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Identification
NameSpaglumic Acid
Accession NumberDB08835
TypeSmall Molecule
GroupsApproved
Description

Spaglumic acid is the β-aspartyl isoform of N-Acetyl-l-aspartylglutamate (isospaglumic Acid is N-(N-Acetyl-l-α-aspartyl)-l-glutamic acid). In eye drops, spaglumic acid is either a magnesium or sodium salt of N-Acetyl-l-aspartylglutamate. Spaglumic acid is a mast cell stabilizer. Thus it is used in allergic conditions such as allergic conjunctivitis. Specifically spaglumic acid is approved in Portugal under the brand name Naabak and in Greece under the brand name Naaxia for use in patients with allergic conjunctivitis.

Structure
Thumb
Synonyms
N-(N-Acetyl-l-β-aspartyl)-l-glutamic acid
N-acetyl-1-aspartylglutamic acid
N-Acetyl-l-aspartylglutamate
N-Acetylaspartylglutamic acid
NAAG
External Identifiers Not Available
Approved Prescription ProductsNot Available
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International Brands
NameCompany
NaabakThea
Brand mixturesNot Available
SaltsNot Available
Categories
UNIIX81L78B3RB
CAS number4910-46-7
WeightAverage: 304.255
Monoisotopic: 304.090665483
Chemical FormulaC11H16N2O8
InChI KeyGUCKKCMJTSNWCU-BQBZGAKWSA-N
InChI
InChI=1S/C11H16N2O8/c1-5(14)12-7(11(20)21)4-8(15)13-6(10(18)19)2-3-9(16)17/h6-7H,2-4H2,1H3,(H,12,14)(H,13,15)(H,16,17)(H,18,19)(H,20,21)/t6-,7-/m0/s1
IUPAC Name
(2S)-2-[(3S)-3-carboxy-3-acetamidopropanamido]pentanedioic acid
SMILES
CC(=O)N[C@@H](CC(=O)N[C@@H](CCC(O)=O)C(O)=O)C(O)=O
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as hybrid peptides. These are compounds containing at least two different types of amino acids (alpha, beta, gamma, delta) linked to each other through a peptide bond.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentHybrid peptides
Alternative Parents
Substituents
  • Hybrid peptide
  • Glutamic acid or derivatives
  • Asparagine or derivatives
  • N-acyl-alpha-amino acid
  • N-acyl-alpha amino acid or derivatives
  • N-acyl-l-alpha-amino acid
  • Alpha-amino acid or derivatives
  • Tricarboxylic acid or derivatives
  • Fatty amide
  • N-acyl-amine
  • Fatty acyl
  • Acetamide
  • Carboxamide group
  • Secondary carboxylic acid amide
  • Carboxylic acid
  • Organooxygen compound
  • Organonitrogen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organic nitrogen compound
  • Organic oxygen compound
  • Carbonyl group
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Pharmacology
IndicationUsed in patients with allergic conjunctivitis.
PharmacodynamicsNot Available
Mechanism of actionSpaglumic acid is a mast cell stabilizer. Mast cells are involved in producing an allergic response by releasing inflammatory mediators such as histamine. Mast cell stablizers block the release of histamine and other mediators by inhibiting mast cell degranulation, which is the process of releasing these mediators. Inhibition occurs through inhibition of specific calcium channels to stabilize the mast cell and prevent degranulation.
Related Articles
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
MetabolismNot Available
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityNot Available
Affected organisms
  • Humans and other mammals
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption-0.8688
Blood Brain Barrier+0.7025
Caco-2 permeable-0.8358
P-glycoprotein substrateNon-substrate0.7019
P-glycoprotein inhibitor INon-inhibitor0.8938
P-glycoprotein inhibitor IINon-inhibitor0.9265
Renal organic cation transporterNon-inhibitor0.9589
CYP450 2C9 substrateNon-substrate0.7215
CYP450 2D6 substrateNon-substrate0.8409
CYP450 3A4 substrateNon-substrate0.6367
CYP450 1A2 substrateNon-inhibitor0.9339
CYP450 2C9 inhibitorNon-inhibitor0.9386
CYP450 2D6 inhibitorNon-inhibitor0.9636
CYP450 2C19 inhibitorNon-inhibitor0.9666
CYP450 3A4 inhibitorNon-inhibitor0.9201
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9817
Ames testNon AMES toxic0.7179
CarcinogenicityNon-carcinogens0.9381
BiodegradationReady biodegradable0.8507
Rat acute toxicity1.7395 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9888
hERG inhibition (predictor II)Non-inhibitor0.9644
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
StateSolid
Experimental PropertiesNot Available
Predicted Properties
PropertyValueSource
Water Solubility3.22 mg/mLALOGPS
logP-1.1ALOGPS
logP-2.3ChemAxon
logS-2ALOGPS
pKa (Strongest Acidic)3.01ChemAxon
pKa (Strongest Basic)-2ChemAxon
Physiological Charge-3ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area170.1 Å2ChemAxon
Rotatable Bond Count9ChemAxon
Refractivity64.06 m3·mol-1ChemAxon
Polarizability27.37 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
References
Synthesis Reference

Reddy AV, Ravindranath B: Synthesis of alpha-, beta- and cyclic spaglumic acids. Int J Pept Protein Res. 1992 Nov;40(5):472-6.

General References
  1. Sala-Rabanal M, Loo DD, Hirayama BA, Turk E, Wright EM: Molecular interactions between dipeptides, drugs and the human intestinal H+ -oligopeptide cotransporter hPEPT1. J Physiol. 2006 Jul 1;574(Pt 1):149-66. Epub 2006 Apr 20. [PubMed:16627568 ]
  2. Sanchis-Merino ME, Montero JA, Ruiz-Moreno JM, Rodriguez AE, Pastor S: Comparative efficacy of topical antihistamines in an animal model of early phase allergic conjunctivitis. Exp Eye Res. 2008 May;86(5):791-7. doi: 10.1016/j.exer.2008.02.007. Epub 2008 Mar 4. [PubMed:18378229 ]
  3. Purello D'Ambrosio F, Gangemi S, Ricciardi L, Cuzzocrea S, Di Lorenzo G: Lodoxamide versus spaglumic acid: a comparative double-blind trial on patients suffering from seasonal allergic conjunctivitis induced by Parietaria pollen. Allergol Immunopathol (Madr). 1997 Sep-Oct;25(5):233-7. [PubMed:9395007 ]
External Links
ATC CodesR01AC05S01GX03
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSDownload (37.4 KB)
Interactions
Drug InteractionsNot Available
Food InteractionsNot Available

Transporters

Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrateOther
General Function:
L-proline transmembrane transporter activity
Specific Function:
Neutral amino acid/proton symporter. Has a pH-dependent electrogenic transport activity for small amino acids such as glycine, alanine and proline. Besides small apolar L-amino acids, it also recognize their D-enantiomers and selected amino acid derivatives such as gamma-aminobutyric acid (By similarity).
Gene Name:
SLC36A1
Uniprot ID:
Q7Z2H8
Molecular Weight:
53075.045 Da
References
  1. Sala-Rabanal M, Loo DD, Hirayama BA, Turk E, Wright EM: Molecular interactions between dipeptides, drugs and the human intestinal H+ -oligopeptide cotransporter hPEPT1. J Physiol. 2006 Jul 1;574(Pt 1):149-66. Epub 2006 Apr 20. [PubMed:16627568 ]
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Drug created on February 19, 2013 16:31 / Updated on August 17, 2016 12:24