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Panobinostat

HCID 6918837
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GrundinformationenÜberblickNamen und BezeichnerEigenschaftenSicherheit und RegulatorischesChemie und IndustrieZugehörige ReaktionenNotizen zur Verbindung
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Grundinformationen

CAS
404950-80-7
Standard-SMILES
Cc1[nH]c2ccccc2c1CCNCc1ccc(/C=C/C(=O)NO)cc1
InChIKey
FPOHNWQLNRZRFC-ZHACJKMWSA-N
Summenformel
C21H23N3O2
Durchschnittliche Molmasse
349,4 g/mol
Monoisotopische Masse
349,17902698

Überblick

Panobinostat is a hydroxamic acid obtained by formal condensation of the carboxy group of (2E)-3-[4-({[2-(2-methylindol-3-yl)ethyl]amino}methyl)phenyl]prop-2-enoic acid with the amino group of hydroxylamine. A histone deacetylase inhibitor used (as its lactate salt) in combination with bortezomib and dexamethasone for the treatment of multiple myeloma. It has a role as an antineoplastic agent, an angiogenesis modulating agent and an EC 3.5.1.98 (histone deacetylase) inhibitor. It is a member of cinnamamides, a hydroxamic acid, a methylindole and a secondary amino compound. It is a conjugate base of a panobinostat(1+).

Namen und Bezeichner

Bevorzugter Name
Panobinostat
IUPAC
(E)-N-hydroxy-3-[4-[[2-(2-methyl-1H-indol-3-yl)ethylamino]methyl]phenyl]prop-2-enamide
Englischer Name
Panobinostat
Summenformel
C21H23N3O2
Molmasse
349.43

Namen und Synonyme

Panobinostat404950-80-7LBH-589FaridakLBH 589NVP-LBH5899647FM7Y3Z(2E)-N-hydroxy-3-[4-({[2-(2-methyl-1H-indol-3-yl)ethyl]amino}methyl)phenyl]prop-2-enamide(E)-N-hydroxy-3-[4-[[2-(2-methyl-1H-indol-3-yl)ethylamino]methyl]phenyl]prop-2-enamideCHEBI:85990DTXSID401935062-Propenamide, N-hydroxy-3-(4-(((2-(2-methyl-1H-indol-3-yl)ethyl)amino)methyl)phenyl)-, (2E)-
Weitere Namen anzeigen
panobinostaCS-422Palcociclib2-AcrylamidePalmer than hePanobinostat D7Panobinostat, >=98%
2-Propenamide, N-hydroxy-3-(4-(((2-(2-methyl-1H-indol-3-yl)ethyl)amino) methyl)phenyl)-, (2E)-2-Propenamide, N-hydroxy-3-[4-[[[2-(2-methyl-1H-indol-3-yl)ethyl]amino]methyl]phenyl]-, (2E)-Panobinostatum(E)-N-hydroxy-3-(4-((2-(2-methyl-1H-indol-3-yl)ethylamino)methyl)phenyl)prop-2-enamide(2E)-N-HYDROXY-3-(4-(((2-(2-METHYL-1H-INDOL-3-YL)ETHYL)AMINO)METHYL)PHENYL)PROP-2-ENAMIDERefChem:56999NVP LBH589DTXCID10115997

Datenbank-Bezeichner

Eigenschaften

Berechnete Struktureigenschaften

XLogP
3
Polarare Oberfläche (TPSA)
77,2 Ų
H-Brücken-Donoren
4
H-Brücken-Akzeptoren
3
Frei drehbare Bindungen
7
Schwere Atome
26
Formalladung
0
Komplexität
474

Experimentelle und physikochemische Eigenschaften

DrugsPharmaceuticals -> Listed in ZINC15
Human DrugsEMA approved medicines: Human medicine

Physikochemische Eigenschaften

Schmelzpunkt
114 · 114-117C
Dichte
1.241 · 1.241±0.06 g/cm3(Predicted)
storage temp.
-20 °C · -20°C Freezer, Under Inert Atmosphere
Löslichkeit
Soluble in DMSO (up to 100 mg/ml) or in Ethanol (up to 5 mg/ml with warming).
pka
8.71 · 8.71±0.23(Predicted)
Aggregatzustand
solid
Farbe
Off-white
Stabilität
1 year · Stable for 1 year from date of purchase as supplied. Solutions in DMSO or ethanol may be stored at -20° for up to 1 month.
InChI
InChI=1S/C21H23N3O2/c1-15-18(19-4-2-3-5-20(19)23-15)12-13-22-14-17-8-6-16(7-9-17)10-11-21(25)24-26/h2-11,22-23,26H,12-14H2,1H3,(H,24,25)/b11-10+

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 · 4 Einträge

Danger

H301+H331 (97.2%): Toxic if swallowed or if inhaled [Danger Acute toxicity, oral; acute toxicity, inhalation]

P203, P260, P261, P264, P264+P265, P270, P271, P280, P301+P316, P302+P352, P304+P340, P305+P354+P338, P316, P317, P318, P319, P321, P330, P332+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 71 reports by companies from 6 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Gefahrenhinweise

Hazard Classes and CategoriesAcute Tox. 3 (98.6%)

Toxikologische Informationen

Hepatotoxicity · 1 Eintrag

Most clinical trials of panobinostat have not reported rates of serum enzyme elevations during therapy and it is typically given in combination with other antineoplastic agents that can cause serum ALT and AST elevations. In the large controlled trial of panobinostat vs placebo in combination with bortezomib and dexamethasone, ALT elevations occurred in similar proportion of patients receiving panobinostat (31%) as placebo (38%) and values above 5 times the upper limit of normal were uncommon (1.8% and 1.3%). In addition, there have been no reports of clinically apparent liver injury with jaundice associated with panobinostat therapy. Thus, panobinostat appears to have little hepatotoxic potential and liver injury from panobinostat must be quite rare, if it occurs at all.

Sicherheitsdaten

wgk
WGK 3
hs_code
29339900

Chemie und Industrie

Pharmakologische Informationen

ATC Code · 3 Einträge

L01XX42

L - Antineoplastic and immunomodulating agents

QL - Antineoplastic and immunomodulating agents

Mechanism of Action · 1 Eintrag

Panobinostat is a deacetylase (DAC) inhibitor. DACs, also known as histone DACs (HDAC), are responsible for regulating the acetylation of about 1750 proteins in the body; their functions are involved in many biological processes including DNA replication and repair, chromatin remodelling, transcription of genes, progression of the cell-cycle, protein degradation and cytoskeletal reorganization. In multiple myeloma, there is an overexpression of DAC proteins. Panobinostat inhibits class I (HDACs 1, 2, 3, 8), class II (HDACs 4, 5, 6, 7, 9, 10) and class IV (HDAC 11) proteins. Panobinostat's antitumor activity is believed to be attributed to epigenetic modulation of gene expression and inhibition of protein metabolism. Panobinostat also exhibits cytotoxic synergy with bortezomib, a proteasome inhibitor concurrently used in treatment of multiple myeloma.

Biological Half-Life30 hours
Metabolism/Metabolites · 1 Eintrag

Panobinostat was extensively metabolized to 77 metabolites. Unchanged panobinostat recovered in urine and feces was 2% and 3%, respectively. Primary metabolic pathways of panobinostat are reduction, hydrolysis, oxidation, and glucuronidation processes. CYP and non-CYP enzymes were found to play significant role in metabolism, CYP2D6 and CYP2C19 playing minor roles.

FDA Pharmacological Classification · 6 Einträge

9647FM7Y3Z

histone deacetylase (HDAC) inhibitor

Established Pharmacologic Class [EPC] - Histone Deacetylase Inhibitor

Mechanisms of Action [MoA] - Histone Deacetylase Inhibitors

Mechanisms of Action [MoA] - Cytochrome P450 2D6 Inhibitors

Histone deacetylase (hdac) inhibitor is a Histone Deacetylase Inhibitor. The mechanism of action of histone deacetylase (hdac) inhibitor is as a Histone Deacetylase Inhibitor and Cytochrome P450 2D6 Inhibitor.

Zugehörige Reaktionen

7
Reaktionsaufzeichnung erstellen
Reaktionsgleichung von HRID 43286
HRID 43286als Produktuspto-grants-2013_09
Reaktionsgleichung von HRID 1669594
HRID 1669594als Eduktuspto-grants-2011_08
Reaktionsgleichung von HRID 1669595
HRID 1669595als Eduktuspto-grants-2011_08
Reaktionsgleichung von HRID 1669596
HRID 1669596als Eduktuspto-grants-2011_08
Reaktionsgleichung von HRID 1669597
HRID 1669597als Eduktuspto-grants-2011_08
Reaktionsgleichung von HRID 1669861
HRID 1669861als Eduktuspto-grants-2011_08
Reaktionsgleichung von HRID 1669862
HRID 1669862als Eduktuspto-grants-2011_08

Notizen zur Verbindung

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Auf dieser SeiteGrundinformationenÜberblickNamen und BezeichnerEigenschaftenSicherheit und RegulatorischesChemie und IndustrieZugehörige ReaktionenNotizen zur Verbindung
CAS
404950-80-7
PubChem CID
6918837
DTXSID
DTXSID40193506
ChEMBL
CHEMBL483254
ChEBI
CHEBI:85990
UNII
9647FM7Y3Z
EC Number
803-814-1
Nikkaji
J2.554.199E、J3.451.397J
InChIKey
FPOHNWQLNRZRFC-ZHACJKMWSA-N
SMILES
C(NO)(=O)/C=C/C1=CC=C(CNCCC2C3=C(NC=2C)C=CC=C3)C=C1
risk_code
22-36/37/38-20
safety_code
24/25
Speicherklasse
6.1C - Combustible acute toxic Cat.3toxic compounds or compounds which causing chronic effects
Hazard Classifications
Acute Tox. 3 InhalationAcute Tox. 3 OralEye Dam. 1Repr. 1BSkin Irrit. 2STOT RE 2 Inhalation
MeSH Pharmacological Classification · 2 Einträge

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.

Absorption, Distribution and ExcretionAfter a 20 mg dose, panobinostat was quickly absorbed with a time to maximum absorption of 2 hours.
Anwendungen · 2 Einträge

BeschreibungPanobinostat is a potent inhibitor of all histone deacetylases (HDACs), with Ki values ranging from 0.6 to 31 nM for HDAC1-11. Through this action, it leads to acetylation of a range of cellular proteins, resulting in cell cycle arrest and apoptosis in cancer cells. It has potential applications in several different forms of cancer as well as in spinal muscular atrophy and HIV therapy.

VerwendenThe novel labelled histone deacetylase inhibitor, LBH589, induces expression of DNA damage response genes and apoptosis in Ph- acute lymphoblastic leukemia cells.

Vor- und nachgelagerte Produkte

Vorgelagerte Rohstoffe

Panobinostat Carboxylic Acid Methyl Ester HydrochlorideHydroxylammoniumchloridNatriumhydroxid

Anbieter100 Anbieter

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Ergänzende Hinweise · 1 Eintrag

DefinitionChEBI: A hydroxamic acid obtained by formal condensation of the carboxy group of (2E)-3-[4-({[2-(2-methylindol-3-yl)ethyl]amino}methyl)phenyl]prop-2-enoic acid with the amino group of hydroxylamine. A histone deacetylase inhibitor used (as its la tate salt) in combination with bortezomib and dexamethasone for the treatment of multiple myeloma.