Eltrombopag
- CAS No.
- 496775-61-2
- Chemical Name:
- Eltrombopag
- Synonyms
- Promacta;Eltrombopa;Eltrombopag [inn];CS-640;Ikuppa;Sb497115;Sb-497115;ltrombopag;Eltrombopag;Unii-S56D65xj9g
- CBNumber:
- CB71463423
- Molecular Formula:
- C25H22N4O4
- Molecular Weight:
- 442.47
- MOL File:
- 496775-61-2.mol
- Modify Date:
- 2024/6/4 15:29:52
| Melting point | 242-244°C |
|---|---|
| Boiling point | 656.8±65.0 °C(Predicted) |
| Density | 1.33 |
| storage temp. | Keep in dark place,Inert atmosphere,Room temperature |
| solubility | Soluble in DMSO (up to 55 mg/ml) or in ethanol (up to 14 mg/ml). |
| form | solid |
| pka | -1.26±0.40(Predicted) |
| color | Orange |
| Stability | Stable for 2 years from date of purchase as supplied. Solutions in DMSO or ethanol may be stored at -20° for up to 3 months. |
| InChI | InChI=1S/C25H22N4O4/c1-14-10-11-19(12-15(14)2)29-24(31)22(16(3)28-29)27-26-21-9-5-8-20(23(21)30)17-6-4-7-18(13-17)25(32)33/h4-13,26,30H,1-3H3,(H,32,33)/b27-22- |
| InChIKey | XDXWLKQMMKQXPV-QYQHSDTDSA-N |
| SMILES | C1(C2=CC=CC(N/N=C3\C(=O)N(C4=CC=C(C)C(C)=C4)N=C\3C)=C2O)=CC=CC(C(O)=O)=C1 |
SAFETY
Risk and Safety Statements
| Symbol(GHS) |     GHS07,GHS08,GHS09,GHS05 |
|||||||||
|---|---|---|---|---|---|---|---|---|---|---|
| Signal word | Danger | |||||||||
| Hazard statements | H318-H373-H410-H302 | |||||||||
| Precautionary statements | P273-P391-P501-P264-P270-P301+P312-P330-P501-P280-P305+P351+P338-P310-P260-P314-P501 | |||||||||
| NFPA 704 |
|
Eltrombopag Chemical Properties,Uses,Production
Description
ITP is an autoimmune disease in which antiplatelet antibodies accelerate the destruction of platelets. In addition, platelet production can be
impaired because the antiplatelet antibodies can also damage megakaryocytes. Although the thrombocytopenia of ITP can be severe, signs of
bleeding are usually only minor.
Eltrombopag is an oral, small-molecule, nonpeptide TPO-receptor agonist. It initiates TPO-receptor signaling by interacting with the
transmembrane domain of the receptor, thereby inducing proliferation
and differentiation of cells in the megakaryocytic lineage. Eltrombopag is
the second TPO-receptor agonist to reach the market behind romiplostim
(Nplate), a recombinant fusion protein launched in 2008. Both drugs are
specifically indicated for the treatment of thrombocytopenia in patients
with chronic ITP who have had an insufficient response to corticosteroids,
immunoglobulins, or splenectomy. Eltrombopag is supplied as the ethanolamine salt (also known as eltrombopag olamine).
The most common adverse reactions associated with eltrombopag were nausea, vomiting, mennorrhagia, myalgia, paresthesia and cataracts. Eltrombopag is derived in five synthetic steps starting from 2-bromo-6-nitroanisole, via Suzuki coupling reaction with 3-carboxyphenylboronic acid to a biphenyl intermediate, followed by cleavage of the methyl ether moiety with hydrobromic acid, and reduction of the nitro group to an amino group under catalytic hydrogenation conditions. Subsequently, the amino group is diazotized with sodium nitrite and hydrochloric acid, and the diazonium intermediate is condensed with 1-(3,4-dimethylphenyl)-3-methyl-2,5-dihydro-1H-pyrazol-5-one to produce eltrombopag.
Chemical Properties
Orange to Red Solid
Uses
Eltrombopag (SB-497115-GR, Promacta, Revolade) is a small molecule agonist of the c-mpl (TpoR) receptor with an IC50 of 0.69 μM for the inhibition of hERG K+ channel tail current. In preclinical studies, the compound was shown to interact selectively with
Definition
ChEBI: A hydrazine in which each nitrogen atom is substituted, one by a 3'-carboxy-2-hydroxy[1,1'-biphenyl]-3-yl group and the other by a 1-(3,4-dimethylphenyl)-3-methyl-5-oxo-1,5-dihydro-4H-pyrazol-4-ylidene group. A small molecule agonist of the c-mpl (TpoR) receptor (the physiological target of the hormone thrombopoietin), it has been developed as a medication for conditions that lead to thrombocytopenia (abnormally low platelet counts).
Synthesis
The synthesis of Eltrombopag is as follows:
At room temperature, add 8.02g (20.0mmol) compound of formula V, 3.98g (24.0mmol) 3-carboxyphenylboronic acid, 8.48g (80.0mmol) sodium carbonate, 1.46g (2.0mmol) PdCl2dppf into a 250mL three-necked flask, 80mL ethanol, 65mL water, nitrogen protection, heated to 80, reacted for 10h, cooled to room temperature, added 60mL water, filtered, the filtrate was adjusted to pH 1-2 with 2M hydrochloric acid, a red solid was precipitated, filtered, and the filter cake was ethanol/water ( v/v=1:1, 40mL) beating, filtering, and drying to obtain 7.58g, the yield is 85.8%, and the purity is 99.40%.
Eltrombopag Preparation Products And Raw materials
Raw materials
Preparation Products
| Supplier | Tel | Country | ProdList | Advantage | Inquiry |
|---|---|---|---|---|---|
| GLR Innovations | +91 9891111994 | New Delhi, India | 4542 | 58 | Inquiry |
| SKVen Technologies Pvt.Ltd. | +91-7032295152 +91-7032295152 | Hyderabad, India | 81 | 58 | Inquiry |
| Styrax Pharma Pvt Ltd | +91-4048583333 +91-9848912103 | Telangana, India | 24 | 58 | Inquiry |
| Shilpa Medicare Limited (SML) | +91-8532238704 +91-9320649838 | Karnataka, India | 61 | 58 | Inquiry |
| Opulant Pharmaceuticals Pvt Ltd | +91-8105130349 +91-8105130349 | Telangana, India | 66 | 58 | Inquiry |
| Crams Technologies | 0129-4011068 | New Delhi, India | 39 | 58 | Inquiry |
| Riddhesh Pharmachem | +91-9106014993 +91-9106014993 | Gujarat, India | 126 | 58 | Inquiry |
| Pharmaffiliates Analytics and Synthetics P. Ltd | +91-172-5066494 | Haryana, India | 6773 | 58 | Inquiry |
| SynZeal Research Pvt Ltd | +1 226-802-2078 | Gujarat, India | 6522 | 58 | Inquiry |
| Pharma Affiliates | 172-5066494 | Haryana, India | 6761 | 58 | Inquiry |