Omacetaxine Mepesuccinate
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Grundinformationen
- CAS
26833-87-4- Standard-SMILES
COC(=O)C[C@](O)(CCCC(C)(C)O)C(=O)O[C@@H]1C(OC)=C[C@]23CCCN2CCc2cc4c(cc2[C@H]13)OCO4- InChIKey
HYFHYPWGAURHIV-JFIAXGOJSA-N- Summenformel
- C29H39NO9
- Durchschnittliche Molmasse
- 545,6 g/mol
- Monoisotopische Masse
- 545,26248182
Namen und Bezeichner
- Bevorzugter Name
- Omacetaxine Mepesuccinate
- IUPAC
- 1-O-[(2S,3S,6R)-4-methoxy-16,18-dioxa-10-azapentacyclo[11.7.0.02,6.06,10.015,19]icosa-1(20),4,13,15(19)-tetraen-3-yl] 4-O-methyl (2R)-2-hydroxy-2-(4-hydroxy-4-methylpentyl)butanedioate
Namen und Synonyme
Omacetaxine mepesuccinateCeflatoninMyelostatSynriboCGX-635OmaproHomoharringtonin(-)-homoharringtonineNSC-141633mepesuccinate d'omacetaxinemepesuccinato de omacetaxinaCHEBI:71019
Weitere Namen anzeigen
(2'R,3S,4S,5R)-(-)-homoharringtonineomacetaxini mepesuccinas6FG8041S5B1-O-[(2S,3S,6R)-4-methoxy-16,18-dioxa-10-azapentacyclo[11.7.0.02,6.06,10.015,19]icosa-1(20),4,13,15(19)-tetraen-3-yl] 4-O-methyl (2R)-2-hydroxy-2-(4-hydroxy-4-methylpentyl)butanedioateCephalotaxine 4-Methyl (2R)-2-Hydroxy-2-(4-hydroxy-4-methylpentyl)butanedioate (Ester)Cephalotaxine, 4-methyl (2R)-2-hydroxy-2-(4-hydroxy-4-methylpentyl)butanedioate (ester)DTXCID80256781-((1S,3AR,14BS)-2-METHOXY-1,5,6,8,9,14B-HEXAHYDRO-4H-CYCLOPENTA(A)(1,3)DIOXOLO(4,5-H)PYRROLO(2,1-B)(3)BENZAZEPIN-1-YL) 4-METHYL (2R)-2-HYDROXY-2-(4-HYDROXY-4-METHYLPENTYL)BUTANEDIOATE
Datenbank-Bezeichner
- CAS
26833-87-4- PubChem CID
- 285033
- ChEMBL
CHEMBL46286- ChEBI
CHEBI:71019- UNII
- 6FG8041S5B
- Nikkaji
- J123.154E
Eigenschaften
Berechnete StruktureigenschaftenWird ergänzt
- XLogP
- 0,8
- Polarare Oberfläche (TPSA)
- 124 Ų
- H-Brücken-Donoren
- 2
- H-Brücken-Akzeptoren
- 10
- Frei drehbare Bindungen
- 11
- Schwere Atome
- 39
- Formalladung
- 0
- Komplexität
- 968
Experimentelle und physikochemische Eigenschaften
Stability/Shelf Life
Bulk: Room temperature and 60°C stability studies indicate the chemical to be stable for at least 30 days (HPLC). Solution: Room temperature stability studies for homoharringtonine (1mg/mL) in 10% ethanol showed 16% decomposition after 24 hours and 35% decomposition after 96 hours (HPLC).
Sicherheit und Regulatorisches
Sicherheitsangaben dienen nur zur Orientierung und ersetzen weder das Sicherheitsdatenblatt (SDB) des Lieferanten noch geltende Vorschriften oder eine fachliche Bewertung.
Gefahrenhinweise
Regulatory InformationCephalotaxine, 4-methyl (2R)-2-hydroxy-2-(4-hydroxy-4-methylpentyl)butanedioate (ester): Does not have an individual approval but may be used under an appropriate group standard
Toxikologische Informationen
Drug Induced Liver Injury
Drug Induced Liver Injury Rank (DILIrank 2.0)
Omacetaxine mepesuccinate
Ambiguous-DILI-concern
4
Adverse reactions
DOI:10.1016/j.drudis.2016.02.015
Toxicity Data
Mouse(ip): LD50: 1960 ug/kg
Mouse(ip): LD50: 6.5 mg/kg
Regulatorische Informationen
Regulatory InformationCephalotaxine, 4-methyl (2R)-2-hydroxy-2-(4-hydroxy-4-methylpentyl)butanedioate (ester): Does not have an individual approval but may be used under an appropriate group standard
Chemie und Industrie
Pharmakologische Informationen
ATC Code
L - Antineoplastic and immunomodulating agents；L01 - Antineoplastic agents；L01X - Other antineoplastic agents；L01XX - Other antineoplastic agents；L01XX40 - Omacetaxine mepesuccinate
QL - Antineoplastic and immunomodulating agents；QL01 - Antineoplastic agents；QL01X - Other antineoplastic agents；QL01XX - Other antineoplastic agents；QL01XX40 - Omacetaxine mepesuccinate
Protein BindingPlasma protein binding is equal or less than 50%.
PharmacodynamicsThe pharmacodynamics of homoharringtonine is not fully understood. It is known that homoharringtonine is involved with protein synthesis inhibition and this leads to its antineoplastic activity.
Mechanism of ActionHomoharringtonine inhibits protein synthesis by not directly binding to Bcr-Abl. It binds to the A-site cleft in the large ribosomal subunit, which affects chain elongation and prevents protein synthesis.
Biological Half-LifeHomoharringtonine has a half life of about 6 hours after subcutaneous administration.
Metabolism/MetabolitesHomoharringtonine has undergoes little hepatic metabolism and is mostly metabolized to 4’-DMHHT by plasma esterase hydrolysis.
MeSH Pharmacological Classification
Agents obtained from higher plants that have demonstrable cytostatic or antineoplastic activity.
Compounds which inhibit the synthesis of proteins. They are usually ANTI-BACTERIAL AGENTS or toxins. Mechanism of the action of inhibition includes the interruption of peptide-chain elongation, the blocking the A site of ribosomes, the misreading of the genetic code or the prevention of the attachment of oligosaccharide side chains to glycoproteins.
Absorption, Distribution and Excretion
Homoharringtonine absorption was not quantified, but maximum concentration is reached after about 30 mins.
Zugehörige Reaktionen
5
Notizen zur Verbindung
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