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
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.
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.
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.
Nebenwirkungen
Common side effects of Naproxen may include indigestion, heartburn, stomach pain, nausea, headache, dizziness, drowsiness, bruising, itching, rash, swelling, or ringing in the ears. Seek immediate medical attention if you have any of the following serious drug reactions. For example: shortness of breath, swelling or rapid weight gain, rash, signs of stomach bleeding (bloody or tarry stools, coughing up blood or vomit that looks like coffee grounds), liver problems (nausea, upper stomach pain, itching, feeling tired, flu-like symptoms, loss of appetite, dark urine, clay-coloured stools, jaundice), kidney problems (little or no urination, pain or difficulty in urinating, swelling of the feet or ankles, feeling tired or shortness of breath), low red blood cells (anaemia), etc. In addition, in rare cases, a severe allergic reaction to naproxen may occur. You may also suffer from stomach ulcers and other adverse reactions when taking it for a long time.
Naproxen Upstream-Materialien And Downstream Produkte
Upstream-Materialien
Downstream Produkte
