Sulfobutylbetadex sodium
[CAS# 182410-00-0]

Identification

• Classification: Chemical reagent >> Organic reagent >> Cyclodextrin
• Name: Sulfobutylbetadex sodium
• Synonyms: Captisol; disodium 4-[[(1S,3R,5R,6S,8R,10R,11S,13R,15R,16S,18S,20S,21R,23S,25S,26R,28S,30S,31R,33R,35R,36R,37R,38S,39S,40S,41S,42S,43S,44R,45R,46S,47R,48R,49R)-36,37,38,39,40,41,42,43,44,45,46,48,49-tridecahydroxy-5,15,20,25,30,35-hexakis(hydroxymethyl)-47-(4-sulfonatobutoxy)-2,4,7,9,12,14,17,19,22,24,27,29,32,34-tetradecaoxaoctacyclo[31.2.2.23,6.28,11.213,16.218,21.223,26.228,31]nonatetracontan-10-yl]methoxy]butane-1-sulfonate; beta-Cyclodextrin sulfobutyl ethers sodium salts
• Molecular Formula: C₅₀H₈₄Na₂O₄₁S₂
• Molecular Weight: 1451.29
• CAS Registry Number: 182410-00-0
• EC Number: 417-710-5
• SMILES: C(CCS(=O)(=O)[O-])COC[C@@H]1[C@@H]2[C@@H]([C@H]([C@H](O1)O[C@@H]3[C@H](O[C@@H]([C@@H]([C@H]3O)O)O[C@@H]4[C@H](O[C@@H]([C@@H]([C@H]4O)O)O[C@H]5[C@@H](O[C@H]([C@H]([C@@H]5O)O)O[C@H]6[C@@H](O[C@H]([C@H]([C@@H]6O)O)O[C@H]7[C@@H](O[C@H]([C@H]([C@@H]7O)O)O[C@@H]8[C@H](O[C@H](O2)[C@@H]([C@H]8O)O)CO)CO)CO)CO)CO)CO)OCCCCS(=O)(=O)[O-])O.[Na+].[Na+]

Properties

• Melting point: 234.5 - 236 °C

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H317
• Safety Statements: P280-P302+P352

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Skin sensitization	Skin Sens.	1	H317

Discovery and Applications

Sulfobutylbetadex sodium is a modified form of beta-cyclodextrin, a cyclic oligosaccharide known for its ability to form inclusion complexes with various molecules. The modification involves the attachment of sulfobutyl groups to the beta-cyclodextrin structure, rendering it more water-soluble and ionizable, which enhances its performance in pharmaceutical applications. This compound is primarily used as an excipient to improve the solubility, stability, and bioavailability of poorly soluble drugs.

The discovery of sulfobutylbetadex sodium was driven by the need to address limitations in drug formulation, particularly with drugs that have poor water solubility. Traditional beta-cyclodextrin has been used for encapsulating hydrophobic molecules, but its limited solubility posed challenges in some formulations. The introduction of sulfobutyl groups to the beta-cyclodextrin structure increased its solubility in water, while the sodium salt form further improved its performance as a drug delivery system. This allowed sulfobutylbetadex sodium to solubilize a broader range of drugs and enhance their bioavailability when administered.

One of the primary applications of sulfobutylbetadex sodium is in the formulation of injectable drugs. Many drugs with low solubility present challenges in parenteral administration due to their inability to dissolve adequately in aqueous solutions. Sulfobutylbetadex sodium acts as a solubilizer, forming inclusion complexes with hydrophobic drugs and enabling their administration in solution form. This property is particularly valuable for improving the pharmacokinetics and efficacy of drugs that otherwise might not reach therapeutic levels in the body.

In addition to its solubilizing properties, sulfobutylbetadex sodium also enhances the stability of drugs by protecting them from degradation. By forming complexes with the drug molecules, the compound helps shield them from environmental factors such as light, heat, or oxidation. This contributes to extending the shelf life of drugs and maintaining their potency over time, making it a vital component in the formulation of stable drug products.

Sulfobutylbetadex sodium is also used in oral and topical drug formulations. In oral formulations, it helps improve the dissolution rate of poorly soluble drugs, leading to enhanced absorption in the gastrointestinal tract. In topical formulations, it can improve the delivery of active ingredients through the skin by forming complexes that enhance the penetration of the drug.

The use of sulfobutylbetadex sodium in drug formulations has expanded the possibilities for developing effective pharmaceutical products, especially for drugs with solubility challenges. Its role as a solubilizer and stabilizer continues to contribute to advancements in drug delivery technologies.

References

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