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  1. General Info
  2. Source Info
  3. Effects Info
  4. Reference
Phytochemical Details
01. General Information
Name Dihydroartemisinin
PubChem CID 3000518
Molecular Weight 284.35g/mol
Synonyms

(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-ol, 3alpha-hydroxydeoxydihydroartemisinin, 8alpha-hydroxydeoxyartemisinin, 9alpha-hydroxydeoxyartemisinin, Alaxin, artemisinin, dihydro-, artenimol, Cotecxin, Cotexin, dihydroartemisinin, dihydroartemisinine, dihydroqinghaosu, dihydroquinghaosu, dihydroquinghaosu, (3R-(3alpha,5abeta,6beta,8abeta,9alpha,10alpha,12alpha,12aR*))-isomer, dihydroquinghaosu, (3R-(3alpha,5abeta,6beta,8abeta,9alpha,10beta,12alpha,12aR*))-isomer, quinghaosu, dihydro-, Salaxin, Santecxin
Formula C₁₅H₂₄O₅
SMILES CC1CCC2C(C(OC3C24C1CCC(O3)(OO4)C)O)C
InChI 1S/C15H24O5/c1-8-4-5-11-9(2)12(16)17-13-15(11)10(8)6-7-14(3,18-13)19-20-15/h8-13,16H,4-7H2,1-3H3/t8-,9-,10+,11+,12+,13-,14-,15-/m1/s1
InChIKey BJDCWCLMFKKGEE-ISOSDAIHSA-N
CAS Number 71939-50-9
ChEBI ID CHEBI:135921
Herb ID HBIN023813
Drug Bank ID DB11638
KEGG ID D07362
Toxicity Organism Test Type Route(Dose)
rat LD50 intraperitoneal(165 mg/kg)
mouse LD50 intraperitoneal(254 mg/kg)
rat LD50 oral(322 mg/kg)
Structure 2D-img
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2D MOL 3D MOL
02. Source Information of Phytochemical
Artemisia annua Cold
Chineses Pinyin QingHao
Use Part Whole Grass
Habitat China
Flavor Bitter, Pungent
Meridian Tropism Liver, Gallbladder
Species
>Kingdom: Viridiplantae
　-->Phylum: Streptophyta
　　-->Class: Equisetopsida
　　　-->Order: Asterales
　　　　-->Family: Asteraceae
　　　　　-->Genus: Artemisia
　　　　　　-->Species: Artemisia annua
03. Combinatorial Therapeutic Effect(s)
Synergistic Effect
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Drug(s) whose efficacy can be enhanced by this phytochemical
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Combination Pair ID: 165
Ref_2
Pair Name Dihydroartemisinin, Sorafenib
Partner Name Sorafenib
Disease Info [ICD-11: 2C12] Hepatocellular carcinoma Investigative
Biological Phenomena Induction-->Ferroptosis
Gene Regulation Down-regulation Expression GCLC hsa2729
Down-regulation Expression GPX4 hsa2879
Down-regulation Expression GSS hsa2937
Down-regulation Expression HMOX1 hsa3162
Up-regulation Expression ROS1 hsa6098
Down-regulation Expression SLC7A11 hsa23657
Up-regulation Expression SMG1 hsa23049
In Vitro Model Hep-G2 Hepatoblastoma Homo sapiens (Human) CVCL_0027
SW480 Colon adenocarcinoma Homo sapiens (Human) CVCL_0546
In Vivo Model 5×10⁶ of HepG2 cells were injected into the right flank of 6-week-old athymic female mice (Balb/c nude mice).
Result DHA and Sora had the same mechanism, and the combined application of them could have a synergistic anti-tumor effect by inducing ferroptosis and inhibiting energy metabolism in HepG2 cells.
Combination Pair ID: 166
Ref_3
Pair Name Dihydroartemisinin, Oxaliplatin
Partner Name Oxaliplatin
Disease Info [ICD-11: 2B91] Colorectal cancer Investigative
Biological Phenomena Induction-->Oxidative Stress
Gene Regulation Up-regulation Expression ATF4 hsa468
Down-regulation Expression BCL2 hsa596
Up-regulation Cleavage CASP3 hsa836
Up-regulation Phosphorylation EIF2S1 hsa1965
Up-regulation Expression MAPK14 hsa1432
Up-regulation Expression MAPK8 hsa5599
Down-regulation Expression PRDX2 hsa7001
Up-regulation Expression ROS1 hsa6098
Down-regulation Expression STAT3 hsa6774
In Vitro Model HCT 116 Colon carcinoma Homo sapiens (Human) CVCL_0291
RKO Colon carcinoma Homo sapiens (Human) CVCL_0504
In Vivo Model The cells were subcutaneously injected into the flanks of nude mice at a concentration of 5×10⁶ cells in 100 μl of PBS/Matrigel mixture (1: 1).
Result We demonstrated an improved therapeutic strategy for CRC patients by combining DHA and oxaliplatin treatments.
Combination Pair ID: 167
Ref_4
Pair Name Dihydroartemisinin, Gefitinib
Partner Name Gefitinib
Disease Info [ICD-11: 2C25] Lung cancer Investigative
Biological Phenomena Induction-->Ferroptosis
Gene Regulation Up-regulation Expression ROS1 hsa6098
In Vitro Model A-549 Lung adenocarcinoma Homo sapiens (Human) CVCL_0023
Result Dihydroartemisinin enhances gefitinib cytotoxicity against lung adenocarcinoma cells by inducing ROS-dependent apoptosis and ferroptosis
Combination Pair ID: 673
Ref_5
Pair Name Dihydroartemisinin, Doxorubicin
Partner Name Doxorubicin
Disease Info [ICD-11: 2C60] Breast cancer Investigative
Biological Phenomena Induction-->Apoptosis
Gene Regulation Up-regulation Cleavage CASP7 hsa840
Up-regulation Cleavage CASP9 hsa842
Up-regulation Cleavage PARP1 hsa142
In Vitro Model MCF-7 Invasive breast carcinoma of no special type Homo sapiens (Human) CVCL_0031
MDA-MB-231 Breast adenocarcinoma Homo sapiens (Human) CVCL_0062
T-47D Invasive breast carcinoma of no special type Homo sapiens (Human) CVCL_0553
Result This study presented a new opportunity to enhance the effectiveness of future treatment regimens of breast cancer using DOX.
Combination Pair ID: 1001
Ref_6
Pair Name Dihydroartemisinin, Doxorubicin
Partner Name Doxorubicin
Disease Info [ICD-11: 2A81] Primary effusion lymphoma Investigative
Biological Phenomena Induction-->Apoptosis
Gene Regulation Up-regulation Cleavage CASP3 hsa836
Up-regulation Cleavage CASP8 hsa841
Up-regulation Cleavage CASP9 hsa842
In Vivo Model An inhibitory effect on PEL growth was evaluated in a PEL-xenograft mouse model，DHA treatment also demonstrated an inhibitory effect on PEL cell growth in an in-vivo xenograft model.
Result DHA is a potentially effective candidate drug for PEL treatment.
Combination Pair ID: 1002
Ref_7
Pair Name Dihydroartemisinin, Capecitabine
Partner Name Capecitabine
Disease Info [ICD-11: 2B91] Colorectal cancer Investigative
Gene Regulation Down-regulation Expression CTNNB1 hsa1499
Down-regulation Expression GSK3B hsa2932
Down-regulation Expression MKI67 hsa4288
Down-regulation Expression MMP9 hsa4318
Down-regulation Expression PECAM1 hsa5175
Down-regulation Expression TCF7 hsa6932
In Vitro Model HCT 116 Colon carcinoma Homo sapiens (Human) CVCL_0291
DLD-1 Colon adenocarcinoma Homo sapiens (Human) CVCL_0248
HCT 15 Colon adenocarcinoma Homo sapiens (Human) CVCL_0292
SW620 Colon adenocarcinoma Homo sapiens (Human) CVCL_0547
CT26 Mouse colon adenocarcinoma Mus musculus (Mouse) CVCL_7254
In Vivo Model CT26 cells (8×10⁵) were injected into the tail vein of BALB/c mice to establish the lung metastasis model. HCT116 cells (2×106) were injected into the tail vein of BALB/c nude mice to establish the peritoneal metastasis model.
Result DHA in combination with Cap could be a novel therapeutic strategy for CRC with improved efficacy and reduced side effects.
Drug(s) whose resistance can be reversed by this phytochemical
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Combination Pair ID: 164
Ref_8
Pair Name Dihydroartemisinin, Osimertinib
Partner Name Osimertinib
Disease Info [ICD-11: 2C25] Lung cancer Investigative
Biological Phenomena Induction-->ROS generation
Gene Regulation Down-regulation Expression HMOX1 hsa3162
Up-regulation Expression ROS1 hsa6098
In Vitro Model PC-9 Lung adenocarcinoma Homo sapiens (Human) CVCL_B260
PC-9/GR4 Lung adenocarcinoma Homo sapiens (Human) CVCL_DH34
In Vivo Model PC-9 or PC9-GR4-AZD1 cells (4×10⁶ cells resuspended in 200 μl of 1:1 mixture of PBS / Corning Matrigel Basement Membrane Matrix) were injected subcutaneously into the right flank of mice.
Result The results suggest that DHA is able to reverse the resistance to osimertinib in EGFR-mutant NSCLC by elevating ROS level and impair heme metabolism.
Drug(s) whose toxicity can be decreased by this phytochemical
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Combination Pair ID: 163
Ref_1
Pair Name Dihydroartemisinin, Cisplatin
Partner Name Cisplatin
Disease Info [ICD-11: 2C10] Pancreatic cancer Investigative
Biological Phenomena Induction-->Ferroptosis
Gene Regulation Up-regulation Expression FTH1 hsa2495
In Vitro Model PANC-1 Pancreatic ductal adenocarcinoma Homo sapiens (Human) CVCL_0480
SW1990 Pancreatic adenocarcinoma Homo sapiens (Human) CVCL_1723
In Vivo Model All animals were injected subcutaneously with 2×10⁶ PANC-1 cells into the right dorsal flank.
Result DHA exhibits synergistic therapeutic efficacy with cisplatin to induce ferroptosis in pancreatic ductal adenocarcinoma via modulation of iron metabolism
04. Reference
No. Title Href
1 DHA exhibits synergistic therapeutic efficacy with cisplatin to induce ferroptosis in pancreatic ductal adenocarcinoma via modulation of iron metabolism. Cell Death Dis. 2021 Jul 15;12(7):705. doi: 10.1038/s41419-021-03996-y. Click
2 Dihydroartemisinin enhances the inhibitory effect of sorafenib on HepG2 cells by inducing ferroptosis and inhibiting energy metabolism. J Pharmacol Sci. 2022 Jan;148(1):73-85. doi: 10.1016/j.jphs.2021.09.008. Click
3 Dihydroartemisinin enhances the anti-tumor activity of oxaliplatin in colorectal cancer cells by altering PRDX2-reactive oxygen species-mediated multiple signaling pathways. Phytomedicine. 2022 Apr;98:153932. doi: 10.1016/j.phymed.2022.153932. Click
4 Dihydroartemisinin enhances gefitinib cytotoxicity against lung adenocarcinoma cells by inducing ROS-dependent apoptosis and ferroptosis. Kaohsiung J Med Sci. 2023 Jul;39(7):699-709. doi: 10.1002/kjm2.12684. Click
5 Synergistic anti-cancer activity of the combination of dihydroartemisinin and doxorubicin in breast cancer cells. Pharmacol Rep. 2013;65(2):453-9. doi: 10.1016/s1734-1140(13)71021-1. Click
6 Dihydroartemisinin Induced Apoptosis and Synergized With Chemotherapy in Pleural Effusion Lymphoma Cells. Anticancer Res. 2023 Mar;43(3):1139-1148. doi: 10.21873/anticanres.16259. Click
7 Dihydroartemisinin inhibits the development of colorectal cancer by GSK-3β/TCF7/MMP9 pathway and synergies with capecitabine. Cancer Lett. 2024 Feb 1;582:216596. doi: 10.1016/j.canlet.2023.216596. Click
8 Dihydroartemisinin overcomes the resistance to osimertinib in EGFR-mutant non-small-cell lung cancer. Pharmacol Res. 2021 Aug;170:105701. doi: 10.1016/j.phrs.2021.105701. Click
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