Demannose

Possibly Marketed Outside US

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C6H12O6
Molecular Weight	180.1561
Optical Activity	UNSPECIFIED
Defined Stereocenters	4 / 4
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)C=O

InChI

InChIKey=GZCGUPFRVQAUEE-KVTDHHQDSA-N

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-/m1/s1

HIDE SMILES / InChI

Molecular Formula	C6H12O6
Molecular Weight	180.1561
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	4 / 4
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: http://www.douglaslabs.com/media/DL99471.pdf
Curator's Comment: description was created based on several sources, including http://www.rxlist.com/d-mannose-page2/supplements.htm | https://www.ncbi.nlm.nih.gov/pubmed/6753135 | https://www.ncbi.nlm.nih.gov/pubmed/9736238

D-mannose is a simple sugar found naturally in fruits such as cranberries and pineapples. Unlike many sugars, it is not metabolised or stored in the liver. Much of it is excreted in the urine, where it interferes with particle attachment and prevents certain kind of bacteria from sticking to the walls and causing infection. Mannose supplement is also indicated for treatment of carbohydrate-deficient glycoprotein syndrome, however clinical trials failed to prove its efficacy.

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Adhesin protein fimH 1 Target ID: CHEMBL4837 Sources: https://www.ncbi.nlm.nih.gov/pubmed/15659162	Inhibitor 8504		2300.0 nM [Kd]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Urinary tract infections 207 Sources: http://www.rxlist.com/d-mannose-page2/supplements.htm	Curative		Approved 8583	D-MANNOSE Approved Use D-mannose may be a useful dietary supplement for individuals wishing to support normal urinary tract health
Carbohydrate-deficient glycoprotein syndrome 1 Sources: http://www.rxlist.com/d-mannose-page2/supplements.htm	Primary		Approved 8583	D-MANNOSE Approved Use D-mannose is used for treating carbohydrate-deficient glycoprotein syndrome, an inherited metabolic disorder.

Doses

Dose	Population	Adverse events
1 g 3 times / day multiple, oral Studied dose Dose: 1 g, 3 times / day Route: oral Route: multiple Dose: 1 g, 3 times / day Sources: https://clinicaltrials.gov/ct2/show/results/NCT01808755?term=MANNOSE%2C+D-&recrs=e&rslt=With&draw=2&rank=1	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: F Food Status: UNKNOWN Sources: https://clinicaltrials.gov/ct2/show/results/NCT01808755?term=MANNOSE%2C+D-&recrs=e&rslt=With&draw=2&rank=1	Sources: https://clinicaltrials.gov/ct2/show/results/NCT01808755?term=MANNOSE%2C+D-&recrs=e&rslt=With&draw=2&rank=1
2 g 1 times / day steady, oral Studied dose Dose: 2 g, 1 times / day Route: oral Route: steady Dose: 2 g, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/23633128/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/23633128/	Sources: https://pubmed.ncbi.nlm.nih.gov/23633128/

PubMed

Title	Date	PubMed
2-Deoxy-D-glucose activates autophagy via endoplasmic reticulum stress rather than ATP depletion.	2011-04	20593179
New approaches in the diagnosis and treatment of latent tuberculosis infection.	2010-12-03	21126375
Molecular epidemiology of zoonotic streptococcosis/lactococcosis in rainbow trout (Oncorhynchus mykiss) aquaculture in Iran.	2010-12	22347573
Acceptor substrate discrimination in phosphatidyl-myo-inositol mannoside synthesis: structural and mutational analysis of mannosyltransferase Corynebacterium glutamicum PimB'.	2010-11-26	20843801
Escherichia coli global gene expression in urine from women with urinary tract infection.	2010-11-11	21085611
Modular approach to triazole-linked 1,6-α-D-oligomannosides to the discovery of inhibitors of Mycobacterium tuberculosis cell wall synthetase.	2010-10-01	20822121
Oral tolerance to food-induced systemic anaphylaxis mediated by the C-type lectin SIGNR1.	2010-10	20835248
Structural and functional basis of resistance to neuraminidase inhibitors of influenza B viruses.	2010-09-09	20695427
Crystal structures of a novel anti-HIV mannose-binding lectin from Polygonatum cyrtonema Hua with unique ligand-binding property and super-structure.	2010-09	20546901
In vivo expression of innate immunity markers in patients with Mycobacterium tuberculosis infection.	2010-08-18	20718957
Cloning, expression and efficient refolding of carbohydrate-peptide mimicry recognizing single chain antibody 2D10.	2010-08	20363331
Structure-based drug design and optimization of mannoside bacterial FimH antagonists.	2010-06-24	20507142
Extracellular SOD-derived H2O2 promotes VEGF signaling in caveolae/lipid rafts and post-ischemic angiogenesis in mice.	2010-04-21	20422004
A multifunctional mannosyltransferase family in Candida albicans determines cell wall mannan structure and host-fungus interactions.	2010-04-16	20164191
A proteomic study of cMyc improvement of CHO culture.	2010-03-22	20307306
Structure and kinetic investigation of Streptococcus pyogenes family GH38 alpha-mannosidase.	2010-02-03	20140249
Mechanistic insights into a Ca2+-dependent family of alpha-mannosidases in a human gut symbiont.	2010-02	20081828
Taurolidine antiadhesive properties on interaction with E. coli; its transformation in biological environment and interaction with bacteria cell wall.	2010-01-28	20126631
Structural basis of the affinity for oligomannosides and analogs displayed by BC2L-A, a Burkholderia cenocepacia soluble lectin.	2010-01	19770128
Interactome analyses identify ties of PrP and its mammalian paralogs to oligomannosidic N-glycans and endoplasmic reticulum-derived chaperones.	2009-10	19798432
Understanding how diverse beta-mannanases recognize heterogeneous substrates.	2009-07-28	19441796
Colon cancer releases alpha-tocopherol from its O-glycosides better than normal colon tissue.	2009-07-08	19579594
The two-domain LysX protein of Mycobacterium tuberculosis is required for production of lysinylated phosphatidylglycerol and resistance to cationic antimicrobial peptides.	2009-07	19649276
Structure of the Michaelis complex of beta-mannosidase, Man2A, provides insight into the conformational itinerary of mannoside hydrolysis.	2009-05-14	19532864
Synthesis, conformation, and biological characterization of a sugar derivative of morphine that is a potent, long-lasting, and nontolerant antinociceptive.	2009-05-14	19351163
Controlled enlargement of the glycoprotein vesicle surrounding a volvox embryo requires the InvB nucleotide-sugar transporter and is required for normal morphogenesis.	2009-04	19346464
Global analysis of the glycoproteome in Saccharomyces cerevisiae reveals new roles for protein glycosylation in eukaryotes.	2009	19756047
Non-invasive molecular imaging of fibrosis using a collagen-targeted peptidomimetic of the platelet collagen receptor glycoprotein VI.	2009	19440310
PIM2 Induced COX-2 and MMP-9 expression in macrophages requires PI3K and Notch1 signaling.	2009	19290049
Mannose-based molecular patterns on stealth microspheres for receptor-specific targeting of human antigen-presenting cells.	2008-10-21	18785716
Syntheses of phosphatidyl-beta-D-glucoside analogues to probe antigen selectivity of monoclonal antibody 'DIM21'.	2008-08-01	18625561
Expeditive synthesis of glycodendrimer scaffolds based on versatile TRIS and mannoside derivatives.	2008-07-18	18572921
Probing the substrate specificity of Golgi alpha-mannosidase II by use of synthetic oligosaccharides and a catalytic nucleophile mutant.	2008-07-16	18558690
Crystal structure of squid rhodopsin with intracellularly extended cytoplasmic region.	2008-06-27	18463093
Mannoside hydrolysis: it's a boat!	2008-05	18421282
Intervening with urinary tract infections using anti-adhesives based on the crystal structure of the FimH-oligomannose-3 complex.	2008-04-30	18446213
Role of antibody paratope conformational flexibility in the manifestation of molecular mimicry.	2008-02-15	18032557
Tetra- and hexavalent mannosides inhibit the pro-apoptotic, antiproliferative and cell surface clustering effects of concanavalin-A: impact on MT1-MMP functions in marrow-derived mesenchymal stromal cells.	2008-02	18065811
EmbA is an essential arabinosyltransferase in Mycobacterium tuberculosis.	2008-01	18174142
Identification of hexose diastereomers by means of tandem mass spectrometry of oxocarbenium ions followed by neural networks analysis.	2008-01	17968854
Multi-mannosides based on a carbohydrate scaffold: synthesis, force field development, molecular dynamics studies, and binding affinities for lectin Con A.	2007-11-23	17979282
Anti-pig IgM antibodies in human serum react predominantly with Gal(alpha 1-3)Gal epitopes.	1993-12-01	7504304
Intravenous administration of phosphorylated acid alpha-glucosidase leads to uptake of enzyme in heart and skeletal muscle of mice.	1991-02	1991835
Automated screening of urine samples for carbohydrates, organic and amino acids after treatment with urease.	1991-01-02	2026685
Lysosomal tartrate sensitive acid phosphatase deficiency in cells which contain lysosomal "high uptake forms".	1990-03-16	2322240
Quantitative analysis of polyols in human plasma and cerebrospinal fluid.	1989-12-29	2625478
Inhibition of cyclic AMP-dependent induction of ornithine aminotransferase by simple carbohydrates in cultured hepatocytes.	1987-12	2827574
Relationships between glucose and mannose during late gestation in normal pregnancy and pregnancy complicated by diabetes mellitus: concurrent concentrations in maternal plasma and amniotic fluid.	1986-05	3958133
Lectin cytochemical evaluation of somatosensory neurons and their peripheral and central processes in rat and man.	1986	3757018
Concanavalin A binding glycoprotein in human stratum corneum.	1984-03	6421939

Patents

Sample Use Guides

In Vivo Use Guide

3 x 1000mg tablets every three hours for a couple of days plus a middle of the night dose is a good guide for most people who need urgent support. Reduce slowly as symptoms improve.

Route of Administration: Oral

In Vitro Use Guide

Two rows of serial two fold dilutions of bacterial suspension in PBS were dispensed in microtiter plates. To each well in the first row an aliquot of a yeast suspension was added; to each raw in the second row an aliquote of washed 3% human group A erythrocytes was added. The plates were gently shaken. Yeast agglutination was scored after 30 min at room temperature, hemagglutination was assessed after the plates were kept overnight at 4°C. To establish whether the agglutination was mannose sensitive or mannose resistant, the bacteria 10^9 cells/ml were suspended in PBS containing 2.5 % methyl alpha-D-mannoside prior to the assay.

Substance Class	Chemical Created by `admin` on `Mon Mar 31 17:33:50 GMT 2025` Edited by `admin` on `Mon Mar 31 17:33:50 GMT 2025`
Record UNII	PHA4727WTP
Record Status	`FAILED`
Record Version

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Name

Type

Language

MANNOSE

Preferred Name

English

Demannose

Official Name

English

MANNOSE, D-

Preferred Name

English

NSC-26247

Code

English

demannose [INN]

Common Name

English

DEMANNOSE [USAN]

Common Name

English

D-mannose [WHO-DD]

Common Name

English

SEMINOSE

Common Name

English

CARUBINOSE

Common Name

English

D-MANNOSE [MI]

Common Name

English

MANNOSE [VANDF]

Common Name

English

(2S,3S,4R,5R)-2,3,4,5,6-pentahydroxyhexanal

Systematic Name

English

D-MANNOSE

Systematic Name

English

MANNOSE [USP-RS]

Common Name

English

MANNOSE, D- [II]

Common Name

English

CERC-802

Code

English

Classification Tree Code System Code

DSLD

2627 (Number of products:112)