U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ACHIRAL
Molecular Formula C15H20NO4.Na
Molecular Weight 301.3134
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of SALCAPROZATE SODIUM

SMILES

[Na+].OC1=C(C=CC=C1)C(=O)NCCCCCCCC([O-])=O

InChI

InChIKey=UOENJXXSKABLJL-UHFFFAOYSA-M
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

HIDE SMILES / InChI

Molecular Formula C15H20NO4
Molecular Weight 278.3236
Charge -1
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula Na
Molecular Weight 22.9898
Charge 1
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Salcaprozate sodium (SNAC), an oral absorption promoter that was discovered as part of a screen to identify carrier-based permeation enhancers (Pes) that could “chaperone” poorly permeable payloads across the intestine. Its potential therapeutic application as a delivery agent was tested in many formats: taste-masked liquids, tablets, and soft gelatin capsules. SNAC is the most extensively tested carrier and the only PE approved in an oral formulation designed to improve oral bioavailabilities. The mechanism of action of this compound is not clear. However, Novo Nordisk offered a mechanism of action for SNAC in its non-enteric coated tablet of the glucagon-like peptide 1 analog, semaglutide. SNAC formed a complex around the semaglutide in the stomach and caused a transient increase in local pH around the molecule. It is claimed that semaglutide is protected against pepsin by SNAC and that solubility was increased, resulting in an increased concentration-dependent flux of semaglutide across the gastric mucosa, using a transcellular mechanism as the tablet comes in intimate contact with the epithelium. Clinical trials for patients with Type 2 Diabetes have shown that the oral semaglutide co-formulated with 300 mg SNAC could be used for further clinical development.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
PubMed

PubMed

TitleDatePubMed
Subchronic oral toxicity of salcaprozate sodium (SNAC) in Sprague-Dawley and Wistar rats.
2009 Jul-Aug
Peri- and postnatal developmental toxicity of salcaprozate sodium (SNAC) in Sprague-Dawley rats.
2009 Jul-Aug
Absorption enhancers: applications and advances.
2012 Mar
Intestinal Permeation Enhancers for Oral Delivery of Macromolecules: A Comparison between Salcaprozate Sodium (SNAC) and Sodium Caprate (C(10)).
2019 Feb 13
Safety and Pharmacokinetics of Single and Multiple Ascending Doses of the Novel Oral Human GLP-1 Analogue, Oral Semaglutide, in Healthy Subjects and Subjects with Type 2 Diabetes.
2019 Jun
Patents

Sample Use Guides

In a single-dose, first-in-human trial, 135 healthy males received oral semaglutide (2-20 mg semaglutide co-formulated with 150-600 mg SNAC (SALCAPROZATE SODIUM )) or placebo with SNAC. In a 10-week, once-daily, multiple-dose trial, 84 healthy males received 20 or 40 mg oral semaglutide (with 300 mg SNAC), placebo, or placebo with SNAC, and 23 males with type 2 diabetes (T2D) received 40 mg oral semaglutide (with 300 mg SNAC), placebo, or placebo with SNAC.
Route of Administration: Oral
Substance Class Chemical
Created
by admin
on Fri Dec 15 15:32:24 GMT 2023
Edited
by admin
on Fri Dec 15 15:32:24 GMT 2023
Record UNII
1YTW0422YU
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
SALCAPROZATE SODIUM
USAN  
USAN  
Official Name English
E-414
Code English
E414
Code English
SALCAPROZATE SODIUM [USAN]
Common Name English
Sodium 8-[(2-hydroxybenzoyl)amino]octanoate
Systematic Name English
Classification Tree Code System Code
NCI_THESAURUS C2140
Created by admin on Fri Dec 15 15:32:24 GMT 2023 , Edited by admin on Fri Dec 15 15:32:24 GMT 2023
Code System Code Type Description
USAN
OO-09
Created by admin on Fri Dec 15 15:32:24 GMT 2023 , Edited by admin on Fri Dec 15 15:32:24 GMT 2023
PRIMARY
NCI_THESAURUS
C75026
Created by admin on Fri Dec 15 15:32:24 GMT 2023 , Edited by admin on Fri Dec 15 15:32:24 GMT 2023
PRIMARY
SMS_ID
100000171991
Created by admin on Fri Dec 15 15:32:24 GMT 2023 , Edited by admin on Fri Dec 15 15:32:24 GMT 2023
PRIMARY
PUBCHEM
23669833
Created by admin on Fri Dec 15 15:32:24 GMT 2023 , Edited by admin on Fri Dec 15 15:32:24 GMT 2023
PRIMARY
CAS
203787-91-1
Created by admin on Fri Dec 15 15:32:24 GMT 2023 , Edited by admin on Fri Dec 15 15:32:24 GMT 2023
PRIMARY
RXCUI
2200637
Created by admin on Fri Dec 15 15:32:24 GMT 2023 , Edited by admin on Fri Dec 15 15:32:24 GMT 2023
PRIMARY
EPA CompTox
DTXSID50174306
Created by admin on Fri Dec 15 15:32:24 GMT 2023 , Edited by admin on Fri Dec 15 15:32:24 GMT 2023
PRIMARY
MESH
C111140
Created by admin on Fri Dec 15 15:32:24 GMT 2023 , Edited by admin on Fri Dec 15 15:32:24 GMT 2023
PRIMARY
DAILYMED
1YTW0422YU
Created by admin on Fri Dec 15 15:32:24 GMT 2023 , Edited by admin on Fri Dec 15 15:32:24 GMT 2023
PRIMARY
FDA UNII
1YTW0422YU
Created by admin on Fri Dec 15 15:32:24 GMT 2023 , Edited by admin on Fri Dec 15 15:32:24 GMT 2023
PRIMARY
ChEMBL
CHEMBL16503
Created by admin on Fri Dec 15 15:32:24 GMT 2023 , Edited by admin on Fri Dec 15 15:32:24 GMT 2023
PRIMARY
Related Record Type Details
PARENT -> SALT/SOLVATE