Artemisinin
[CAS# 63968-64-9]

Identification

• Classification: API >> Antiparasitic drug >> Antimalarial
• Name: Artemisinin
• Synonyms: (+)-Arteannuin; Qinghaosu; [3R-(3R,5aS,6S,8aS,9R,10R,12S,12aR**)]-Decahydro-3,6,9-trimethyl-3,12-epoxy-12H-pyrano[4,3-j]-1,2-benzodioxepin-10-one
• Molecular Formula: C₁₅H₂₂O₅
• Molecular Weight: 282.33
• CAS Registry Number: 63968-64-9
• EC Number: 700-290-5
• SMILES: C[C@@H]1CC[C@H]2[C@H](C(=O)O[C@H]3[C@@]24[C@H]1CC[C@](O3)(OO4)C)C

Properties

• Density: 1.2±0.1 g/cm³ Calc.^*
• Melting point: 156 - 157 ºC (Expl.)
• Boiling point: 389.9±42.0 ºC 760 mmHg (Calc.)^*
• Flash point: 172.0±27.9 ºC (Calc.)^*
• Solubility: DMSO: 57 mg/mL, water: 10 mM (Expl.)
• Index of refraction: 1.533 (Calc.)^*
• Alpha: 76 º (c=0.5, MeOH) (Expl.)

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software.

Safety Data

• Hazard Symbols: GHS02;GHS09 Danger
• Hazard Statements: H242-H400-H410
• Precautionary Statements: P210-P234-P235-P240-P273-P280-P370+P378-P391-P403-P410-P411-P420-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Chronic hazardous to the aquatic environment	Aquatic Chronic	1	H410
Organic peroxides	Org. Perox.	E	H242
Acute hazardous to the aquatic environment	Aquatic Acute	1	H400
Eye irritation	Eye Irrit.	2A	H319
Organic peroxides	Org. Perox.	D	H242
Specific target organ toxicity - single exposure	STOT SE	3	H335
Skin irritation	Skin Irrit.	2	H315

Discovory and Applicatios

Artemisinin is a sesquiterpene lactone with a unique endoperoxide bridge, naturally occurring in the plant Artemisia annua, commonly known as sweet wormwood. Its discovery was the result of systematic studies of traditional Chinese medicine in the 1970s, aimed at identifying compounds effective against malaria. Tu Youyou and her colleagues successfully isolated artemisinin from the plant and demonstrated its potent antimalarial activity, leading to a paradigm shift in malaria treatment and earning Tu Youyou the Nobel Prize in Physiology or Medicine in 2015.

The structure of artemisinin, characterized by a peroxide linkage within a sesquiterpene lactone skeleton, was elucidated using modern spectroscopic methods. This structural feature is critical to its antimalarial activity, as it allows the generation of reactive oxygen species in the presence of ferrous ions found in the malaria parasite, leading to parasite death. The discovery of artemisinin and its derivatives, including artesunate, artemether, and dihydroartemisinin, provided a new class of antimalarial drugs with rapid action against *Plasmodium* species, including strains resistant to previous treatments.

Artemisinin and its derivatives are widely used in artemisinin-based combination therapies (ACTs), which are now the standard treatment for uncomplicated malaria. ACTs combine artemisinin derivatives with partner drugs, enhancing efficacy and reducing the risk of resistance development. The rapid parasite clearance and potent activity of artemisinin make it especially valuable in regions with high malaria burden and drug-resistant *Plasmodium falciparum*.

Beyond antimalarial activity, artemisinin has been investigated for additional pharmacological effects. Studies indicate potential anticancer activity, with in vitro and in vivo experiments showing that artemisinin can induce apoptosis and inhibit proliferation in various cancer cell lines. This effect is believed to be mediated through the generation of reactive oxygen species and interference with cellular signaling pathways. Artemisinin has also demonstrated anti-inflammatory, antiviral, and immunomodulatory properties, suggesting broader therapeutic applications, although these are still under investigation and not yet widely applied clinically.

The pharmacokinetics of artemisinin are characterized by rapid absorption and metabolism, necessitating the use of combination therapy to ensure sustained antimalarial efficacy. Formulation strategies, including oral, intravenous, and intramuscular preparations, have been developed to optimize bioavailability and therapeutic outcomes.

Historically, the discovery of artemisinin exemplifies the successful integration of traditional medicine with modern scientific research. The identification of its unique chemical structure and pharmacological activity has had a transformative impact on global health, substantially reducing malaria morbidity and mortality. Research continues to explore novel derivatives and improved formulations to enhance efficacy, stability, and accessibility, especially in endemic regions.

Overall, artemisinin is a sesquiterpene lactone with a distinctive endoperoxide bridge, discovered from *Artemisia annua*, and is primarily used as a potent antimalarial agent. Its development has revolutionized malaria treatment, with artemisinin-based combination therapies providing rapid and effective parasite clearance. Emerging research on its anticancer, anti-inflammatory, and antiviral properties further underscores its potential as a versatile bioactive compound.

References

2007. Malaria-Infected Mice Are Cured by a Single Dose of Novel Artemisinin Derivatives. Journal of Medicinal Chemistry, 50(8).
DOI: 10.1021/jm070149m

2005. Synthesis and Cytotoxicity Studies of Artemisinin Derivatives Containing Lipophilic Alkyl Carbon Chains. Organic Letters, 7(7).
DOI: 10.1021/ol050230o

2003. Artemisinin, a Novel Antimalarial Drug: Biochemical and Molecular Approaches for Enhanced Production. Planta Medica, 69(4).
DOI: 10.1055/s-2003-38871