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artesunate

Structure via PubChem · Public domain (PubChem)

EntityQ707939· pop 22· linked from 96 articles

artesunate

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Also known as Arsumax, artesunato, artesunatum, artesunic acid, AS, butanedioic acid, 1-[(3R,5aS,6R,8aS,9R,10S,12R,12aR)-decahydro-3,6,9-trimethyl-3,12-epoxy-12H-pyrano[4,3-j]-1,2-benzodioxepin-10-yl] ester, dihydroqinghasu hemsuccinate

Artesunate is a medication used to treat malaria. The intravenous form is preferred to quinine for severe malaria. Often it is used as part of combination therapy, such as artesunate plus mefloquine. It is not used for the prevention of malaria. Artesunate can be given by injection into a vein, injection into a muscle, by mouth, and by rectum.

Key facts

Drug.image
Artesunate.svg
Drug.Verifiedfields
changed
Drug.Watchedfields
changed
Drug.verifiedrevid
457818909
Drug.image_class
skin-invert-image
Drug.image2
Artesunate ball-and-stick model from xtal 2002.png
Drug.image_class2
bg-transparent
Drug.pronounce
ahr-tez′ŭ-nāt
Drug.tradename
many
Drug.DailyMedID
Artesunate
Drug.routes_of_administration
By mouth, intravenous, intramuscular
Drug.class
Artemisinin
Drug.ATC_prefix
P01
Drug.ATC_suffix
BE03
Drug.legal_CA
Rx-only
Drug.legal_US
Rx-only
Drug.legal_EU
Rx-only
Drug.index2_label
as salt

via Wikipedia infobox

Chemical data

Formula
C19H28O8
Molecular weight
384.4 g/mol
IUPAC name
4-oxo-4-[[(1R,4S,5R,8S,9R,10S,12R,13R)-1,5,9-trimethyl-11,14,15,16-tetraoxatetracyclo[10.3.1.04,13.08,13]hexadecan-10-yl]oxy]butanoic acid
SMILES
C[C@@H]1CC[C@H]2[C@H]([C@@H](O[C@H]3[C@@]24[C@H]1CC[C@](O3)(OO4)C)OC(=O)CCC(=O)O)C
InChIKey
FIHJKUPKCHIPAT-AHIGJZGOSA-N
XLogP
2.5
Polar surface area
101 Ų
H-bond donors
1
H-bond acceptors
8
Formal charge
0

via PubChem

~10 min read

Encyclopedic overview

12 sections
Contents
  • Medical uses
  • Pregnancy
  • Children
  • Adverse effects
  • Contraindications
  • Mechanisms of action
  • Pharmacokinetics
  • Chemical synthesis
  • Research
  • History
  • References
  • External links

Artesunate is a medication used to treat malaria. The intravenous form is preferred to quinine for severe malaria. Often it is used as part of combination therapy, such as artesunate plus mefloquine. It is not used for the prevention of malaria. Artesunate can be given by injection into a vein, injection into a muscle, by mouth, and by rectum.

The most common side effects include kidney failure requiring dialysis, hemoglobinuria (the presence of hemoglobin in urine) and jaundice.

Excerpted from Wikipedia’s “artesunate” article, available under the CC BY-SA 4.0 licence.