ContaminantDB: Repaglinide

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-05-22 03:45:48 UTC

Update Date

2016-11-09 01:15:29 UTC

Accession Number

CHEM016862

Identification

Common Name

Repaglinide

Class

Small Molecule

Description

Repaglinide is an oral antihyperglycemic agent used for the treatment of non-insulin-dependent diabetes mellitus (NIDDM). It belongs to the meglitinide class of short-acting insulin secretagogues, which act by binding to β cells of the pancreas to stimulate insulin release. Repaglinide induces an early insulin response to meals decreasing postprandial blood glucose levels. It should only be taken with meals and meal-time doses should be skipped with any skipped meal. Approximately one month of therapy is required before a decrease in fasting blood glucose is seen. Meglitnides may have a neutral effect on weight or cause a slight increase in weight. The average weight gain caused by meglitinides appears to be lower than that caused by sulfonylureas and insulin and appears to occur only in those naïve to oral antidiabetic agents. Due to their mechanism of action, meglitinides may cause hypoglycemia although the risk is thought to be lower than that of sulfonylureas since their action is dependent on the presence of glucose. In addition to reducing postprandial and fasting blood glucose, meglitnides have been shown to decrease glycosylated hemoglobin (HbA1c) levels, which are reflective of the last 8-10 weeks of glucose control. Meglitinides appear to be more effective at lowering postprandial blood glucose than metformin, sulfonylureas and thiazolidinediones. Repaglinide is extensively metabolized in the liver and excreted in bile. Repaglinide metabolites do not possess appreciable hypoglycemic activity. Approximately 90% of a single orally administered dose is eliminated in feces and 8% in urine.

Contaminant Sources

HMDB Contaminants - Urine
STOFF IDENT Compounds
ToxCast & Tox21 Chemicals

Contaminant Type

Not Available

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
Prandin	Kegg
Surepost	Kegg
AG-ee 388 ZW	HMDB
AG-ee 623 ZW	HMDB
Glaxo wellcome brand OF replaginide	HMDB
Novo nordisk brand 2 OF repaglinide	HMDB
Repa-glinide	HMDB
2-Ethoxy-4-(2-((3-methyl-1-(2-(1-piperidinyl)phenyl)butyl)amino)-2-oxoethyl)benzoic acid	HMDB
Novo nordisk brand OF repaglinide	HMDB
NovoNorm	HMDB
Repaglinide, (+-)-isomer	HMDB
2-Ethoxy-N-(alpha-(2-methyl-1-propyl)-2-piperidinobenzyl)-4-carbamoylmethylbenzoic acid	HMDB
AG-ee 388	HMDB
GlucoNorm	HMDB

Chemical Formula

C₂₇H₃₆N₂O₄

Average Molecular Mass

452.586 g/mol

Monoisotopic Mass

452.268 g/mol

CAS Registry Number

135062-02-1

IUPAC Name

2-ethoxy-4-({[(1S)-3-methyl-1-[2-(piperidin-1-yl)phenyl]butyl]carbamoyl}methyl)benzoic acid

Traditional Name

repaglinide

SMILES

CCOC1=C(C=CC(CC(=O)N[C@@H](CC(C)C)C2=CC=CC=C2N2CCCCC2)=C1)C(O)=O

InChI Identifier

InChI=1S/C27H36N2O4/c1-4-33-25-17-20(12-13-22(25)27(31)32)18-26(30)28-23(16-19(2)3)21-10-6-7-11-24(21)29-14-8-5-9-15-29/h6-7,10-13,17,19,23H,4-5,8-9,14-16,18H2,1-3H3,(H,28,30)(H,31,32)/t23-/m0/s1

InChI Key

FAEKWTJYAYMJKF-QHCPKHFHSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as phenylpiperidines. Phenylpiperidines are compounds containing a phenylpiperidine skeleton, which consists of a piperidine bound to a phenyl group.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Piperidines

Sub Class

Phenylpiperidines

Direct Parent

Phenylpiperidines

Alternative Parents

Substituents

Phenylpiperidine
Phenylacetamide
Benzoic acid or derivatives
Benzoic acid
Phenoxy compound
Benzoyl
Phenol ether
Tertiary aliphatic/aromatic amine
Dialkylarylamine
Aniline or substituted anilines
Alkyl aryl ether
Benzenoid
Monocyclic benzene moiety
Amino acid
Tertiary amine
Carboxamide group
Amino acid or derivatives
Secondary carboxylic acid amide
Monocarboxylic acid or derivatives
Ether
Carboxylic acid
Carboxylic acid derivative
Azacycle
Organonitrogen compound
Hydrocarbon derivative
Carbonyl group
Amine
Organic oxide
Organopnictogen compound
Organooxygen compound
Organic oxygen compound
Organic nitrogen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

piperidines (CHEBI:8805 )

Biological Properties

Status

Detected and Not Quantified

Origin

Not Available

Cellular Locations

Not Available

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Physical Properties

State

Not Available

Appearance

Not Available

Experimental Properties

Property	Value
Melting Point	Not Available
Boiling Point	Not Available
Solubility	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	0.0029 g/L	ALOGPS
logP	5.05	ALOGPS
logP	3.95	ChemAxon
logS	-5.2	ALOGPS
pKa (Strongest Acidic)	3.68	ChemAxon
pKa (Strongest Basic)	4.82	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	78.87 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	131.83 m³·mol⁻¹	ChemAxon
Polarizability	51.49 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0g7j-2958400000-8cbddf3d4598a0fc7340	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-00ei-5260910000-4aaa7a93bda9f63c45e2	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-0udi-0000900000-c0108433e6c3f3bf1c75	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-004i-0009000000-30aa31031f07d8ae52b8	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-002r-0908000000-b76282b9697187110f0a	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-0udi-0000900000-2f6de321d96a7df0cde9	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-0udi-0140900000-4fef8b8042e88aa84955	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-001i-0290000000-4867f74dff429e78bb45	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-001i-0290000000-bdb018b622ca04e9d8b1	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-001i-0590000000-60f613e4ee0d364efcea	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - , positive	splash10-0f89-2791700000-333192fa8176a2febaa5	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-0udi-0140900000-4fef8b8042e88aa84955	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 50V, Positive	splash10-0089-0970000000-602d29c500b424ed363e	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Negative	splash10-004i-0009000000-30aa31031f07d8ae52b8	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-0udi-0000900000-dee9fb6cd200b9ec5dea	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 30V, Positive	splash10-001i-0290000000-eb9b8068f0e4a444f798	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Negative	splash10-0udi-0000900000-c0108433e6c3f3bf1c75	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 30V, Negative	splash10-002r-0908000000-b76282b9697187110f0a	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-001i-0290000000-720a9142676a841f0079	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-0gx0-0590600000-eb3b3f1dce83738e96c9	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-0udi-0000900000-c946d573c5042841c3f6	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0f6t-0181900000-f133163bc1e44e5ff6f3	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0002-1691100000-199236474a5fb7cb930d	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a5a-4940000000-4dc08f986e76785388e2	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0zfr-0010900000-dd8d5e58d8cda3e20087	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0bt9-1554900000-694c7b4171377cee14c4	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-2966000000-f2d3f7a4cbcb2910e30f	Spectrum

Toxicity Profile

Route of Exposure

Not Available

Mechanism of Toxicity

Not Available

Metabolism

Not Available

Toxicity Values

Not Available

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

Not Available

Uses/Sources

Not Available

Minimum Risk Level

Not Available

Health Effects

Not Available

Symptoms

Not Available

Treatment

Not Available

Concentrations

Not Available

External Links

DrugBank ID

DB00912

HMDB ID

HMDB0015048

FooDB ID

Not Available

Phenol Explorer ID

Not Available

KNApSAcK ID

Not Available

BiGG ID

Not Available

BioCyc ID

Not Available

METLIN ID

Not Available

PDB ID

Not Available

Wikipedia Link

Chemspider ID

ChEBI ID

PubChem Compound ID

Kegg Compound ID

YMDB ID

Not Available

ECMDB ID

Not Available

References

Synthesis Reference

Not Available

MSDS

Not Available

General References

1. Massi-Benedetti M, Damsbo P: Pharmacology and clinical experience with repaglinide. Expert Opin Investig Drugs. 2000 Apr;9(4):885-98.

Repaglinide (CHEM016862)

Structure for CHEM016862: Repaglinide