ContaminantDB: Glipizide

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References Targets (3)XML

Record Information

Version

1.0

Creation Date

2009-07-03 22:08:18 UTC

Update Date

2026-03-31 18:00:29 UTC

Accession Number

CHEM002065

Identification

Common Name

Glipizide

Class

Small Molecule

Description

Glipizide is only found in individuals that have used or taken this drug. It is an oral hypoglycemic agent which is rapidly absorbed and completely metabolized. [PubChem]Sulfonylureas likely bind to ATP-sensitive potassium-channel receptors on the pancreatic cell surface, reducing potassium conductance and causing depolarization of the membrane. Depolarization stimulates calcium ion influx through voltage-sensitive calcium channels, raising intracellular concentrations of calcium ions, which induces the secretion, or exocytosis, of insulin.

Contaminant Sources

HMDB Contaminants - Urine
STOFF IDENT Compounds
T3DB toxins
ToxCast & Tox21 Chemicals

Contaminant Type

Amide
Amine
Drug
Hypoglycemic Agent
Metabolite
Organic Compound
Synthetic Compound

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
1-Cyclohexyl-3-({p-[2-(5-methylpyrazinecarboxamido)ethyl]phenyl}sulfonyl)urea	ChEBI
Aldiab	ChEBI
CP 28,720	ChEBI
CP 28720	ChEBI
CP-28,720	ChEBI
Digrin	ChEBI
Dipazide	ChEBI
Glibenese	ChEBI
Glibetin	ChEBI
Glican	ChEBI
Glidiab	ChEBI
Glipid	ChEBI
Glipizida	ChEBI
Glipizidum	ChEBI
Gluco-rite	ChEBI
Glucolip	ChEBI
Glucotrol	ChEBI
Glucozide	ChEBI
Glupitel	ChEBI
Glupizide	ChEBI
Glyde	ChEBI
Glydiazinamide	ChEBI
K 4024	ChEBI
Melizide	ChEBI
Mindiab	ChEBI
Minidab	ChEBI
Minidiab	ChEBI
Minodiab	ChEBI
N-{4-[beta-(5-methylpyrazine-2-carboxamido)ethyl]benzenesulphonyl}-n'-cyclohexylurea	ChEBI
Napizide	ChEBI
Ozidia	ChEBI
Sucrazide	ChEBI
1-Cyclohexyl-3-({p-[2-(5-methylpyrazinecarboxamido)ethyl]phenyl}sulphonyl)urea	Generator
N-{4-[b-(5-methylpyrazine-2-carboxamido)ethyl]benzenesulfonyl}-n'-cyclohexylurea	Generator
N-{4-[b-(5-methylpyrazine-2-carboxamido)ethyl]benzenesulphonyl}-n'-cyclohexylurea	Generator
N-{4-[beta-(5-methylpyrazine-2-carboxamido)ethyl]benzenesulfonyl}-n'-cyclohexylurea	Generator
N-{4-[β-(5-methylpyrazine-2-carboxamido)ethyl]benzenesulfonyl}-n'-cyclohexylurea	Generator
N-{4-[β-(5-methylpyrazine-2-carboxamido)ethyl]benzenesulphonyl}-n'-cyclohexylurea	Generator
Glibenese brand OF glipizide	HMDB
Glidiazinamide	HMDB
Glypidizine	HMDB
Kenfarma brand OF glipizide	HMDB
Pfizer brand 2 OF glipizide	HMDB
Alphapharm brand OF glipizide	HMDB
Lacer brand OF glipizide	HMDB
Pfizer brand 1 OF glipizide	HMDB
Glipizide kenfarma brand	HMDB
Lilly brand OF glipizide	HMDB

Chemical Formula

C₂₁H₂₇N₅O₄S

Average Molecular Mass

445.535 g/mol

Monoisotopic Mass

445.178 g/mol

CAS Registry Number

29094-61-9

IUPAC Name

N-[2-(4-{[(cyclohexylcarbamoyl)amino]sulfonyl}phenyl)ethyl]-5-methylpyrazine-2-carboxamide

Traditional Name

glipizide

SMILES

CC1=CN=C(C=N1)C(=O)NCCC1=CC=C(C=C1)S(=O)(=O)NC(=O)NC1CCCCC1

InChI Identifier

InChI=1S/C21H27N5O4S/c1-15-13-24-19(14-23-15)20(27)22-12-11-16-7-9-18(10-8-16)31(29,30)26-21(28)25-17-5-3-2-4-6-17/h7-10,13-14,17H,2-6,11-12H2,1H3,(H,22,27)(H2,25,26,28)

InChI Key

ZJJXGWJIGJFDTL-UHFFFAOYSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as benzenesulfonamides. These are organic compounds containing a sulfonamide group that is S-linked to a benzene ring.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Benzenesulfonamides

Direct Parent

Benzenesulfonamides

Alternative Parents

Substituents

Benzenesulfonamide
Benzenesulfonyl group
Sulfonylurea
Pyrazine
Organic sulfonic acid or derivatives
Heteroaromatic compound
Aminosulfonyl compound
Sulfonyl
Organosulfonic acid or derivatives
Carboximidic acid
Carboximidic acid derivative
Azacycle
Organoheterocyclic compound
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Organic nitrogen compound
Hydrocarbon derivative
Organic oxide
Organosulfur compound
Organooxygen compound
Organonitrogen compound
Organopnictogen compound
Organic oxygen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

pyrazines (CHEBI:5384 )
monocarboxylic acid amide (CHEBI:5384 )
aromatic amide (CHEBI:5384 )
N-sulfonylurea (CHEBI:5384 )

Biological Properties

Status

Detected and Not Quantified

Origin

Exogenous

Cellular Locations

Cytoplasm
Membrane

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

hypoglycemic agent

Biological Roles

EC 2.7.1.33 (pantothenate kinase) inhibitor

Chemical Roles

EC 2.7.1.33 (pantothenate kinase) inhibitor

Physical Properties

State

Solid

Appearance

White powder.

Experimental Properties

Property	Value
Melting Point	200-203°C
Boiling Point	Not Available
Solubility	37.2 mg/L

Predicted Properties

Property	Value	Source
Water Solubility	0.016 g/L	ALOGPS
logP	1.83	ALOGPS
logP	1.43	ChemAxon
logS	-4.4	ALOGPS
pKa (Strongest Acidic)	4.32	ChemAxon
pKa (Strongest Basic)	0.059	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	130.15 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	115.62 m³·mol⁻¹	ChemAxon
Polarizability	47.64 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	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	splash10-0udj-9433200000-0daa174c6f208f739d92	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 , Positive	splash10-014i-0119600000-895a0f8ef34678f1200d	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-qTof , Positive	splash10-014i-0009600000-3a2ab7e8e725ab4b2090	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-qTof , Positive	splash10-0v4i-3941000000-57ab7532afaad5f9a2ac	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - , positive	splash10-014i-0009600000-3a2ab7e8e725ab4b2090	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - , positive	splash10-00di-0329000000-a6f7044e9dfe397cfcdd	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - , positive	splash10-014i-0119600000-895a0f8ef34678f1200d	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - , positive	splash10-00di-1429000000-60bdb648d5355af7a75b	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - , positive	splash10-0v4i-3941000000-57ab7532afaad5f9a2ac	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 60V, Negative	splash10-00bc-9400000000-e36d6f6a0eb4114e661c	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 45V, Negative	splash10-00di-3900000000-e23bb49f877be3901320	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 75V, Negative	splash10-004l-9100000000-688c676b3e072ae42071	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 90V, Negative	splash10-01tc-9100000000-4c0399e69298b606717a	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 30V, Positive	splash10-0gi9-0946000000-e87ed6360a6302adddaf	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 60V, Positive	splash10-0w30-1900000000-b3353b86c5a566797995	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 90V, Positive	splash10-01tc-9100000000-1058c878e881b259b2e6	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 45V, Positive	splash10-0gc9-0910000000-97927d7e80b6e6c9c189	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 30V, Positive	splash10-0gi9-0946000000-1bd55371a0002464d88d	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 45V, Positive	splash10-0gc9-0910000000-4c6c3446c687a5f55469	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 60V, Positive	splash10-0w30-1900000000-91618f445cb7066cc191	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-006t-1209300000-c14d0f75f56599ec527f	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0002-7903000000-63e0326a933897ad8d58	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-05mk-9700000000-3dea1f33244b9e19e407	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0007-5208900000-36b94e0ee176fc17450f	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00kb-4529000000-18be67f87a3195a21fff	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0007-9310000000-3bae0e1f24a4fc985c6b	Spectrum

Toxicity Profile

Route of Exposure

Oral. Gastrointestinal absorption is uniform, rapid, and essentially complete.

Mechanism of Toxicity

Sulfonylureas likely bind to ATP-sensitive potassium-channel receptors on the pancreatic cell surface, reducing potassium conductance and causing depolarization of the membrane. Depolarization stimulates calcium ion influx through voltage-sensitive calcium channels, raising intracellular concentrations of calcium ions, which induces the secretion, or exocytosis, of insulin.

Metabolism

Hepatic. The major metabolites of glipizide are products of aromatic hydroxylation and have no hypoglycemic activity. A minor metabolite which accounts for less than 2% of a dose, an acetylaminoethyl benzine derivatives, is reported to have 1/10 to 1/3 as much hypoglycemic activity as the parent compound. Route of Elimination: The primary metabolites are inactive hydroxylation products and polar conjugates and are excreted mainly in the urine. Half Life: 2-5 hours

Toxicity Values

The acute oral toxicity was extremely low in all species tested (LD50 greater than 4 g/kg).

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

No indication of carcinogenicity to humans (not listed by IARC).

Uses/Sources

For use as an adjunct to diet for the control of hyperglycemia and its associated symptomatology in patients with non-insulin-dependent diabetes mellitus (NIDDM; type II), formerly known as maturity-onset diabetes, after an adequate trial of dietary therapy has proved unsatisfactory.

Minimum Risk Level

Not Available

Health Effects

Not Available

Symptoms

The acute oral toxicity was extremely low in all species tested (LD50 greater than 4 g/kg). Overdosage of sulfonylureas including glipizide can produce hypoglycemia.

Treatment

Not Available

Concentrations

Not Available

External Links

DrugBank ID

DB01067

HMDB ID

HMDB0015200

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

Not Available

YMDB ID

Not Available

ECMDB ID

Not Available

References

Synthesis Reference

Suresh Kumar Gidwani, Purushottam Singnurkar, Prashant Kumar Tewari, “Sustained release pharmaceutical composition containing glipizide and method for producing same.” U.S. Patent US6270797, issued February, 2000.

MSDS

Link

General References

1. https://www.ncbi.nlm.nih.gov/pubmed/?term=11147395

2. https://www.ncbi.nlm.nih.gov/pubmed/?term=20797618

3. https://www.ncbi.nlm.nih.gov/pubmed/?term=23230096

4. https://www.ncbi.nlm.nih.gov/pubmed/?term=24418334

5. https://www.ncbi.nlm.nih.gov/pubmed/?term=24444583

6. https://www.ncbi.nlm.nih.gov/pubmed/?term=2665487

7. https://www.ncbi.nlm.nih.gov/pubmed/?term=3143256

8. https://www.ncbi.nlm.nih.gov/pubmed/?term=389600

9. https://www.ncbi.nlm.nih.gov/pubmed/?term=3923454

10. https://www.ncbi.nlm.nih.gov/pubmed/?term=7660535

Glipizide (CHEM002065)

Structure for CHEM002065: Glipizide