Introduction：Basic information about CAS 26833-85-2|Harringtonine, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.
| Common Name | Harringtonine |
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| CAS Number | 26833-85-2 | Molecular Weight | 531.595 |
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| Density | 1.4±0.1 g/cm3 | Boiling Point | 679.4±55.0 °C at 760 mmHg |
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| Molecular Formula | C28H37NO9 | Melting Point | 73-75ºC |
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| MSDS | / | Flash Point | 364.7±31.5 °C |
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Names
| Name | Harringtonin |
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| Synonym | More Synonyms |
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Harringtonine BiologicalActivity
| Description | Harringtonine is a natural Cephalotaxus alkaloid that inhibits protein synthesis. |
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| Related Catalog | Signaling Pathways >>Others >>OthersResearch Areas >>Cancer |
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| In Vitro | Harringtonine inhibits the elongation phase of translation by preventing substrate binding to the acceptor site on the 60-S ribosome subunit and therefore block aminoacyl-tRNA binding and peptide bond formation[1]. Harringtonine displays potent inhibition of Chikungunya virus infection with an EC50 of 0.24 μM. Harringtonine could inhibit other alphaviruses[2]. Harringtonine inhibits the growth of human myeloid leukemia cells in vitro at low concentrations. The mechanism of the antitumor action of harringtonine is considered to be an effect on protein synthesis and is characterized by breakdown of polysomes to monosomes[3]. |
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| Cell Assay | For harringtonine treatment studies with Sindbis virus, BHK21 cells are seeded into 96-well plates and infected with Sindbis virus at an MOI of 1 for 1 h prior to being washed twice with PBS and incubated with various concentrations of harringtonine (0.1 μM, 1 μM, 5 μM, and 10 μM) at 37°C with 5% CO2. Cell supernatants are harvested for plaque assays at 24 h postinfection[2]. |
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| References | [1]. Fresno M, et al. Inhibition of translation in eukaryotic systems by harringtonine. Eur J Biochem. 1977 Jan;72(2):323-30. [2]. Kaur P, et al. Inhibition of chikungunya virus replication by harringtonine, a novel antiviral that suppresses viral protein expression. Antimicrob Agents Chemother. 2013 Jan;57(1):155-67. [3]. Piao YF, et al. Growth inhibition of human myeloid leukemia cells in vitro by harringtonine. Gan To Kagaku Ryoho. 1990 Feb;17(2):281-5. |
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Chemical & Physical Properties
| Density | 1.4±0.1 g/cm3 |
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| Boiling Point | 679.4±55.0 °C at 760 mmHg |
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| Melting Point | 73-75ºC |
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| Molecular Formula | C28H37NO9 |
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| Molecular Weight | 531.595 |
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| Flash Point | 364.7±31.5 °C |
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| Exact Mass | 531.246826 |
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| PSA | 123.99000 |
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| LogP | 2.58 |
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| Vapour Pressure | 0.0±2.2 mmHg at 25°C |
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| Index of Refraction | 1.610 |
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| InChIKey | HAVJATCHLFRDHY-KSZYUSJVSA-N |
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| SMILES | COC(=O)CC(O)(CCC(C)(C)O)C(=O)OC1C(OC)=CC23CCCN2CCc2cc4c(cc2C13)OCO4 |
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| Storage condition | -20℃ |
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Toxicological Information
CHEMICAL IDENTIFICATION - RTECS NUMBER :
- FK0250000
- CHEMICAL NAME :
- Cephalotaxine, 4-methyl-, 2-hydroxy-2-(3-hydroxy-3-methylbutyl)butanedioate (ester), (3(R))-
- CAS REGISTRY NUMBER :
- 26833-85-2
- LAST UPDATED :
- 199703
- DATA ITEMS CITED :
- 7
- MOLECULAR FORMULA :
- C28-H37-N-O9
- MOLECULAR WEIGHT :
- 531.66
- WISWESSER LINE NOTATION :
- T5 H5 F675 1A T AX IO KO QN BU JHT&&TTJ CO1 DOVXQ1VQ2XQ1&1 T1
HEALTH HAZARD DATAACUTE TOXICITY DATA - TYPE OF TEST :
- LD50 - Lethal dose, 50 percent kill
- ROUTE OF EXPOSURE :
- Intraperitoneal
- SPECIES OBSERVED :
- Rodent - mouse
- DOSE/DURATION :
- 4170 ug/kg
- TOXIC EFFECTS :
- Details of toxic effects not reported other than lethal dose value
- TYPE OF TEST :
- LD50 - Lethal dose, 50 percent kill
- ROUTE OF EXPOSURE :
- Intravenous
- SPECIES OBSERVED :
- Rodent - mouse
- DOSE/DURATION :
- 4500 ug/kg
- TOXIC EFFECTS :
- Details of toxic effects not reported other than lethal dose value
- TYPE OF TEST :
- TDLo - Lowest published toxic dose
- ROUTE OF EXPOSURE :
- Intravenous
- SPECIES OBSERVED :
- Mammal - dog
- DOSE/DURATION :
- 4200 ug/kg/5D-I
- TOXIC EFFECTS :
- Cardiac - pulse rate increase, without fall in BP Blood - leukopenia Nutritional and Gross Metabolic - weight loss or decreased weight gain
- TYPE OF TEST :
- TDLo - Lowest published toxic dose
- ROUTE OF EXPOSURE :
- Intravenous
- SPECIES OBSERVED :
- Rodent - rabbit
- DOSE/DURATION :
- 5200 ug/kg/5D-I
- TOXIC EFFECTS :
- Cardiac - pulse rate increase, without fall in BP Blood - leukopenia Related to Chronic Data - death
- TYPE OF TEST :
- Micronucleus test
MUTATION DATA - TYPE OF TEST :
- Cytogenetic analysis
- TEST SYSTEM :
- Rodent - hamster Lung
- DOSE/DURATION :
- 200 ug/L
- REFERENCE :
- CYLPDN Zhongguo Yaoli Xuebao. Acta Pharmacologica Sinica. Chinese Journal of Pharmacology. (China International Book Trading Corp., POB 2820, Beijing, Peop. Rep. China) V.1- 1980- Volume(issue)/page/year: 7,173,1986
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Safety Information
| Hazard Codes | Xi |
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| RIDADR | UN 1544 |
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| Packaging Group | II |
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| Hazard Class | 6.1(a) |
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Synonyms
| harringtonine |
| O-[(2R)-2,5-Dihydroxy-2-(2-methoxy-2-oxoethyl)-5-methylhexanoyl]cephalotaxine |
| Cephalotaxine, O-[(2R)-2,5-dihydroxy-2-(2-methoxy-2-oxoethyl)-5-methyl-1-oxohexyl]- |
| Harringtonine (8CI) |
