Salcaprozate sodium
[CAS# 203787-91-1]

Identification

• Classification: API >> Digestive system medication
• Name: Salcaprozate sodium
• Synonyms: Sodium 8-(salicyloylamino)octanoate; Sodium 8-[(2-hydroxybenzoyl)amino]caprylate; Sodium 8-[(2-hydroxybenzoyl)amino]octanoate; Sodium N-[8-(2-hydroxybenzoyl)amino]caprylate
• Molecular Formula: C₁₅H₂₀NO₄.Na
• Molecular Weight: 301.31
• CAS Registry Number: 203787-91-1
• EC Number: 807-387-2
• SMILES: C1=CC=C(C(=C1)C(=O)NCCCCCCCC(=O)[O-])O.[Na+]

Properties

• Melting point: 183-185 °C

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H302-H315-H319
• Safety Statements: P261-P305+P351+P338

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Eye irritation	Eye Irrit.	2	H319
Acute toxicity	Acute Tox.	4	H302
Specific target organ toxicity - single exposure	STOT SE	3	H335

Discovery and Applications

Saprozan sodium (SNAC) is a compound recognized for its role as an oral absorption enhancer in pharmaceuticals. SNAC, with the chemical formula C18H27NO7S, has gained attention for its ability to enhance the delivery of therapeutic peptides and proteins, which are often difficult to administer orally due to poor gastrointestinal absorption.

The discovery of saprozan sodium stemmed from the need to overcome a major challenge in drug delivery: the effective oral delivery of large biomolecules. Peptides and proteins are essential in modern medicine, providing targeted treatments for a variety of diseases. However, their large size and susceptibility to degradation by gastrointestinal enzymes make oral administration inefficient. Traditionally, these drugs are administered by injection, which can be inconvenient and reduce patient compliance.

Research into improving the oral bioavailability of these drugs has led to the development of various absorption enhancers. Among them, SNAC is a promising candidate due to its unique properties. Saprozan sodium works by temporarily altering the permeability of the gastrointestinal epithelium, allowing larger molecules to pass more easily. It does this by interacting with the lipid bilayer of the cell membrane, thereby facilitating the transport of co-administered therapeutic agents.

One of the most important applications of SNAC is the oral administration of semaglutide, a GLP-1 receptor agonist used to treat type 2 diabetes. Semaglutide typically requires injection, but the development of an oral formulation containing SNAC has revolutionized its administration. Oral semaglutide (marketed as Rybelsus) effectively lowers blood glucose levels while offering the convenience of oral administration, greatly improving patient compliance and quality of life.

Beyond diabetes management, the potential of SNAC extends to other therapeutic areas where oral administration of peptides and proteins is required. This includes treatments for obesity, osteoporosis, and various metabolic disorders. The ability to take these drugs orally could change the treatment paradigm, making therapies more accessible and acceptable to patients.

Clinical trials have thoroughly evaluated the safety and efficacy of semaglutide sodium. Studies have shown that SNAC is well tolerated and does not cause significant long-term changes to the gastrointestinal mucosa. Its transient effect on membrane permeability ensures that gastrointestinal function returns to normal quickly after absorption of the therapeutic.

In addition to enhancing drug absorption, SNAC has been studied for its potential to improve the bioavailability of poorly soluble small molecules. This expands its application beyond peptides and proteins, providing a versatile solution for enhancing the efficacy of a wide range of oral drugs.

Despite its many advantages, the use of saccaproate sodium is not without its challenges. SNAC-based drug formulations require careful optimization to balance efficacy and safety. In addition, the regulatory approval process requires comprehensive studies to ensure that the use of absorption enhancers does not compromise the therapeutic index of the drug.

In summary, the discovery of saccaproate sodium represents a major advance in pharmaceutical science, providing a solution to the long-standing challenges of oral administration of peptides and proteins. Its use in oral drugs such as semaglutide demonstrates its potential to improve patient compliance and treatment outcomes. As research continues, SNAC is expected to play a key role in the development of new oral therapies, expanding the possibility of effective and convenient treatment options in various fields of medicine.

References

2024. The Synthesis of SNAC Phenolate Salts and the Effect on Oral Bioavailability of Semaglutide. Molecules, 29(16).
DOI: 10.3390/molecules29163909

2019. Materials for oral delivery of proteins and peptides. Nature Reviews Materials, 5(2).
DOI: 10.1038/s41578-019-0156-6

1997. Oral Delivery of Heparin in Combination with Sodium N-[8-(2-Hydroxybenzoyl)amino]caprylate: Pharmacological Considerations. Pharmaceutical Research, 14(12).
DOI: 10.1023/a:1012160703533