CAS 145375-43-5 Mitiglinide (HCID 121891)

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Grundinformationen

CAS: 145375-43-5
Standard-SMILES: O=C(O)[C@H](CC(=O)N1C[C@H]2CCCC[C@H]2C1)Cc1ccccc1
InChIKey: WPGGHFDDFPHPOB-BBWFWOEESA-N
Summenformel: C19H25NO3
Durchschnittliche Molmasse: 315,4 g/mol
Monoisotopische Masse: 315,18344366

Namen und Bezeichner

Bevorzugter Name: Mitiglinide
IUPAC: (2S)-4-[(3aR,7aS)-1,3,3a,4,5,6,7,7a-octahydroisoindol-2-yl]-2-benzyl-4-oxobutanoic acid
Englischer Name: [2(S)-cis]-Octahydro-gamma-oxo-alpha-(phenylmethyl)-2H-isoindole-2-butanoic acid
Summenformel: C19H25NO3
Molmasse: 315.41

Namen und Synonyme

Mitiglinide145375-43-5mitiglinidaD86I0XLB13DTXSID40483032-Benzyl-3-(hexahydro-2-isoindolinylcarbonyl)propionatemitiglinidummiti-glinideRefChem:159078DTXCID2028278A10BX08(2S)-4-((3aR,7aS)-octahydro-1H-isoindol-2-yl)-2-benzyl-4-oxobutanoic acid

Weitere Namen anzeigen

Unii-D86I0xlb13Mitiglinide (S21403)Mitiglinide Impurity Ⅱ[2(S)-cis]-Octahydro-γ-oxo-α-(phenylmethyl)-2H-isoindole-2-butanoic acid(2S)-4-[(3aR,7aS)-octahydro-1H-isoindol-2-yl]-2-benzyl-4-oxobutanoic acid2H-Isoindole-2-butanoic acid, octahydro-γ-oxo-α-(phenylmethyl)-, (αS,3aR,7aS)-[2(S)-cis]-Octahydro-gamma-oxo-alpha-(phenylmethyl)-2H-isoindole-2-butanoic acid USP/EP/BP

2H-Isoindole-2-butanoic acid, octahydro-gamma-oxo-alpha-(phenylmethyl)-, calcium salt, (2(S)-cis)-Mitiglinide [INN](2S)-4-[(3aS,7aR)-1,3,3a,4,5,6,7,7a-octahydroisoindol-2-yl]-2-benzyl-4-oxobutanoic acid(S)-2-Benzyl-4-((3aR,7aS)-octahydro-2H-isoindol-2-yl)-4-oxobutanoic acid(2S)-4-[(3aR,7aS)-1,3,3a,4,5,6,7,7a-octahydroisoindol-2-yl]-4-oxidanylidene-2-(phenylmethyl)butanoic acid(2S)-4-[(3aR,7aS)-1,3,3a,4,5,6,7,7a-octahydroisoindol-2-yl]-2-benzyl-4-oxobutanoic acidMITIGLINIDE [MI][2(s)-cis]-octahydro-gamma-oxo-alpha-(phenylmethyl)-2h-isoindole-2-butanoic acid

Eigenschaften

Berechnete Struktureigenschaften

XLogP: 3
Polarare Oberfläche (TPSA): 57,6 Å²
H-Brücken-Donoren: 1
H-Brücken-Akzeptoren: 3
Frei drehbare Bindungen: 5
Schwere Atome: 23
Formalladung: 0
Komplexität: 416

Experimentelle und physikochemische Eigenschaften

LogP2.9

Physikochemische Eigenschaften

Siedepunkt: 519.6 · 519.6±43.0 °C(Predicted)
Dichte: 1.175 · 1.175
pka: 4.37 · 4.37±0.10(Predicted)

Sicherheit und Regulatorisches

Toxikologische Informationen

Drug Induced Liver Injury · 4 Einträge

Drug-Induced Liver Injury Severity and Toxicity (DILIst)

Mitiglinide

DILI Positive

DOI:10.1016/j.drudis.2019.09.022

Chemie und Industrie

Pharmakologische Informationen

ATC Code · 2 Einträge

A - Alimentary tract and metabolism；A10 - Drugs used in diabetes；A10B - Blood glucose lowering drugs, excl. insulins；A10BX - Other blood glucose lowering drugs, excl. insulins；A10BX08 - Mitiglinide

QA - Alimentary tract and metabolism；QA10 - Drugs used in diabetes；QA10B - Blood glucose lowering drugs, excl. insulins；QA10BX - Other blood glucose lowering drugs, excl. insulins；QA10BX08 - Mitiglinide

PharmacodynamicsMitiglinide belongs to the meglitinide class of blood glucose-lowering drugs. It is approved for use in Japan but has not yet gained FDA approval.

Mechanism of Action · 1 Eintrag

Mitiglinide is thought to stimulate insulin secretion by binding to and blocking ATP-sensitive K(+) (K(ATP)) channels (Kir6.2/SUR1 complex, KATP channels) in pancreatic beta-cells. Closure of potassium channels causes depolarization which stimulates calcium influx through voltage-gated calcium channels. High intracellular calcium subsequently triggers the exocytosis of insulin granules.

MeSH Pharmacological ClassificationSubstances which lower blood glucose levels.