Sodium butyrate

Details

Stereochemistry	ACHIRAL
Molecular Formula	C4H7O2.Na
Molecular Weight	110.0869
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

[Na+].CCCC([O-])=O

InChI

InChIKey=MFBOGIVSZKQAPD-UHFFFAOYSA-M

InChI=1S/C4H8O2.Na/c1-2-3-4(5)6;/h2-3H2,1H3,(H,5,6);/q;+1/p-1

HIDE SMILES / InChI

Molecular Formula	C4H7O2
Molecular Weight	87.0972
Charge	-1
Count

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

Molecular Formula	Na
Molecular Weight	22.9898
Charge	1
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/28702095 | https://www.ncbi.nlm.nih.gov/pubmed/24868283 | https://www.ncbi.nlm.nih.gov/pubmed/24868272

Butyric acid (butanoic acid) belongs to a group of short-chain fatty acids and is thought to play several beneficial roles in the gastrointestinal tract. The butyric anion is easily absorbed by enteric cells and used as a main source of energy. Moreover, butyric acid is an important regulator of colonocyte proliferation and apoptosis, gastrointestinal tract motility and bacterial microflora composition in addition to its involvement in many other processes including immunoregulation and anti-inflammatory activity. Butyric acid shows a protective effect in inflammatory response secondary to inflammatory bowel diseases. A beneficial effect of butyric acid as one constituent of a multifaceted mechanism modulating gastrointestinal function has also been stressed in patients with the stoma and coexisting constipation. Butyric acid supplementation combined with the use of probiotics should be adopted as one of the basic therapeutic strategies in this patient group, preceding treatment with laxatives. Sodium butyrate in the form of enemas (combined in a mixture with A-300 silicon dioxide) may be a successful method of therapeutic management in patients with radiation proctitis. Sodium butyrate may also prevent diarrhea through an increased passive absorption of water in the colon and its effects on the gut microflora.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Potency
Histone deacetylase 3 35 Target ID: CHEMBL1829 Sources: https://www.ncbi.nlm.nih.gov/pubmed/21874153	Inhibitor 8297	9.0 µM [IC50]
Histone deacetylase 2 37 Target ID: CHEMBL1937 Sources: https://www.ncbi.nlm.nih.gov/pubmed/21874153	Inhibitor 8297	12.0 µM [IC50]
Histone deacetylase 8 17 Target ID: CHEMBL3192 Sources: https://www.ncbi.nlm.nih.gov/pubmed/21874153	Inhibitor 8297	15.0 µM [IC50]
Histone deacetylase 1 51 Target ID: CHEMBL325 Sources: https://www.ncbi.nlm.nih.gov/pubmed/21874153	Inhibitor 8297	16.0 µM [IC50]

Conditions

Condition	Modality	Highest Phase	Product
Ulcerative colitis 123 Sources: https://www.ncbi.nlm.nih.gov/pubmed/18614971 https://www.ncbi.nlm.nih.gov/pubmed/1612357	Primary	Phase I 428	Unknown Approved Use Unknown
Ulcerative proctosigmoiditis 2 Sources: https://www.ncbi.nlm.nih.gov/pubmed/9293933 https://www.ncbi.nlm.nih.gov/pubmed/8304299	Palliative	Phase I 428	Unknown Approved Use Unknown
Obesity 203 Sources: https://clinicaltrials.gov/ct2/show/NCT02721953	Primary	Phase III 656	Unknown Approved Use Unknown
Schizophrenia 298 Sources: https://clinicaltrials.gov/ct2/show/NCT03010865	Primary	Phase III 656	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Synthesis of the antistroke drug lubeluzole and its enantiomer. Lipase-catalyzed resolution of chiral building block.	2001	11270322
[Volatile compounds in air and oral saliva in healthy people, and in periodontitis and gingivitis patients].	2001	11236158
Epstein-Barr virus latently infected cells are selectively deleted in simulated-microgravity cultures.	2001 Apr	11409687
Histone deacetylase inhibitors promote apoptosis and differential cell cycle arrest in anaplastic thyroid cancer cells.	2001 Apr	11349829
Inactivation of hepatitis B virus in plasma by hospital in-use chemical disinfectants assessed by a modified HepG2 cell culture.	2001 Apr	11289771
SCFA increase intestinal Na absorption by induction of NHE3 in rat colon and human intestinal C2/bbe cells.	2001 Apr	11254495
Differential regulation of placental and germ cell alkaline phosphatases by glucocorticoid and sodium butyrate in human gastric carcinoma cell line TMK-1.	2001 Apr 1	11361139
dSIR2 and dHDAC6: two novel, inhibitor-resistant deacetylases in Drosophila melanogaster.	2001 Apr 15	11281647
Enhanced maturation of porcine neonatal pancreatic cell clusters with growth factors fails to improve transplantation outcome.	2001 Apr 27	11374418
Synergistic growth inhibition of prostate cancer cells by 1 alpha,25 Dihydroxyvitamin D(3) and its 19-nor-hexafluoride analogs in combination with either sodium butyrate or trichostatin A.	2001 Apr 5	11313934
Evaluation of the activity and localization of 15-lipoxygenase-1 after introduction into human colorectal carcinoma Caco-2 cells.	2001 Apr-May	11418015
Effect of the liquid upflow velocity on thermophilic sulphate reduction in acidifying granular sludge reactors.	2001 Feb	11349377
Isolation and preliminary characterization of the medium-chain fatty acid:CoA ligase responsible for activation of short- and medium-chain fatty acids in colonic mucosa from swine.	2001 Feb	11281196
Role of type II thioesterases: evidence for removal of short acyl chains produced by aberrant decarboxylation of chain extender units.	2001 Feb	11251294
In vitro fermentation characteristics of native and processed cereal grains and potato starch using ileal chyme from dogs.	2001 Feb	11219453
Dietary fiber fraction of germinated barley foodstuff attenuated mucosal damage and diarrhea, and accelerated the repair of the colonic mucosa in an experimental colitis.	2001 Feb	11207896
Radiolabeled cholinesterase substrates: in vitro methods for determining structure-activity relationships and identification of a positron emission tomography radiopharmaceutical for in vivo measurement of butyrylcholinesterase activity.	2001 Feb	11176278
Overexpression of BCL-X(L) underlies the molecular basis for resistance to staurosporine-induced apoptosis in PC-3 cells.	2001 Feb 15	11245486
Pharmacological characterisation of human 5-HT2 receptor subtypes.	2001 Feb 23	11230991
Butyrate alters the expression and activity of cell cycle components in anaplastic thyroid carcinoma cells.	2001 Jan	11272092
Effect of lipids and oleic acid on biomass development in anaerobic fixed-bed reactors. Part I: Biofilm growth and activity.	2001 Jan	11257880
Rapid and simple method for detection of fenofibric acid in human serum by high-performance liquid chromatography.	2001 Jan	11210669
A survey of lipolytic and glycolytic end-products in commercial Cheddar enzyme-modified cheese.	2001 Jan	11210051
Differential effects of adenovirus-p16 on bladder cancer cell lines can be overcome by the addition of butyrate.	2001 Jan	11205911
Downregulation of MLL-CBP fusion gene expression is associated with differentiation of SN-1 cells with t(11;16)(q23;p13).	2001 Jan 18	11313967
Evidence of a functional role for the cyclin-dependent kinase-inhibitor p21WAF1/CIP1/MDA6 in promoting differentiation and preventing mitochondrial dysfunction and apoptosis induced by sodium butyrate in human myelomonocytic leukemia cells (U937).	2001 Jul	11408941
HMG-CoA reductase inhibitor mevastatin enhances the growth inhibitory effect of butyrate in the colorectal carcinoma cell line Caco-2.	2001 Jul	11408350
Effect of temperature increase from 55 to 65 degrees C on performance and microbial population dynamics of an anaerobic reactor treating cattle manure.	2001 Jul	11394779
Characterization of the reaction mechanism for the XL-I form of bovine liver xenobiotic/medium-chain fatty acid:CoA ligase.	2001 Jul 1	11415461
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
Inhibition of growth of methane-producing bacteria of the ruminant forestomach by hydroxymethylglutaryl-SCoA reductase inhibitors.	2001 Jun	11417704
Enhanced inducible mGlu1alpha receptor expression in Chinese hamster ovary cells.	2001 Jun	11413250
Identification of new triarylethylene oxyalkanoic acid analogues as bone selective estrogen mimetics.	2001 Jun	11408177
p21 gene regulation during enterocyte differentiation.	2001 Jun 1	11368530
Purification of recombinant cutinase by extraction in an aqueous two-phase system facilitated by a fatty acid substrate.	2001 Jun 20	11344451
Genes modulated by histone acetylation as new effectors of butyrate activity.	2001 Jun 22	11423116
p21 Waf1/Cip1 can protect human colon carcinoma cells against p53-dependent and p53-independent apoptosis induced by natural chemopreventive and therapeutic agents.	2001 Jun 7	11423989
Dehalogenation of dichloroethene in a contaminated soil: fatty acids and alcohols as electron donors and an apparent requirement for tetrachloroethene.	2001 Mar	11330721
Anthelmintic activity of the stem bark extracts of Berlina grandiflora and one of its active principles, Betulinic acid.	2001 Mar	11315752
Methotrexate stimulates lung fibroblasts and epithelial cells to release eosinophil chemotactic activity.	2001 Mar	11296949
Therapeutic effects of sodium butyrate on glioma cells in vitro and in the rat C6 glioma model.	2001 Mar	11270553
Slow-release pellets of sodium butyrate do not modify azoxymethane (AOM)-induced intestinal carcinogenesis in F344 rats.	2001 Mar	11238196
Synergistic efficacy of 3n-butyrate and 5-fluorouracil in human colorectal cancer xenografts via modulation of DNA synthesis.	2001 Mar	11231942
Antitumor activity of tributyrin in murine melanoma model.	2001 Mar 26	11179828
Comamonas nitrativorans sp. nov., a novel denitrifier isolated from a denitrifying reactor treating landfill leachate.	2001 May	11411724
Clostridium uliginosum sp. nov., a novel acid-tolerant, anaerobic bacterium with connecting filaments.	2001 May	11411680
Dietary inulin improves distal colitis induced by dextran sodium sulfate in the rat.	2001 May	11374687
Short-chain fatty acid derivatives stimulate cell proliferation and induce STAT-5 activation.	2001 May 15	11342457
Removal of ethylacetate vapor from waste gases by a trickle-bed air biofilter.	2001 May 4	11278036
Olfactory response to mushroom composting emissions as a function of chemical concentration.	2001 May-Jun	11401265

Patents

Sample Use Guides

In Vivo Use Guide

Dietary Supplement: Sodium Butyrate 4.38 gms of sodium butyrate per day for 12 weeks

Route of Administration: Oral

In Vitro Use Guide

A study by Zhang et al. analyzing human colorectal cancer cell lines (HCT-116 and HT-29) treated with sodium butyrate at concentrations ranging from 0.5–5 mM found that sodium butyrate inhibited the growth of the studied cancer cells, stimulated autophagy and induced apoptotic cell death.

Substance Class	Chemical Created by `admin` on `Fri Dec 15 15:33:46 GMT 2023` Edited by `admin` on `Fri Dec 15 15:33:46 GMT 2023`
Record UNII	8RAS91C36W
Record Status	`Validated (UNII)`
Record Version

Download

Name

Type

Language

Sodium butyrate

Systematic Name

English

NSC-174280

Code

English

SODIUM BUTYRATE [WHO-DD]

Common Name

English

BUTYRIC ACID SODIUM SALT

Common Name

English

SODIUM BUTYRATE [USP-RS]

Common Name

English

SODIUM BUTYRATE [USP MONOGRAPH]

Common Name

English

BUTYRIC ACID, SODIUM SALT

Common Name

English

SODIUM BUTYRATE [HSDB]

Common Name

English

Classification Tree Code System Code

EU-Orphan Drug

EU/3/05/284