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

Molecular Formula	C4H9NO
Molecular Weight	87.1204
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

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 1430
fetal-globin synthesis 1 Target ID: fetal-globin synthesis Sources: https://www.ncbi.nlm.nih.gov/pubmed/8844444	Activator 1430

PubMed

Title	Date	PubMed
Isobutyramide activates transcription of human fetal gamma- and murine embryonic epsilon(y)-globin genes.	2001 Dec	12903753
Overexpression of Bcl-2 regulates sodium butyrate- and/or docetaxel-induced apoptosis in human bladder cancer cells both in vitro and in vivo.	2001 Jul 1	11391617
Design, synthesis and QSAR studies on N-aryl heteroarylisopropanolamines, a new class of non-peptidic HIV-1 protease inhibitors.	2002 Aug	12057640
In vitro neuropharmacological evaluation of piperovatine, an isobutylamide from Piper piscatorum (Piperaceae).	2002 Dec	12426087
Larvicidal activity of isobutylamides identified in Piper nigrum fruits against three mosquito species.	2002 Mar 27	11902925
Separation of alkamides from Echinacea purpurea extracts by cyclodextrin-modified micellar electrokinetic chromatography.	2002 Sep	12207319
Induction of fetal hemoglobin expression by the histone deacetylase inhibitor apicidin.	2003 Mar 1	12393499
Evidence for an isobutylamide associated with host-plant resistance to western flower thrips, Frankliniella occidentalis, in chrysanthemum.	2005 Jan	15839483
In vitro and in vivo immune stimulating effects of a new standardized Echinacea angustifolia root extract (Polinacea).	2005 Jul	15949903
Mass spectral characterization of fatty acid amides from alfalfa trichomes and their deterrence against the potato leafhopper.	2005 Mar	15721945
Echinacea: a miracle herb against aging and cancer? Evidence in vivo in mice.	2005 Sep	16136209
High performance liquid chromatography/electrospray ionization mass spectrometry for simultaneous analysis of alkamides and caffeic acid derivatives from Echinacea purpurea extracts.	2006 Jan 27	16298376
Cloning and nucleotide sequence of carbaryl hydrolase gene (cahA) from Arthrobacter sp. RC100.	2006 May	16781470
Phytotherapeutic effects of Echinacea purpurea in gamma-irradiated mice.	2007 Dec	17993747
Binding to DPF-motif by the POB1 EH domain is responsible for POB1-Eps15 interaction.	2007 Dec 21	18154663
A novel thermostable nitrilase superfamily amidase from Geobacillus pallidus showing acyl transfer activity.	2007 Jun	17347819
Structural evidence for a ligand coordination switch in liver alcohol dehydrogenase.	2007 May 8	17429946
Metabolic control analysis: a tool for designing strategies to manipulate metabolic pathways.	2008	18629230
Chemical dissection of the link between streptozotocin, O-GlcNAc, and pancreatic cell death.	2008 Aug 25	18721751
Vasorelaxant and antioxidant activities of Spilanthes acmella Murr.	2008 Dec	19330100
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	18193826
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	18289688
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	18560664
R-stereoselective amidase from Rhodococcus erythropolis No. 7 acting on 4-chloro-3-hydroxybutyramide.	2008 Mar	18388476
Utilization of aliphatic nitriles under haloalkaline conditions by Bacillus alkalinitrilicus sp. nov. isolated from soda solonchak soil.	2008 Nov	18801047
N,N'-Bis(4-methyl-phen-yl)naphthalene-1,4-dicarboxamide N,N-dimethyl-acetamide disolvate.	2008 Nov 20	21581351
2-Substituted piperazine-derived imidazole carboxamides as potent and selective CCK1R agonists for the treatment of obesity.	2008 Sep 1	18684621
Multiple conformational states in crystals and in solution in alphagamma hybrid peptides. Fragility of the C12 helix in short sequences.	2008 Sep 5	18662036
Inhibition of androstenediol-dependent LNCaP tumour growth by 17alpha-ethynyl-5alpha-androstane-3alpha, 17beta-diol (HE3235).	2009 Apr 7	19337256
Thalassaemia intermedia: an update.	2009 Aug 29	21415986
Binding of NIR-conPK and NIR-6T to astrocytomas and microglial cells: evidence for a protein related to TSPO.	2009 Dec 18	20020060
N,N'-Bis(4-bromo-phen-yl)naphthalene-1,4-dicarboxamide N,N-dimethyl-acetamide disolvate.	2009 Dec 4	21580134
Formation and properties of stabilized aluminum nanoparticles.	2009 Mar	20355993
Histone deacetylase inhibition improves differentiation of dendritic cells from leukemic blasts of patients with TEL/AML1-positive acute lymphoblastic leukemia.	2009 Mar	19129484
Characteristic and spectroscopic properties of the Schiff-base model compounds.	2009 Nov	19748307
Natural toxins for use in pest management.	2010 Aug	22069667
A new acylamidase from Rhodococcus erythropolis TA37 can hydrolyze N-substituted amides.	2010 Aug	21073421
Acetazolamide-based fungal chitinase inhibitors.	2010 Dec 1	21044846
Preparation of N-acetyl, tert-butyl amide derivatives of the 20 natural amino acids.	2010 Mar	19333720
Psychophysical evaluation of a sanshool derivative (alkylamide) and the elucidation of mechanisms subserving tingle.	2010 Mar 3	20209090
LC-MS profiling of N-alkylamides in Spilanthes acmella extract and the transmucosal behaviour of its main bio-active spilanthol.	2010 Nov 2	20227845
Preliminary studies on local anesthetic and antipyretic activities of Spilanthes acmella Murr. in experimental animal models.	2010 Oct	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 Sep	20724102

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)

Substance Class	Chemical Created by `admin` on `Fri Dec 15 15:53:59 GMT 2023` Edited by `admin` on `Fri Dec 15 15:53:59 GMT 2023`
Record UNII	82UOE7B38Z
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

ISOBUTYRAMIDE

Systematic Name

English

NSC-8423

Code

English

2-METHYLPROPIONAMIDE

Systematic Name

English

Classification Tree Code System Code

FDA ORPHAN DRUG

82494