Avatrombopag
Chemical compound
From Wikipedia, the free encyclopedia
Avatrombopag, sold under the brand name Doptelet, is a medication that is used for certain conditions that lead to thrombocytopenia (low platelets) such as thrombocytopenia associated with chronic liver disease in adults who are to undergo a planned medical or dental procedure.[8][9] It was approved for medical use in the United States in May 2018,[10][11] the European Union in June 2019,[7] and Australia in January 2023.[1]
| |
| Clinical data | |
|---|---|
| Pronunciation | a" va trom' boe pag |
| Trade names | Doptelet |
| AHFS/Drugs.com | Monograph |
| MedlinePlus | a618032 |
| License data |
|
| Pregnancy category |
|
| Routes of administration | By mouth |
| ATC code | |
| Legal status | |
| Legal status | |
| Identifiers | |
| |
| CAS Number | |
| PubChem CID | |
| DrugBank | |
| ChemSpider | |
| UNII | |
| KEGG | |
| ChEMBL | |
| CompTox Dashboard (EPA) | |
| Chemical and physical data | |
| Formula | C29H34Cl2N6O3S2 |
| Molar mass | 649.65 g·mol−1 |
| 3D model (JSmol) | |
| |
| |
  (what is this?) | |
It acts as a thrombopoietin receptor agonist.[12]
Synthesis
The chemical synthesis of avatrombopag was recently reported:[13]
The halogenation of 2-acetyl-4-chlorothiophene [34730-20-6] (1) gave 2-bromo-1-(4-chloro-2-thienyl)ethanone [677007-73-7] (2). Condensation with thiourea produced 4-(4-chlorothiophen-2-yl)-1,3-thiazol-2-amine [570407-10-2] (3). Halogenation with N-bromosuccinimide (NBS) in DMF have an intermediate which was used for nucleophilic aromatic substitution with 1-cyclohexylpiperazine [17766-28-8] (4) to provide [570407-42-0] (5). Schotten-Baumann reaction with 5,6-dichloronicotinic acid [41667-95-2] (6) gave the corresponding nicotinamide [570403-04-2] (7). A second nucleophilic aromatic substitution ethyl isonipecotate [1126-09-6] (8) gave [570403-14-4] (9). Subsequent saponification completed the synthesis of avatrombopag (10).
