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Identification
- Summary
Spaglumic acid is the β-aspartyl isoform of N-Acetyl-l-aspartylglutamate, a naturally occurring neurotransmitter, used in allergic eye conditions due to its ability to stabilize mast cells.
- Generic Name
- Spaglumic acid
- DrugBank Accession Number
- DB08835
- Background
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.
- Type
- Small Molecule
- Groups
- Experimental
- Structure
Structure for Spaglumic acid (DB08835)
- Weight
- Average: 304.255
Monoisotopic: 304.090665483 - Chemical Formula
- C11H16N2O8
- Synonyms
- N-Acetyl-L-β-aspartyl-L-glutamic acid
- Spaglumic acid
Pharmacology
- Indication
Used in patients with allergic conjunctivitis.
Reduce drug development failure ratesBuild, train, & validate machine-learning modelswith evidence-based and structured datasets.Build, train, & validate predictive machine-learning models with structured datasets.- Associated Conditions
Indication Type Indication Combined Product Details Approval Level Age Group Patient Characteristics Dose Form Treatment of Ocular inflammation •••••••••••• •••••••• • ••••• Treatment of Ocular inflammation •••••••••••• •••••••• • ••••• Treatment of Ocular inflammation •••••••••••• •••••••• • ••••• - Contraindications & Blackbox Warnings
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Not Available
- Mechanism of action
Spaglumic 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.
Target Actions Organism UGlutamate carboxypeptidase 2 ligandHumans - Absorption
Not Available
- Volume of distribution
Not Available
- Protein binding
Not Available
- Metabolism
- Not Available
- Route of elimination
Not Available
- Half-life
Not Available
- Clearance
Not Available
- Adverse Effects
Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.- Toxicity
Not Available
- 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.Not Available
- Food Interactions
- Take with or without food.
Products
Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.- International/Other Brands
- Naabak (Thea)
Categories
- ATC Codes
- R01AC05 — Spaglumic acid
- R01AC — Antiallergic agents, excl. corticosteroids
- R01A — DECONGESTANTS AND OTHER NASAL PREPARATIONS FOR TOPICAL USE
- R01 — NASAL PREPARATIONS
- R — RESPIRATORY SYSTEM
- Drug Categories
- Chemical TaxonomyProvided by Classyfire
- Description
- This 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.
- Kingdom
- Organic compounds
- Super Class
- Organic acids and derivatives
- Class
- Peptidomimetics
- Sub Class
- Hybrid peptides
- Direct Parent
- Hybrid peptides
- Alternative Parents
- Glutamic acid and derivatives / Asparagine and derivatives / N-acyl-L-alpha-amino acids / Tricarboxylic acids and derivatives / N-acyl amines / Acetamides / Secondary carboxylic acid amides / Carboxylic acids / Organopnictogen compounds / Organonitrogen compounds show 3 more
- Substituents
- Acetamide / Aliphatic acyclic compound / Alpha-amino acid or derivatives / Asparagine or derivatives / Carbonyl group / Carboxamide group / Carboxylic acid / Carboxylic acid derivative / Fatty acyl / Fatty amide show 15 more
- Molecular Framework
- Aliphatic acyclic compounds
- External Descriptors
- Not Available
- Affected organisms
- Humans and other mammals
Chemical Identifiers
- UNII
- X81L78B3RB
- CAS number
- 4910-46-7
- InChI Key
- GUCKKCMJTSNWCU-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
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
- 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. [Article]
- 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. [Article]
- 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. [Article]
- External Links
- KEGG Drug
- D07374
- PubChem Compound
- 210320
- PubChem Substance
- 175427113
- ChemSpider
- 182277
- ChEBI
- 135289
- ChEMBL
- CHEMBL2105616
- ZINC
- ZINC000002504638
- Drugs.com
- Drugs.com Drug Page
- Wikipedia
- N-Acetylaspartylglutamic_acid
- MSDS
- Download (37.4 KB)
Clinical Trials
- Clinical Trials
Clinical Trial & Rare Diseases Add-on Data Package
Explore 4,000+ rare diseases, orphan drugs & condition pairs, clinical trial why stopped data, & more. Preview package Phase Status Purpose Conditions Count Start Date Why Stopped 100+ additional columns Unlock 175K+ rows when you subscribe.View sample data4 Completed Treatment Allergic Conjunctivitis (AC) 1 somestatus stop reason just information to hide
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
Form Route Strength Solution Ophthalmic 4.9 % Solution / drops Ophthalmic Solution / drops Ophthalmic 49 MG/ML Solution Ophthalmic 4.9 g/100ml - Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
- Not Available
- Predicted Properties
Property Value Source Water Solubility 3.22 mg/mL ALOGPS logP -1 ALOGPS logP -2.3 Chemaxon logS -2 ALOGPS pKa (Strongest Acidic) 3.01 Chemaxon pKa (Strongest Basic) -2 Chemaxon Physiological Charge -3 Chemaxon Hydrogen Acceptor Count 8 Chemaxon Hydrogen Donor Count 5 Chemaxon Polar Surface Area 170.1 Å2 Chemaxon Rotatable Bond Count 9 Chemaxon Refractivity 64.06 m3·mol-1 Chemaxon Polarizability 27.37 Å3 Chemaxon Number of Rings 0 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter No Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption - 0.8688 Blood Brain Barrier + 0.7025 Caco-2 permeable - 0.8358 P-glycoprotein substrate Non-substrate 0.7019 P-glycoprotein inhibitor I Non-inhibitor 0.8938 P-glycoprotein inhibitor II Non-inhibitor 0.9265 Renal organic cation transporter Non-inhibitor 0.9589 CYP450 2C9 substrate Non-substrate 0.7215 CYP450 2D6 substrate Non-substrate 0.8409 CYP450 3A4 substrate Non-substrate 0.6367 CYP450 1A2 substrate Non-inhibitor 0.9339 CYP450 2C9 inhibitor Non-inhibitor 0.9386 CYP450 2D6 inhibitor Non-inhibitor 0.9636 CYP450 2C19 inhibitor Non-inhibitor 0.9666 CYP450 3A4 inhibitor Non-inhibitor 0.9201 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.9817 Ames test Non AMES toxic 0.7179 Carcinogenicity Non-carcinogens 0.9381 Biodegradation Ready biodegradable 0.8507 Rat acute toxicity 1.7395 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9888 hERG inhibition (predictor II) Non-inhibitor 0.9644
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS splash10-06rb-0891000000-218620ca674b8145ee6a Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS splash10-0006-0890000000-98cc2cfa8c57b62bbea0 Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS splash10-03di-0910000000-b1ff6e899b9821160ee8 Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS splash10-0007-0910000000-51b4b33020b6f64c38e0 Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS splash10-03di-4900000000-2c18199f4113a28911c1 Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS splash10-001l-9600000000-886b5539ddf30fa41928 Predicted 1H NMR Spectrum 1D NMR Not Applicable Predicted 13C NMR Spectrum 1D NMR Not Applicable - Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 176.0104257 predictedDarkChem Lite v0.1.0 [M-H]- 163.88947 predictedDeepCCS 1.0 (2019) [M+H]+ 176.0257257 predictedDarkChem Lite v0.1.0 [M+H]+ 166.24747 predictedDeepCCS 1.0 (2019) [M+Na]+ 176.4779257 predictedDarkChem Lite v0.1.0 [M+Na]+ 173.41151 predictedDeepCCS 1.0 (2019)
Targets
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- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Ligand
- General Function
- Has both folate hydrolase and N-acetylated-alpha-linked-acidic dipeptidase (NAALADase) activity. Has a preference for tri-alpha-glutamate peptides. In the intestine, required for the uptake of folate. In the brain, modulates excitatory neurotransmission through the hydrolysis of the neuropeptide, N-aceylaspartylglutamate (NAAG), thereby releasing glutamate. Involved in prostate tumor progression
- Specific Function
- Ac-Asp-Glu binding
- Gene Name
- FOLH1
- Uniprot ID
- Q04609
- Uniprot Name
- Glutamate carboxypeptidase 2
- Molecular Weight
- 84330.015 Da
References
- Bandari RP, Jiang Z, Reynolds TS, Bernskoetter NE, Szczodroski AF, Bassuner KJ, Kirkpatrick DL, Rold TL, Sieckman GL, Hoffman TJ, Connors JP, Smith CJ: Synthesis and biological evaluation of copper-64 radiolabeled [DUPA-6-Ahx-(NODAGA)-5-Ava-BBN(7-14)NH2], a novel bivalent targeting vector having affinity for two distinct biomarkers (GRPr/PSMA) of prostate cancer. Nucl Med Biol. 2014 Apr;41(4):355-63. doi: 10.1016/j.nucmedbio.2014.01.001. Epub 2014 Jan 10. [Article]
Transporters
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- SubstrateOther
- General Function
- Electrogenic proton/amino acid symporter with selectivity for small apolar L-amino acids, their D-enantiomers and selected amino acid derivatives such as 4-aminobutanoate/GABA (PubMed:12527723, PubMed:12809675, PubMed:19549785). May be involved in the efflux from the lysosomal compartment of neutral amino acids resulting from proteolysis (By similarity). May play a role in specifying sites for exocytosis in neurons (By similarity)
- Specific Function
- alanine transmembrane transporter activity
- Gene Name
- SLC36A1
- Uniprot ID
- Q7Z2H8
- Uniprot Name
- Proton-coupled amino acid transporter 1
- Molecular Weight
- 53075.045 Da
References
- 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. [Article]
Drug created at February 19, 2013 23:31 / Updated at June 12, 2021 10:53