Naproxen

Structural formula
General
Non-proprietary name	Naproxen
other names	( S ) -2- (6-methoxy-2-naphthyl) propionic acid NAPROXEN ( INCI )
Molecular formula	C 14 H 14 O 3 (naproxen) C 14 H 13 NaO 3 (naproxen sodium salt )
Brief description	white solid
External identifiers / databases
CAS number 22204-53-1 (naproxen) 26159-34-2 (naproxen sodium salt ) EC number 244-838-7 ECHA InfoCard 100.040.747 PubChem 156391 ChemSpider 137720 DrugBank DB00788 Wikidata Q1215575
Drug information
ATC code	G02 CC02 , M01 AE02 , M02 AA12
Drug class	NSAIDs
Mechanism of action	COX inhibitors
properties
Molar mass	230.26 g mol −1
Melting point	152 ° C (naproxen) 244–246 ° C (naproxen sodium salt)
solubility	47 ± 7 mg l −1 (37 ° C, pH 1.2) 153 ± 1 mg l −1 (37 ° C, pH 4.5)
safety instructions
Please note the exemption from the labeling requirement for drugs, medical devices, cosmetics, food and animal feed GHS labeling of hazardous substances danger H and P phrases H: 301 P: 301 + 310
Toxicological data	248 mg kg −1 ( LD 50 ,  rat ,  oral ) 1234 mg kg −1 ( LD 50 ,  mouse ,  oral ) 435 mg kg −1 ( LD 50 ,  mouse ,  iv )
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Naproxen is a drug that has analgesic, antipyretic and anti-inflammatory effects. Naproxen is chiral , only the ( S ) enantiomer is used as a medicinal substance.

history

Naproxen was patented in 1968 by the Mexican company Syntex and introduced in 1973; Naproxen sodium by Hoffmann-La Roche 1980. In March 2002 it was released from the prescription requirement in Germany for single doses below 250 mg.

Manufacturing

Several processes are described for the chemical synthesis of naproxen, including the resolution of ( RS ) -2- (6-methoxy-2-naphthyl) propionic acid and an asymmetric synthesis.

Stereoisomerism

Naproxen is used as a medicinal substance exclusively as an ( S ) -enantiomer. Only this is effective as a non-steroidal anti - inflammatory drug .

Effect and mode of action

Naproxen inhibits the formation of prostaglandins not only by inhibiting cyclooxygenase , but also the hormone-sensitive lipase . Prostaglandins are messenger substances that irritate the nerve endings, which then send pain signals to the brain. Since this process is inhibited, the pain signal no longer reaches the brain, and this is how the analgesic effect occurs. Chemically, it is an aryl propionate with a very long plasma half-life for nonsteroidal anti-inflammatory drugs ( NSAIDs ) .

• Plasma half-life: 12-15 hours
• Metabolism: hepatic
• Elimination: renal

Applications

Naproxen is women against menstrual cramps or after inserting a spiral administered. Other areas of application are rheumatism and swellings and inflammations of all kinds (e.g. after operations), but also as pain relievers for smaller operations such as tooth extractions . Naproxen is common as a general pain reliever in the United States.

Side effects

Side effects can occur. The following are the most important:

• Liver and kidney disorders
• Stomach / intestinal ulcers
• Nausea , vomiting
• Skin irritation (general allergic reactions such as urticaria )
• Swelling of the face
• asthma
• diarrhea
• Bleeding from the stomach lining (can be fatal)
• Central nervous disorders dizziness , fatigue , headache , visual disturbances (flashes in front of the eye), dizziness
• anaphylactic shock as a result of an allergic reaction
• Increased risk of stroke

Naproxen has the lowest risk of heart attacks and strokes compared to other NSAIDs. Children and adolescents under the age of 12 should not take naproxen. Older people should adhere to low doses. In addition, enough water should be drunk with it.

Interactions

In the case of drugs with a similar effect, the risk of the side effects listed above is significantly increased. If you take anticoagulant drugs ( Marcumar , Clopidogrel ) at the same time , there is an increased risk of bleeding. Naproxen can increase or decrease the effects of other drugs.

pregnancy and breast feeding period

The drug must not be used in certain phases of pregnancy. The drug should not be used during breastfeeding unless the attending physician deems it urgent.

Trade names

Monopreparations : Alacetan (D), Aleve (D, A, CH, USA), Analgesin Forte (Hungary), Apranax (CH), Dolormin for women (D), Dolormin GS (D), Dysmenalgit (D), Miranax (A ), Mobilat Schmerztabletten (D), Naprobene (A), Naproxen (D), Proxen (D, A, CH), numerous generic drugs (D, A, CH)

Combination preparations : Vimovo (D, A, CH): In addition to naproxen, the preparation contains the proton pump inhibitor esomeprazole .

Individual evidence

1. ↑ Entry on NAPROXEN in the CosIng database of the EU Commission, accessed on June 27, 2020.
2. ↑ ^{a b c d e} data sheet Naproxene at Sigma-Aldrich , accessed on May 12, 2017 ( PDF ).
3. ^ The Merck Index . An Encyclopaedia of Chemicals, Drugs and Biologicals . 14th edition, 2006, ISBN 978-0-911910-00-1 , p. 1109.
4. ↑ ^{a b} K. Tsinman, A. Avdeef, O. Tsinman, D. Voloboy: Powder Dissolution Method for Estimating Rotating Disk Intrinsic Dissolution Rates of Low Solubility Drugs in Pharm Res 26 (2009) 2093-2100, doi: 10.1007 / s11095- 009-9921-3 .
5. ^ ^{A b c} Römpp Lexikon Chemie, Georg Thieme Verlag, Stuttgart - New York, 10th edition, 1998, p. 2813 f.
6. ^ Govi-Verlag Pharmazeutischer Verlag: Pharmazeutische Zeitung online: Naproxen preparations in the test. In: pharmische-zeitung.de. December 20, 2004, accessed June 6, 2015 . 
7. ^ C. Giordano M. Villa, S. Panossian Panossian: Naproxen: Industrial Asymmetric Synthesis. In: AN Collins, GN Sheldrake, J. Crosby (Eds.): Chirality in Industry Wiley, 1992, ISBN 0-471-93595-6 , pp. 303-312.
8. ^ Carsten Schmuck, Bernd Engels, Tanja Schirmeister, Reinhold Fink: Chemistry for Medicine , Pearson Studies, ISBN 978-3-8273-7286-4 , p. 413.
9. ↑ MO Taha, LA Dahabiyeh, Y. Bustanji, H. Zalloum, S. Saleh: Combining ligand-based pharmacophore modeling, quantitative structure-activity relationship analysis and in silico screening for the discovery of new potent hormone sensitive lipase inhibitor. In: Journal of medicinal chemistry. Volume 51, Number 20, October 2008, pp. 6478-6494, doi: 10.1021 / jm800718k , PMID 18808096 .
10. ^ Entry on naproxen in the DrugBank of the University of Alberta , accessed June 6, 2015.
11. ↑ MD Haag, MJ Bos, A. Hofman, PJ Koudstaal, MM Breteler, BH Stricker: Cyclooxygenase selectivity of nonsteroidal anti-inflammatory drugs and risk of stroke. In: Archives of internal medicine . Volume 168, Number 11, June 2008, pp. 1219-1224, doi: 10.1001 / archinte.168.11.1219 , PMID 18541831 .
12. ↑ NAPROXEN NEW STANDARD - drug telegram. In: arznei-telegramm.de. January 12, 2007, accessed November 13, 2016 . 
13. ↑ patienteninfo-service.de: Vimovo 500 mg / 20 mg tablets with modified release of active ingredients (accessed on March 7, 2013).

This article is about a health issue. It is not used for self-diagnosis and does not replace a diagnosis by a doctor. Please note the information on health issues !