleib schädigen. Reproduktionstoxizität Kategorie 2 Warnung P201, P202, P281, P308+P313, P405,P501
H370 Schädigt die Organe. Spezifische Zielorgan-Toxizität (einmalige Exposition) Kategorie 1 Achtung P260, P264, P270, P307+P311, P321,P405, P501
Sicherheit
P201 Vor Gebrauch besondere Anweisungen einholen.
P202 Vor Gebrauch alle Sicherheitshinweise lesen und verstehen.
P210 Von Hitze, heißen Oberflächen, Funken, offenen Flammen und anderen Zündquellenarten fernhalten. Nicht rauchen.
P260 Dampf/Aerosol/Nebel nicht einatmen.
P261 Einatmen von Staub vermeiden.
P264 Nach Gebrauch gründlich waschen.
P264 Nach Gebrauch gründlich waschen.
P270 Bei Gebrauch nicht essen, trinken oder rauchen.
P280 Schutzhandschuhe/Schutzkleidung/Augenschutz tragen.
P311 GIFTINFORMATIONSZENTRUM/Arzt anrufen.
P301+P310 BEI VERSCHLUCKEN: Sofort GIFTINFORMATIONSZENTRUM/Arzt/... (geeignete Stelle für medizinische Notfallversorgung vom Hersteller/Lieferanten anzugeben) anrufen.
P305+P351+P338 BEI KONTAKT MIT DEN AUGEN: Einige Minuten lang behutsam mit Wasser spülen. Eventuell vorhandene Kontaktlinsen nach Möglichkeit entfernen. Weiter spülen.

Naproxen Chemische Eigenschaften,Einsatz,Produktion Methoden

R-Sätze Betriebsanweisung:

R22:Gesundheitsschädlich beim Verschlucken.

S-Sätze Betriebsanweisung:

S36/37:Bei der Arbeit geeignete Schutzhandschuhe und Schutzkleidung tragen.

Beschreibung

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.

Chemische Eigenschaften

white to light yellow crystal powde

Originator

Naprosyn,Syntex,UK,1973

Verwenden

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.

Verwenden

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

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.

Trademarks

Naprosyn (Roche).

Therapeutic Function

Antiinflammatory

Synthesis Reference(s)

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

Allgemeine Beschreibung

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).

Pharmakokinetik

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 Upstream-Materialien And Downstream Produkte

Upstream-Materialien

Downstream Produkte


Naproxen Anbieter Lieferant Produzent Hersteller Vertrieb Händler.

Global( 470)Lieferanten
Firmenname Telefon Fax E-Mail Land Produktkatalog Edge Rate
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
+8618371201331
020-81716319 sales@pipitech.com;87478684@qq.com China 3245 55
Hefei TNJ Chemical Industry Co.,Ltd.
+86-0551-65418679
86-0551-65418697 info@tnjchem.com China 3000 55
Hebei Minshang Biotechnology Co., Ltd
+86-13582176207 +86-13582176207
cathy@hbminshang.cn CHINA 304 58
Shanxi Naipu Import and Export Co.,Ltd
+8613734021967
kaia@neputrading.com CHINA 1009 58
career henan chemical co
+86-371-86658258
sales@coreychem.com CHINA 29954 58
HEBEI YINGONG NEW MATERIAL TECHNOLOGY CO.,LTD
+8619933070948
claire@hbyingong.com China 443 58
SHANDONG ZHI SHANG CHEMICAL CO.LTD
+86 18953170293
+86 0531-67809011 sales@sdzschem.com CHINA 2941 58

22204-53-1(Naproxen)Verwandte Suche:


  • ()-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
  • (+)-2-naphthaleneaceticaci
  • (+)-6-Methoxy-alpha-methyl-2-napthaleneacetic acid
  • (s)-2-naphthaleneaceticaci
  • 2-Naphthaleneacetic acid, 6-methoxy-alpha-methyl-, (+)-
  • 2-Naphthaleneacetic acid, 6-methoxy-alpha-methyl-, (S)-
  • 6-Methoxy-methyl-2-naphthaleneaceticacid
  • axer
  • Bonyl
  • calosen
  • CG 3117
  • cg3117
  • Prexan
  • primeral
  • Propionic acid, 2-(6-methoxy-2-naphthyl)-, (+)-
  • Proxen
  • Proxine
  • Reuxen
  • RS-3540
  • Veradol
  • Xenar
  • (S)-6-Methoxy-α-methyl-2-naphthaleneacetic Acid
  • (dl)-propionic acid
  • NAPROXEN FREE BASE
  • Naproxen (base and/or unspecified salts)
  • (+)-2-(6-Methoxy-2-naphthyl)-propionic acid
  • (S)-(+)-2-(6-Methoxy-2-naphthyl)propionic acid, (S)-(+)-6-Methoxy-α-methyl-2-naphthaleneacetic acid
  • (S)-(+)-2-(6-Methoxy-2-naphthyl)propionic acid, Naproxen, (S)-(+)-6-Methoxy-α-methyl-2-naphthaleneacetic acid
  • (1)-2-(6-Methoxy-2-naphthyl)propionic acid
  • Naphthaleneacetic acid, 6-methoxy-.alpha.-methyl-, (S)-
  • (+)-(S)-2-(6-METHOXYNAPTHALENE-2-YL)PROPIONIC ACID
  • (S)-(+)-6-Methoxy-α-methyl-2-naphthaleneacetic acid,(S)-(+)-2-(6-Methoxy-2-naphthyl)propionic acid, Naproxen
  • Naproxen (200 mg)
  • (2S)-2-(6-Methoxynaphth-2-yl)propanoic acid
  • Naproxen (INN)
  • Aproxen
  • po-Naproxen
  • Xenar-CR
  • Naproxen API
  • (S)-(+)-6-Methoxy-alpha-methyl-2-naphthaleneacetic Acid Naproxen
  • (S)-(+)-6-Methoxy-α-Methyl-2-naphthaleneacetic
  • 2-Naphthaleneacetic acid, 6- methoxy-α-methyl,(S)-
  • (2S)-2-(6-Methoxynaphth-2-yl)propanoic acid 98+%
  • d-2-(6’-methoxy-2’-naphthyl)-propionsaeure
  • d-2-(6'-Methoxy-2'-naphthyl)-propionsaeure
  • Diocodal
  • (+)-6-Methoxy-alpha-methyl-2-naphthaleneacetic acid~Naproxen
  • NAPROXEN BASE
  • NAPROXEN USP /BP2000
  • Naproxen USP,BP.CP
  • (S)-6-METHOXY-A-METHYL-2-*NAPHTHALENEACE TIC ACID FR
  • NAPROXEN, FREE ACID, USP
  • NAPROXEN VETRANAL, 250 MG
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