Identification
- Generic Name
- Galactose
- DrugBank Accession Number
- DB11735
- Background
Galactose has been used in trials studying the treatment and diagnosis of Hepatitis C, Hepatic Cancer, Wilsons Disease, Diabetic Macular Oedema, and Focal Segmental Glomerulosclerosis, among others. There are even proposals for its use in accelerating senescence in mice, rats, and Drosophila, for its association with ovarian cancer, or even for the potential treatment of focal segmental glomerulosclerosis. Nevertheless, none of these ongoing studies have yet provided formal elucidation for their proposals.
As a naturally occurring sugar, it may be found in a number dairy products. Even then, however, it is not generally used as a sweetener considering it is only about 30% as sweet as sucrose. Regardless, although it is predominantly used as a pathway to generate glucose fuel for the human body, galactose is involved as an ingredient in some commonly used vaccines and non-prescription products.
- Type
- Small Molecule
- Groups
- Approved, Investigational
- Structure
Structure for Galactose (DB11735)
- Weight
- Average: 180.1559
Monoisotopic: 180.063388116 - Chemical Formula
- C6H12O6
- Synonyms
- D-Galactose
- D(+)-Galactose
- Galactose
Pharmacology
- Indication
There are limited therapeutic uses for which galactose is formally indicated. Some predominant indications include (a) the use of galactose to facilitate the construction of structurally and immunologically effective attenuated vaccines 12,14, and (b) the role galactose plays as an essential element in the formation of lactulose - a synthetic disaccharide indicated for the treatment of constipation and/or hepatic encephalopathy (HE); hepatic coma 13.
Nevertheless, there are many studies looking into a variety of possible uses for galactose, including the use of the monosaccharide sugar for accelerating senescence in mice, rats, and Drosophila 1,2, the proposed association between galactose in consumed milk and ovarian cancer 3,4, a possible role in the therapy of focal segmental glomerulosclerosis 5, among various others. Regardless, none of these proposed indications have yet been formally elucidated for practical use.
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Galactose is a naturally occurring monosaccharide that forms the disaccharide lactose when combined with glucose (another monosaccharide) 6. Subsequently, when lactose or small amounts of free galactose found in various common dairy products (and other foods) are consumed, the hydrolysis of lactose to glucose and galactose occurs and galactose is itself further metabolized to generate glucose 6. Such glucose is, of course, ultimately relied upon and used as the primary metabolic fuel for humans in a variety of biological reactions.
Conversely, however, the ways in which galactose is commonly used in therapeutic agents generally do not rely upon such pharmacodynamics, even though they ultimately remain the most important ways in which galactose exerts or elicits useful biological actions for the human body.
- Mechanism of action
In the development of typhoid Ty21a live oral vaccine, the use of exogenous galactose is critical. When dealing with Salmonella typhimurium, it has been shown that rough strains with incomplete lipopolysaccharide (LPS) lacking O-specific side chains are much less virulent than smooth strains with complete LPS with O-specific side chains 12. Salmonella typhimurium gal E mutants used to produce the vaccine are effectively avirulent and highly protective but lack the specific UDP-galactose 4-epimerase enzyme which allows for the normal synthesis of UDP-galactose from UDP-glucose 12. The consequence of this mutant defect is that the gal E mutants can only generate incomplete LPS without O-specific antigen side chains, which are not capable enough as the complete LPS with O-specific side chains at generating an immunologic response 12. When exogenous galactose is added to the vaccine medium, however, it allows the mutants to generate UDP-galactose via galactose 1-phosphate 12. This ultimately allows the mutants to form smooth-type LPS with O-specific side chains 12. Regardless, the mutant's epimerase defect ultimately results in the accumulation of such intermediary products like galactose 1-phosphate and UDP-galactose, which consequently causes lysis of the mutant cells. The resultant vaccine is subsequently effective enough to elicit an immunologic response while the bacteriolysis prevents the mutant cells from regaining virulence under conditions where smooth type LPS similar to the active parental strain is synthesized 12.
Galactose is also an essential element to the chemical structure of the commonly used laxative solution lactulose. Lactulose itself is a synthetic disaccharide that is made in parts from lactose, galactose, and various other sugars 15. It is poorly absorbed from the gastrointestinal tract and no enzyme capable of hydrolysis of lactulose is present in human gastrointestinal tissue 15. Oral doses of lactulose subsequently arrive at the colon largely unchanged 15. At the colon, lactulose is finally broken down predominantly to lactic acid, and also small amounts of formic and acetic acids by the action of colonic bacteria, which results in an increase in osmotic pressure and slight acidification of the colonic contents 15. This action consequently causes an increase in stool water content and softens the stool for a laxative effect 15.
- Absorption
The absorption of galactose from the human jejunum was calculated to be 1.0 g per minute per 30 cm of the gut 7.
- Volume of distribution
It has been documented that galactose distributes in a volume equivalent to 40% of body weight 8.
- Protein binding
Readily accessible data regarding the protein binding of galactose is not available.
- Metabolism
The primary pathway for galactose metabolism is called the Leloir pathway, so named after Luis Federico Leloir. The initial stage of this pathway is the conversion of beta-D-galactose to alpha-D-galactose by the enzyme galactose mutarotase (GALM) 6. The pathway then performs the conversion of alpha-D-galactose to UDP-glucose by way of three principal enzymes and their reactions: galactokinase (GALK) phosphorylates alpha-D-galactose to galactose-1-phosphate (Gal-1-P); galactose-1-phosphate uridyltransferase (GALT) transfers a UMP group from UDP-glucose to Gal-1-P to form UDP-galactose; and finally, UDP galactose-4-epimerase (GALE) interconverts UDP-galactose and UDP-glucose, which completes the pathway 6.
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- Route of elimination
The primary route of elimination for galactose is hepatic 14,6.
- Half-life
Readily accessible data regarding the half-life of galactose is not available.
- Clearance
In subjects with no liver disease, systemic galactose clearance was calculated to be 1.5 +/- 0.1 L/min 9.
- Adverse Effects
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It is typically uncommon to experience an overdosage situation with dietary galactose or from galactose as an ingredient in a therapeutic agent. At the same time, the experiencing a situation characterized by excessive amounts of galactose in the body defines the challenge with galactosemia, which is itself a rare genetic metabolic disorder. In individuals with galactosemia, the enzymes needed for further metabolism of galactose (ie. such as galactose-1-phosphate uridyltransferase) are severely diminished or missing entirely, leading to toxic levels of galactose 1-phosphate in various tissues 10. This toxic excess typically results in hepatomegaly, cirrhosis, renal failure, cataracts, vomiting, hypoglycemia, lethargy, brain damage, and ovarian failure 10. Without treatment, mortality in infants with galactosemia is about 75% 11.
- 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.Not Available
- 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.- Mixture Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image Echovist Galactose (13.5 mL / vial) + Galactose (3 g / vial) Kit; Powder, for suspension Intrauterine Berlex Laboratories, Inc. 1999-02-15 2004-02-12 Canada 
Echovist Galactose (13.5 mL / vial) + Galactose (3 g / vial) Kit; Powder, for suspension Intrauterine Berlex Laboratories, Inc. 1999-02-15 2004-02-12 Canada Levovist - Pws IV (4g Granules /vial) Galactose (999 mg / g) + Palmitic Acid (1 mg / g) Powder, for solution Intravenous Berlex Laboratories, Inc. 1997-12-19 2003-06-26 Canada
Categories
- ATC Codes
- V08DA02 — Microparticles of galactoseV04CE01 — Galactose
- Drug Categories
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as hexoses. These are monosaccharides in which the sugar unit is a is a six-carbon containing moeity.
- Kingdom
- Organic compounds
- Super Class
- Organic oxygen compounds
- Class
- Organooxygen compounds
- Sub Class
- Carbohydrates and carbohydrate conjugates
- Direct Parent
- Hexoses
- Alternative Parents
- Medium-chain aldehydes / Beta-hydroxy aldehydes / Alpha-hydroxyaldehydes / Secondary alcohols / Polyols / Primary alcohols / Organic oxides / Hydrocarbon derivatives
- Substituents
- Alcohol / Aldehyde / Aliphatic acyclic compound / Alpha-hydroxyaldehyde / Beta-hydroxy aldehyde / Carbonyl group / Hexose monosaccharide / Hydrocarbon derivative / Medium-chain aldehyde / Organic oxide
- Molecular Framework
- Aliphatic acyclic compounds
- External Descriptors
- aldehydo-galactose, D-galactose (CHEBI:17118)
- Affected organisms
- Not Available
Chemical Identifiers
- UNII
- X2RN3Q8DNE
- CAS number
- 59-23-4
- InChI Key
- GZCGUPFRVQAUEE-KCDKBNATSA-N
- InChI
- InChI=1S/C6H12O6/c7-1-3(9)5(11)6(12)4(10)2-8/h1,3-6,8-12H,2H2/t3-,4+,5+,6-/m0/s1
- IUPAC Name
- (2R,3S,4S,5R)-2,3,4,5,6-pentahydroxyhexanal
- SMILES
- [H]C(=O)[C@H](O)[C@@H](O)[C@@H](O)[C@H](O)CO
References
- General References
- Pourmemar E, Majdi A, Haramshahi M, Talebi M, Karimi P, Sadigh-Eteghad S: Intranasal Cerebrolysin Attenuates Learning and Memory Impairments in D-galactose-Induced Senescence in Mice. Exp Gerontol. 2017 Jan;87(Pt A):16-22. doi: 10.1016/j.exger.2016.11.011. Epub 2016 Nov 25. [Article]
- Cui X, Zuo P, Zhang Q, Li X, Hu Y, Long J, Packer L, Liu J: Chronic systemic D-galactose exposure induces memory loss, neurodegeneration, and oxidative damage in mice: protective effects of R-alpha-lipoic acid. J Neurosci Res. 2006 Aug 15;84(3):647-54. doi: 10.1002/jnr.20899. [Article]
- Cramer DW: Lactase persistence and milk consumption as determinants of ovarian cancer risk. Am J Epidemiol. 1989 Nov;130(5):904-10. [Article]
- Cramer DW, Harlow BL, Willett WC, Welch WR, Bell DA, Scully RE, Ng WG, Knapp RC: Galactose consumption and metabolism in relation to the risk of ovarian cancer. Lancet. 1989 Jul 8;2(8654):66-71. [Article]
- Savin VJ, McCarthy ET, Sharma R, Charba D, Sharma M: Galactose binds to focal segmental glomerulosclerosis permeability factor and inhibits its activity. Transl Res. 2008 Jun;151(6):288-92. doi: 10.1016/j.trsl.2008.04.001. Epub 2008 May 2. [Article]
- Sunehag A, Tigas S, Haymond MW: Contribution of plasma galactose and glucose to milk lactose synthesis during galactose ingestion. J Clin Endocrinol Metab. 2003 Jan;88(1):225-9. doi: 10.1210/jc.2002-020768. [Article]
- HOLDSWORTH CD, DAWSON AM: THE ABSORPTION OF MONOSACCHARIDES IN MAN. Clin Sci. 1964 Dec;27:371-9. [Article]
- WICK AN, DRURY DR: Action of insulin on volume of distribution of galactose in the body. Am J Physiol. 1953 May;173(2):229-32. doi: 10.1152/ajplegacy.1953.173.2.229. [Article]
- Keiding S: Galactose clearance measurements and liver blood flow. Gastroenterology. 1988 Feb;94(2):477-81. [Article]
- Leslie ND: Insights into the pathogenesis of galactosemia. Annu Rev Nutr. 2003;23:59-80. doi: 10.1146/annurev.nutr.23.011702.073135. Epub 2003 Apr 9. [Article]
- Karadag N, Zenciroglu A, Eminoglu FT, Dilli D, Karagol BS, Kundak A, Dursun A, Hakan N, Okumus N: Literature review and outcome of classic galactosemia diagnosed in the neonatal period. Clin Lab. 2013;59(9-10):1139-46. [Article]
- Rene Germanier (2012). Bacterial Vaccines. Academic Press. [ISBN:0323140211]
- Electronic Medicines Compendium: Duphalac (lactulose) monograph [Link]
- ScienceDirect: Galactose Profile [Link]
- Lactulose Solution USP Label [File]
- External Links
- MSDS
- Download (38.6 KB)
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 Withdrawn Treatment Hepatic neoplasms malignant 1 3 Completed Treatment Mucopolysaccharidosis Type IVA 1 3 Recruiting Treatment Brain Metastases / Breast Cancer / Cognitive Impairment (CI) / Gangliosidosis, GM1 / Radiotherapy Side Effects 1 2 Completed Treatment Focal Segmental Glomerulosclerosis (FSGS) 1 2 Completed Treatment Mucopolysaccharidosis Type IVA 1
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
Form Route Strength Kit; powder, for suspension Intrauterine Powder, for solution Intravenous - Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Not Available
- Experimental Properties
- Not Available
- Predicted Properties
Property Value Source Water Solubility 261.0 mg/mL ALOGPS logP -2.4 ALOGPS logP -3.6 Chemaxon logS 0.16 ALOGPS pKa (Strongest Acidic) 12.26 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 37.35 m3·mol-1 Chemaxon Polarizability 16.13 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
- Not Available
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 136.1736761 predictedDarkChem Lite v0.1.0 [M-H]- 144.27483 predictedDeepCCS 1.0 (2019) [M+H]+ 137.2987761 predictedDarkChem Lite v0.1.0 [M+H]+ 146.66057 predictedDeepCCS 1.0 (2019) [M+Na]+ 135.6626761 predictedDarkChem Lite v0.1.0 [M+Na]+ 152.5731 predictedDeepCCS 1.0 (2019)
Drug created at October 20, 2016 20:43 / Updated at May 04, 2023 00:49