[4-[(Hydroxyamino)carbonyl]phenyl]carbamic acid [6-[(diethylamino)methyl]-2-naphthalenyl]methyl ester CAS#: 497833-27-9

[4-[(Hydroxyamino)carbonyl]phenyl]carbamic acid [6-[(diethylamino)methyl]-2-naphthalenyl]methyl ester Basic information

Product Name:

[4-[(Hydroxyamino)carbonyl]phenyl]carbamic acid [6-[(diethylamino)methyl]-2-naphthalenyl]methyl ester

Synonyms:

[4-[(Hydroxyamino)carbonyl]phenyl]carbamic acid [6-[(diethylamino)methyl]-2-naphthalenyl]methyl ester
Givinostat
Givinostat(ITF-2357)
Carbamic acid, N-[4-[(hydroxyamino)carbonyl]phenyl]-, [6-[(diethylamino)methyl]-2-naphthalenyl]methylester
Gavinostat
[6-(diethylaminomethyl)naphthalen-2-yl]methyl N-[4-(hydroxycarbamoyl)phenyl]carbamate
CS-2025
Givinostat(free base)

CAS:

497833-27-9

MF:

C24H27N3O4

MW:

421.49

Mol File:

497833-27-9.mol

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[4-[(Hydroxyamino)carbonyl]phenyl]carbamic acid [6-[(diethylamino)methyl]-2-naphthalenyl]methyl ester Chemical Properties

Density: 1.259
storage temp.: Store at -20°C
solubility: Soluble in DMSO
pka: 8.97±0.10(Predicted)
form: Solid
color: White to light yellow
InChI: InChI=1S/C24H27N3O4/c1-3-27(4-2)15-17-5-7-21-14-18(6-8-20(21)13-17)16-31-24(29)25-22-11-9-19(10-12-22)23(28)26-30/h5-14,30H,3-4,15-16H2,1-2H3,(H,25,29)(H,26,28)
InChIKey: YALNUENQHAQXEA-UHFFFAOYSA-N
SMILES: C(OCC1=CC=C2C(=C1)C=CC(CN(CC)CC)=C2)(=O)NC1=CC=C(C(NO)=O)C=C1

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[4-[(Hydroxyamino)carbonyl]phenyl]carbamic acid [6-[(diethylamino)methyl]-2-naphthalenyl]methyl ester Usage And Synthesis

Uses

Givinostat (ITF-2357) is a HDAC inhibitor with an IC50 of 198 and 157 nM for HDAC1 and HDAC3, respectively. Givinostat can be used for Duchenne muscular dystrophy (DMD) research[1].

Definition

ChEBI: N-[4-[(hydroxyamino)-oxomethyl]phenyl]carbamic acid [6-(diethylaminomethyl)-2-naphthalenyl]methyl ester is a carbamate ester.

in vivo

Givinostat (ITF2357) at 10 mg/kg is used as a positive control and, as expected, reduced serum TNFα by 60%. Strikingly, pretreatment of ITF3056 starting at 0.1 mg/kg significantly reduces the circulating TNFα by nearly 90%. To achieve a significant increase in serum IL-1β production, a higher dose of LPS is injected (10 mg/kg), and blood is collected after 4 h. Similarly, when pretreated with lower doses of Givinostat (ITF-2357) (1 or 5 mg/kg), there is a 22% reduction for 1 mg/kg and 40% for 5 mg/kg^[1].

IC 50

hHDAC3: 157 nM (IC₅₀); HD1-B: 7.5 nM (IC₅₀); HD1-A: 16 nM (IC₅₀); HD2: 10 nM (IC₅₀); hHDAC1: 198 nM (IC₅₀); hHDAC11: 292 nM (IC₅₀); hHDAC6: 315 nM (IC₅₀); hHDAC2: 325 nM (IC₅₀); hHDAC10: 340 nM (IC₅₀); hHDAC7: 524 nM (IC₅₀); hHDAC5: 532 nM (IC₅₀); hHDAC9: 541 nM (IC₅₀); hHDAC8: 854 nM (IC₅₀); hHDAC4: 1059 nM (IC₅₀)

References

[1] Li S, et al. Specific inhibition of histone deacetylase 8 reduces gene expression and production of proinflammatory cytokines in vitro and in vivo. J Biol Chem. 2015 Jan 23;290(4):2368-78. DOI:10.1074/jbc.M114.618454
[2] Leoni F, et al. The histone deacetylase inhibitor ITF2357 reduces production of pro-inflammatory cytokines in vitro and systemic inflammation in vivo. Mol Med. 2005 Jan-Dec;11(1-12):1-15. DOI:10.2119/2006-00005.Dinarello
[3] Wang YG, et al. Givinostat inhibition of hepatic stellate cell proliferation and protein acetylation. World J Gastroenterol. 2015 Jul 21;21(27):8326-39. DOI:10.3748/wjg.v21.i27.8326

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