CAS 16409-34-0 Sodium glycodeoxycholate - Vaccine Lab / Alfa Chemistry

Sodium Glycodeoxycholate as an Epithelial Permeation Enhancer

Sodium glycodeoxycholate and sodium deoxycholate as epithelial permeation enhancers: in vitro and ex vivo intestinal and buccal bioassays Brayden DJ, et al. European Journal of Pharmaceutical Sciences, 2021, 159, 105737.

Sodium glycodeoxycholate (SGC) is a bile salt that has been studied as an epithelial permeation enhancer (PE) for intestinal and buccal drug delivery. Despite its potential, it is less popular due to concerns over non-specific action and potential toxicity.
Methodology: This study revisited SGC, comparing their efficacy and toxicity using in vitro and ex vivo models. Cytotoxicity assays were performed on Caco-2 cells to assess cellular changes at various concentrations. Both agents were tested at 10 mM concentrations in Ussing chambers to evaluate their effect on transepithelial resistance (TEER) and permeability across isolated rat colonic mucosae. Additionally, SGC and DC were tested on a buccal epithelial cell line (TR146) and isolated porcine buccal mucosae to assess their impact on cellular parameters and permeability.
Results: At concentrations greater than 2 mM, SGC altered cellular parameters over 60 minutes. The agent significantly reduced TEER and increased the permeability (Papp) of [3H]-octreotide across rat colonic mucosae. SGC, at 10 mM, also increased the Papp of paracellular markers like FITC-dextran 4000 (FD4) and the fluorescent peptide FITC-LKP without damaging tissue histology. In buccal models, SGC demonstrated high potency and efficacy, particularly in increasing the Papp of [14C]-mannitol and [3H]-octreotide across porcine buccal tissue, again without causing tissue damage.
Conclusion: SGC is an effective PE in both intestinal and buccal models, enhancing paracellular fluxes of hydrophilic molecules, including peptides. These findings suggest that SGC, in particular, holds promise for enhancing drug delivery through epithelial tissues.

Sodium Glycodeoxycholate as a Penetration Enhancer for the Preparation of Buccal Adhesive Tablets

Histological and bioadhesion studies on buccal bioadhesive tablets containing a penetration enhancer sodium glycodeoxycholate Şenel S, et al. International Journal of Pharmaceutics, 1998, 170(2), 239-245.

Sodium glycodeoxycholate (GDC) was incorporated as a penetration enhancer into a formulation containing hydroxypropyl methylcellulose (HPMC) and carbomer to create buccal adhesive tablets. GDC does not compromise the adhesiveness of the tablets and is a suitable excipient for buccal adhesive drug delivery systems.
Tablet Preparation:
The tablets were produced via direct compression, with HPMC and carbomer mixed in an 8:2 ratio. GDC was included at a concentration of 5% w/w to enhance penetration, while magnesium stearate was added at 1% w/w as a lubricant. The tablets were designed to have a surface area of 1.15 cm² exposed to the buccal mucosa.

Catalog Number	ACM16409340-3
CAS	16409-34-0
Structure
Synonyms	Glycodeoxycholic acid sodium salt; N-(3α,12α-Dihydroxy-24-oxocholan-24-yl)glycine
IUPAC Name	Sodium;2-[[(4R)-4-[(3R,5R,8R,9S,10S,12S,13R,14S,17R)-3,12-dihydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]pentanoyl]amino]acetate
Molecular Weight	471.61
Molecular Formula	C26H42NNaO5
Canonical SMILES	CC(CCC(=O)NCC(=O)[O-])C1CCC2C1(C(CC3C2CCC4C3(CCC(C4)O)C)O)C.[Na+]
InChI	InChI=1S/C26H43NO5.Na/c1-15(4-9-23(30)27-14-24(31)32)19-7-8-20-18-6-5-16-12-17(28)10-11-25(16,2)21(18)13-22(29)26(19,20)3;/h15-22,28-29H,4-14H2,1-3H3,(H,27,30)(H,31,32);/t15-,16-,17-,18+,19-,20+,21+,22+,25+,26-;/m1./s1
InChI Key	IIYSTUUVIASHBG-YEUHZSMFSA-N
Melting Point	245-250 °C
Purity	97%
Solubility	0.1 M (in water at 20 °C), clear, colorless
Appearance	White solid
Storage	Solid
Complexity	727
Covalently-Bonded Unit Count	2
Defined Atom Stereocenter Count	10
EC Number	240-455-4
Exact Mass	472.30389275
Heavy Atom Count	33
Hydrogen Bond Acceptor Count	5
Hydrogen Bond Donor Count	4
Isomeric SMILES	C[C@H](CCC(=O)NCC(=O)O)[C@H]1CC[C@@H]2[C@@]1([C@H](C[C@H]3[C@H]2CC[C@H]4[C@@]3(CC[C@H](C4)O)C)O)C.[Na]
MDL Number	MFCD00036742
Monoisotopic Mass	472.30389275
Physical State	Solid
Rotatable Bond Count	6
Topological Polar Surface Area	107 Å²