Abexinostat
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Grundinformationen
- CAS
783355-60-2- Standard-SMILES
CN(C)Cc1c(C(=O)NCCOc2ccc(C(=O)NO)cc2)oc2ccccc12- InChIKey
MAUCONCHVWBMHK-UHFFFAOYSA-N- Summenformel
- C21H23N3O5
- Durchschnittliche Molmasse
- 397,4 g/mol
- Monoisotopische Masse
- 397,16377084
Überblick
Abexinostat is a 1-benzofuran substituted by {2-[4-(hydroxycarbamoyl)phenoxy]ethyl}aminocarbonyl and (dimethylamino)methyl groups at positions 2 and 3, respectively. It is a potent pan-HDAC inhibitor whose major target is HDAC1 (Ki = 7 nM). It has a role as a radiosensitizing agent, an autophagy inducer, an antineoplastic agent, an EC 3.5.1.98 (histone deacetylase) inhibitor and an apoptosis inducer. It is a secondary carboxamide, a hydroxamic acid, an aromatic ether, a member of 1-benzofurans and a tertiary amino compound.
Namen und Bezeichner
- Bevorzugter Name
- Abexinostat
- IUPAC
- 3-[(dimethylamino)methyl]-N-[2-[4-(hydroxycarbamoyl)phenoxy]ethyl]-1-benzofuran-2-carboxamide
- Englischer Name
- CRA-02478
- Summenformel
- C21H23N3O5
- Molmasse
- 397.42
Namen und Synonyme
ABEXINOSTAT783355-60-2PCI-24781PCI 24781CRA-024781CRA 024781CRA 24781PCI24781CRA024781IYO470654U3-[(dimethylamino)methyl]-N-{2-[4-(hydroxycarbamoyl)phenoxy]ethyl}-1-benzofuran-2-carboxamidePZP115891
Weitere Namen anzeigen
CS-423CRA-02478PCI-24781, >=98%CRA-02478CRA-02478 PCI-24781PCI-24781(CRA-024781)
S78454PZP-115891DTXSID30229005S-784542-Benzofurancarboxamide, 3-((dimethylamino)methyl)-N-(2-(4-((hydroxyamino)carbonyl)phenoxy)ethyl)-3-[(dimethylamino)methyl]-N-[2-[4-(hydroxycarbamoyl)phenoxy]ethyl]-1-benzofuran-2-carboxamide3-((DIMETHYLAMINO)METHYL)-N-(2-(4-(HYDROXYCARBAMOYL)PHENOXY)ETHYL)-1-BENZOFURAN-2-CARBOXAMIDEabexinostatum
Datenbank-Bezeichner
- CAS
783355-60-2- PubChem CID
- 11749858
- DTXSID
DTXSID30229005- ChEMBL
CHEMBL2103863
Eigenschaften
Berechnete StruktureigenschaftenWird ergänzt
- XLogP
- 2,2
- Polarare Oberfläche (TPSA)
- 104 Ų
- H-Brücken-Donoren
- 3
- H-Brücken-Akzeptoren
- 6
- Frei drehbare Bindungen
- 8
- Schwere Atome
- 29
- Formalladung
- 0
- Komplexität
- 550
Experimentelle und physikochemische Eigenschaften
DrugsPharmaceuticals -> Listed in ZINC15
Physikochemische Eigenschaften
- Schmelzpunkt
- 198 · 198-202oC (dec.)
- Dichte
- 1.284 · 1.284
- storage temp.
- Refrigerator
- Löslichkeit
- DMSO (Slightly), Methanol (Slightly, Heated)
- Aggregatzustand
- Solid
- pka
- 9.04 · 9.04±0.10(Predicted)
- Farbe
- White
- InChI
- 1S/C21H23N3O5/c1-24(2)13-17-16-5-3-4-6-18(16)29-19(17)21(26)22-11-12-28-15-9-7-14(8-10-15)20(25)23-27/h3-10,27H,11-13H2,1-2H3,(H,22,26)(H,23,25)
- InChIKey
- MAUCONCHVWBMHK-UHFFFAOYSA-N
- SMILES
- N(O)C(=O)c1ccc(cc1)OCCNC(=O)c2[o]c3c(c2CN(C)C)cccc3 || CN(C)CC1=C(C(NCCOC2=CC=C(C(NO)=O)C=C2)=O)OC3=CC=CC=C31
Sicherheit und Regulatorisches
Sicherheitsangaben dienen nur zur Orientierung und ersetzen weder das Sicherheitsdatenblatt (SDB) des Lieferanten noch geltende Vorschriften oder eine fachliche Bewertung.
GHS-Klassifizierung
GHS Classification
Danger
H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]
P203, P260, P262, P264, P264+P265, P270, P273, P280, P301+P317, P301+P330+P331, P302+P352, P302+P361+P354, P304+P340, P305+P354+P338, P316, P317, P318, P319, P321, P330, P361+P364, P363, P391, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 2 reports by companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Gefahrenhinweise
Hazard Classes and CategoriesAcute Tox. 4 (100%)
Sicherheitsdaten
- Speicherklasse
- 11 - Combustible Solids
Chemie und Industrie
Pharmakologische Informationen
Mechanism of Action
Abexinostat is a novel histone deacetylase (HDAC) inhibitor. HDAC inhibitors target HDAC enzymes and inhibit the proliferation of cancer cells and induce cancer cell death, or apoptosis. Histone deacetylation is carried out by a family of related HDAC enzymes. Inhibition of these enzymes causes changes to chromatin structure and to gene expression patterns, which results in the inhibition of proliferation of cancer cells, and induction of apoptosis.
MeSH Pharmacological ClassificationCompounds that inhibit HISTONE DEACETYLASES. This class of drugs may influence gene expression by increasing the level of acetylated HISTONES in specific CHROMATIN domains.
Anwendungen
VerwendenPCI-24781 is a novel hydroxamic acid HDAC inhibitor (histone deacetylase inhibitor). PCI-24781 exerts cytotoxicity and histone H3 alterations via caspase-8 and FADD in leukemia cells.
Zugehörige Reaktionen
1
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