Salcaprozate sodium | CAS#203787-91-1 | Intestinal permeation enhancer

MedKoo Cat#: 463293 | Name: Salcaprozate sodium

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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Salcaprozate sodium, also known as SNAC, is an intestinal permeation enhancer (PE). It can be used as a delivery agent to promote the oral absorption of certain macromolecules with poor bioavailability such as insulin and heparin. SNAC has been applied in the development of the first oral glucagon-like peptide-1 receptor agonist semaglutide (RYBELSUS) approved in 2017. SNAC increases passive transcellular permeation across the small intestinal epithelia based on noncovalent macromolecule complexation and is associated with a pH-elevating, monomer-inducing, and pepsin-inhibiting effect in the stomach.

Chemical Structure

Salcaprozate sodium

CAS#203787-91-1 (sodium)

Theoretical Analysis

MedKoo Cat#: 463293

Name: Salcaprozate sodium

CAS#: 203787-91-1 (sodium)

Chemical Formula: C15H20NNaO4

Exact Mass: 0.0000

Molecular Weight: 301.32

Elemental Analysis: C, 59.79; H, 6.69; N, 4.65; Na, 7.63; O, 21.24

Price and Availability

Size	Price	Availability
1g	USD 250.00	2 Weeks
2g	USD 450.00	2 Weeks
5g	USD 950.00	2 Weeks
10g	USD 1,450.00	2 Weeks
25g	USD 2,450.00	2 Weeks
50g	USD 3,450.00	2 Weeks

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Related CAS #

203787-91-1 (sodium) 183990-46-7 (free acid)

Synonym

Salcaprozate sodium; E 414; E414; E-414; SNAC; Salcaprozic acid, sodium salt;

IUPAC/Chemical Name

sodium 8-(2-hydroxybenzamido)octanoate

InChi Key

UOENJXXSKABLJL-UHFFFAOYSA-M

InChi Code

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

SMILES Code

Oc1c(C(NCCCCCCCC([O-])=O)=O)cccc1.[Na+]

Appearance

Solid powder

Purity

>97% (or refer to the Certificate of Analysis

Shipping Condition

Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition

Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility

Soluble in DMSO

Shelf Life

>3 years if stored properly

Drug Formulation

This drug may be formulated in DMSO

Stock Solution Storage

0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code

2934.99.9001

More Info

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 301.32 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

1: Kang C, Bernaldez M, Stamatis SD, Rose JP, Sun R. Interaction between Permeation Enhancers and Lipid Bilayers. J Phys Chem B. 2024 Feb 22;128(7):1668-1679. doi: 10.1021/acs.jpcb.3c06448. Epub 2024 Jan 17. PMID: 38232311. 2: Akinbote OE, Verana G, Dandekar AA, Tijani AO, Mishra D, Puri A, Dinh S. Effects of Sodium Salts of Fatty Acids and Their Derivatives on Skin Permeation of Cromolyn Sodium. AAPS PharmSciTech. 2023 Nov 2;24(8):221. doi: 10.1208/s12249-023-02676-8. PMID: 37919402. 3: Kim JC, Park EJ, Na DH. Gastrointestinal Permeation Enhancers for the Development of Oral Peptide Pharmaceuticals. Pharmaceuticals (Basel). 2022 Dec 19;15(12):1585. doi: 10.3390/ph15121585. PMID: 36559036; PMCID: PMC9781085. 4: Mortensen JS, Bohr SS, Harloff-Helleberg S, Hatzakis NS, Saaby L, Nielsen HM. Physical and barrier changes in gastrointestinal mucus induced by the permeation enhancer sodium 8-[(2-hydroxybenzoyl)amino]octanoate (SNAC). J Control Release. 2022 Dec;352:163-178. doi: 10.1016/j.jconrel.2022.09.034. Epub 2022 Oct 19. PMID: 36314534. 5: Twarog C, Fattal E, Noiray M, Illel B, Brayden DJ, Taverna M, Hillaireau H. Characterization of the physicochemical interactions between exenatide and two intestinal permeation enhancers: Sodium caprate (C10) and salcaprozate sodium (SNAC). Int J Pharm. 2022 Oct 15;626:122131. doi: 10.1016/j.ijpharm.2022.122131. Epub 2022 Aug 24. PMID: 36028084. 6: Holman M, Tijani A, Klein J, Frempong D, Dinh S, Puri A. Penetration Enhancement Strategies for Intradermal Delivery of Cromolyn Sodium. AAPS PharmSciTech. 2022 Jun 23;23(6):171. doi: 10.1208/s12249-022-02328-3. PMID: 35739411. 7: Kneiszl R, Hossain S, Larsson P. In Silico-Based Experiments on Mechanistic Interactions between Several Intestinal Permeation Enhancers with a Lipid Bilayer Model. Mol Pharm. 2022 Jan 3;19(1):124-137. doi: 10.1021/acs.molpharmaceut.1c00689. Epub 2021 Dec 16. PMID: 34913341; PMCID: PMC8728740. 8: Burshtein G, Itin C, Tang JCY, Galitzer H, Fraser WD, Schwartz P. The combined effect of permeation enhancement and proteolysis inhibition on the systemic exposure of orally administrated peptides: Salcaprozate sodium, soybean trypsin inhibitor, and teriparatide study in pigs. Int J Pharm X. 2021 Oct 8;3:100097. doi: 10.1016/j.ijpx.2021.100097. PMID: 34704013; PMCID: PMC8524144. 9: Hossain S, Joyce P, Parrow A, Jõemetsa S, Höök F, Larsson P, Bergström CAS. Influence of Bile Composition on Membrane Incorporation of Transient Permeability Enhancers. Mol Pharm. 2020 Nov 2;17(11):4226-4240. doi: 10.1021/acs.molpharmaceut.0c00668. Epub 2020 Oct 8. PMID: 32960068; PMCID: PMC7610231. 10: Fattah S, Ismaiel M, Murphy B, Rulikowska A, Frias JM, Winter DC, Brayden DJ. Salcaprozate sodium (SNAC) enhances permeability of octreotide across isolated rat and human intestinal epithelial mucosae in Ussing chambers. Eur J Pharm Sci. 2020 Nov 1;154:105509. doi: 10.1016/j.ejps.2020.105509. Epub 2020 Aug 8. PMID: 32777258. 11: Tomono T, Yagi H, Ukawa M, Ishizaki S, Miwa T, Nonomura M, Igi R, Kumagai H, Miyata K, Tobita E, Kobayashi H, Sakuma S. Nasal absorption enhancement of protein drugs independent to their chemical properties in the presence of hyaluronic acid modified with tetraglycine-L-octaarginine. Eur J Pharm Biopharm. 2020 Sep;154:186-194. doi: 10.1016/j.ejpb.2020.07.003. Epub 2020 Jul 15. PMID: 32681963. 12: Twarog C, Liu K, O'Brien PJ, Dawson KA, Fattal E, Illel B, Brayden DJ. A head-to-head Caco-2 assay comparison of the mechanisms of action of the intestinal permeation enhancers: SNAC and sodium caprate (C10). Eur J Pharm Biopharm. 2020 Jul;152:95-107. doi: 10.1016/j.ejpb.2020.04.023. Epub 2020 May 6. PMID: 32387703. 13: Twarog C, Fattah S, Heade J, Maher S, Fattal E, Brayden DJ. Intestinal Permeation Enhancers for Oral Delivery of Macromolecules: A Comparison between Salcaprozate Sodium (SNAC) and Sodium Caprate (C10). Pharmaceutics. 2019 Feb 13;11(2):78. doi: 10.3390/pharmaceutics11020078. PMID: 30781867; PMCID: PMC6410172. 14: Brito A, Habeych E, Silva-Zolezzi I, Galaffu N, Allen LH. Methods to assess vitamin B12 bioavailability and technologies to enhance its absorption. Nutr Rev. 2018 Oct 1;76(10):778-792. doi: 10.1093/nutrit/nuy026. PMID: 29931214. 15: Riley MG, Castelli MC, Paehler EA. Subchronic oral toxicity of salcaprozate sodium (SNAC) in Sprague-Dawley and Wistar rats. Int J Toxicol. 2009 Jul- Aug;28(4):278-93. doi: 10.1177/1091581809337737. PMID: 19636071. 16: Riley MG, York RG. Peri- and postnatal developmental toxicity of salcaprozate sodium (SNAC) in Sprague-Dawley rats. Int J Toxicol. 2009 Jul- Aug;28(4):266-77. doi: 10.1177/1091581809337736. PMID: 19636070. 17: Mousa SA, Zhang F, Aljada A, Chaturvedi S, Takieddin M, Zhang H, Chi L, Castelli MC, Friedman K, Goldberg MM, Linhardt RJ. Pharmacokinetics and pharmacodynamics of oral heparin solid dosage form in healthy human subjects. J Clin Pharmacol. 2007 Dec;47(12):1508-20. doi: 10.1177/0091270007307242. PMID: 18048572; PMCID: PMC4135515.