Structure via PubChem · Public domain (PubChem)
repaglinide
Sign in to saveAlso known as (-)-repaglinide, AGEE-623ZW, AG-EE 388 ZW, AG-EE 623 ZW
Repaglinide is an antidiabetic drug in the class of medications known as meglitinides, and was invented in 1983. Repaglinide is a medication used in addition to diet and exercise for blood sugar control in type 2 diabetes. The mechanism of action of repaglinide involves promoting insulin release from β-islet cells of the pancreas; like other antidiabetic drugs, a main side effect concern is hypoglycemia. It is sold by Novo Nordisk under the name of Prandin in the United States, Gluconorm in Canada, Surepost in Japan, Repaglinide in Egypt, and Novonorm elsewhere. In Japan it is produced by Dain
Chemical data
- Formula
- C27H36N2O4
- Molecular weight
- 452.6 g/mol
- IUPAC name
- 2-ethoxy-4-[2-[[(1S)-3-methyl-1-(2-piperidin-1-ylphenyl)butyl]amino]-2-oxoethyl]benzoic acid
- SMILES
- CCOC1=C(C=CC(=C1)CC(=O)N[C@@H](CC(C)C)C2=CC=CC=C2N3CCCCC3)C(=O)O
- InChIKey
- FAEKWTJYAYMJKF-QHCPKHFHSA-N
- XLogP
- 5.2
- Polar surface area
- 78.9 Ų
- H-bond donors
- 2
- H-bond acceptors
- 5
- Formal charge
- 0
via PubChem
Research
1,006 papers- Repaglinide.Drugs & aging · 1998
- Repaglinide: prandial glucose regulation in clinical practice.Diabetes, obesity & metabolism · 2000
- Repaglinide: a review of its use in type 2 diabetes mellitus.Drugs · 2012
- Repaglinide, a new oral antidiabetic agent: a review of recent preclinical studies.European journal of clinical investigation · 1999
- Repaglinide as monotherapy in Type 2 diabetes.Experimental and clinical endocrinology & diabetes : official journal, German Society of Endocrinology [and] German Diabetes Association · 1999
via PubMed
Wikidata facts
- Mass
- 452.267508
Show 6 more facts
- chemical formula
- C₂₇H₃₆N₂O₄
- defined daily dose
- 4
- World Health Organisation international non-proprietary name
- repaglinide
- isomeric SMILES
- CCOC1=C(C=CC(=C1)CC(=O)N[C@@H](CC(C)C)C2=CC=CC=C2N3CCCCC3)C(=O)O
- canonical SMILES
- CCOC1=C(C=CC(=C1)CC(=O)NC(CC(C)C)C2=CC=CC=C2N3CCCCC3)C(=O)O
- Commons category
- Repaglinide
Sources (6)
via Wikidata · CC0
~8 min read
Article
12 sectionsContents
- Medical uses
- Contraindications
- Adverse events
- Special populations
- Drug interactions
- Pharmacology
- Mechanism of action
- Pharmacokinetics
- History
- Intellectual property
- References
- External links
{{Drugbox | verifiedrevid = 464380887 | image = Repaglinide.svg | image_class = skin-invert-image | image2 = Repaglinide ball-and-stick.png | image_class2 = bg-transparent
| tradename = Prandin, Novonorm, Enyglid, others | Drugs.com = | MedlinePlus = a600010 | licence_EU = yes | DailyMedID = Repaglinide | licence_US = Prandin | pregnancy_AU = C | routes_of_administration = By mouth | ATC_prefix = A10 | ATC_suffix = BX02 | legal_AU = S4 | legal_CA = Rx-only | legal_UK = POM | legal_US = Rx-only | legal_EU = Rx-only