Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | C4H9NO |
| Molecular Weight | 87.1204 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
CC(C)C(N)=O
InChI
InChIKey=WFKAJVHLWXSISD-UHFFFAOYSA-N
InChI=1S/C4H9NO/c1-3(2)4(5)6/h3H,1-2H3,(H2,5,6)
Isobutyramide (VX-366) is an orally available branched chain amide that may offer an alternative to current treatments for beta-hemoglobinopathy. Isobutyramide has been shown to increase fetal hemoglobin (HbF) in patients with beta-hemoglobinopathies. Isobutyramide was originated at the Children's Hospital Oakland Research Institute which, in 1993, granted exclusive worldwide rights for the agent to Vertex. However, development of Isobutyramide has been discontinued for sickle cell anaemia and thalassaemia.
Originator
Approval Year
PubMed
| Title | Date | PubMed |
|---|---|---|
| Medicinal and ethnoveterinary remedies of hunters in Trinidad. | 2001 |
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| Isobutyramide activates transcription of human fetal gamma- and murine embryonic epsilon(y)-globin genes. | 2001 Dec |
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| Design, synthesis and QSAR studies on N-aryl heteroarylisopropanolamines, a new class of non-peptidic HIV-1 protease inhibitors. | 2002 Aug |
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| In vitro neuropharmacological evaluation of piperovatine, an isobutylamide from Piper piscatorum (Piperaceae). | 2002 Dec |
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| Separation of alkamides from Echinacea purpurea extracts by cyclodextrin-modified micellar electrokinetic chromatography. | 2002 Sep |
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| Induction of fetal hemoglobin expression by the histone deacetylase inhibitor apicidin. | 2003 Mar 1 |
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| Isobutylamides of unsaturated fatty acids from Chrysanthemum morifolium associated with host-plant resistance against the western flower thrips. | 2003 Sep |
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| Investigating the effect of hydrogen bonding environments in amide cleavage reactions at zinc(II) complexes with intramolecular amide oxygen co-ordination. | 2004 Dec 21 |
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| Zinc(II) complexes with intramolecular amide oxygen coordination as models of metalloamidases. | 2004 Jan 7 |
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| Purification and properties of an enantioselective and thermoactive amidase from the thermophilic actinomycete Pseudonocardia thermophila. | 2004 Jul |
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| Rendering poly(amidoamine) or poly(propylenimine) dendrimers temperature sensitive. | 2004 Oct 13 |
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| Evidence for an isobutylamide associated with host-plant resistance to western flower thrips, Frankliniella occidentalis, in chrysanthemum. | 2005 Jan |
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| In vitro and in vivo immune stimulating effects of a new standardized Echinacea angustifolia root extract (Polinacea). | 2005 Jul |
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| Mass spectral characterization of fatty acid amides from alfalfa trichomes and their deterrence against the potato leafhopper. | 2005 Mar |
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| Echinacea: a miracle herb against aging and cancer? Evidence in vivo in mice. | 2005 Sep |
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| High performance liquid chromatography/electrospray ionization mass spectrometry for simultaneous analysis of alkamides and caffeic acid derivatives from Echinacea purpurea extracts. | 2006 Jan 27 |
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| Cloning and nucleotide sequence of carbaryl hydrolase gene (cahA) from Arthrobacter sp. RC100. | 2006 May |
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| Phytotherapeutic effects of Echinacea purpurea in gamma-irradiated mice. | 2007 Dec |
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| Binding to DPF-motif by the POB1 EH domain is responsible for POB1-Eps15 interaction. | 2007 Dec 21 |
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| A novel thermostable nitrilase superfamily amidase from Geobacillus pallidus showing acyl transfer activity. | 2007 Jun |
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| Structural evidence for a ligand coordination switch in liver alcohol dehydrogenase. | 2007 May 8 |
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| Metabolic control analysis: a tool for designing strategies to manipulate metabolic pathways. | 2008 |
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| New trisubstituted 1,2,4-triazole derivatives as potent ghrelin receptor antagonists. 3. Synthesis and pharmacological in vitro and in vivo evaluations. | 2008 Feb 14 |
|
| Diorganotin(IV) complexes of dipeptides containing the alpha-aminoisobutyryl residue (Aib): preparation, structural characterization, antibacterial and antiproliferative activities of [(n-Bu)2 Sn(H(-1)L)] (LH=H-Aib-L-Leu-OH, H-Aib-L-Ala-OH). | 2008 Jul |
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| Terminal nickel(ii) amide, alkoxide, and thiolate complexes containing amido diphosphine ligands of the type [N(o-C6H4PR2)2]- (R = Ph, (i)Pr, Cy). | 2008 Jul 7 |
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| R-stereoselective amidase from Rhodococcus erythropolis No. 7 acting on 4-chloro-3-hydroxybutyramide. | 2008 Mar |
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| N,N'-Bis(4-methyl-phen-yl)naphthalene-1,4-dicarboxamide N,N-dimethyl-acetamide disolvate. | 2008 Nov 20 |
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| Thalassaemia intermedia: an update. | 2009 Aug 29 |
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| N,N'-Bis(4-bromo-phen-yl)naphthalene-1,4-dicarboxamide N,N-dimethyl-acetamide disolvate. | 2009 Dec 4 |
|
| Formation and properties of stabilized aluminum nanoparticles. | 2009 Mar |
|
| Histone deacetylase inhibition improves differentiation of dendritic cells from leukemic blasts of patients with TEL/AML1-positive acute lymphoblastic leukemia. | 2009 Mar |
|
| Characteristic and spectroscopic properties of the Schiff-base model compounds. | 2009 Nov |
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| A new acylamidase from Rhodococcus erythropolis TA37 can hydrolyze N-substituted amides. | 2010 Aug |
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| Acetazolamide-based fungal chitinase inhibitors. | 2010 Dec 1 |
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| Psychophysical evaluation of a sanshool derivative (alkylamide) and the elucidation of mechanisms subserving tingle. | 2010 Mar 3 |
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| Preliminary studies on local anesthetic and antipyretic activities of Spilanthes acmella Murr. in experimental animal models. | 2010 Oct |
|
| Establishment of steady-state metabolism of ethanol in perfused rat liver: the quantitative analysis using kinetic mechanism-based rate equations of alcohol dehydrogenase. | 2010 Sep |
Patents
Sample Use Guides
Isobutyramide was administered as a suspension over a period of 3 months, from a starting dose of 50 mg/kg/day up to 150 mg/kg/day, to four adult sickle cell (SS) anemia patients. The maximum dose was maintained for 3 weeks.
Route of Administration:
Oral
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FDA ORPHAN DRUG |
82494
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FDA ORPHAN DRUG |
71792
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563-83-7
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DTXSID1060340
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C030197
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68424
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209-265-9
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ISOBUTYRAMIDE
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8423
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1653517
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82UOE7B38Z
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SUBSTANCE RECORD
