Identification
- Generic Name
- Tagatose
- DrugBank Accession Number
- DB04936
- Background
Tagatose is a functional sweetener. It is a naturally occurring monosaccharide, specifically a hexose. It is commonly found in dairy with a similar texture and sweetened capacity to sucrose but with only a third of the calories. It is approved as a food additive as a low calorie sweetener. Additionally, it is under investigation by Spherix for the treatment of obesity and type II diabetes.
- Type
- Small Molecule
- Groups
- Investigational
- Structure
Structure for Tagatose (DB04936)
- Weight
- Average: 180.1559
Monoisotopic: 180.063388116 - Chemical Formula
- C6H12O6
- Synonyms
- (3S,4S,5R)-1,3,4,5,6-pentahydroxyhexan-2-one
- D-lyxo-hex-2-ulose
- D-lyxo-hexulose
- D-tag
- D-tagatose
- keto-D-tagatose
Pharmacology
- Indication
Intended for use as a therapeutic adjunct in the treatment of type II diabetes.
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Oral tagatose significantly blunts the rise in plasma glucose seen after oral glucose in patients with diabetes mellitus in a dose-dependent manner without significantly affecting insulin levels. The minimal elevation of plasma tagatose levels in normal patients and the adverse gastrointestinal effects seen following larger doses of tagatose support poor absorption of this hexose and suggest that tagatose may act by attenuating glucose absorption in the intestine.
- Mechanism of action
he steps in the metabolism of tagatose are identical to those for fructose or fruit sugar but tagatose is incompletely absorbed. Only 15-20 percent of tagatose is absorbed in the small intestine. The major part of ingested tagatose is fermented in the colon by indigenous microflora, resulting in the production of short-chain fatty acids. The short chain fatty acids are absorbed almost completely and metabolized.
- Absorption
Only 15-20 percent of tagatose is absorbed in the small intestine.
- Volume of distribution
Not Available
- Protein binding
Not Available
- Metabolism
Tagatose does not influence the level of blood glucose nor insulin levels.
- Route of elimination
Not Available
- Half-life
Not Available
- Clearance
Not Available
- Adverse Effects
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Not Available
- Pathways
- Not Available
- 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.
Drug Interaction Integrate drug-drug
interactions in your softwareTechnetium Tc-99m oxidronate Tagatose may decrease effectiveness of Technetium Tc-99m oxidronate as a diagnostic agent. - Food Interactions
- Not Available
Products
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- Naturlose
Categories
- Drug Categories
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as monosaccharides. These are compounds containing one carbohydrate unit not glycosidically linked to another such unit, and no set of two or more glycosidically linked carbohydrate units. Monosaccharides have the general formula CnH2nOn.
- Kingdom
- Organic compounds
- Super Class
- Organic oxygen compounds
- Class
- Organooxygen compounds
- Sub Class
- Carbohydrates and carbohydrate conjugates
- Direct Parent
- Monosaccharides
- Alternative Parents
- Beta-hydroxy ketones / Acyloins / Alpha-hydroxy ketones / Secondary alcohols / Polyols / Primary alcohols / Organic oxides / Hydrocarbon derivatives
- Substituents
- Acyloin / Alcohol / Aliphatic acyclic compound / Alpha-hydroxy ketone / Beta-hydroxy ketone / Carbonyl group / Hydrocarbon derivative / Ketone / Monosaccharide / Organic oxide
- Molecular Framework
- Aliphatic acyclic compounds
- External Descriptors
- tagatose, D-tagatose (CHEBI:47693)
- Affected organisms
- Humans and other mammals
Chemical Identifiers
- UNII
- T7A20Y888Y
- CAS number
- 87-81-0
- InChI Key
- BJHIKXHVCXFQLS-PQLUHFTBSA-N
- InChI
- InChI=1S/C6H12O6/c7-1-3(9)5(11)6(12)4(10)2-8/h3,5-9,11-12H,1-2H2/t3-,5+,6-/m1/s1
- IUPAC Name
- (3S,4S,5R)-1,3,4,5,6-pentahydroxyhexan-2-one
- SMILES
- OC[C@@H](O)[C@H](O)[C@H](O)C(=O)CO
References
- General References
- Donner TW, Wilber JF, Ostrowski D: D-tagatose, a novel hexose: acute effects on carbohydrate tolerance in subjects with and without type 2 diabetes. Diabetes Obes Metab. 1999 Sep;1(5):285-91. [Article]
- External Links
- Human Metabolome Database
- HMDB0003418
- PubChem Compound
- 92092
- PubChem Substance
- 175426910
- ChemSpider
- 83142
- ChEBI
- 47693
- ZINC
- ZINC000002516866
- PDBe Ligand
- TAG
- Wikipedia
- Tagatose
- PDB Entries
- 2qum / 3vnl / 7dz4 / 8u01
- MSDS
- Download (69.8 KB)
Clinical Trials
- Clinical Trials
Phase Status Purpose Conditions Count 3 Completed Treatment Type 2 Diabetes Mellitus 1 2 Completed Treatment Type 2 Diabetes Mellitus 1
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
- Not Available
- Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 133-135 °C Not Available - Predicted Properties
Property Value Source Water Solubility 399.0 mg/mL ALOGPS logP -2.2 ALOGPS logP -3.3 Chemaxon logS 0.35 ALOGPS pKa (Strongest Acidic) 12.16 Chemaxon pKa (Strongest Basic) -3 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 6 Chemaxon Hydrogen Donor Count 5 Chemaxon Polar Surface Area 118.22 Å2 Chemaxon Rotatable Bond Count 5 Chemaxon Refractivity 37.56 m3·mol-1 Chemaxon Polarizability 16.44 Å3 Chemaxon Number of Rings 0 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 + 0.7519 Blood Brain Barrier - 0.5821 Caco-2 permeable - 0.8899 P-glycoprotein substrate Non-substrate 0.6377 P-glycoprotein inhibitor I Non-inhibitor 0.9527 P-glycoprotein inhibitor II Non-inhibitor 0.9369 Renal organic cation transporter Non-inhibitor 0.9292 CYP450 2C9 substrate Non-substrate 0.8653 CYP450 2D6 substrate Non-substrate 0.8805 CYP450 3A4 substrate Non-substrate 0.7379 CYP450 1A2 substrate Non-inhibitor 0.8273 CYP450 2C9 inhibitor Non-inhibitor 0.9441 CYP450 2D6 inhibitor Non-inhibitor 0.9417 CYP450 2C19 inhibitor Non-inhibitor 0.9346 CYP450 3A4 inhibitor Non-inhibitor 0.9195 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.9652 Ames test Non AMES toxic 0.8597 Carcinogenicity Non-carcinogens 0.7946 Biodegradation Ready biodegradable 0.913 Rat acute toxicity 1.4430 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9837 hERG inhibition (predictor II) Non-inhibitor 0.9306
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 137.1892761 predictedDarkChem Lite v0.1.0 [M-H]- 137.1770761 predictedDarkChem Lite v0.1.0 [M-H]- 138.2437761 predictedDarkChem Lite v0.1.0 [M-H]- 141.73415 predictedDeepCCS 1.0 (2019) [M+H]+ 137.8672761 predictedDarkChem Lite v0.1.0 [M+H]+ 139.5044761 predictedDarkChem Lite v0.1.0 [M+H]+ 137.4385761 predictedDarkChem Lite v0.1.0 [M+H]+ 144.12971 predictedDeepCCS 1.0 (2019) [M+Na]+ 136.6953761 predictedDarkChem Lite v0.1.0 [M+Na]+ 143.4711901 predictedDarkChem Standard v0.1.0 [M+Na]+ 137.3883761 predictedDarkChem Lite v0.1.0 [M+Na]+ 150.04222 predictedDeepCCS 1.0 (2019)
Drug created at October 21, 2007 22:23 / Updated at June 12, 2020 16:52