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Ophthalmic acid information


Ophthalmic acid[1]
Stereo, skeletal formula of ophthalmic acid
Names
IUPAC name
(N-(L-γ-Glutamyl)-(2S)-2-aminobutyryl)glycine
Identifiers
CAS Number
  • 495-27-2 checkY
3D model (JSmol)
  • Interactive image
ChEBI
  • CHEBI:84058 ☒N
ChemSpider
  • 5381695 checkY
MeSH ophthalmic+acid
PubChem CID
  • 7018721
UNII
  • 3A60475Q1Q checkY
CompTox Dashboard (EPA)
  • DTXSID40895053 Edit this at Wikidata
InChI
  • InChI=1S/C11H19N3O6/c1-2-7(10(18)13-5-9(16)17)14-8(15)4-3-6(12)11(19)20/h6-7H,2-5,12H2,1H3,(H,13,18)(H,14,15)(H,16,17)(H,19,20)/t6-,7-/m0/s1 checkY
    Key: JCMUOFQHZLPHQP-BQBZGAKWSA-N checkY
SMILES
  • CC[C@H](NC(=O)CC[C@H](N)C(O)=O)C(=O)NCC(O)=O
Properties
Chemical formula
C11H19N3O6
Molar mass 289.288 g·mol−1
Appearance White crystals
Related compounds
Related alkanoic acids
  • N-Acetylaspartylglutamic acid
  • Glycylglycine
  • α-Aminobutyric acid
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Ophthalmic acid (OPH), also known as ophthalmate (chemically L-γ-glutamyl-L-α-aminobutyrylglycine), is a tripeptide analog of glutathione. However, instead of the cysteine essential for many of glutathione's diverse functions, it contains L-2-aminobutyrate, a non-proteinogenic amino acid lacking the nucleophilic thiol group. Because of this, it has been widely, and incorrectly, considered an accidental byproduct of glutathione synthesis.

In 2024, an article published by the federation of European biochemistry societies compiled evidence to put forward the major hypothesis that OPH serves as a glutathione regulating tripeptide, affecting both cellular and organelle influx and efflux of GSH, as well as modulating GSH-dependent reactions and signaling.[2]

  1. ^ Ophthalmic acid
  2. ^ Schomakers, Bauke V.; Jillings, Sonia L.; van Weeghel, Michel; Vaz, Frédéric M.; Salomons, Gajja S.; Janssens, Georges E.; Houtkooper, Riekelt H. (2024-01-20). "Ophthalmic acid is a glutathione regulating tripeptide". The FEBS Journal. doi:10.1111/febs.17061. ISSN 1742-464X.

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Ophthalmic acid

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Ophthalmic acid (OPH), also known as ophthalmate (chemically L-γ-glutamyl-L-α-aminobutyrylglycine), is a tripeptide analog of glutathione. However, instead...

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Glutathione

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mass spectrometry. Reductive stress Glutathione synthetase deficiency Ophthalmic acid roGFP, a tool to measure the cellular glutathione redox potential...

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Tripeptide

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(MSH) Ophthalmic acid (L-γ-glutamyl-L-α-aminobutyryl-glycine) is an analogue of glutathione isolated from crystalline lens Norophthalmic acid...

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Hyaluronic acid

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biomedical companies also produce brands of hyaluronan for ophthalmic surgery. Native hyaluronic acid has a relatively short half-life (shown in rabbits) so...

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Prednisolone acetate ophthalmic suspension (eye drops) is an adrenocortical steroid product, prepared as a sterile ophthalmic suspension and used to...

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C11H19N3O6

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molecular formula C11H19N3O6 (molar mass: 289.285 g/mol) may refer to: Ophthalmic acid Tabtoxin, or wildfire toxin This set index page lists chemical structure...

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Vicryl

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of Johnson and Johnson. A monofilament version is also made for use in ophthalmic practice. It is indicated for soft tissue approximation and ligation....

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Flurbiprofen

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acid derivative family of nonsteroidal anti-inflammatory drugs (NSAIDs). It is primarily indicated as a pre-operative anti-miotic (in an ophthalmic solution)...

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demonstration, the elimination of latanoprost acid from plasma is rapid (half-life 17 minutes) after either ophthalmic or intravenous administration. Steroid...

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States, with more than 11 million prescriptions. It is available as its acid or in two salts, as either diclofenac sodium or potassium. It is also widely...

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Ophthalmic drug administration is the administration of a drug to the eyes, most typically as an eye drop formulation. Topical formulations are used to...

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interactions with drugs taken by mouth or through any route other than topical ophthalmic are very unlikely. Corticosteroids mediate their anti-inflammatory effects...

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embolization into the ophthalmic and retinal arteries can occur. Fillers are made of polysaccharides such as hyaluronic acids, a naturally occurring...

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intravenous NSAID. The Syntex company, of Palo Alto, California developed the ophthalmic solution Acular around 2006, which is currently licensed by Allergan,...

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Hiroshi (1997). "A Case of Contact Dermatitis Due to Sodium Bisulfite in an Ophthalmic Solution". The Journal of Dermatology. 24 (10): 675–677. doi:10.1111/j...

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Balanced salt solution

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hydrochloric acid (to adjust pH), and water for injection. The pH is approximately 7.5. The osmolality is approximately 300 mOsm/Kg. BSS Plus (ophthalmic irrigation...

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Travoprost

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Travoprost acid and its metabolites are mainly excreted via the kidney with a terminal half-life of 45 minutes. "Travoprost ophthalmic Use During Pregnancy"...

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brimonidine's tartrate formulation in a concentration of 0.025%, as an ophthalmic vasoconstrictor under the brand name Lumify. Intended to relieve redness...

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hydrate the skin. Creams containing a high percentage of urea or lactic acid have been shown to work exceptionally well in some cases. Application of...

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solvent than ethanol. Vinegar, being acidic, is a better solvent for obtaining alkaloids but a poorer solvent for acidic components. For individuals who choose...

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Suprofen

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subsequently used exclusively as a topical ophthalmic solution, typically to prevent miosis during and after ophthalmic surgery. This application has been discontinued...

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Alcaftadine

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Retrieved 20 May 2024. "Drug Approval Package: Lastacaft (alcaftadine) Ophthalmic Solution NDA #022134". U.S. Food and Drug Administration (FDA). 24 December...

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Sodium hyaluronate

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hyaluronic acid, a glycosaminoglycan found in various connective tissue of humans. Sodium hyaluronate is the sodium salt of hyaluronic acid. It is a glycosaminoglycan...

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