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)

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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
Medicinal and ethnoveterinary remedies of hunters in Trinidad.	2001	11737880
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
Chemical dissection of the link between streptozotocin, O-GlcNAc, and pancreatic cell death.	2008 Aug 25	18721751
Utilization of aliphatic nitriles under haloalkaline conditions by Bacillus alkalinitrilicus sp. nov. isolated from soda solonchak soil.	2008 Nov	18801047
Characteristic and spectroscopic properties of the Schiff-base model compounds.	2009 Nov	19748307
Acetazolamide-based fungal chitinase inhibitors.	2010 Dec 1	21044846
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
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)

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