ISOBUTYRAMIDE

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

Structure Search

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)

HIDE SMILES / InChI

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/8844444 | https://www.ncbi.nlm.nih.gov/pubmed/10772882 | https://www.ncbi.nlm.nih.gov/pubmed/10772882 | https://adisinsight.springer.com/drugs/800006007

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

Targets

Primary Target	Pharmacology	Condition	Potency
gamma-globin synthesis 1 Target ID: gamma-globin synthesis Sources: https://www.ncbi.nlm.nih.gov/pubmed/8844444	Activator 1447
fetal-globin synthesis 1 Target ID: fetal-globin synthesis Sources: https://www.ncbi.nlm.nih.gov/pubmed/8844444	Activator 1447

PubMed

Title	Date	PubMed
Acetazolamide-based fungal chitinase inhibitors.	2010-12-01	21044846
LC-MS profiling of N-alkylamides in Spilanthes acmella extract and the transmucosal behaviour of its main bio-active spilanthol.	2010-11-02	20227845
Preliminary studies on local anesthetic and antipyretic activities of Spilanthes acmella Murr. in experimental animal models.	2010-10	21206617
Establishment of steady-state metabolism of ethanol in perfused rat liver: the quantitative analysis using kinetic mechanism-based rate equations of alcohol dehydrogenase.	2010-09	20724102
Natural toxins for use in pest management.	2010-08	22069667
A new acylamidase from Rhodococcus erythropolis TA37 can hydrolyze N-substituted amides.	2010-08	21073421
Psychophysical evaluation of a sanshool derivative (alkylamide) and the elucidation of mechanisms subserving tingle.	2010-03-03	20209090
Preparation of N-acetyl, tert-butyl amide derivatives of the 20 natural amino acids.	2010-03	19333720
Binding of NIR-conPK and NIR-6T to astrocytomas and microglial cells: evidence for a protein related to TSPO.	2009-12-18	20020060
N,N'-Bis(4-bromo-phen-yl)naphthalene-1,4-dicarboxamide N,N-dimethyl-acetamide disolvate.	2009-12-04	21580134
Characteristic and spectroscopic properties of the Schiff-base model compounds.	2009-11	19748307
Thalassaemia intermedia: an update.	2009-08-29	21415986
Inhibition of androstenediol-dependent LNCaP tumour growth by 17alpha-ethynyl-5alpha-androstane-3alpha, 17beta-diol (HE3235).	2009-04-07	19337256
Formation and properties of stabilized aluminum nanoparticles.	2009-03	20355993
Histone deacetylase inhibition improves differentiation of dendritic cells from leukemic blasts of patients with TEL/AML1-positive acute lymphoblastic leukemia.	2009-03	19129484
Vasorelaxant and antioxidant activities of Spilanthes acmella Murr.	2008-12	19330100
N,N'-Bis(4-methyl-phen-yl)naphthalene-1,4-dicarboxamide N,N-dimethyl-acetamide disolvate.	2008-11-20	21581351
Utilization of aliphatic nitriles under haloalkaline conditions by Bacillus alkalinitrilicus sp. nov. isolated from soda solonchak soil.	2008-11	18801047
Multiple conformational states in crystals and in solution in alphagamma hybrid peptides. Fragility of the C12 helix in short sequences.	2008-09-05	18662036
2-Substituted piperazine-derived imidazole carboxamides as potent and selective CCK1R agonists for the treatment of obesity.	2008-09-01	18684621
Chemical dissection of the link between streptozotocin, O-GlcNAc, and pancreatic cell death.	2008-08-25	18721751
Terminal nickel(ii) amide, alkoxide, and thiolate complexes containing amido diphosphine ligands of the type [N(o-C6H4PR2)2]- (R = Ph, (i)Pr, Cy).	2008-07-07	18560664
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).	2008-07	18289688
R-stereoselective amidase from Rhodococcus erythropolis No. 7 acting on 4-chloro-3-hydroxybutyramide.	2008-03	18388476
New trisubstituted 1,2,4-triazole derivatives as potent ghrelin receptor antagonists. 3. Synthesis and pharmacological in vitro and in vivo evaluations.	2008-02-14	18193826
Metabolic control analysis: a tool for designing strategies to manipulate metabolic pathways.	2008	18629230
Binding to DPF-motif by the POB1 EH domain is responsible for POB1-Eps15 interaction.	2007-12-21	18154663
Phytotherapeutic effects of Echinacea purpurea in gamma-irradiated mice.	2007-12	17993747
A novel thermostable nitrilase superfamily amidase from Geobacillus pallidus showing acyl transfer activity.	2007-06	17347819
Structural evidence for a ligand coordination switch in liver alcohol dehydrogenase.	2007-05-08	17429946
Cloning and nucleotide sequence of carbaryl hydrolase gene (cahA) from Arthrobacter sp. RC100.	2006-05	16781470
High performance liquid chromatography/electrospray ionization mass spectrometry for simultaneous analysis of alkamides and caffeic acid derivatives from Echinacea purpurea extracts.	2006-01-27	16298376
Echinacea: a miracle herb against aging and cancer? Evidence in vivo in mice.	2005-09	16136209
In vitro and in vivo immune stimulating effects of a new standardized Echinacea angustifolia root extract (Polinacea).	2005-07	15949903
Mass spectral characterization of fatty acid amides from alfalfa trichomes and their deterrence against the potato leafhopper.	2005-03	15721945
Evidence for an isobutylamide associated with host-plant resistance to western flower thrips, Frankliniella occidentalis, in chrysanthemum.	2005-01	15839483
Investigating the effect of hydrogen bonding environments in amide cleavage reactions at zinc(II) complexes with intramolecular amide oxygen co-ordination.	2004-12-21	15573171
Rendering poly(amidoamine) or poly(propylenimine) dendrimers temperature sensitive.	2004-10-13	15469255
Purification and properties of an enantioselective and thermoactive amidase from the thermophilic actinomycete Pseudonocardia thermophila.	2004-07	15103424
Zinc(II) complexes with intramolecular amide oxygen coordination as models of metalloamidases.	2004-01-07	15356757
Isobutylamides of unsaturated fatty acids from Chrysanthemum morifolium associated with host-plant resistance against the western flower thrips.	2003-09	14510603
Induction of fetal hemoglobin expression by the histone deacetylase inhibitor apicidin.	2003-03-01	12393499
In vitro neuropharmacological evaluation of piperovatine, an isobutylamide from Piper piscatorum (Piperaceae).	2002-12	12426087
Separation of alkamides from Echinacea purpurea extracts by cyclodextrin-modified micellar electrokinetic chromatography.	2002-09	12207319
Design, synthesis and QSAR studies on N-aryl heteroarylisopropanolamines, a new class of non-peptidic HIV-1 protease inhibitors.	2002-08	12057640
Larvicidal activity of isobutylamides identified in Piper nigrum fruits against three mosquito species.	2002-03-27	11902925
Isobutyramide activates transcription of human fetal gamma- and murine embryonic epsilon(y)-globin genes.	2001-12	12903753
Redox-induced terpyridyl substitution in the Os(VI)-hydrazido complex, trans-[Os(VI)(tpy)(Cl)(2)(NN(CH(2))(4)O)](2+).	2001-07-30	11466041
Effects of semen filtration and dilution rate on morphology and fertility of frozen gander spermatozoa.	2001-06-01	11414487
Medicinal and ethnoveterinary remedies of hunters in Trinidad.	2001	11737880

Patents

Sample Use Guides

In Vivo Use Guide

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

In Vitro Use Guide

Isobutyramide is essentially an uncompetitive inhibitor of purified rat liver alcohol dehydrogenase (Kii = 0.33 mM)

Name

Type

Language

NSC-8423

Preferred Name

English

ISOBUTYRAMIDE

Systematic Name

English

2-METHYLPROPIONAMIDE

Systematic Name

English

Classification Tree Code System Code

FDA ORPHAN DRUG

82494