Dimebutic Acid

Details

Stereochemistry	ACHIRAL
Molecular Formula	C6H12O2
Molecular Weight	116.1583
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CCC(C)(C)C(O)=O

InChI

InChIKey=VUAXHMVRKOTJKP-UHFFFAOYSA-N

InChI=1S/C6H12O2/c1-4-6(2,3)5(7)8/h4H2,1-3H3,(H,7,8)

HIDE SMILES / InChI

Molecular Formula	C6H12O2
Molecular Weight	116.1583
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/23828223 | https://www.prnewswire.com/news-releases/hemaquest-pharmaceuticals-announces-first-patient-enrolled-in-phase-2-clinical-study-of-hqk-1001-in-patients-with-sickle-cell-disease-120655659.html | https://adisinsight.springer.com/drugs/800029658

2,2-DIMETHYLBUTYRIC ACID (HQK-1001) is an orally administered SCFAD (Short Chain Fatty Acid Derivative), which has shown an excellent safety profile and biologic effects on fetal hemoglobin induction and red blood cell production in the laboratory, relevant animal models, and in clinical trials carried out in healthy human subjects as well as patients with sickle cell disease and beta thalassemia. The compound has received Orphan Drug Designation in the United States and Europe for both sickle cell disease and beta thalassemia. HemaQuest Pharmaceuticals was developing HQK-1001 for the oral treatment of sickle cell anaemia and beta thalassaemia. HQK-1001 has been evaluated in phase II trials for beta thalassaemia and sickle cell anaemia.

Originator

Approval Year

PubMed

Title	Date	PubMed
Differential effects of short-chain fatty acids on head and neck squamous carcinoma cells.	2002 Apr	12150517
Simvastatin.	2003 Aug	12909768
[Chemical components of essential oils from the herb of Ligularia virgaurea].	2003 Jul	15139106
New polynuclear manganese clusters from the use of the hydrophobic carboxylate ligand 2,2-dimethylbutyrate.	2005 Jun 27	15962962
Novel short chain fatty acids restore chloride secretion in cystic fibrosis.	2006 Mar 31	16472777
A top-down systems biology view of microbiome-mammalian metabolic interactions in a mouse model.	2007	17515922
Top-down systems biology integration of conditional prebiotic modulated transgenomic interactions in a humanized microbiome mouse model.	2008	18628745
Probiotic modulation of symbiotic gut microbial-host metabolic interactions in a humanized microbiome mouse model.	2008	18197175
Liquid chromatography-mass spectrometric assay for quantitation of the short-chain fatty acid, 2,2-dimethylbutyrate (NSC 741804), in rat plasma.	2008 Feb 1	18155649
Fetal globin gene inducers: novel agents and new potential.	2010 Aug	20712788
Biotechnological production and applications of statins.	2010 Jan	19820926
Beta-thalassemia.	2010 May 21	20492708

Patents

Sample Use Guides

In Vivo Use Guide

Hemoglobin SS or S/β(0) thalassemia: HQK-1001 was administered daily for 26 weeks at 30 mg/kg (n = 15), 40 mg/kg (n = 18) and 50 mg/kg (n = 19), either alone (n = 21) or with hydroxyurea (n = 31).

Route of Administration: Oral

Substance Class	Chemical Created by `admin` on `Sat Dec 16 02:08:32 GMT 2023` Edited by `admin` on `Sat Dec 16 02:08:32 GMT 2023`
Record UNII	AY606CN05O
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

Dimebutic Acid

Official Name

English

NSC-16045

Code

English

NSC-741804

Code

English

2,2-DIMETHYLBUTANOIC ACID

Systematic Name

English

Butanoic acid, 2,2-dimethyl-

Systematic Name

English

Dimebutic acid [INN]

Common Name

English

2,2-DIMETHYLBUTYRIC ACID

Systematic Name

English

Classification Tree Code System Code

FDA ORPHAN DRUG

746120