Identification
- Summary
Gliquidone is a sulfonylurea drug used in the management of diabetes mellitus type 2.
- Generic Name
- Gliquidone
- DrugBank Accession Number
- DB01251
- Background
Gliquidone is a sulfonylurea drug used to treat diabetes mellitus type 2. It is an ATP-dependent K+ (KATP) channel blocker. This block causes a depolarization which leads to activation of voltage-dependent Ca channels and Ca2+ influx, and eventually increases insulin release.
- Type
- Small Molecule
- Groups
- Approved, Investigational
- Structure
Structure for Gliquidone (DB01251)
- Weight
- Average: 527.632
Monoisotopic: 527.209006493 - Chemical Formula
- C27H33N3O6S
- Synonyms
- Gliquidona
- Gliquidone
- Gliquidonum
- External IDs
- ARDF 26
- ARDF-26
Pharmacology
- Indication
Used in the treatment of diabetes mellitus type 2.
Reduce drug development failure ratesBuild, train, & validate machine-learning modelswith evidence-based and structured datasets.Build, train, & validate predictive machine-learning models with structured datasets.- Associated Conditions
Indication Type Indication Combined Product Details Approval Level Age Group Patient Characteristics Dose Form Management of Type 2 diabetes mellitus •••••••••••• •••• ••• •••••••• ••• •••••••••• ••• •••••••• ••••••• •••••• - Contraindications & Blackbox Warnings
Prevent Adverse Drug Events TodayTap into our Clinical API for life-saving information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events with our Clinical API- Pharmacodynamics
Gliquidone is an anti-diabetic drug in the sulfonylurea class. In patients with diabetes mellitus, there is a deficiency or absence of a hormone manufactured by the pancreas called insulin. Insulin is the main hormone responsible for the control of sugar in the blood. Gliquidone is an antidiabetic medication which is used in those patients with adult maturity onset or non-insulin dependent diabetes (NIDDM). It works by lowering blood sugar levels by stimulating the production and release of insulin from the pancreas. It also promotes the movement of sugar from the blood into the cells in the body which need it.
- Mechanism of action
The mechanism of action of gliquidone in lowering blood glucose appears to be dependent on stimulating the release of insulin from functioning pancreatic beta cells, and increasing sensitivity of peripheral tissues to insulin. Gliquidone likely binds to ATP-sensitive potassium channel receptors on the pancreatic cell surface, reducing potassium conductance and causing depolarization of the membrane. Membrane depolarization stimulates calcium ion influx through voltage-sensitive calcium channels. This increase in intracellular calcium ion concentration induces the secretion of insulin.
Target Actions Organism AATP-binding cassette sub-family C member 8 inhibitorHumans AATP-sensitive inward rectifier potassium channel 8 inhibitorHumans - Absorption
Not Available
- Volume of distribution
Not Available
- Protein binding
Not Available
- Metabolism
- Not Available
- Route of elimination
Not Available
- Half-life
The mean terminal half-life was approximately 8 hours (range 5.7-9.4 hours)
- Clearance
Not Available
- Adverse Effects
Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.- Toxicity
Not Available
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">
- Not Available
Interactions
- Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Drug Interaction Integrate drug-drug
interactions in your softwareAbatacept The metabolism of Gliquidone can be increased when combined with Abatacept. Abrocitinib The metabolism of Abrocitinib can be decreased when combined with Gliquidone. Acarbose The risk or severity of hypoglycemia can be increased when Acarbose is combined with Gliquidone. Acebutolol The therapeutic efficacy of Gliquidone can be increased when used in combination with Acebutolol. Aceclofenac The protein binding of Gliquidone can be decreased when combined with Aceclofenac. - Food Interactions
- Not Available
Products
Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.- International/Other Brands
- Devotan (Menarini) / Fordiab (Hexpharm Jaya) / Glidiab (Soho) / Glunormal (Ying Yuan) / Glurenor (Guidotti) / Glurenorm (Boehringer Ingelheim) / Jie Shi (Tianjin Institute of Pharmaceutical Research Pharmaceutical) / Ka Rui Lin (Anjielun) / Lodem (Dexa Medica)
Categories
- ATC Codes
- A10BB08 — Gliquidone
- Drug Categories
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as 1,3-isoquinolinediones. These are isoquinoline derivatives carrying one C=O group at positions 1, and 3 respectively.
- Kingdom
- Organic compounds
- Super Class
- Organoheterocyclic compounds
- Class
- Isoquinolines and derivatives
- Sub Class
- 1,3-isoquinolinediones
- Direct Parent
- 1,3-isoquinolinediones
- Alternative Parents
- Isoquinolones and derivatives / Tetrahydroisoquinolines / Benzenesulfonamides / Benzenesulfonyl compounds / Anisoles / Sulfonylureas / Alkyl aryl ethers / N-substituted carboxylic acid imides / Organosulfonic acids and derivatives / Aminosulfonyl compounds show 8 more
- Substituents
- 1,3-isoquinolinedione / Alkyl aryl ether / Aminosulfonyl compound / Anisole / Aromatic heteropolycyclic compound / Azacycle / Benzenesulfonamide / Benzenesulfonyl group / Benzenoid / Carbonyl group show 23 more
- Molecular Framework
- Aromatic heteropolycyclic compounds
- External Descriptors
- Not Available
- Affected organisms
- Humans and other mammals
Chemical Identifiers
- UNII
- C7C2QDD75P
- CAS number
- 33342-05-1
- InChI Key
- LLJFMFZYVVLQKT-UHFFFAOYSA-N
- InChI
- InChI=1S/C27H33N3O6S/c1-27(2)23-14-11-20(36-3)17-22(23)24(31)30(25(27)32)16-15-18-9-12-21(13-10-18)37(34,35)29-26(33)28-19-7-5-4-6-8-19/h9-14,17,19H,4-8,15-16H2,1-3H3,(H2,28,29,33)
- IUPAC Name
- 3-cyclohexyl-1-{4-[2-(7-methoxy-4,4-dimethyl-1,3-dioxo-1,2,3,4-tetrahydroisoquinolin-2-yl)ethyl]benzenesulfonyl}urea
- SMILES
- COC1=CC2=C(C=C1)C(C)(C)C(=O)N(CCC1=CC=C(C=C1)S(=O)(=O)NC(=O)NC1CCCCC1)C2=O
References
- Synthesis Reference
U.S. Patent 3,708,486.
- General References
- Not Available
- External Links
- Human Metabolome Database
- HMDB0015381
- KEGG Drug
- D02430
- PubChem Compound
- 91610
- PubChem Substance
- 46508425
- ChemSpider
- 82719
- BindingDB
- 50248247
- 25793
- ChEBI
- 93416
- ChEMBL
- CHEMBL383634
- ZINC
- ZINC000001482077
- Therapeutic Targets Database
- DAP000924
- PharmGKB
- PA164744895
- Wikipedia
- Gliquidone
Clinical Trials
- Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
Phase Status Purpose Conditions Count 4 Completed Treatment Diabetes / Type 2 Diabetes Mellitus 1 Not Available Completed Not Available Type 2 Diabetes Mellitus 3
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
Form Route Strength Tablet Oral Tablet Oral 30 MG - Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 180-182 U.S. Patent 3,708,486. logP 4.5 Not Available - Predicted Properties
Property Value Source Water Solubility 0.0022 mg/mL ALOGPS logP 3.59 ALOGPS logP 4.14 Chemaxon logS -5.4 ALOGPS pKa (Strongest Acidic) 4.32 Chemaxon pKa (Strongest Basic) -4.8 Chemaxon Physiological Charge -1 Chemaxon Hydrogen Acceptor Count 6 Chemaxon Hydrogen Donor Count 2 Chemaxon Polar Surface Area 121.88 Å2 Chemaxon Rotatable Bond Count 6 Chemaxon Refractivity 139.48 m3·mol-1 Chemaxon Polarizability 57.3 Å3 Chemaxon Number of Rings 4 Chemaxon Bioavailability 1 Chemaxon Rule of Five No Chemaxon Ghose Filter No Chemaxon Veber's Rule No Chemaxon MDDR-like Rule Yes Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.9157 Blood Brain Barrier + 0.625 Caco-2 permeable - 0.6185 P-glycoprotein substrate Substrate 0.7457 P-glycoprotein inhibitor I Inhibitor 0.6115 P-glycoprotein inhibitor II Inhibitor 0.805 Renal organic cation transporter Non-inhibitor 0.7921 CYP450 2C9 substrate Substrate 0.5166 CYP450 2D6 substrate Non-substrate 0.8162 CYP450 3A4 substrate Substrate 0.594 CYP450 1A2 substrate Non-inhibitor 0.9046 CYP450 2C9 inhibitor Non-inhibitor 0.6454 CYP450 2D6 inhibitor Non-inhibitor 0.9231 CYP450 2C19 inhibitor Non-inhibitor 0.9025 CYP450 3A4 inhibitor Inhibitor 0.7961 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.5173 Ames test Non AMES toxic 0.6124 Carcinogenicity Non-carcinogens 0.7477 Biodegradation Not ready biodegradable 0.8693 Rat acute toxicity 2.3506 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.8418 hERG inhibition (predictor II) Inhibitor 0.6182
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 245.6939086 predictedDarkChem Lite v0.1.0 [M-H]- 246.7259086 predictedDarkChem Lite v0.1.0 [M-H]- 221.78117 predictedDeepCCS 1.0 (2019) [M+H]+ 246.4388086 predictedDarkChem Lite v0.1.0 [M+H]+ 246.5821086 predictedDarkChem Lite v0.1.0 [M+H]+ 224.17674 predictedDeepCCS 1.0 (2019) [M+Na]+ 246.1543086 predictedDarkChem Lite v0.1.0 [M+Na]+ 246.7972086 predictedDarkChem Lite v0.1.0 [M+Na]+ 230.08926 predictedDeepCCS 1.0 (2019)
Targets
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- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Inhibitor
- General Function
- Sulfonylurea receptor activity
- Specific Function
- Subunit of the beta-cell ATP-sensitive potassium channel (KATP). Regulator of ATP-sensitive K(+) channels and insulin release.
- Gene Name
- ABCC8
- Uniprot ID
- Q09428
- Uniprot Name
- ATP-binding cassette sub-family C member 8
- Molecular Weight
- 176990.36 Da
References
- Gribble FM, Ashcroft FM: Sulfonylurea sensitivity of adenosine triphosphate-sensitive potassium channels from beta cells and extrapancreatic tissues. Metabolism. 2000 Oct;49(10 Suppl 2):3-6. [Article]
- Harrower A: Gliclazide modified release: from once-daily administration to 24-hour blood glucose control. Metabolism. 2000 Oct;49(10 Suppl 2):7-11. [Article]
- Lawrence CL, Proks P, Rodrigo GC, Jones P, Hayabuchi Y, Standen NB, Ashcroft FM: Gliclazide produces high-affinity block of KATP channels in mouse isolated pancreatic beta cells but not rat heart or arterial smooth muscle cells. Diabetologia. 2001 Aug;44(8):1019-25. [Article]
- Reimann F, Ashcroft FM, Gribble FM: Structural basis for the interference between nicorandil and sulfonylurea action. Diabetes. 2001 Oct;50(10):2253-9. [Article]
- Proks P, Reimann F, Green N, Gribble F, Ashcroft F: Sulfonylurea stimulation of insulin secretion. Diabetes. 2002 Dec;51 Suppl 3:S368-76. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Inhibitor
- General Function
- Inward rectifier potassium channel activity
- Specific Function
- This potassium channel is controlled by G proteins. Inward rectifier potassium channels are characterized by a greater tendency to allow potassium to flow into the cell rather than out of it. Their...
- Gene Name
- KCNJ8
- Uniprot ID
- Q15842
- Uniprot Name
- ATP-sensitive inward rectifier potassium channel 8
- Molecular Weight
- 47967.455 Da
References
- Szewczyk A, Wojcik G, Lobanov NA, Nalecz MJ: The mitochondrial sulfonylurea receptor: identification and characterization. Biochem Biophys Res Commun. 1997 Jan 23;230(3):611-5. [Article]
- Sato T, Costa AD, Saito T, Ogura T, Ishida H, Garlid KD, Nakaya H: Bepridil, an antiarrhythmic drug, opens mitochondrial KATP channels, blocks sarcolemmal KATP channels, and confers cardioprotection. J Pharmacol Exp Ther. 2006 Jan;316(1):182-8. Epub 2005 Sep 20. [Article]
- Hill RA, Rudra S, Peng B, Roane DS, Bounds JK, Zhang Y, Adloo A, Lu T: Hydroxyl-substituted sulfonylureas as potent inhibitors of specific [3H]glyburide binding to rat brain synaptosomes. Bioorg Med Chem. 2003 May 1;11(9):2099-113. [Article]
Enzymes
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- Steroid hydroxylase activity
- Specific Function
- Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
- Gene Name
- CYP2C9
- Uniprot ID
- P11712
- Uniprot Name
- Cytochrome P450 2C9
- Molecular Weight
- 55627.365 Da
References
- May M, Schindler C: Clinically and pharmacologically relevant interactions of antidiabetic drugs. Ther Adv Endocrinol Metab. 2016 Apr;7(2):69-83. doi: 10.1177/2042018816638050. Epub 2016 Mar 31. [Article]
Drug created at March 30, 2007 14:35 / Updated at June 16, 2021 12:30