Aspartame

Identification

Generic Name
Aspartame
DrugBank Accession Number
DB00168
Background

Flavoring agent sweeter than sugar, metabolized as phenylalanine and aspartic acid.

Type
Small Molecule
Groups
Investigational, Nutraceutical
Structure
Weight
Average: 294.3031
Monoisotopic: 294.121571696
Chemical Formula
C14H18N2O5
Synonyms
  • 1-Methyl N-L-alpha-aspartyl-L-phenylalanate
  • 1-methyl N-L-α-aspartyl-L-phenylalanate
  • 3-Amino-N-(alpha-carboxyphenethyl)succinamic acid N-methyl ester
  • 3-Amino-N-(alpha-methoxycarbonylphenethyl) succinamic acid
  • 3-Amino-N-(α-carboxyphenethyl)succinamic acid N-methyl ester
  • 3-Amino-N-(α-methoxycarbonylphenethyl) succinamic acid
  • Asp-phe-ome
  • Aspartam
  • Aspartame
  • Aspartamo
  • Aspartamum
  • Aspartylphenylalanine methyl ester
  • L-Aspartyl-L-phenylalanine methyl ester
External IDs
  • E-951
  • SC-18862

Pharmacology

Indication

Used as a diet supplement and sugar substitute.

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Associated Therapies
Contraindications & Blackbox Warnings
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Pharmacodynamics

Aspartame (L-alpha-aspartyl-L-phenylalanine methyl ester) is a low-calorie sweetener used to sweeten a wide variety of low- and reduced-calorie foods and beverages, including low-calorie tabletop sweeteners. Aspartame is composed of two amino acids, aspartic acid and phenylalanine, as the methyl ester. Aspartic acid and phenylalanine are also found naturally in protein containing foods, including meats, grains and dairy products. Methyl esters are also found naturally in many foods such as fruits and vegetable and their juices. Upon digestion, aspartame breaks down into three components (aspartic acid, phenylalanine and methanol), which are then absorbed into the blood and used in normal body processes. Neither aspartame nor its components accumulates in the body. These components are used in the body in the same ways as when they are derived from common foods.

Mechanism of action

180 to 200 times sweeter than sucrose, it is metabolized as a protein and its subsequent amino-acids used up in there respective mechanisms.

TargetActionsOrganism
UTaste receptor type 1 member 3Not AvailableHumans
UTaste receptor type 1 member 2
agonist
Humans
UTransient receptor potential cation channel subfamily V member 1
inducer
Humans
Absorption

Absorbed in the small intestine, aspartame is metabolized and absorbed very quickly.

Volume of distribution

Not Available

Protein binding

Not Available

Metabolism

Approximately 10% of aspartame (by weight) is broken down into methanol in the small intestine. Most of the methanol is absorbed and quickly converted into formaldehyde. Approximately 50% of aspartame (by weight) is broken down into phenylalanine. Approximately 40% of aspartame (by mass) is broken down into aspartic acid.

Route of elimination

Not Available

Half-life

At room temperature, aspartame is most stable at pH 4.3, where its half-life is nearly 300 days. At pH 7, its half-life is shortened to only a few days.

Clearance

Not Available

Adverse Effects
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Toxicity

Mild gastrointestinal side effects including diarrhea have been reported.

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
AcamprosateThe excretion of Acamprosate can be decreased when combined with Aspartame.
AcyclovirThe excretion of Acyclovir can be decreased when combined with Aspartame.
Adefovir dipivoxilThe excretion of Adefovir dipivoxil can be decreased when combined with Aspartame.
AllopurinolThe excretion of Allopurinol can be decreased when combined with Aspartame.
Aminohippuric acidThe excretion of Aminohippuric acid can be decreased when combined with Aspartame.
Food Interactions
Not Available

Products

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International/Other Brands
Aminosweet (Ajinomoto) / Canderel (Merisant) / Equal (Merisant) / Nutrasweet (NutraSweet)
Over the Counter Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
แอสพาร์เทม ชนิดผงPowder38 mg/1sachetOralบริษัท โรงงานเภสัชกรรมแหลมทองการแพทย์ จำกัด จำกัด2000-04-04Not applicableThailand flag
แอสพาร์เทม เม็ดTablet20 mgOralบริษัท โรงงานเภสัชกรรมแหลมทองการแพทย์ จำกัด จำกัด2000-09-03Not applicableThailand flag
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
HEPASELAMİN AMİNOASİT IV İNFÜZYON ÇÖZELTİSİ 500 ML SETLİ ŞİŞEAspartame (0.9 %) + Ademetionine (0.24 %) + Adenine (0.8 %) + Ascorbic acid (0.6 %) + Biotin (0.1 %) + Calcifediol (0.9 %) + Cysteine (0.066 %) + Lysine (0.61 %) + Methionine (0.5 %) + NADH (0.45 %) + Phosphoric acid (0.115 %) + Thiamine (0.02 %) + Tryptophan (1.1 %) + Tyrosine (0.1 %) + Valine (0.77 %) + Vitamin A (0.84 %)SolutionIntravenousOSEL İLAÇ SAN. VE TİC. A.Ş.2003-12-31Not applicableTurkey flag
HEPASELAMİN AMİNOASİT IV İNFÜZYON ÇÖZELTİSİ 500 ML SETSİZ ŞİŞEAspartame (0.9 %) + Ademetionine (0.24 %) + Adenine (0.8 %) + Ascorbic acid (0.6 %) + Biotin (0.1 %) + Calcifediol (0.9 %) + Cysteine (0.066 %) + Lysine (0.61 %) + Methionine (0.5 %) + NADH (0.45 %) + Phosphoric acid (0.115 %) + Thiamine (0.02 %) + Tryptophan (1.1 %) + Tyrosine (0.1 %) + Valine (0.77 %) + Vitamin A (0.84 %)SolutionIntravenousOSEL İLAÇ SAN. VE TİC. A.Ş.2003-12-31Not applicableTurkey flag
HEPATAMINE %8 500 ML(SETLI)Aspartame (0.9 %) + Ademetionine (0.24 %) + Adenine (0.8 %) + Ascorbic acid (0.6 %) + Biotin (0.1 %) + Calcifediol (0.9 %) + Cysteine (0.066 %) + Lysine (0.61 %) + Methionine (0.5 %) + NADH (0.45 %) + Phosphoric acid (0.115 %) + Sodium bisulfite (0.01 %) + Thiamine (0.02 %) + Tryptophan (1.1 %) + Tyrosine (0.1 %) + Valine (0.77 %) + Vitamin A (0.84 %)SolutionIntravenousECZACIBAŞI-BAXTER HASTANE ÜRÜNLERİ SAN.VE TİC. A.Ş.1990-01-162024-01-23Turkey flag
HEPATAMINE %8 500 ML(SETSIZ)Aspartame (0.9 %) + Ademetionine (0.24 %) + Adenine (0.8 %) + Ascorbic acid (0.6 %) + Biotin (0.1 %) + Calcifediol (0.9 %) + Cysteine (0.066 %) + Lysine (0.61 %) + Methionine (0.5 %) + NADH (0.45 %) + Phosphoric acid (0.115 %) + Sodium bisulfite (0.01 %) + Thiamine (0.02 %) + Tryptophan (1.1 %) + Tyrosine (0.1 %) + Valine (0.77 %) + Vitamin A (0.84 %)SolutionIntravenousECZACIBAŞI-BAXTER HASTANE ÜRÜNLERİ SAN.VE TİC. A.Ş.1990-01-162024-01-23Turkey flag

Categories

Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as peptides. These are compounds containing an amide derived from two or more amino carboxylic acid molecules (the same or different) by formation of a covalent bond from the carbonyl carbon of one to the nitrogen atom of another.
Kingdom
Organic compounds
Super Class
Organic acids and derivatives
Class
Carboxylic acids and derivatives
Sub Class
Amino acids, peptides, and analogues
Direct Parent
Peptides
Alternative Parents
Phenylalanine and derivatives / Alpha amino acid esters / N-acyl-alpha amino acids and derivatives / Beta amino acids and derivatives / Amphetamines and derivatives / Fatty acid esters / Dicarboxylic acids and derivatives / Methyl esters / Amino acids / Propargyl-type 1,3-dipolar organic compounds
show 7 more
Substituents
Alpha peptide / Alpha-amino acid ester / Alpha-amino acid or derivatives / Amine / Amino acid / Amino acid or derivatives / Amphetamine or derivatives / Aromatic homomonocyclic compound / Benzenoid / Beta amino acid or derivatives
show 23 more
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
dipeptide, methyl ester, carboxylic acid (CHEBI:2877)
Affected organisms
  • Humans and other mammals

Chemical Identifiers

UNII
Z0H242BBR1
CAS number
22839-47-0
InChI Key
IAOZJIPTCAWIRG-QWRGUYRKSA-N
InChI
InChI=1S/C14H18N2O5/c1-21-14(20)11(7-9-5-3-2-4-6-9)16-13(19)10(15)8-12(17)18/h2-6,10-11H,7-8,15H2,1H3,(H,16,19)(H,17,18)/t10-,11-/m0/s1
IUPAC Name
(3S)-3-amino-3-{[(2S)-1-methoxy-1-oxo-3-phenylpropan-2-yl]carbamoyl}propanoic acid
SMILES
COC(=O)[C@H](CC1=CC=CC=C1)NC(=O)[C@@H](N)CC(O)=O

References

Synthesis Reference

Josef Tsau, "Convenient to use aspartame and method of making." U.S. Patent US5582351, issued August, 1972.

US5582351
General References
Not Available
Human Metabolome Database
HMDB0001894
KEGG Drug
D02381
KEGG Compound
C11045
PubChem Compound
134601
PubChem Substance
46507278
ChemSpider
118630
BindingDB
50240005
RxNav
1311524
ChEBI
2877
ChEMBL
CHEMBL171679
ZINC
ZINC000001532132
PharmGKB
PA448493
PDBe Ligand
PME
Wikipedia
Aspartame
PDB Entries
1a8j
MSDS
Download (71.9 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
3CompletedTreatmentBowel preparation therapy1
1CompletedNot AvailableHuman Immunodeficiency Virus (HIV) Infections1
Not AvailableCompletedTreatmentDiabetes / Hyperglycemia / Kidney Transplantation1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
  • Medisca Inc.
Dosage Forms
FormRouteStrength
SolutionIntravenous
TabletOral10 mg
TabletOral20 mg
Powder, for solution40 mg
PowderOral3 g
PowderOral38 mg/1sachet
Prices
Unit descriptionCostUnit
Aspartame powder1.68USD g
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)about 190 and 245-247Schlatter, J.M.; US.Patent 3,492,131; January 27, 1970; assigned to G.D. Searle & Co.
water solubilityThe solubility of aspartame in water is dependent on pH and temperature, the maximum solubility is reached at pH 2.2 (20 mg/mL at 25 °C) and the minimum solubility at pH 5.2 (pHi) is 13.5 mg/mL at 25 °C.Not Available
logP-0.1Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.651 mg/mLALOGPS
logP-1.2ALOGPS
logP-2.2Chemaxon
logS-2.6ALOGPS
pKa (Strongest Acidic)3.53Chemaxon
pKa (Strongest Basic)8.53Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count5Chemaxon
Hydrogen Donor Count3Chemaxon
Polar Surface Area118.72 Å2Chemaxon
Rotatable Bond Count8Chemaxon
Refractivity73.22 m3·mol-1Chemaxon
Polarizability29.56 Å3Chemaxon
Number of Rings1Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption-0.8218
Blood Brain Barrier-0.5562
Caco-2 permeable-0.8956
P-glycoprotein substrateSubstrate0.5137
P-glycoprotein inhibitor INon-inhibitor0.9286
P-glycoprotein inhibitor IINon-inhibitor0.9772
Renal organic cation transporterNon-inhibitor0.9573
CYP450 2C9 substrateNon-substrate0.833
CYP450 2D6 substrateNon-substrate0.8474
CYP450 3A4 substrateNon-substrate0.6928
CYP450 1A2 substrateNon-inhibitor0.8972
CYP450 2C9 inhibitorNon-inhibitor0.894
CYP450 2D6 inhibitorNon-inhibitor0.9549
CYP450 2C19 inhibitorNon-inhibitor0.9484
CYP450 3A4 inhibitorNon-inhibitor0.9437
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9792
Ames testNon AMES toxic0.7963
CarcinogenicityNon-carcinogens0.9284
BiodegradationNot ready biodegradable0.7073
Rat acute toxicity1.6896 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9948
hERG inhibition (predictor II)Non-inhibitor0.9467
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSsplash10-000i-9220000000-2625126bd17025b83933
MS/MS Spectrum - Quattro_QQQ 10V, PositiveLC-MS/MSsplash10-00ns-0690000000-e92f66ca1ae82b0ccd81
MS/MS Spectrum - Quattro_QQQ 25V, PositiveLC-MS/MSsplash10-00di-2900000000-8eec324eec1e64466b1c
MS/MS Spectrum - Quattro_QQQ 40V, PositiveLC-MS/MSsplash10-01b9-2900000000-e8415697953bc139924b
LC-MS/MS Spectrum - LC-ESI-qTof , PositiveLC-MS/MSsplash10-0080-0890000000-b2e2c2a89ceaf3d1f9db
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-00e9-0930000000-d8dbb5a34c019dc70708
MS/MS Spectrum - , positiveLC-MS/MSsplash10-0080-0890000000-b2e2c2a89ceaf3d1f9db
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-00ub-1970000000-9a4891d7e6e0a151e8ab
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-002f-0190000000-4aa50b1c6e5f60a7f909
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-01b9-2900000000-8d574788d68a24601047
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-016r-1930000000-0b7e566c73fe94f752d3
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0g4l-5900000000-c0cd73ebaaa8ee60ad14
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-014i-2900000000-3b4037485f7b5fb492ec
1H NMR Spectrum1D NMRNot Applicable
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
[1H,13C] 2D NMR Spectrum2D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-172.3735177
predicted
DarkChem Lite v0.1.0
[M-H]-177.0424177
predicted
DarkChem Lite v0.1.0
[M-H]-176.0097177
predicted
DarkChem Lite v0.1.0
[M-H]-175.18747
predicted
DeepCCS 1.0 (2019)
[M+H]+171.5815177
predicted
DarkChem Lite v0.1.0
[M+H]+176.9302177
predicted
DarkChem Lite v0.1.0
[M+H]+175.0552177
predicted
DarkChem Lite v0.1.0
[M+H]+177.54567
predicted
DeepCCS 1.0 (2019)
[M+Na]+171.1424177
predicted
DarkChem Lite v0.1.0
[M+Na]+176.0215177
predicted
DarkChem Lite v0.1.0
[M+Na]+175.7310177
predicted
DarkChem Lite v0.1.0
[M+Na]+184.24998
predicted
DeepCCS 1.0 (2019)

Targets

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insights and accelerate drug research.
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Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Taste receptor activity
Specific Function
Putative taste receptor. TAS1R1/TAS1R3 responds to the umami taste stimulus (the taste of monosodium glutamate). TAS1R2/TAS1R3 recognizes diverse natural and synthetic sweeteners. TAS1R3 is essenti...
Gene Name
TAS1R3
Uniprot ID
Q7RTX0
Uniprot Name
Taste receptor type 1 member 3
Molecular Weight
93385.155 Da
References
  1. Maillet EL, Cui M, Jiang P, Mezei M, Hecht E, Quijada J, Margolskee RF, Osman R, Max M: Characterization of the Binding Site of Aspartame in the Human Sweet Taste Receptor. Chem Senses. 2015 Oct;40(8):577-86. doi: 10.1093/chemse/bjv045. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Agonist
General Function
Taste receptor activity
Specific Function
Putative taste receptor. TAS1R2/TAS1R3 recognizes diverse natural and synthetic sweeteners.
Gene Name
TAS1R2
Uniprot ID
Q8TE23
Uniprot Name
Taste receptor type 1 member 2
Molecular Weight
95182.54 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [Article]
  3. Xu H, Staszewski L, Tang H, Adler E, Zoller M, Li X: Different functional roles of T1R subunits in the heteromeric taste receptors. Proc Natl Acad Sci U S A. 2004 Sep 28;101(39):14258-63. Epub 2004 Sep 7. [Article]
  4. Cui M, Jiang P, Maillet E, Max M, Margolskee RF, Osman R: The heterodimeric sweet taste receptor has multiple potential ligand binding sites. Curr Pharm Des. 2006;12(35):4591-600. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inducer
General Function
Transmembrane signaling receptor activity
Specific Function
Ligand-activated non-selective calcium permeant cation channel involved in detection of noxious chemical and thermal stimuli. Seems to mediate proton influx and may be involved in intracellular aci...
Gene Name
TRPV1
Uniprot ID
Q8NER1
Uniprot Name
Transient receptor potential cation channel subfamily V member 1
Molecular Weight
94955.33 Da
References
  1. Riera CE, Vogel H, Simon SA, le Coutre J: Artificial sweeteners and salts producing a metallic taste sensation activate TRPV1 receptors. Am J Physiol Regul Integr Comp Physiol. 2007 Aug;293(2):R626-34. Epub 2007 Jun 13. [Article]

Transporters

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Sodium-independent organic anion transmembrane transporter activity
Specific Function
Involved in the renal elimination of endogenous and exogenous organic anions. Functions as organic anion exchanger when the uptake of one molecule of organic anion is coupled with an efflux of one ...
Gene Name
SLC22A6
Uniprot ID
Q4U2R8
Uniprot Name
Solute carrier family 22 member 6
Molecular Weight
61815.78 Da
References
  1. Jung KY, Takeda M, Kim DK, Tojo A, Narikawa S, Yoo BS, Hosoyamada M, Cha SH, Sekine T, Endou H: Characterization of ochratoxin A transport by human organic anion transporters. Life Sci. 2001 Sep 21;69(18):2123-35. [Article]
  2. Tsuda M, Sekine T, Takeda M, Cha SH, Kanai Y, Kimura M, Endou H: Transport of ochratoxin A by renal multispecific organic anion transporter 1. J Pharmacol Exp Ther. 1999 Jun;289(3):1301-5. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Sodium-independent organic anion transmembrane transporter activity
Specific Function
Plays an important role in the excretion/detoxification of endogenous and exogenous organic anions, especially from the brain and kidney. Involved in the transport basolateral of steviol, fexofenad...
Gene Name
SLC22A8
Uniprot ID
Q8TCC7
Uniprot Name
Solute carrier family 22 member 8
Molecular Weight
59855.585 Da
References
  1. Jung KY, Takeda M, Kim DK, Tojo A, Narikawa S, Yoo BS, Hosoyamada M, Cha SH, Sekine T, Endou H: Characterization of ochratoxin A transport by human organic anion transporters. Life Sci. 2001 Sep 21;69(18):2123-35. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Sodium-independent organic anion transmembrane transporter activity
Specific Function
Mediates saturable uptake of estrone sulfate, dehydroepiandrosterone sulfate and related compounds.
Gene Name
SLC22A11
Uniprot ID
Q9NSA0
Uniprot Name
Solute carrier family 22 member 11
Molecular Weight
59970.945 Da
References
  1. Babu E, Takeda M, Narikawa S, Kobayashi Y, Enomoto A, Tojo A, Cha SH, Sekine T, Sakthisekaran D, Endou H: Role of human organic anion transporter 4 in the transport of ochratoxin A. Biochim Biophys Acta. 2002 Jun 12;1590(1-3):64-75. [Article]

Drug created at June 13, 2005 13:24 / Updated at January 02, 2024 23:42