Entinostat
Grundinformationen
- CAS
209783-80-2- Standard-SMILES
Nc1ccccc1NC(=O)c1ccc(CNC(=O)OCc2cccnc2)cc1- InChIKey
INVTYAOGFAGBOE-UHFFFAOYSA-N- Summenformel
- C21H20N4O3
- Durchschnittliche Molmasse
- 376,4 g/mol
- Monoisotopische Masse
- 376,1535405
Überblick
Entinostat is a member of the class of benzamides resulting from the formal condensation of the carboxy group of the pyridin-3-ylmethyl carbamate derivative of p-(aminomethyl)benzoic acid with one of the amino groups of benzene-1,2-diamine. It is an inhibitor of histone deacetylase isoform 1 (HDAC1) and isoform 3 (HDAC3). It has a role as an antineoplastic agent, an EC 3.5.1.98 (histone deacetylase) inhibitor and an apoptosis inducer. It is a member of benzamides, a carbamate ester, a member of pyridines, a substituted aniline and a primary amino compound. It is functionally related to a 1,2-phenylenediamine.
Namen und Bezeichner
- Bevorzugter Name
- Entinostat
- IUPAC
- pyridin-3-ylmethyl N-[[4-[(2-aminophenyl)carbamoyl]phenyl]methyl]carbamate
- Englischer Name
- Entinostat
- Summenformel
- C21H20N4O3
- Molmasse
- 376.41
Namen und Synonyme
Entinostat209783-80-2ms-275SNDX-275MS 275MS-27-275SNDX 275MS 27-275entinostatumpyridin-3-ylmethyl N-[[4-[(2-aminophenyl)carbamoyl]phenyl]methyl]carbamate1ZNY4FKK9HBAY 86-5274
Weitere Namen anzeigen
RivipanselCS-189MS 2275EntenotMS 275-27MS275D4-EntinostatMS275
N-(2-aminophenyl)-4-(N-(pyridin-3-ylmethoxycarbonyl)aminomethyl)benzamideNSC706995BAY86-5274Carbamic acid, N-[[4-[[(2-aminophenyl)amino]carbonyl]phenyl]methyl]-, 3-pyridinylmethyl esterMS-275-27DTXSID0041068CHEBI:132082(pyridin-3-yl)methyl N-({4-[(2-aminophenyl)carbamoyl]phenyl}methyl)carbamate
Datenbank-Bezeichner
- CAS
209783-80-2- PubChem CID
- 4261
- DTXSID
DTXSID0041068- ChEMBL
CHEMBL27759- ChEBI
CHEBI:132082- UNII
- 1ZNY4FKK9H
Eigenschaften
Berechnete Struktureigenschaften
- XLogP
- 2
- Polarare Oberfläche (TPSA)
- 106 Ų
- H-Brücken-Donoren
- 3
- H-Brücken-Akzeptoren
- 5
- Frei drehbare Bindungen
- 7
- Schwere Atome
- 28
- Formalladung
- 0
- Komplexität
- 508
Experimentelle und physikochemische Eigenschaften
DrugsPharmaceuticals -> Listed in ZINC15
LogP1.26
Physikochemische Eigenschaften
- Schmelzpunkt
- 159 · 159-160 ºC
- Siedepunkt
- 566.7 · 566.7±50.0 °C(Predicted)
- Dichte
- 1.315 · 1.315
- storage temp.
- -20 °C · Keep in dark place,Sealed in dry,Store in freezer, under -20°C
- Löslichkeit
- 38 mg/mL, · DMSO: 38 mg/mL, soluble
- Aggregatzustand
- solid
- pka
- 11.32 · 11.32±0.46(Predicted)
- Farbe
- Pale yellow
- Stabilität
- 1 year · Stable for 1 year from date of purchase as supplied. Solutions in DMSO may be stored at -20° for up to 1 week.
- InChI
- InChI=1S/C21H20N4O3/c22-18-5-1-2-6-19(18)25-20(26)17-9-7-15(8-10-17)13-24-21(27)28-14-16-4-3-11-23-12-16/h1-12H,13-14,22H2,(H,24,27)(H,25,26)
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
H301 (98.6%): Toxic if swallowed [Danger Acute toxicity, oral]
P203, P261, P264, P264+P265, P270, P271, P280, P301+P316, P302+P352, P304+P340, P305+P351+P338, P318, P319, P321, P330, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 74 reports by companies from 8 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Gefahrenhinweise
Hazard Classes and CategoriesAcute Tox. 3 (98.6%)
Sicherheitsdaten
- wgk
- 3
- ridadr
- UN 2811 6.1 / PGIII
- hs_code
- 29333990
- risk_code
- 36/37/38-62-48/25-25-61
- hazard_code
- Xi,T
- safety_code
- 26-36-45
- Speicherklasse
- 6.1C - Combustible acute toxic Cat.3toxic compounds or compounds which causing chronic effects
- Hazard Classifications
- Acute Tox. 3 OralRepr. 1A
Chemie und Industrie
Pharmakologische Informationen
ATC Code
L - Antineoplastic and immunomodulating agents
QL - Antineoplastic and immunomodulating agents
MeSH Pharmacological Classification
Substances that inhibit or prevent the proliferation of NEOPLASMS.
Compounds that inhibit HISTONE DEACETYLASES. This class of drugs may influence gene expression by increasing the level of acetylated HISTONES in specific CHROMATIN domains.
Anwendungen
BeschreibungEntinostat (SNDX-275, MS-275) belongs to benzamide class HDACi and inhibits HDAC1 and 2, 3 and 9 and has low effect against HDAC4, 6, 7 and 8 (Khan et al. 2007). Entinostat is in phase II clinical trial for treatment of Hodgkin's lymphoma and advanced breast cancer (in combination with aromatase inhibitors) and metastatic lung cancer (in combination with erlotinib).
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