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Details

Stereochemistry ABSOLUTE
Molecular Formula 2C14H25N3O4S.5H2O
Molecular Weight 752.938
Optical Activity UNSPECIFIED
Defined Stereocenters 4 / 4
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ALITAME

SMILES

O.O.O.O.O.C[C@@H](NC(=O)[C@@H](N)CC(O)=O)C(=O)NC1C(C)(C)SC1(C)C.C[C@@H](NC(=O)[C@@H](N)CC(O)=O)C(=O)NC2C(C)(C)SC2(C)C

InChI

InChIKey=NUFKRGBSZPCGQB-FLBSXDLDSA-N
InChI=1S/2C14H25N3O4S.5H2O/c2*1-7(16-11(21)8(15)6-9(18)19)10(20)17-12-13(2,3)22-14(12,4)5;;;;;/h2*7-8,12H,6,15H2,1-5H3,(H,16,21)(H,17,20)(H,18,19);5*1H2/t2*7-,8+;;;;;/m11...../s1

HIDE SMILES / InChI

Description

Alitame [l-α-aspartyl-N-(2,2,4,4-tetramethyl-3-thioethanyl)-d-alaninamide] is an amino acid-based sweetener developed by Pfizer Central Research from l-aspartic acid, d-alanine, and 2,2,4,4-tetraethylthioethanyl amine. A terminal amide group instead of the methyl ester constituent of aspartame was used to improve the hydrolytic stability. The incorporation of d-alanine as a second amino acid in place of l-phenylalanine has resulted in optimum sweetness. The increased steric and lipophilic bulk on a small ring with a sulfur derivative has provided a very sweet product and good taste qualities. Alitame is noncariogenic. From an oral intake, 7–22% is unabsorbed and excreted in the feces. The remainder is hydrolyzed to aspartic acid and alanine amide. The aspartic acid is normally metabolized, and the alanine amide is excreted in the urine as a sulfoxide isomer, sulfone, or conjugated with glucuronic acid. U.S. Food and Drug Administration has approved alitame for use as per acceptable daily intake (ADI) value.

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency
50.0 µM [Kd]

PubMed

Patents

Sample Use Guides

In Vivo Use Guide
An acceptable daily intake (ADI) of 0–1 mg per kilogram of body weight was allocated. The estimated daily intake is 0.34 mg per kilogram of body weight, which represents the amount if alitame is the only sweetener in the diet.
Route of Administration: Oral