Avn 944
Grundinformationen
- CAS
297730-17-7- Standard-SMILES
CC[C@H](CC#N)OC(=O)N[C@@H](C)c1cccc(NC(=O)Nc2ccc(-c3cnco3)c(OC)c2)c1- InChIKey
GYCPCOJTCINIFZ-OXJNMPFZSA-N- Summenformel
- C25H27N5O5
- Durchschnittliche Molmasse
- 477,5 g/mol
- Monoisotopische Masse
- 477,20121898
Überblick
AVN944 is a biotech drug that demonstrated a statistically meaningful impact on IMPDH and other proteins that are critical to activities in cancer cells, including nucleotide biosynthesis, energy and metabolism, DNA replication, apoptosis and cell cycle control. AVN944 has been associated with cancer cell death in clinical trials. It is being investigated for the treatment of patients with advanced hematologic malignancies.
Namen und Bezeichner
- Bevorzugter Name
- Avn 944
- IUPAC
- [(2R)-1-cyanobutan-2-yl] N-[(1S)-1-[3-[[3-methoxy-4-(1,3-oxazol-5-yl)phenyl]carbamoylamino]phenyl]ethyl]carbamate
- Englischer Name
- AVN-944
- Summenformel
- C25H27N5O5
- Molmasse
- 477.51
Namen und Synonyme
AVN-944297730-17-7AVN944AVN 944I3NPL1V48QDTXSID80183921RefChem:560415DTXCID20106412(R)-1-cyanobutan-2-yl ((S)-1-(3-(3-(3-methoxy-4-(oxazol-5-yl)phenyl)ureido)phenyl)ethyl)carbamateVX-944501345-02-4(R)-1-Cyanobutan-2-yl (S)-1-(3-(3-(3-methoxy-4-(oxazol-5-yl)phenyl)ureido)phenyl)ethylcarbamate
Weitere Namen anzeigen
VX944VX 944CS-1604AVN944 (VX-944)VX 944AVN-944, 10 mM in DMSOCarbamic acid, N-[(1S)-1-[3-[[[[3-methoxy-4-(5-oxazolyl)phenyl]amino]carbonyl]amino]phenyl]ethyl]-, (1R)-1-(cyanomethyl)propyl ester
[(2R)-1-cyanobutan-2-yl] N-[(1S)-1-[3-[[3-methoxy-4-(1,3-oxazol-5-yl)phenyl]carbamoylamino]phenyl]ethyl]carbamateCarbamic acid, ((1S)-1-(3-((((3-methoxy-4-(5-oxazolyl)phenyl)amino)carbonyl)amino)phenyl)ethyl)-, (1R)-1-(cyanomethyl)propyl esterUNII-I3NPL1V48QMFCD22200574orb320202orb1225405orb1306875AVN 944 [WHO-DD]
Datenbank-Bezeichner
- CAS
297730-17-7- PubChem CID
- 9918559
- DTXSID
DTXSID80183921- ChEMBL
CHEMBL3349001- UNII
- I3NPL1V48Q
Eigenschaften
Berechnete Struktureigenschaften
- XLogP
- 3,1
- Polarare Oberfläche (TPSA)
- 139 Ų
- H-Brücken-Donoren
- 3
- H-Brücken-Akzeptoren
- 7
- Frei drehbare Bindungen
- 10
- Schwere Atome
- 35
- Formalladung
- 0
- Komplexität
- 743
Physikochemische Eigenschaften
- Siedepunkt
- 597.4 · 597.4±50.0 °C(Predicted)
- Dichte
- 1.277 · 1.277±0.06 g/cm3(Predicted)
- storage temp.
- -20 °C · Store at -20°C
- Löslichkeit
- DMSO:PBS (pH 7.2) (1:3):0.25(Max Conc. mg/mL);0.52(Max Conc. mM)DMF:30.0(Max Conc. mg/mL);62.83(Max Conc. mM)
- Aggregatzustand
- A crystalline solid
- pka
- 11.38 · 11.38±0.46(Predicted)
- Farbe
- White to off-white
- InChIKey
- GYCPCOJTCINIFZ-OXJNMPFZSA-N
- SMILES
- N([C@@H](C)c1cc(ccc1)NC(=O)Nc2cc(c(cc2)c3[o]cnc3)OC)C(=O)O[C@H](CC)CC#N
Sicherheit und Regulatorisches
Sicherheitsangaben dienen nur zur Orientierung und ersetzen weder das Sicherheitsdatenblatt (SDB) des Lieferanten noch geltende Vorschriften oder eine fachliche Bewertung.
Sicherheitsdaten
- wgk
- WGK 3
- Speicherklasse
- 11 - Combustible Solids
Chemie und Industrie
Pharmakologische Informationen
Pharmacodynamics
IMPDH is highly upregulated in most hematological cancers and in many solid tumors. AVN944 is a biotech drug that demonstrated a statistically meaningful impact in inhibiting IMPDH and other proteins that are critical to activities in cancer cells, including nucleotide biosynthesis, energy and metabolism, DNA replication, apoptosis and cell cycle control. AVN944 has been associated with cancer cell death in clinical trials. It is being investigated for the treatment of patients with advanced hematologic malignancies.
Mechanism of Action
AVN944 inhibits IMPDH and appears to induce apoptosis. Specifically, it was found that the gene HspA1A, a marker of stress response found to correlate with depleted GTP pools in cancer cell lines, is induced within hours upon the first treatment of the drug in patients, even at the trial's lowest doses. Following continued dosing of AVN944, this marker of disease cell stress was elevated even in the absence of circulating levels of the drug between doses.
Anwendungen
BeschreibungAVN944 is a selective, noncompetitive inhibitor of inosine-5''-monophosphate dehydrogenase (IMPDH; Ki = 6-10 nM for both human IMPDH isoforms), a rate-limiting enzyme involved in the de novo synthesis of purine nucleotides. Inhibition of IMPDH results in disruption of DNA and RNA synthesis, inhibition of cell proliferation, and the induction of apoptosis. AVN944 has been shown to inhibit the proliferation of multiple myeloma cells in vitro by inducing caspase-independent apoptosis. It is also reported to have antitumor properties in androgen-sensitive and androgen-independent prostate cancer cells in vitro.
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