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Identification
- Summary
Gluconolactone is a polyhydroxy acid used in the dissolution of calculi and used as an additive in various drug products to maintain consistency and other characteristics.
- Brand Names
- Renacidin
- Generic Name
- Gluconolactone
- DrugBank Accession Number
- DB04564
- Background
Gluconolactone is a naturally-occurring food additive used as a sequestrant, an acidifier, or a curing, pickling, or leavening agent. It is a cyclic ester of D-gluconic acid. Pure gluconolactone is a white odorless crystalline powder.
- Type
- Small Molecule
- Groups
- Approved, Experimental
- Structure
Structure for Gluconolactone (DB04564)
- Weight
- Average: 178.14
Monoisotopic: 178.047738052 - Chemical Formula
- C6H10O6
- Synonyms
- 1,5-D-gluconolactone
- 1,5-Gluconolactone
- D-gluconic acid delta-lactone
- D-glucono-1,5-lactone
- D-threo-Aldono-1,5-lactone
- delta-gluconolactone
- GDL
- Gluconic acid lactone
- Glucono delta-lactone
- Glucono-delta-lactone
- Gluconolactone
- External IDs
- E-575
- INS NO.575
- INS-575
- NSC-34393
Pharmacology
- Indication
Not Available
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Indication Type Indication Combined Product Details Approval Level Age Group Patient Characteristics Dose Form Used in combination to treat Bladder calculus Combination Product in combination with: Magnesium carbonate (DB09481), Citric acid (DB04272) •••••••••••• •••••••• Used in combination for prophylaxis of Catheter site calcification Combination Product in combination with: Citric acid (DB04272), Magnesium carbonate (DB09481) •••••••••••• •••••••••• •••••••• ••••••••• Used in combination for prophylaxis of Medical device site calcification Combination Product in combination with: Magnesium carbonate (DB09481), Citric acid (DB04272) •••••••••••• ••••••••••• ••••• •••••••• - Contraindications & Blackbox Warnings
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Not Available
- Mechanism of action
Target Actions Organism ULactase/phlorizin hydrolase Not Available Humans - Absorption
Not Available
- Volume of distribution
Not Available
- Protein binding
Not Available
- Metabolism
- Not Available
- Route of elimination
Not Available
- Half-life
Not Available
- Clearance
Not Available
- Adverse Effects
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Not Available
- Pathways
Pathway Category Transaldolase Deficiency Disease Glucose-6-phosphate Dehydrogenase Deficiency Disease Pentose Phosphate Pathway Metabolic Ribose-5-phosphate Isomerase Deficiency Disease - Pharmacogenomic Effects/ADRs
- Not Available
Interactions
- Drug Interactions
- 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.Not Available
- Food Interactions
- No interactions found.
Products
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Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image Renacidin Gluconolactone (0.198 g/100mL) + Citric acid (6.6 g/100mL) + Magnesium carbonate (3.376 g/100mL) Solution Irrigation United-Guardian, Inc. 1991-01-01 2018-06-01 US 
Renacidin Gluconolactone (0.198 g/100mL) + Citric acid (6.602 g/100mL) + Magnesium carbonate (3.268 g/100mL) Solution Irrigation United-Guardian, Inc. 2016-02-01 Not applicable US
Categories
- Drug Categories
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as gluconolactones. These are polyhydroxy acids containing a gluconolactone molecule, which is characterized by a tetrahydropyran substituted by three hydroxyl groups, one ketone group, and one hydroxymethyl group.
- Kingdom
- Organic compounds
- Super Class
- Organic oxygen compounds
- Class
- Organooxygen compounds
- Sub Class
- Carbohydrates and carbohydrate conjugates
- Direct Parent
- Gluconolactones
- Alternative Parents
- Delta valerolactones / Oxanes / Secondary alcohols / Carboxylic acid esters / Polyols / Oxacyclic compounds / Monocarboxylic acids and derivatives / Primary alcohols / Organic oxides / Hydrocarbon derivatives show 1 more
- Substituents
- Alcohol / Aliphatic heteromonocyclic compound / Carbonyl group / Carboxylic acid derivative / Carboxylic acid ester / Delta valerolactone / Delta_valerolactone / Gluconolactone / Hydrocarbon derivative / Lactone show 8 more
- Molecular Framework
- Aliphatic heteromonocyclic compounds
- External Descriptors
- aldono-1,5-lactone, gluconolactone (CHEBI:16217)
- Affected organisms
- Not Available
Chemical Identifiers
- UNII
- WQ29KQ9POT
- CAS number
- 90-80-2
- InChI Key
- PHOQVHQSTUBQQK-SQOUGZDYSA-N
- InChI
- InChI=1S/C6H10O6/c7-1-2-3(8)4(9)5(10)6(11)12-2/h2-5,7-10H,1H2/t2-,3-,4+,5-/m1/s1
- IUPAC Name
- (3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-one
- SMILES
- OC[C@H]1OC(=O)[C@H](O)[C@@H](O)[C@@H]1O
References
- General References
- Not Available
- External Links
- Human Metabolome Database
- HMDB0000150
- KEGG Drug
- D04332
- KEGG Compound
- C00198
- PubChem Compound
- 7027
- PubChem Substance
- 46506698
- ChemSpider
- 6760
- BindingDB
- 50366565
- 25842
- ChEBI
- 16217
- ChEMBL
- CHEMBL1200829
- ZINC
- ZINC000002539702
- PDBe Ligand
- LGC
- Wikipedia
- Gluconolactone
- PDB Entries
- 1e6x / 2e40 / 2vwg / 2w39 / 3azz / 3eqo / 3vif / 4ynu / 4zlg / 4zob … show 4 more
Clinical Trials
- Clinical Trials
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Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
Form Route Strength Solution Irrigation - Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source water solubility 5.9E+005 mg/L (at 25 °C) MERCK INDEX (1996) - Predicted Properties
Property Value Source Water Solubility 586.0 mg/mL ALOGPS logP -2.2 ALOGPS logP -2.7 Chemaxon logS 0.52 ALOGPS pKa (Strongest Acidic) 11.62 Chemaxon pKa (Strongest Basic) -3 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 5 Chemaxon Hydrogen Donor Count 4 Chemaxon Polar Surface Area 107.22 Å2 Chemaxon Rotatable Bond Count 1 Chemaxon Refractivity 34.78 m3·mol-1 Chemaxon Polarizability 15.53 Å3 Chemaxon Number of Rings 1 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter No Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption - 0.6673 Blood Brain Barrier + 0.5748 Caco-2 permeable - 0.8709 P-glycoprotein substrate Non-substrate 0.6469 P-glycoprotein inhibitor I Non-inhibitor 0.9477 P-glycoprotein inhibitor II Non-inhibitor 0.9759 Renal organic cation transporter Non-inhibitor 0.8928 CYP450 2C9 substrate Non-substrate 0.8421 CYP450 2D6 substrate Non-substrate 0.8852 CYP450 3A4 substrate Non-substrate 0.6784 CYP450 1A2 substrate Non-inhibitor 0.9831 CYP450 2C9 inhibitor Non-inhibitor 0.9724 CYP450 2D6 inhibitor Non-inhibitor 0.9668 CYP450 2C19 inhibitor Non-inhibitor 0.9771 CYP450 3A4 inhibitor Non-inhibitor 0.9594 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.98 Ames test Non AMES toxic 0.5908 Carcinogenicity Non-carcinogens 0.9631 Biodegradation Ready biodegradable 0.9489 Rat acute toxicity 1.0920 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9764 hERG inhibition (predictor II) Non-inhibitor 0.9507
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 134.0673724 predictedDarkChem Lite v0.1.0 [M-H]- 134.7590724 predictedDarkChem Lite v0.1.0 [M-H]- 135.81691 predictedDeepCCS 1.0 (2019) [M+H]+ 135.8652724 predictedDarkChem Lite v0.1.0 [M+H]+ 136.3474724 predictedDarkChem Lite v0.1.0 [M+H]+ 138.21034 predictedDeepCCS 1.0 (2019) [M+Na]+ 133.8556724 predictedDarkChem Lite v0.1.0 [M+Na]+ 134.0495724 predictedDarkChem Lite v0.1.0 [M+Na]+ 144.5572 predictedDeepCCS 1.0 (2019)
Targets
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- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Broad specificity glycosidase of the intestinal brush border membrane that hydrolyzes lactose, the main sugar in mammalian milk, to produce D-glucose and D-galactose (PubMed:12594539, PubMed:16400612, PubMed:3929764, PubMed:9762914). The mature protein is composed of two domains that catalyze the hydrolysis of beta-glucopyranosides and beta-galactopyranosides, with a preference for hydrophilic aglycones (in lactose and cellobiose) for one domain and hydrophobic aglycones (in phlorizin and glycosylceramides) for the other (PubMed:12594539, PubMed:3929764, PubMed:9762914)
- Specific Function
- beta-glucosidase activity
- Gene Name
- LCT
- Uniprot ID
- P09848
- Uniprot Name
- Lactase/phlorizin hydrolase
- Molecular Weight
- 218584.77 Da
References
- Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [Article]
Drug created at June 13, 2005 13:24 / Updated at February 21, 2021 18:51