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Substance Name: Artemisinin [INN]
RN: 63968-64-9
UNII: 9RMU91N5K2
InChIKey: BLUAFEHZUWYNDE-NNWCWBAJSA-N

Note

  • Antimalarial from Chinese medicinal herb Artemisia annua.

Molecular Formula

  • C15-H22-O5

Molecular Weight

  • 282.334
 

Classification Codes

  • Anti-Infective Agents
  • Drug / Therapeutic Agent
  • Natural Product
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Names and Synonyms

Name of Substance

  • Artemisinin [INN]
  • Artemisinine

Synonyms

  • (+)-Artemisinin
  • (3R,5aS,6R,8aS,9R,12S,12aR)-Octahydro-3,6,9-trimethyl-3,12-epoxy-12H-pyrano(4,3-j)-1,2-benzodioxepin-10(3H)-one
  • Arteannuin
  • Artemisia annua L., extract
  • Artemisine
  • Artemisinin
  • Artemisinina
  • Artemisinina [Spanish]
  • Artemisinine
  • Artemisinine [French]
  • Artemisininum
  • Artemisininum [Latin]
  • BRN 4194670
  • EC 700-290-5
  • Huanghuahaosu
  • NSC 369397
  • Octahydro-3,6,9-trimethyl-3,12-epoxy-12H-pyrano(4,3-j)-1,2-benzodioxepin-10(3H)-one
  • Qing Hau Sau
  • Qing Hau Sau [Chinese]
  • Qing Hau SU
  • Qinghaosu
  • Qinghaosu [Chinese]
  • Qinghosu
  • UNII-9RMU91N5K2

Systematic Names

  • (3R,5aS,6R,8aS,9R,12S,12aR)-3,6,9-Trimethyloctahydro-3,12-epoxypyrano(4,3-j)(1,2)benzodioxepin-10(3H)-one
  • (3R,5aS,6R,8aS,9R,12S,12aR)-Octahydro-3,6,9-trimethyl-3,12-epoxy-12H-pyrano(4,3-j)-1,2-benzodioxepin-10(3H)-one
  • 3,12-Epoxy-12H-pyranol(4,3-j)-1,2-benzodioxepin-10(3H)-one, octahydro-3,6,9-trimethyl-, (3-alpha,5a-beta,6-beta,8a-beta,9-alpha,12-beta,12aR*)-(+)-

Registry Numbers

CAS Registry Number

  • 63968-64-9

FDA UNII

  • 9RMU91N5K2

System Generated Number

  • 0063968649

Structure Descriptors

InChI

1S/C15H22O5/c1-8-4-5-11-9(2)12(16)17-13-15(11)10(8)6-7-14(3,18-13)19-20-15/h8-11,13H,4-7H2,1-3H3/t8-,9-,10+,11+,13-,14-,15-/m1/s1

InChIKey

BLUAFEHZUWYNDE-NNWCWBAJSA-N

Smiles

C1([C@@H]([C@@H]2CC[C@H]([C@@H]3CC[C@@]4(O[C@@H]([C@@]23OO4)O1)C)C)C)=O

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
dog LD intramuscular > 800mg/kg (800mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD Journal of Traditional Chinese Medicine Vol. 2, Pg. 31, 1982.
mouse LD unreported > 2gm/kg (2000mg/kg)   Antimicrobial Agents and Chemotherapy. Vol. 37, Pg. 1108, 1993.
mouse LD50 intramuscular 2800mg/kg (2800mg/kg)   Chinese Medical Journal Vol. 92, Pg. 811, 1979.
mouse LD50 intraperitoneal 1558mg/kg (1558mg/kg)   Chinese Medical Journal Vol. 92, Pg. 811, 1979.
mouse LD50 oral 4228mg/kg (4228mg/kg) BEHAVIORAL: ALTERED SLEEP TIME (INCLUDING CHANGE IN RIGHTING REFLEX)

BEHAVIORAL: ATAXIA

BEHAVIORAL: TREMOR
Journal of Traditional Chinese Medicine Vol. 2, Pg. 31, 1982.
rat LD50 intramuscular 2571mg/kg (2571mg/kg) BEHAVIORAL: ALTERED SLEEP TIME (INCLUDING CHANGE IN RIGHTING REFLEX)

BEHAVIORAL: ATAXIA

BEHAVIORAL: TREMOR
Journal of Traditional Chinese Medicine Vol. 2, Pg. 31, 1982.
rat LD50 oral 5576mg/kg (5576mg/kg) BEHAVIORAL: TREMOR

BEHAVIORAL: ALTERED SLEEP TIME (INCLUDING CHANGE IN RIGHTING REFLEX)

BEHAVIORAL: ATAXIA
Journal of Traditional Chinese Medicine Vol. 2, Pg. 31, 1982.

Physical Properties

Physical Property Value Units Temp (deg C) Source
log P (octanol-water) 2.9 (none)   EXP
Water Solubility 51.9 mg/L 25 EST
Vapor Pressure 2.18E-06 mm Hg 25 EST
Henry's Law Constant 4.92E-09 atm-m3/mole 25 EST
Atmospheric OH Rate Constant 4.33E-11 cm3/molecule-sec 25 EST

Physical property data is provided to ChemIDplus by SRC, Inc.