Structure via PubChem · Public domain (PubChem)
epalrestat
Sign in to saveAlso known as 2-[(5Z)-5-[(E)-3-phenil-2-methylprop-2-enylidene]-4-oxo-2-thioxo-3-thiazolidinyl]acetic acid
Epalrestat is a carboxylic acid derivative and a noncompetitive and reversible aldose reductase inhibitor used for the treatment of diabetic neuropathy, which is one of the most common long-term complications in patients with diabetes mellitus. It reduces the accumulation of intracellular sorbitol which is believed to be the cause of diabetic neuropathy, retinopathy and nephropathy It is well tolerated, with the most commonly reported adverse effects being gastrointestinal issues such as nausea and vomiting, as well as increases in certain liver enzymes. Chemically, epalrestat is unusual in th
Chemical data
- Formula
- C15H13NO3S2
- Molecular weight
- 319.4 g/mol
- IUPAC name
- 2-[(5Z)-5-[(E)-2-methyl-3-phenylprop-2-enylidene]-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl]acetic acid
- SMILES
- C/C(=C\C1=CC=CC=C1)/C=C\2/C(=O)N(C(=S)S2)CC(=O)O
- InChIKey
- CHNUOJQWGUIOLD-NFZZJPOKSA-N
- XLogP
- 3.8
- Polar surface area
- 115 Ų
- H-bond donors
- 1
- H-bond acceptors
- 5
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Max clinical phase
- Approved
- Molecule type
- Small molecule
- First approval
- 1992
- Admin. routes
- oral
- Indications
- breast cancer, Charcot-Marie-Tooth disease
via ChEMBL · EBI
Wikidata facts
- Mass
- 319.03368527599997
Show 5 more facts
- chemical formula
- C₁₅H₁₃NO₃S₂
- subject has role
- enzyme inhibitor
- isomeric SMILES
- C/C(=C\C1=CC=CC=C1)/C=C\2/C(=O)N(C(=S)S2)CC(=O)O
- canonical SMILES
- CC(=CC1=CC=CC=C1)C=C2C(=O)N(C(=S)S2)CC(=O)O
- Commons category
- Epalrestat
Sources (2)
via Wikidata · CC0
~3 min read
Encyclopedic overview
3 sectionsContents
- Evidence
- Brand names
- References
{{Chembox | Verifiedfields = changed | Watchedfields = changed | verifiedrevid = 406013101 | ImageFile = Epalrestat.svg | ImageClass = skin-invert-image | ImageSize = 222 | PIN = {(5Z)-5-[(2E)-2-Methyl-3-phenylprop-2-en-1-ylidene]-4-oxo-2-sulfanylidene-1,3-thiazolidin-3-yl}acetic acid | OtherNames =
|Section1 =
Excerpted from Wikipedia’s “epalrestat” article, available under the CC BY-SA 4.0 licence.