Salcaprozate sodium

Salcaprozate sodium (SNAC), an oral absorption promoter, and has the potential as a delivery agent for oral forms of heparin and insulin. Salcaprozate sodium could increase passive transcellular permeation across small intestinal epithelia based on increased lipophilicity arising from non-covalent macromolecule complexation.

Designed for biological research and industrial applications, not intended for individual clinical or medical purposes.
Salcaprozate sodium(CAS 203787-91-1)

CAT No: R1937

CAS No:203787-91-1

Synonyms/Alias:Salcaprozate sodium;203787-91-1;sodium 8-(2-hydroxybenzamido)octanoate;SNAC;Salcaprozate sodium [USAN];sodium 8-[(2-hydroxybenzoyl)amino]octanoate;Sodium salcaprozate;sodium;8-[(2-hydroxybenzoyl)amino]octanoate;E414;Octanoic acid, 8-[(2-hydroxybenzoyl)amino]-, monosodium salt;UNII-1YTW0422YU;Salcaprozic acid, sodium salt;1YTW0422YU;Salcaprozate (sodium);MFCD00952954;Salcaprozate sodium (USAN);E 414;E-414;Sodium 8-((2-hydroxybenzoyl)amino)octanoate;DTXSID50174306;sodium,8-[(2-hydroxybenzoyl)amino]octanoate;Octanoic acid, 8-((2-hydroxybenzoyl)amino)-, monosodium salt;Salcaprozic acid sodium salt;P414;C15H20NNaO4;Octanoic acid, 8-[(2-hydroxybenzoyl)amino]-, sodium salt;SNAC sodium;SCHEMBL825599;CHEMBL2107027;DTXCID3096797;Salcaprozate (sodium) (Standard);UOENJXXSKABLJL-UHFFFAOYSA-M;EX-A3434;Sodium 8-(salicyloylamino)octanoate;sodium8-(2-hydroxybenzamido)octanoate;AKOS027252576;HY-114299R;AC-31357;AS-65676;DA-67382;FS168567;SY111977;HY-114299;CS-0081977;D05787;I10998;Q27253228;SODIUM 8-[(2-HYDROXYPHENYL)FORMAMIDO]OCTANOATE;807-387-2;

Chemical Name:sodium;8-[(2-hydroxybenzoyl)amino]octanoate

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M.F/Formula
C15H20NNaO4
M.W/Mr.
301.31
Application
Delivery agent

Salcaprozate sodium is a synthetic amphiphilic compound classified as an absorption enhancer, widely recognized for its utility in biochemical and pharmaceutical research settings. Structurally, it is an N-acyl amino acid derivative, specifically the sodium salt of the salicyloyl caproic acid, which imparts both hydrophilic and lipophilic properties. These characteristics enable the molecule to interact with biological membranes, modulating their permeability and facilitating the transport of otherwise poorly absorbed substances across epithelial barriers. Its unique mechanism of action and compatibility with a range of chemical entities make it a valuable tool for scientists investigating molecular transport phenomena, formulation science, and drug delivery technologies.

Permeation enhancement studies: Salcaprozate sodium is extensively employed in studies focused on enhancing the paracellular and transcellular transport of macromolecules across epithelial cell layers. Its amphiphilic nature allows it to transiently modulate tight junctions and membrane fluidity, making it a model compound for elucidating the mechanisms by which absorption enhancers facilitate the passage of peptides, proteins, and other hydrophilic agents through intestinal or buccal mucosa. Researchers utilize this absorption enhancer in in vitro and ex vivo models to assess its effects on barrier integrity and molecular flux, thereby advancing the understanding of epithelial transport dynamics.

Formulation development: The compound serves as a critical excipient in the design and optimization of oral, nasal, and transmucosal delivery systems for challenging active pharmaceutical ingredients. Its ability to increase the bioavailability of large or hydrophilic molecules underpins its inclusion in advanced formulation studies, where it is assessed for compatibility, stability, and functional performance in various dosage forms. Scientists leverage its properties to overcome solubility and permeability barriers during the preclinical evaluation of novel drug candidates, facilitating the development of more effective delivery platforms.

In vitro absorption modeling: Researchers employ salcaprozate sodium in the construction of in vitro models that simulate human intestinal absorption. By incorporating it into Caco-2 cell monolayers or other epithelial tissue models, scientists can investigate the compound's impact on drug permeability, efflux transporter activity, and cellular uptake. These studies are crucial for predicting in vivo absorption profiles, screening new chemical entities for oral bioavailability, and informing the rational design of next-generation absorption enhancers.

Mechanistic biochemical research: The unique interaction of this absorption enhancer with membrane phospholipids and tight junction proteins makes it a valuable probe for mechanistic studies. Investigators use it to dissect the molecular pathways involved in membrane perturbation, tight junction opening, and cellular signaling cascades triggered by amphiphilic agents. Such research provides insights into the safety, reversibility, and selectivity of absorption enhancement strategies, supporting the development of compounds with improved efficacy and minimized risk.

Analytical method development: Salcaprozate sodium is also applied as a reference standard or functional additive in the development and validation of analytical methodologies for absorption enhancers. Its well-characterized physicochemical properties allow for the calibration of chromatographic and spectroscopic techniques, as well as the benchmarking of permeability assays. By serving as a model enhancer, it supports the establishment of robust, reproducible analytical protocols for quantitative and qualitative assessment in research and quality control environments.

Long-term Storage Conditions
10 mM in DMSO
InChI
InChI=1S/C15H21NO4.Na/c17-13-9-6-5-8-12(13)15(20)16-11-7-3-1-2-4-10-14(18)19;/h5-6,8-9,17H,1-4,7,10-11H2,(H,16,20)(H,18,19);/q;+1/p-1
InChI Key
UOENJXXSKABLJL-UHFFFAOYSA-M
Canonical SMILES
C1=CC=C(C(=C1)C(=O)NCCCCCCCC(=O)[O-])O.[Na+]
References
1. Riley MGI, et, al. Subchronic oral toxicity of salcaprozate sodium (SNAC) in Sprague-Dawley and Wistar rats. Int J Toxicol. Jul-Aug 2009; 28(4):278-93.
2. Twarog C, et, al. Intestinal Permeation Enhancers for Oral Delivery of Macromolecules: A Comparison between Salcaprozate Sodium (SNAC) and Sodium Caprate (C 10). Pharmaceutics. 2019 Feb 13; 11(2):78.
3. Li Y, et, al. Impact of Sodium N-[8-(2-Hydroxybenzoyl)amino]-caprylate on Intestinal Permeability for Notoginsenoside R1 and Salvianolic Acids in Caco-2 Cells Transport and Rat Pharmacokinetics. Molecules. 2018 Nov 16; 23(11):2990.

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