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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
Structure of HARRINGTONIN

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

HIDE SMILES / InChI

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

Curator's Comment: Paudler et al. isolated harringtonine and cephalotaxine from Cephalotaxus harringtonia in 1963 for the first time.

Approval Year

Sourcing

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

TitleDatePubMed
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

Acute nonlymphocytic leukemia treatment: 2- 4 mg intravenously daily, 5 - 7 days
Route of Administration: Intravenous
In Vitro Use Guide
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 Fri Dec 15 19:16:58 GMT 2023
Edited
by admin
on Fri Dec 15 19:16:58 GMT 2023
Record UNII
088662H40F
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
HARRINGTONIN
Common Name English
2'R-HARRINGTONINE
Common Name English
CEPHALOTAXINE, 4-METHYL (2R)-2-HYDROXY-2-(3-HYDROXY-3-METHYLBUTYL)BUTANEDIOATE (ESTER)
Systematic Name English
HARRINGTONINE
Common Name English
NSC-124147
Code English
Harringtonine [WHO-DD]
Common Name English
Code System Code Type Description
SMS_ID
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
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FDA UNII
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
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CAS
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
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NSC
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
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PUBCHEM
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
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EPA CompTox
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
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EVMPD
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
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