Homoharringtonine
- CAS No.
- 26833-87-4
- Chemical Name:
- Homoharringtonine
- Synonyms
- HHT;HHT2;ORW2;SKR3;ACVRL1;ACVRLK1;CGX 635;Myelostat;Ceflatonin;NSC 141633
- CBNumber:
- CB2278852
- Molecular Formula:
- C29H39NO9
- Molecular Weight:
- 545.63
- MOL File:
- 26833-87-4.mol
- MSDS File:
- SDS
- Modify Date:
- 2024/1/5 22:10:32
| Melting point | 144-146 C |
|---|---|
| Boiling point | 619.03°C (rough estimate) |
| Density | 1.2395 (rough estimate) |
| refractive index | 1.6290 (estimate) |
| storage temp. | 2-8°C |
| solubility | DMSO: soluble20mg/mL, clear |
| pka | 11.60±0.29(Predicted) |
| form | powder |
| color | white to beige |
| optical activity | [α]/D -120 to -140°, c = 1 in chloroform-d |
| InChIKey | DJIVDDPFKDEQIR-XSEHADPMSA-N |
SAFETY
Risk and Safety Statements
| Symbol(GHS) |  GHS06 |
|||||||||
|---|---|---|---|---|---|---|---|---|---|---|
| Signal word | Danger | |||||||||
| Hazard statements | H300+H310+H330 | |||||||||
| Precautionary statements | P262-P280-P301+P310+P330-P302+P352+P310-P304+P340+P310 | |||||||||
| Hazard Codes | T+,Xi | |||||||||
| Risk Statements | 26/27/28-36/37/38-28 | |||||||||
| Safety Statements | 36/37/39-45-27-26-36/37-28 | |||||||||
| RIDADR | UN 1544 6.1/PG 2 | |||||||||
| WGK Germany | 3 | |||||||||
| RTECS | FK0260000 | |||||||||
| HazardClass | 6.1(a) | |||||||||
| PackingGroup | II | |||||||||
| NFPA 704 |
|
Homoharringtonine price More Price(3)
| Manufacturer | Product number | Product description | CAS number | Packaging | Price | Updated | Buy |
|---|---|---|---|---|---|---|---|
| Sigma-Aldrich(India) | SML1091 | Homoharringtonine ≥98% (HPLC) | 26833-87-4 | 10MG | ₹12383.8 | 2022-06-14 | Buy |
| Sigma-Aldrich(India) | SML1091 | Homoharringtonine ≥98% (HPLC) | 26833-87-4 | 50MG | ₹49935.73 | 2022-06-14 | Buy |
| Sigma-Aldrich(India) | SAB1412002 | ANTI-ACVRL1 antibody produced in mouse clone 1E7, purified immunoglobulin, buffered aqueous solution | 26833-87-4 | 100μG | ₹52347.6 | 2022-06-14 | Buy |
Homoharringtonine Chemical Properties,Uses,Production
Description
Omacetaxine mepesuccinate (also known as homoharringtonine) was approved by the US FDA in October 2012 for the treatment of patients with chronic or accelerated phase chronic myeloid leukemia (CML) with resistance or intolerance to at least two tyrosine kinase inhibitors (TKIs). Omacetaxine is a protein synthesis inhibitor that was studied in the 1970s for the treatment of acute myeloid leukemia (AML) and in the 1990s for CML. Emergence of resistance to first- and second-generation TKIs has lead to renewed interest in omacetaxine due to its differentiated mode of action. Omacetaxine acts on the initial step of protein translation andresults in the rapid loss of a number of short-lived proteins that regulate proliferation and cell survival. Omacetaxine induces apoptosis and shows in vitro activity in anumberof leukemia cell lines andinmurine leukemiamodels. Omacetaxineis a naturally occurring alkaloid isolated from Cephalotaxus coniferous shrubs that are indigenous to Asia. Extracts of the bark have been used by practitioners of traditional Chinese medicine for the treatment of cancer. Although omacetaxine could be isolated directly from bark and roots, a more efficient approach is semi-synthesis by esterification of the abundant biosynthetic precursor cephalotaxine, which can be extracted from leaves rather than nonrenewable sources. Esterification is carried out with an activated ester in which the diol side-chain is protected as a tetrahydropyran; after ester formation, the diol is released in two steps under mild conditions.
Chemical Properties
Off-white Cryst
Physical properties
Appearance: an almost white or pale yellow crystalline powder or an amorphous friable solid. It has the hygroscopic nature. It darkens on exposure to light. Solubility: easily soluble in chloroform, ethanol and methanol, and slightly soluble in ether and water. Melting point: 143–147?°C.
History
In China, especially in Fujian, etc., doctors have treated tumor with Cephalotaxus harringtonia long ago. In the early 1970s, American scientists Powell et?al. isolated and identified the alkaloids of the Cephalotaxus plant and studied its antitumor activity. One type of the alkaloids (Cephalotaxine ester, including harringtonine, homoharringtonine, isoharringtonine, deoxyharringtonine, and pseudodeoxyharringtonine) was found to have the effect of inhibiting the proliferation of mouse leukemia cells . Chinese scientists also isolated a large number of harringtonine and homoharringtonine and used them to treat leukemia. Then, the United States and other developed countries’ scientists carried out the Phase I and II clinical research and toxicology research of homoharringtonine.
Uses
Homoharringtonine (HHT) combined with some botanical drugs could induce cancer cells to resemble normal cells. HHT was prepared by a semi-synthetic method from Cephalotaxine, a major alkaloid of Cepahlotaxus species through the formation of a-ketoes
Definition
ChEBI: A cephalotaxine-derived alkaloid ester obtained from Cephalotaxus harringtonia; used for the treatment of chronic or accelerated phase chronic myeloid leukaemia.
Indications
This product is recorded in the Pharmacopoeia of the People’s Republic of China (2015).
Its main dosage form is homoharringtonine injection, which is mainly used for
the treatment of chronic myelocytic leukemia and acute myeloid leukemia.
Biological Activity
Inhibitor of protein synthesis. Blocks elongation phase of translation by binding to the 60-S ribosome subunit. Antileukemic.
Pharmacology
Induce apoptosis: Homoharringtonine was found to activate HL-60 cell apoptosis through caspase-3 mediated Bcl-2-Bax, -MAPK pathway .
3. Induce cell differentiation: Homoharringtonine could induce HL-60 cell differentiation by downregulating the expression of CD44 gene, thereby increasing p27 and p21 expression and inhibition of cyclin E activity.
Structure-Activity Relationship (SAR) The methyl acetate group of 2′ position in the C-3 acyl side chain is an active essential group. R group plays a role in regulating the polarity of the molecule, and the size of the R group can affect the molecular activity. The olefinic carbon instead of the 2′ position chiral carbon is still active .
Clinical Use
Synribo® (Omacetaxine mepesuccinate) was approved by the FDA for the treatment of adult patients with chronic or accelerated phase chronic myeloid leukemia (CML) exhibiting resistance or intolerance to tyrosine kinase inhibitors (TKI’s). Omacetaxine mepesuccinate inhibits protein synthesis and prevents aminoacyl-tRNA binding during the elongation phase and targets myeloma-promoting molecules Mcl-1, XIAP, and β-catenin, which are particularly important in the survival of myeloma cells. Omacetaxine mepesuccinate is also known as homoharringtonine, an alkaloid originally discovered and structurally identified from Cephalotaxus harringtonia, which occurs naturally in Japan and eastern Asia.
Anticancer Research
This compound is isolated from Cephalotaxus harringtonia. A racemic mixture ofharringtonine and homoharringtonine is used for acute and chronic myelogenousleukemia (Shoeb 2006).
Homoharringtonine Preparation Products And Raw materials
Raw materials
Preparation Products
| Supplier | Tel | Country | ProdList | Advantage | Inquiry |
|---|---|---|---|---|---|
| Pharmaffiliates Analytics and Synthetics P. Ltd | +91-172-5066494 | Haryana, India | 6773 | 58 | Inquiry |
| CLEARSYNTH LABS LTD. | +91-22-45045900 | Hyderabad, India | 6351 | 58 | Inquiry |
| Shanghai Daken Advanced Materials Co.,Ltd | +86-371-66670886 | China | 16914 | 58 | Inquiry |
| Henan Tianfu Chemical Co.,Ltd. | +86-0371-55170693 +86-19937530512 | China | 21668 | 55 | Inquiry |
| career henan chemical co | +86-0371-86658258 +8613203830695 | China | 29894 | 58 | Inquiry |
| Chengdu Biopurify Phytochemicals Ltd. | +8618080483897 | China | 3777 | 58 | Inquiry |
| Shaanxi Pioneer Biotech Co., Ltd . | +8613259417953 | China | 3000 | 58 | Inquiry |
| Chongqing Chemdad Co., Ltd | +86-023-6139-8061 +86-86-13650506873 | China | 39916 | 58 | Inquiry |
| CONIER CHEM AND PHARMA LIMITED | +8618523575427 | China | 49391 | 58 | Inquiry |
| Hubei Ipure Biology Co., Ltd | +8613367258412 | China | 10326 | 58 | Inquiry |
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