Structure via PubChem · Public domain (PubChem)
avatrombopag
Sign in to saveAvatrombopag, 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. It was approved for medical use in the United States in May 2018, the European Union in June 2019, and Australia in January 2023.
Chemical data
- Formula
- C29H34Cl2N6O3S2
- Molecular weight
- 649.7 g/mol
- IUPAC name
- 1-[3-chloro-5-[[4-(4-chlorothiophen-2-yl)-5-(4-cyclohexylpiperazin-1-yl)-1,3-thiazol-2-yl]carbamoyl]-2-pyridinyl]piperidine-4-carboxylic acid
- SMILES
- C1CCC(CC1)N2CCN(CC2)C3=C(N=C(S3)NC(=O)C4=CC(=C(N=C4)N5CCC(CC5)C(=O)O)Cl)C6=CC(=CS6)Cl
- InChIKey
- OFZJKCQENFPZBH-UHFFFAOYSA-N
- XLogP
- 4
- Polar surface area
- 158 Ų
- H-bond donors
- 2
- H-bond acceptors
- 10
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Max clinical phase
- Approved
- Molecule type
- Small molecule
- First approval
- 2018
- Admin. routes
- oral
- Indications
- liver disease, autoimmune thrombocytopenic purpura, Thrombocytopenia, hemorrhage
via ChEMBL · EBI
Wikidata facts
- Subclass of
- chemical compound
- Mass
- 648.151
- Has use
- medication
Show 2 more facts
- canonical SMILES
- C1CCC(CC1)N2CCN(CC2)C3=C(N=C(S3)NC(=O)C4=CC(=C(N=C4)N5CCC(CC5)C(=O)O)Cl)C6=CC(=CS6)Cl
- chemical formula
- C₂₉H₃₄Cl₂N₆O₃S₂
Sources (2)
via Wikidata · CC0
~2 min read
Encyclopedic overview
2 sectionsContents
- Synthesis
- References
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. It was approved for medical use in the United States in May 2018, the European Union in June 2019, and Australia in January 2023.
It acts as a thrombopoietin receptor agonist. ==Synthesis== The chemical synthesis of avatrombopag was recently reported: skin-invert-image|700px|center 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). == References ==
Excerpted from Wikipedia’s “avatrombopag” article, available under the CC BY-SA 4.0 licence.