| Identification | Back Directory | [Name]
Pracinostat | [CAS]
929016-96-6 | [Synonyms]
SB939
CS-60
Pracinostat
SB939, >98%
Pracinostat, >=98%
Pracinostat (SB939)
SB 939 Pracinostat
SB939; SB-939; SB 939
Pracinostat USP/EP/BP
PRACINOSTAT (SB939), >98%
Pracinostat Hydrochloride
PRACINOSTAT (SB939);SB939; SB-939
KaeMpferol 3-O-β-D-(6-E-p-CouMaroylglucoside)
(E)-3-[2-butyl-1-[2-(diethylamino)ethyl]benzimidazol-5-yl]-N-hydroxyprop-2-enamide
(2E)-3-[2-Butyl-1-[2-(diethylaMino)ethyl]-1H-benziMidazol-5-yl]-N-hydroxyacrylaMide
(E)-3-[2-Butyl-1-(2-diethylaMinoethyl)-1H-benziMidazol-5-yl]-N-hydroxy-2-propenaMide
(E)-3-(2-BUTYL-1-(2-(DIETHYLAMINO)ETHYL)-1H-BENZO[D]IMIDAZOL-5-YL)-N-HYDROXYACRYLAMIDE
(2E)-3-[2-Butyl-1-[2-(diethylaMino)ethyl]-1H-benziMidazol-5-yl]-N-hydroxy-2-propenaMide
2-Propenamide, 3-[2-butyl-1-[2-(diethylamino)ethyl]-1H-benzimidazol-5-yl]-N-hydroxy-, (2E)-
(2E)-3-[2-Butyl-1-[2-(diethylamino)ethyl]-1H-benzimidazol-5-yl]-N-hydroxyacrylamide Pracinostat (SB939) | [Molecular Formula]
C20H30N4O2 | [MDL Number]
MFCD17215206 | [MOL File]
929016-96-6.mol | [Molecular Weight]
358.478 |
| Chemical Properties | Back Directory | [density ]
1.11 | [storage temp. ]
Store at -20°C | [solubility ]
insoluble in H2O; ≥11.4 mg/mL in DMSO; ≥24.8 mg/mL in EtOH with ultrasonic | [form ]
solid | [pka]
8.67±0.23(Predicted) | [color ]
White to light brown | [InChI]
InChI=1S/C20H30N4O2/c1-4-7-8-19-21-17-15-16(10-12-20(25)22-26)9-11-18(17)24(19)14-13-23(5-2)6-3/h9-12,15,26H,4-8,13-14H2,1-3H3,(H,22,25)/b12-10+ | [InChIKey]
JHDKZFFAIZKUCU-ZRDIBKRKSA-N | [SMILES]
C(NO)(=O)/C=C/C1=CC=C2N(CCN(CC)CC)C(CCCC)=NC2=C1 |
| Hazard Information | Back Directory | [Uses]
Pracinostat is a potent and orally active histone deacetylase (HDAC) inhibitor with high tumor exposure and efficacy in mouse models of colorectal cancer. The selectivity of Pracinostat for tumor tissues makes it a promising therapeutic candidate for use in patients with advanced solid malignancies. | [Definition]
ChEBI: Pracinostat is a hydroxamic acid that is N-hydroxyacrylamide which is substituted at position 3 by a 2-butyl-1-[2-(diethylamino)ethyl]-1H-benzimidazol-5-yl group (the E isomer). An orally available pan-histone deacetylase inhibitor with demonstrated activity in the treatment of advanced solid tumours. It has a role as an EC 3.5.1.98 (histone deacetylase) inhibitor, an antineoplastic agent, an apoptosis inducer and an antimalarial. It is an olefinic compound, a hydroxamic acid, a benzimidazole and a tertiary amino compound. | [Biological Activity]
pracinostat, also known as sb939, is a potent and orally available inhibitor of histone deacetylase (hdac) with a relatively stronger selectivity (more than 1000-fold) for class i, class ii and class iv hdacs rather than class iii hdacs. pracinostat potently suppresses proliferation in a wide range of cancer cell lines, including colon cancer, ovarian cancer, prostate carcinomas, acute myeloid leukaemia (aml) and b cell lymphoma. recent study results have shown that sb939 induces the accumulation of acetylated histone h3 (ach3) and acetylated α-tubulin and increases the expression of the cyclin dependent kinase inhibitor p21 in cancer cells.razak ar, hotte sj, siu ll, chen ex, hirte hw, powers j, walsh w, stayner la, laughlin a, novotny-diermayr v, zhu j, eisenhauer ea. phase i clinical, pharmacokinetic and pharmacodynamic study of sb939, an oral histone deacetylase (hdac) inhibitor, in patients with advanced solid tumours. br j cancer. 2011;104(5):756-762. | [in vivo]
Pracinostat (SB939, 25-100 mg/kg) shows significant dose-dependent growth inhibition of HCT-116 xenografts. SB939 selectively accumulates in tumor tissue. SB939 (50 or 75 mg/kg) exhibits anti-tumor activities in the Apcmin genetic colon cancer mouse model[1]. Pracinostat (25 or 50?mg/kg per day for 21 days) induces significant inhibition of tumor growth (TGI), by 59 and 116%, respectively, in mice bearing MV4-11 xenografts. Pracinostat (75?mg/kg, q.o.d) in combination with pacritinib is efficacious and synergistic in vivo in two different models of human AML. Pracinostat and pacritinib have synergistic effects on AML-induced plasma cytokines/growth factors/chemokines[3]. | [target]
HDAC1 | [IC 50]
HDAC10: 40 nM (IC50); HDAC3: 43 nM (IC50); HDAC5: 47 nM (IC50); HDAC1: 49 nM (IC50); HDAC4: 56 nM (IC50); HDAC9: 70 nM (IC50); HDAC11: 93 nM (IC50); HDAC2: 96 nM (IC50); HDAC7: 137 nM (IC50); HDAC8: 140 nM (IC50); HDAC6: 1008 nM (IC50); MBLAC2: <10 nM (EC50) | [storage]
Store at -20°C |
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