Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C28H37NO9 |
Molecular Weight | 531.5947 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 4 / 4 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
[H][C@@]12[C@H](OC(=O)[C@@](O)(CCC(C)(C)O)CC(=O)OC)C(OC)=C[C@@]13CCCN3CCC4=C2C=C5OCOC5=C4
InChI
InChIKey=HAVJATCHLFRDHY-KSZYUSJVSA-N
InChI=1S/C28H37NO9/c1-26(2,32)8-9-28(33,15-22(30)35-4)25(31)38-24-21(34-3)14-27-7-5-10-29(27)11-6-17-12-19-20(37-16-36-19)13-18(17)23(24)27/h12-14,23-24,32-33H,5-11,15-16H2,1-4H3/t23-,24-,27+,28-/m1/s1
Molecular Formula | C28H37NO9 |
Molecular Weight | 531.5947 |
Charge | 0 |
Count |
|
Stereochemistry | ABSOLUTE |
Additional Stereochemistry | No |
Defined Stereocenters | 4 / 4 |
E/Z Centers | 0 |
Optical Activity | UNSPECIFIED |
Harringtonine is a cephalotaxine alkaloid originally found in Cephalotaxus hainanensis Li; it exhibits antiviral and anticancer activities. Harringtonine immobilizes initiated ribosomes, inhibiting protein translation by binding the A site of the 60 S ribosomal subunit and preventing aminoacyl-tRNA binding. Harringtonine inhibits chikungunya virus infection, suppressing replication, RNA production, and viral protein expression. Alone, harringtonine downregulates production of Mcl-1, increases cleavage of PARP, and inhibits cell growth in acute promyelocytic leukemia (APL) cells. Additionally, this compound improves the efficacy of co-administered chemotherapeutic compounds, further inhibiting proliferation and inducing apoptosis in leukemia cells. Harringtonine and homoharringtonine isolated from Cephalotaxus hainanesis have exhibited significant antileukemia activity and are widely used in clinics in China.
Originator
Sources: https://www.ncbi.nlm.nih.gov/pubmed/24387717
Curator's Comment: Paudler et al. isolated harringtonine and cephalotaxine from Cephalotaxus harringtonia in 1963 for the first time.
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: Chikungunya virus Sources: https://www.ncbi.nlm.nih.gov/pubmed/23275491 |
0.24 µM [EC50] | ||
Target ID: GO:0006412 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | Unknown Approved UseUnknown |
|||
Primary | Unknown Approved UseUnknown |
PubMed
Title | Date | PubMed |
---|---|---|
Harringtonine, an inhibitor of initiation of protein biosynthesis. | 1975 Sep |
|
Highlight on the studies of anticancer drugs derived from plants in China. | 1994 Jan |
|
Simultaneous multi-parameter observation of Harringtonine-treating HL-60 cells with both two-photon and confocal laser scanning microscopy. | 2001 Aug |
|
Inhibition of chikungunya virus replication by harringtonine, a novel antiviral that suppresses viral protein expression. | 2013 Jan |
Patents
Sample Use Guides
In Vivo Use Guide
Sources: https://link.springer.com/article/10.1007/BF02997235
Acute nonlymphocytic leukemia treatment: 2- 4 mg intravenously daily, 5 - 7 days
Route of Administration:
Intravenous
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/1237080
Curator's Comment: The effect of harringtonine (HA) in various concentrations on HL-60 was evaluated. 0.10 ug/ml HA showed a strong cell killing effect, and 0.025 microgram/ml HA a weak differentiation induction accompanied by cell growth retardation. https://www.ncbi.nlm.nih.gov/pubmed/2512060
DNA synthesis in HeLa cells is partially inhibited by a 200 nM concentration of Harringtonine.
Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Dec 15 19:16:58 GMT 2023
by
admin
on
Fri Dec 15 19:16:58 GMT 2023
|
Record UNII |
088662H40F
|
Record Status |
Validated (UNII)
|
Record Version |
|
-
Download
Name | Type | Language | ||
---|---|---|---|---|
|
Common Name | English | ||
|
Common Name | English | ||
|
Systematic Name | English | ||
|
Common Name | English | ||
|
Code | English | ||
|
Common Name | English |
Code System | Code | Type | Description | ||
---|---|---|---|---|---|
|
100000137716
Created by
admin on Fri Dec 15 19:16:58 GMT 2023 , Edited by admin on Fri Dec 15 19:16:58 GMT 2023
|
PRIMARY | |||
|
088662H40F
Created by
admin on Fri Dec 15 19:16:58 GMT 2023 , Edited by admin on Fri Dec 15 19:16:58 GMT 2023
|
PRIMARY | |||
|
26833-85-2
Created by
admin on Fri Dec 15 19:16:58 GMT 2023 , Edited by admin on Fri Dec 15 19:16:58 GMT 2023
|
PRIMARY | |||
|
124147
Created by
admin on Fri Dec 15 19:16:58 GMT 2023 , Edited by admin on Fri Dec 15 19:16:58 GMT 2023
|
PRIMARY | |||
|
276389
Created by
admin on Fri Dec 15 19:16:58 GMT 2023 , Edited by admin on Fri Dec 15 19:16:58 GMT 2023
|
PRIMARY | |||
|
DTXSID50101680
Created by
admin on Fri Dec 15 19:16:58 GMT 2023 , Edited by admin on Fri Dec 15 19:16:58 GMT 2023
|
PRIMARY | |||
|
SUB76293
Created by
admin on Fri Dec 15 19:16:58 GMT 2023 , Edited by admin on Fri Dec 15 19:16:58 GMT 2023
|
PRIMARY |