Artemether

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Structural formula
Structure of Artemether
General
Non-proprietary name Artemether
other names

(3 R , 5a S , 6 R , 8a S , 9 R , 10 S , 12 R , 12a R ) -Decahydro-10-methoxy-3,6,9-trimethyl-3,12-epoxy-12 H -pyrano [4,3- j ] -1,2-benzodioxepine ( IUPAC )

Molecular formula C 16 H 26 O 5
External identifiers / databases
CAS number 71963-77-4
EC number 663-549-0
ECHA InfoCard 100.189.847
PubChem 68911
ChemSpider 62138
DrugBank DB06697
Wikidata Q416199
Drug information
ATC code

P01 BE02 , P01 BE52

Drug class

Antiprotozoic

properties
Molar mass 298.37 g mol −1
Physical state

firmly

Melting point

86-88 ° C

safety instructions
Please note the exemption from the labeling requirement for drugs, medical devices, cosmetics, food and animal feed
GHS labeling of hazardous substances
07 - Warning

Caution

H and P phrases H: 302
P: no P-phrases
Toxicological data

263 mg kg −1 ( LD 50 ,  mouse ,  im )

As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Artemether is an from Artemisinin derived semi-synthetic drug for the treatment of by Plasmodium falciparum causing malaria . The active ingredient Artemether was included in 1997 by the World Health Organization (WHO) in the list of essential medicines of the World Health Organization .

Pharmacological properties

Artemether has a significantly improved bioavailability compared to artemisinin . Like all artemisinin derivatives, it acts via an endogenous peroxide group that presumably forms radicals that are toxic to the plasmodia in infected erythrocytes . The absorption of the lipid-soluble substance is facilitated in the case of oral administration by a meal that is as high in fat as possible. The relatively short half-life of around two hours is problematic. Artemether is metabolized in the liver by the enzyme cytochrome P450 3A4 .

use

The main focus for the application of Artemether is the treatment of the uncomplicated Malaria tropica , especially with Plasmodia, which are resistant to other drugs like chloroquine . The World Health Organization advises against using it as a single substance in order to reduce the risk of developing resistance to artemisinin derivatives. Artemether is therefore used exclusively as a combination preparation for the therapy of malaria.

Artemether is being used experimentally in cancer therapy.

Manufacturing

Annual mugwort ( Artemisia annua )

Artemether is produced by reacting dihydroartemisinin obtained from Artemisia annua with methanol in an acidic medium. Artemether is insoluble in water.

It is sold in Germany, Austria and Switzerland in combination with Lumefantrine under the trade name Riamet ® and worldwide under the trade name Coartem ® .

Finished medicinal products

  • in a fixed combination (Artemether 20.mg with Lumefantrine 120 mg) under the trademark Riamet ® ( inter alia in D , A , CH , GB , F , S , NL ) and under the trademark Coartem ® ( inter alia in USA , ZA )

Individual evidence

  1. ↑ a b The Merck Index. An Encyclopaedia of Chemicals, Drugs and Biologicals. 14th edition. Merck, Whitehouse Station NJ 2006, ISBN 0-911910-00-X , p. 133.
  2. ↑ a b Artemether data sheet at Sigma-Aldrich , accessed on May 9, 2017 ( PDF ).
  3. ↑ Artemether WHO Model Lists of Essential Medicines (PDF; 442 kB), accessed on August 13, 2012.
  4. ↑ WHO on artemisinin monopreparations .
  5. ↑ Narendra P. Singh, Vijay Kumar Panwar: Case report of a pituitary macroadenoma treated with artemether . (PDF) In: Integrative Cancer Therapies . Vol. 5, No. 4, December 2006, pp. 391-394. doi : 10.1177 / 1534735406295311 . PMID 17101767 .
  6. ↑ Zhi-Ping Wu, Cheng-Wei Gao, Yong-Gui Wu, Qi-Shun Zhu, Yan Chen, Xin Liu, Chuen Liu: Inhibitive effect of artemether on tumor growth and angiogenesis in the rat C6 orthotopic brain gliomas model . In: Integrative Cancer Therapies . Vol. 8, No. 1, March 2009, pp. 88-92. doi : 10.1177 / 1534735408330714 . PMID 19174507 .