ChemicalBook > CAS DataBase List > Eltrombopag

Eltrombopag

Product Name
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
Formula Weight
442.47
MOL File
496775-61-2.mol
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Eltrombopag Property

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
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Safety

Hazardous Substances Data
496775-61-2(Hazardous Substances Data)
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Danger
Hazard statements

H302Harmful if swallowed

H318Causes serious eye damage

H373May cause damage to organs through prolonged or repeated exposure

H410Very toxic to aquatic life with long lasting effects

Precautionary statements

P260Do not breathe dust/fume/gas/mist/vapours/spray.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P270Do not eat, drink or smoke when using this product.

P273Avoid release to the environment.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P301+P312IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P310Immediately call a POISON CENTER or doctor/physician.

P314Get medical advice/attention if you feel unwell.

P330Rinse mouth.

P391Collect spillage. Hazardous to the aquatic environment

P501Dispose of contents/container to..…

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N-Bromosuccinimide Price

Cayman Chemical
Product number
13247
Product name
Eltrombopag
Purity
≥98%
Packaging
1mg
Price
$32
Updated
2024/03/01
Cayman Chemical
Product number
13247
Product name
Eltrombopag
Purity
≥98%
Packaging
5mg
Price
$86
Updated
2024/03/01
Cayman Chemical
Product number
13247
Product name
Eltrombopag
Purity
≥98%
Packaging
10mg
Price
$117
Updated
2024/03/01
Cayman Chemical
Product number
13247
Product name
Eltrombopag
Purity
≥98%
Packaging
25mg
Price
$214
Updated
2024/03/01
TRC
Product number
E508000
Product name
Eltrombopag
Packaging
2mg
Price
$55
Updated
2021/12/16
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Eltrombopag Chemical Properties,Usage,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

Originator

Ligand Pharmaceuticals (US)

Uses

An agonist of the Thrombopoietin (Tpo) receptor, used as treatment for thrombocytopenia.

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).

brand name

Promacta

Clinical Use

Thrombopoetin receptor agonist:
Treatment of chronic immune idiopathic thrombocytopenic purpura (ITP)
Chronic hepatitis C associated thrombocytopenia (HCV)
Severe aplastic anaemia

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%.

Drug interactions

Potentially hazardous interactions with other drugs
Ciclosporin: concentration of eltrombopag reduced.
Statins: increased rosuvastatin concentration, may need to reduce rosuvastatin dose.

Metabolism

Mainly hepatically metabolised through cleavage, oxidation by cytochrome P450 isoenzymes CYP1A2 and CYP 2C8 and conjugation with glucuronic acid, glutathione, or cysteine.
Approximately 31% of a dose is eliminated in the urine as metabolites, and about 59% in the faeces (20% unchanged).

References

1) Xie?et al. (2018), Pharmacological characterization of eltrombopag, a novel orally active human thrombopoietin receptor agonist; J. Cell. Mol. Med.,?22?5367 2) Erickson-Miller?et al.?(2008),?Preclinical activity of eltrombopag (SB-497115), an oral, nonpeptide thrombopoietin receptor agonist; Stem Cells,?27?424 3) Alvarado?et al.?(2019),?Eltrombopag maintains human hematopoietic stem and progenitor cells under inflammatory conditions mediated by IFN-γ; Blood,?133?2043 4) Guenther?et al.?(2019),?Eltrombopag promotes DNA repair in human hematopoietic stem and progenitor cells; Exp. Hematol.?73?1 5) Vlachodimitropoulou?et al.?(2017),?Eltrombopag: a powerful chelator of cellular or extracellular iron (II) alone or combined with a second chelator; Blood,?130?1923 6) Kao?et al.?(2018),?Thrombopoietin receptor-independent stimulation of hematopoietic stem cells by eltrombopag; Science Transl. Med.,?10?eaas9563

Eltrombopag Preparation Products And Raw materials

Raw materials

Preparation Products

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Eltrombopag Suppliers

Canada 1 CHINA 259 China Hong Kong 1 India 13 United Kingdom 2 United States 20 Global 296
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View Lastest Price from Eltrombopag manufacturers

Sinoway Industrial co., ltd.
Product
Eltrombopag 496775-61-2
Price
US $0.00/Kg/Bag
Min. Order
2Kg/Bag
Purity
99% up, High Density
Supply Ability
20 tons
Release date
2023-02-07
Hebei Zhuanglai Chemical Trading Co.,Ltd
Product
Eltrombopag 496775-61-2
Price
US $10.00/kg
Min. Order
1kg
Purity
99%
Supply Ability
20ton
Release date
2024-06-04
shandong perfect biotechnology co.ltd
Product
Eltrombopag 496775-61-2
Price
US $0.00/g
Min. Order
1g
Purity
98% HPLC
Supply Ability
100kg
Release date
2023-08-14

496775-61-2, EltrombopagRelated Search:

Dimethyl sulfone METHYL THIOPHENE-2-CARBOXYLATE Dihydromyrcenol Dimethicone Chlorodimethylphenylsilane Kresoxim-methyl Dimethyl sulfoxide Methyl acrylate Methylparaben N,N-Dimethylacetamide N,N-Dimethylformamide Bensulfuron methyl 1,5-Diphenylcarbazide 1,2-Dimethylhydrazine Dihydrochloride Poly(dimethylsiloxane) Thiophanate-methyl 2-(3,4-Dimethylphenyl)-1,2-dihydro-5-methyl-3H-pyrazol-3-one Methyl

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  • 3'-[2-[(2Z)-1-(3,4-Dimethylphenyl)-1,5-dihydro-3-methyl-5-oxo-4H-pyrazol-4-ylidene]hydrazinyl]-2'-hydroxy-[1,1'-biphenyl]-3-carboxylic acid
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  • (Z)-3'-(2-(1-(3,4-Dimethylphenyl)-3-methyl-5-oxo-1H-pyrazol-4(5H)-ylidene)hydrazinyl)-2'-hydroxy-
  • [1,1'-Biphenyl]-3-carboxylic acid, 3'-[2-[(2Z)-1-(3,4-dimethylphenyl)-1,5-dihydro-3-methyl-5-oxo-4H-pyrazol-4-ylidene]hydrazinyl]-2'-hydroxy-
  • CS-640
  • 3'-[2-[(2Z)-1-(3,4-Dimethylphenyl)-1,5-dihydro-3-methyl-5-oxo-4H-pyrazol-4-ylidene]hydrazinyl]-2'-hydroxy-[1,1'-biphenyl]-3-carboxylic acid Eltrombopag
  • Eltrombopag 3'-[2-[(2Z)-1-(3,4-Dimethylphenyl)-1,5-dihydro-3-methyl-5-oxo-4H-pyrazol-4-ylidene]hydrazinyl]-2'-hydroxy-[1,1'-biphenyl]-3-carboxylic acid
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  • ltrombopag
  • [1,1'-Biphenyl]-3-carboxylic acid, 3'-[(2Z)-2-[1-(3,4-dimethylphenyl)-1,5-dihydro-3-methyl-5-oxo-4H-pyrazol-4-ylidene]hydrazinyl]-2'-hydroxy-
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  • (Z)-3'-(2-(1-(3,4-Dimethylphenyl)-3-methyl-5-oxo-1H-pyrazol-4(5H)-ylidene)hydrazinyl)-2'-hydroxy-[1,1'-biphenyl]-3-carboxylic acid
  • 496775-61-2
  • 496755-61-2
  • SB-497115-GR, Revolade, Promacta
  • Agonist
  • Aromatics
  • Heterocycles
  • Intermediates & Fine Chemicals
  • Pharmaceuticals
  • Inhibitors
  • API