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Repaglinide

HCID 65981
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Basic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
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Basic information

CAS
135062-02-1
Standard SMILES
CCOc1cc(CC(=O)N[C@@H](CC(C)C)c2ccccc2N2CCCCC2)ccc1C(=O)O
InChIKey
FAEKWTJYAYMJKF-QHCPKHFHSA-N
Molecular formula
C27H36N2O4
Average molar mass
452.6 g/mol
Monoisotopic mass
452.26750763

Overview

Repaglinide is a member of piperidines.

Names & identifiers

Preferred name
Repaglinide
IUPAC
2-ethoxy-4-[2-[[(1S)-3-methyl-1-(2-piperidin-1-ylphenyl)butyl]amino]-2-oxoethyl]benzoic acid
English name
Repaglinide
Molecular formula
C27H36N2O4
Molecular weight
452.59

Names & synonyms

Repaglinide135062-02-1PrandinRepaglinidaAG-EE 623 ZWGlucoNormAG-EE 388 ZWRepaglinidumAGEE-623ZWenyglidAG-EE-623ZWDTXSID3023552
Show more names
Repaglinide APIRapaglinideEP5.2CS-1998NOVONORMAG-EE-623ag-ee388zwRepaglinidAG-EE 624ZW
2-ethoxy-4-[2-[[(1S)-3-methyl-1-(2-piperidin-1-ylphenyl)butyl]amino]-2-oxoethyl]benzoic acidNSC-759893AG-EE-623-ZWA10BX02668Z8C33LUDTXCID603552(+)-2-Ethoxy-alpha-(((S)-alpha-isobutyl-o-piperidinobenzyl)carbamoyl)-p-toluic acidrepaglinide impurity E

Database identifiers

CAS
135062-02-1
PubChem CID
65981
DTXSID
DTXSID3023552
ChEMBL
CHEMBL1272
ChEBI
CHEBI:8805
UNII
668Z8C33LU
EC Number
629-921-1
Nikkaji
J555.407A

Properties

Computed structural properties

XLogP
5.2
Topological polar surface area
78.9 Ų
Hydrogen bond donors
2
Hydrogen bond acceptors
5
Rotatable bonds
10
Heavy atoms
33
Formal charge
0
Complexity
619

Experimental & physicochemical properties

DrugsPharmaceuticals -> Listed in ZINC15
LogP · 2 items

5.9

3.2

Solubility · 2 items

2.94e-03 g/L

>67.9 [ug/mL] (The mean of the results at pH 7.4)

Human Drugs · 6 items

Breast Feeding; Lactation; Milk, Human; Hypoglycemic Agents

FDA approved drugs -> Active ingredient

EMA approved medicines: Human medicine

EMA approved medicines: Human medicine

EMA approved medicines: Human medicine

EMA approved medicines: Human medicine

Melting Point · 2 items

130-131 °C

130 - 131 °C

Physical DescriptionSolid
Dissociation Constants3.75

Physicochemical properties

Safety & regulation

Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.

GHS classification

GHS Classification · 4 items

Warning

H361 (96.7%): Suspected of damaging fertility or the unborn child [Warning Reproductive toxicity]

P203, P260, P263, P264, P270, P273, P280, P318, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 60 reports by companies from 8 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Hazard information

Hazard Classes and CategoriesRepr. 2 (96.7%)

Toxicology

Hepatotoxicity · 1 item

In several large clinical trials, serum aminotransferase elevations during repaglinide therapy were uncommon and similar in frequency with placebo. All serum enzyme elevations that occurred were asymptomatic and resolved rapidly with stopping therapy. Since its approval and with wide scale use, there have been a small number of reports of clinically apparent liver injury attributed to repaglinide. The time to onset ranged from 2 to 8 weeks and the pattern of serum enzyme elevations was typically cholestatic or mixed. Jaundice and pruritus were prominent. Immunoallergic features and autoantibodies were not present. All published cases have been self-limited, resolving within 1 to 2 months of stopping.

Adverse Effects · 1 item

The most commonly reported side effect associated with repaglinide monotherapy is hypoglycemia (7% in a study of 76 patients), followed by weight gain (1.8 kg / 16 weeks). Whipple triad for hypoglycemia is defined as the presence of symptoms of hypoglycemia, presence of factual hypoglycemia (Repaglinide has reports showing it to be of greater risk of cardiovascular events than metformin but lesser than sulfonylureas.

Chemistry & industry

Pharmacology

ATC Code · 3 items

A10BX02

A - Alimentary tract and metabolism

QA - Alimentary tract and metabolism

Protein Binding>98% (e.g. to to albumin and α1-acid glycoprotein)
Pharmacodynamics · 1 item

Insulin secretion by pancreatic β cells is partly controlled by cellular membrane potential. Membrane potential is regulated through an inverse relationship between the activity of cell membrane ATP-sensitive potassium channels (ABCC8) and extracellular glucose concentrations. Extracellular glucose enters the cell via GLUT2 (SLC2A2) transporters. Once inside the cell, glucose is metabolized to produce ATP. High concentrations of ATP inhibit ATP-sensitive potassium channels causing membrane depolarization. When extracellular glucose concentrations are low, ATP-sensitive potassium channels open causing membrane repolarization. High glucose concentrations cause ATP-sensitive potassium channels to close resulting in membrane depolarization and opening of L-type calcium channels. The influx of calcium ions stimulates calcium-dependent exocytosis of insulin granules. Repaglinide increases insulin release by inhibiting ATP-sensitive potassium channels in a glucose-dependent manner.

Mechanism of Action · 1 item

Repaglinide activity is dependent on the presence functioning β cells and glucose. In contrast to sulfonylurea insulin secretatogogues, repaglinide has no effect on insulin release in the absence of glucose. Rather, it potentiates the effect of extracellular glucose on ATP-sensitive potassium channel and has little effect on insulin levels between meals and overnight. As such, repaglinide is more effective at reducing postprandial blood glucose levels than fasting blood glucose levels and requires a longer duration of therapy (approximately one month) before decreases in fasting blood glucose are observed. The insulinotropic effects of repaglinide are highest at intermediate glucose levels (3 to 10 mmol/L) and it does not increase insulin release already stimulated by high glucose concentrations (greater than 15 mmol/L). Repaglinide appears to be selective for pancreatic β cells and does not appear to affect skeletal or cardiac muscle or thyroid tissue.

Related reactions

7 records
New reaction record
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HRID 423216As productuspto-grants-2012_01
HRID 858367 reaction equation
HRID 858367As productuspto-grants-2006_12
HRID 1034031 reaction equation
HRID 1034031As productuspto-grants-1994_05
HRID 1034032 reaction equation
HRID 1034032As productuspto-grants-1994_05
HRID 1260168 reaction equation
HRID 1260168As reactantuspto-grants-2013_06
HRID 1857027 reaction equation
HRID 1857027As productuspto-grants-2000_11
HRID 1857028 reaction equation
HRID 1857028As productuspto-grants-2000_11

Compound notes

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On this pageBasic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
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Melting point
129 · 129-130.2 °C
Boiling point
672.9 · 672.9±55.0 °C(Predicted)
alpha
20 · D20 +6.97° (c = 0.975 in methanol); D20 +7.45° (c = 1.06 in methanol)
Density
1.137 · 1.137±0.06 g/cm3(Predicted)
storage temp.
2 · 2-8°C
solubility
34 mg/mL · DMSO: 34 mg/mL
form
solid
pka
4.19 · 4.19±0.10(Predicted)
color
white
Water Solubility
89.99 mg/L · 89.99mg/L(25 ºC)
Merck
14 · 14,8136
InChIKey
FAEKWTJYAYMJKF-QHCPKHFHSA-N
SMILES
C(O)(=O)C1=CC=C(CC(N[C@H](C2=CC=CC=C2N2CCCCC2)CC(C)C)=O)C=C1OCC
CAS DataBase Reference
135062 · 135062-02-1(CAS DataBase Reference)
FDA UNII
668 Z8C33LU · 668Z8C33LU
NCI Drug Dictionary
Prandin
ATC code
10 BX02 · A10BX02
UNSPSC Code
41116107 · 41116107
NACRES
77 · NA.77
Protein binding
98 % · >98%
Excreted unchanged in urine
8 · <8 (mainly as metabolites)
Volume of distribution
30 Litres · 30 Litres
Biological half-life
1 · 1 / 2
Symbol(GHS)
7 · GHS07,GHS08
Signal word
Warning
Hazard statements
302 · H302-H361-H362
Precautionary statements
501 · P501-P263-P260-P270-P202-P201-P264-P280-P308+P313-P301+P312+P330-P405
PPE
95 · Eyeshields, Gloves, type N95 (US)
WGK Germany
2 · 2
RTECS
33825 · 000000033825
HS Code
2933399090 · 2933399090
Storage Class
11 · 11 - Combustible Solids
Toxicity
50 orally · LD50 orally in rats: >1 g/kg (Grell)
Toxicity SummarySevere hypoglycemia may induce seizures, coma, or other neurological impairments and requires immediate hospitalization and medical attention.
Drug Induced Liver Injury · 6 items

Drug Induced Liver Injury Rank (DILIrank 2.0)

Repaglinide

vLess-DILI-concern

5

Adverse reactions

DOI:10.1016/j.drudis.2016.02.015

Effects During Pregnancy and Lactation◉ Summary of Use during Lactation

Safety data

PPE
Eyeshields, Gloves, type N95 (US)
wgk
2
rtecs
000000033825
hs_code
2933399090
Toxicity
LD50 orally in rats: >1 g/kg (Grell)
Signal word
Warning
Symbol(GHS)
GHS07,GHS08
Storage Class
11 - Combustible Solids
Hazard statements
H302-H361-H362
Precautionary statements
P501-P263-P260-P270-P202-P201-P264-P280-P308+P313-P301+P312+P330-P405
Biological Half-Life
1 hour
Metabolism/Metabolites · 2 items

Repaglinide is rapidly metabolized via oxidation and dealkylation by cytochrome P450 3A4 and 2C9 to form the major dicarboxylic acid derivative (M2). Further oxidation produces the aromatic amine derivative (M1). Glucuronidation of the carboxylic acid group of repaglinide yields an acyl glucuronide (M7). Several other unidentified metabolites have been detected. Repaglinide metabolites to not possess appreciable hypoglycemic activity.

Repaglinide has known human metabolites that include Repaglinide aromatic amine, 2-ethoxy-4-[2-[[1-[2-(4-hydroxybutylamino)phenyl]-3-methylbutyl]amino]-2-oxoethyl]benzoic acid, 2-ethoxy-4-[2-[[3-hydroxy-3-methyl-1-(2-piperidin-1-ylphenyl)butyl]amino]-2-oxoethyl]benzoic acid, 2-Hydroxy-4-[2-[[3-methyl-1-(2-piperidin-1-ylphenyl)butyl]amino]-2-oxoethyl]benzoic acid, and 3'-Hydroxy Repaglinide(Mixture of Diastereomers).

FDA Pharmacological Classification · 6 items

668Z8C33LU

REPAGLINIDE

Established Pharmacologic Class [EPC] - Glinide

Mechanisms of Action [MoA] - Potassium Channel Antagonists

Repaglinide is a Glinide. The mechanism of action of repaglinide is as a Potassium Channel Antagonist.

REPAGLINIDE

MeSH Pharmacological ClassificationSubstances which lower blood glucose levels.
Absorption, Distribution and Excretion · 4 items

Rapidly and completely absorbed following oral administration. Peak plasma concentrations are observed within 1 hour (range 0.5-1.4 hours). The absolute bioavailability is approximately 56%. Maximal biological effect is observed within 3-3.5 hours and plasma insulin levels remain elevated for 4-6 hours. When a single 2 mg dose of repaglinide is given to healthy subjects, the area under the curve (AUC) is 18.0 - 18.7 (ng/mL/h)^3.

90% eliminated in feces (<2% as unchanged drug), 8% in urine (0.1% as unchanged drug)

31 L following IV administration in healthy individuals

33-38 L/hour following IV administration

Cellular LocationsCytoplasm
Metabolite PathwaysRepaglinide Action Pathway

Uses & manufacturing

UsesUse (kg; approx.) in Germany (2009): >100
Applications · 9 items

Uses1. Anti-diabetic medicine. Oral non-sulfonylurea hypoglycemic agent, for the treatment of typeⅡdiabetes. 2. Used as hypolycemic agent.

DescriptionRepaglinide was marketed in the US as an orally active hypoglycemic agent in patients with a type Ⅱ diabetes mellitus, to lower blood glucose in synergistic combination with metformin, when hyperglycemia cannot be controlled by diet, exercise or metformin alone. Chiral (S)-repaglinide can be synthesized in several ways, each involving a stereoselective reduction of an imine or enamine group. Repaglinide is a nonsulfonylurea belonging to the meglitinide family, with an insulin-releasing effect mediated by pancreatic betacells, by closing the ATP-sensitive K+ channels that, in turn, increases the cytosolic concentration of Ca++. In several animal models, repaglinide was more efficient than glibenclamide as a dose-dependant promoter of insulin release, but its mechanism of action is probably slightly different. Repaglinide has a rapid onset of action, a short duration of action and a reduced risk of hypoglycemia compared to glyburide.

DescriptionRepaglinide is a metaglitinide antidiabetic agent that blocks ATP-dependent potassium (Kir6) channels in pancreatic β-cells (Kd = 0.42 nM for the sulphonylurea receptor SUR1 when co-expressed with Kir6.2). In vivo, repaglinide lowers blood glucose in fasted rats and dogs (ED50s = 10 and 28.3 μg/kg, respectively). Formulations containing repaglinide have been used to control blood sugar levels in patients with type 2 diabetes.

UsesNon-sulfonylurea oral hypoglycemic agent. Used as an antidiabetic

UsesThe R-enantiomer showed only weak hypoglycemic activity. Repaglinide impurity

Usesantineoplastic

UsesA KIR6 (KATP) channel blocker

General DescriptionRepaglinide is 2-ethoxy-4-[2-[[(1S)-3-methyl-1-[2-(1-piperidinyl)phenyl]butyl]amino]-2-oxoethyl]benzoic acid(Prandin); approvals for generics are pending. Combinationsare available with metformin in the United States(Prandimet), and the drug may also be coprescribed with oneof the thiazolidinediones (typically pioglitazone or rosiglitazone;see previous discussion). To establish the most clinicallyvaluable dose, the patient is titrated while monitoringblood glucose levels and hemoglobin glycosylation (HbA1c)as an index of longer-term overall control.

General DescriptionRepaglinide, (+)-2-ethoxy-4-[N-[3-methyl-1(S)-[2-(1-piperidinyl) phenyl]butyl]carbamoyl-methyl]benzoicacid (Prandin), represents a new class of nonsulfonylureaoral hypoglycemic agents. With a fast onset and ashort duration of action, the medication should be taken withmeals. It is oxidized by CYP 3A4, and the carboxylic acidmay be conjugated to inactive compounds. Less than 0.2%is excreted unchanged by the kidney, which may be an advantagefor elderly patients who are renally impaired. Themost common side effect involves hypoglycemia, resultingin shakiness, headache, cold sweats, anxiety, and changes inmental state.

Upstream & downstream products

Upstream raw materials

Benzenemethanamine, α-(2-methylpropyl)-N-[(1S)-1-phenylethyl]-2-(1-piperidinyl)-, (αS)-Repaglinide Impurity 152-Piperidin-1-yl-benzaldehyde2-Piperidinobenzonitrile(+)-2-Ethoxy-4-(N-3-Methyl-1(S)-(2-(1-Piperidinyl)Phenyl)-Butyl)Carbamoylmethyl)3-methyl-1-(2-(piperidin-1-yl)phenyl)butan-1-one(S)-3-Methyl-1-(2-piperidin-1-ylphenyl)butylaminePiperidine2-Chlorobenzonitrile

Additional notes

DefinitionChEBI: Repaglinide is a member of piperidines.