Glucosamine

Identification

Summary

Glucosamine is a common ingredient in nutritional supplements used for the relief of joint pain.

Generic Name

Glucosamine

DrugBank Accession Number

DB01296

Background

Osteoarthritis (OA) is a progressive and degenerative joint disease marked by loss of cartilage, bone changes, and synovial membrane inflammation.¹⁴ Treatment with chondroprotective drugs, such as glucosamine sulfate may offer additional benefits to nonsteroidal anti-inflammatory drugs treating the painful symptoms of OA. Glucosamine is commonly used over the counter as a treatment for arthritic joint pain, although its acceptance as a medical therapy varies due to contradictory and findings with unclear clinical significance during clinical trials.^6,14 It is currently not approved as a prescription product by the FDA, but is widely available over the counter.

Type

Small Molecule

Groups

Approved, Investigational

Structure

3D

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MOLSDF3D-SDFPDBSMILESInChI

Similar Structures

Structure for Glucosamine (DB01296)

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Weight

Average: 179.1711
Monoisotopic: 179.079372531

Chemical Formula

C₆H₁₃NO₅

Synonyms

• 2-amino-2-deoxy-D-glucose
• Chitosamine
• D-Glucosamine
• Glucosamina
• Glucosamine

Pharmacology

Indication

Glucosamine is generally used over the counter in the symptomatic treatment of osteoarthritis and joint pain,¹ frequently combined with chondroitin sulfate and/or ibuprofen.²⁷

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Associated Conditions

• Back pain
• Joint Pain
• Osteoarthritis (OA)
• Osteoarthritis of the Knee
• Articular inflammation

Contraindications & Blackbox Warnings

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Pharmacodynamics

The administration of glucosamine, in theory, provides a building block towards the synthesis of glycosaminoglycans, slowing the progression of osteoarthritis and relieving symptoms of joint pain. Studies to this date examining the efficacy of glucosamine sulfate have been inconclusive. Glycosaminoglycans contribute to joint cartilage elasticity, strength, and flexibility.¹¹ A systematic review of various studies and guidelines determined that modest improvements were reported for joint pain and function in patients taking glucosamine. A consistent joint space narrowing was observed, but with an unclear clinical significance.⁶

Mechanism of action

The mechanism of action of glucosamine in joint health is unclear,⁶ however there are several possible mechanisms that contribute to its therapeutic effects. Because glucosamine is a precursor for glycosaminoglycans, and glycosaminoglycans are a major component of joint cartilage,¹⁴ glucosamine supplements may help to rebuild cartilage and treat the symptoms of arthritis. Some in vitro studies show evidence that glucosamine reduces inflammation via inhibition of interferon gamma^15,16,17 and Nuclear factor kappa B subunit 65 (NF-κB p65),^16,18 improving the symptoms of arthritis and joint pain. Clinical relevance is unknown at this time.

Target	Actions	Organism
UInterferon gamma	inhibitor	Humans
UTranscription factor p65	inhibitor	Humans

Absorption

In a pharmacokinetic study, glucosamine was 88.7% absorption by the gastrointestinal tract. Absolute oral bioavailability was 44%, likely due to the hepatic first-pass effect.¹² In a pharmacokinetic study of 12 healthy adults receiving oral crystalline glucosamine, plasma levels increased up to 30 times the baseline levels and Cmax was 10 microM with a 1,500 mg once-daily dose. Tmax was about 3 hours. AUC was 20,216 ± 5021 after a 15,000 mg dose.¹³

Volume of distribution

Results of a pharmacokinetic study of 12 healthy volunteers receiving three daily consecutive oral administrations of glucosamine sulfate soluble powder demonstrated glucosamine distribution to extravascular compartments.¹³ Human pharmacokinetic data for glucosamine is limited in the literature, however, a large animal model study of horses revealed a mean apparent volume of distribution of 15.4 L/kg. Concentrations of glucosamine ranged from 9-15 microM after an intravenous dose, and 0.3-0.7 microM after nasogastric dosing. These concentrations remained in the range of 0.1-0.7 microM in the majority of horses 12 hours after dosing,⁵ suggesting effectiveness of a once-daily dose. In rats and dogs, radioactivity from a C-14 labeled dose of glucosamine is detected in the liver, kidneys, articular cartilage, and other areas.¹²

Protein binding

Not Available

Metabolism

Glucosamine undergoes metabolism in the liver.¹² Metabolism information for glucosamine is limited in the literature.

Route of elimination

Fecal excretion of glucosamine in a pharmacokinetic study was 11.3% within 120 hours after administration.¹³ Urinary elimination was found to be 1.19% within the first 8 hours post-administration.¹²

Half-life

The estimated half-life for glucosamine is 15 hours after an oral dose.¹³ After a bolus intravenous injection of 1005 mg crystalline glucosamine sulfate, the parent drug has an apparent half life of 1.11 hours.¹²

Clearance

Not Available

Adverse Effects

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Toxicity

The oral LD50 of glucosamine in rats is >5000 mg/kg.²⁴ Symptoms of an overdose with glucosamine may include nausea, vomiting, abdominal pain, and diarrhea (common side effects of this drug). Severe and life-threatening hypersensitivity reactions to glucosamine may occur in patients with a shellfish allergy or asthma.²⁸

Pathways

Pathway	Category
Amino Sugar Metabolism	Metabolic
G(M2)-Gangliosidosis: Variant B, Tay-Sachs Disease	Disease
Sialuria or French Type Sialuria	Disease
Sialuria or French Type Sialuria	Disease
Salla Disease/Infantile Sialic Acid Storage Disease	Disease
Tay-Sachs Disease	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.

• Approved
• Vet approved
• Nutraceutical
• Illicit
• Withdrawn
• Investigational
• Experimental
• All Drugs

Drug	Interaction
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Abciximab	Glucosamine may increase the antiplatelet activities of Abciximab.
Acenocoumarol	Glucosamine may increase the anticoagulant activities of Acenocoumarol.
Acetylsalicylic acid	Glucosamine may increase the antiplatelet activities of Acetylsalicylic acid.
Anagrelide	Glucosamine may increase the antiplatelet activities of Anagrelide.
Cangrelor	Glucosamine may increase the antiplatelet activities of Cangrelor.
Caplacizumab	Glucosamine may increase the antiplatelet activities of Caplacizumab.
Cilostazol	Glucosamine may increase the antiplatelet activities of Cilostazol.
Clopidogrel	Glucosamine may increase the antiplatelet activities of Clopidogrel.
Defibrotide	Glucosamine may increase the antiplatelet activities of Defibrotide.
Dipyridamole	Glucosamine may increase the antiplatelet activities of Dipyridamole.

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Food Interactions

No interactions found.

Products

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Product Ingredients

Ingredient	UNII	CAS	InChI Key
Glucosamine hydrochloride	750W5330FY	66-84-2	QKPLRMLTKYXDST-NSEZLWDYSA-N
Glucosamine sulfate	1FW7WLR731	14999-43-0	WLNBMPZUVDTASE-HXIISURNSA-N
Glucosamine sulfate potassium chloride	15VQ11I66N	1296149-08-0	UOUQWMJTBOYJTE-YZJMRIMCSA-M
Glucosamine sulfate sodium chloride	7RI65CXJ9S	Not Available	Not applicable

Generic Prescription Products

Name	Dosage	Strength	Route	Labeller	Marketing Start	Marketing End	Region	Image
MYLREG	Drug delivery system	1500.00 mg	Oral		2018-05-18	Not applicable

Over the Counter Products

Name	Dosage	Strength	Route	Labeller	Marketing Start	Marketing End	Region	Image
Appeton Essentials Glucosamine-500mg Tablet	Tablet		Oral	KOTRA PHARMA (M) SDN. BHD.	2020-09-08	Not applicable
Arthroflex	Capsule		Oral	ALLPAC SOLUTIONS SDN. BHD.	2020-09-08	Not applicable
Artrisa Sachet for Oral Solution 1500 mg	Powder, for solution		Oral	AV MANUFACTURING SDN.BHD	2020-09-08	Not applicable
AVM-Artrisa 250mg Capsule	Capsule	250 mg	Oral	AV MANUFACTURING SDN.BHD	2020-09-08	Not applicable
AVM-Artrisa 500mg Capsule	Capsule	500 mg	Oral	AV MANUFACTURING SDN.BHD	2020-09-08	Not applicable
Axcel Glucosamine-500mg Tablet	Tablet		Oral	KOTRA PHARMA (M) SDN. BHD.	2020-09-08	Not applicable
BIO-LIFE GLUCOSAMINE 500MG TABLETS	Tablet	500 MG	Oral	BIO-LIFE MARKETING SDN BHD	2020-09-08	2021-12-12
BiO-LiFE Glucosamine 750mg Tablet	Tablet, film coated		Oral	MEGA LIFESCIENCES SDN. BHD.	2020-09-08	Not applicable
Blackmores Glucosamine 1500 Tablet	Tablet, film coated		Oral	BLACKMORES (MALAYSIA) SDN. BHD.	2020-09-08	Not applicable
BLACKMORES GLUCOSAMINE 500 TABLET	Tablet, film coated	500 mg	Oral	BLACKMORES (MALAYSIA) SDN. BHD.	2020-09-08	Not applicable

Mixture Products

Name	Ingredients	Dosage	Route	Labeller	Marketing Start	Marketing End	Region	Image
Adaxil	Glucosamine sulfate (750 mg) + Chondroitin sulfate sodium (bovine) (600 mg)	Powder	Oral	MYLAN HEALTHCARE SDN. BHD.	2020-09-08	Not applicable
Appeton Essentials Glucosamine 500 + Chondroitin 400 Tablet	Glucosamine sulfate potassium chloride (500 mg) + Chondroitin sulfate sodium (bovine) (400 mg)	Tablet	Oral	KOTRA PHARMA (M) SDN. BHD.	2020-09-08	Not applicable
ARIFLEX	Glucosamine sulfate (1.500 g) + Chondroitin sulfate sodium (bovine) (1.200 g)	Drug delivery system	Oral	Af Operadora De Negocios, s.a. De c.v.	2018-08-30	Not applicable
Arthro Capsule	Glucosamine sulfate (375 mg) + Chondroitin sulfate sodium (bovine) (200 mg)	Capsule	Oral	STERILINE SDN. BHD.	2020-09-08	Not applicable
ARTHRO-S Powder for Oral Solution	Glucosamine sulfate potassium chloride (1500 mg) + Chondroitin sulfate sodium (bovine) (1200 mg)	Powder	Oral	Noripharma Sdn. Bhd.	2020-09-08	Not applicable
ARTROFORT(R) COMPLEX	Glucosamine (750 mg) + Chondroitin sulfate (bovine) (600 mg)	Powder	Oral	บริษัท เมด้า ฟาม่าร์ (ประเทศไทย) จำกัด	2011-11-04	Not applicable
Avance JOINT COMFORT TABLET	Glucosamine (250 mg) + Chondroitin sulfate (200 mg)	Tablet	Oral	BEST WORLD LIFESTYLE SDN. BHD.	2020-09-08	Not applicable
Axcel Glucosatin Dry Powder for Oral Solution	Glucosamine sulfate potassium chloride (1500 mg) + Chondroitin sulfate sodium (bovine) (1200 mg)	Powder, for solution	Oral	KOTRA PHARMA (M) SDN. BHD.	2020-09-08	Not applicable
Axcel GLUCOSATIN TABLET	Glucosamine sulfate potassium chloride (500 mg) + Chondroitin sulfate sodium (bovine) (400 mg)	Tablet	Oral	KOTRA PHARMA (M) SDN. BHD.	2020-09-08	Not applicable
Bio-Life Glucosamine 500mg tablet	Glucosamine hydrochloride (500 mg) + Chondroitin sulfate (bovine) (400 mg)	Tablet	Oral	BIO-LIFE MARKETING SDN BHD	2020-09-08	Not applicable

Unapproved/Other Products

Name	Ingredients	Dosage	Route	Labeller	Marketing Start	Marketing End	Region	Image
Medi-flexx Rx Joint Support Formula	Glucosamine sulfate (500 mg/1) + Chondroitin sulfate (chicken) (400 mg/1) + Dimethyl sulfone (200 mg/1)	Tablet	Oral	Two Hip Consulting, Llc	2014-12-05	2016-04-11
Remaxazon External Patch	Glucosamine (5 g/100g) + Capsaicin (.0285 g/100g) + Chondroitin sulfate sodium (bovine) (3 g/100g) + Lidocaine (4 g/100g)	Patch	Topical	Home Aide Diganostics, Inc.	2015-03-09	Not applicable

Categories

ATC Codes

M01AX05 — Glucosamine

• M01AX — Other antiinflammatory and antirheumatic agents, non-steroids
• M01A — ANTIINFLAMMATORY AND ANTIRHEUMATIC PRODUCTS, NON-STEROIDS
• M01 — ANTIINFLAMMATORY AND ANTIRHEUMATIC PRODUCTS
• M — MUSCULO-SKELETAL SYSTEM

Drug Categories

• Amino Sugars
• Antiinflammatory and Antirheumatic Products
• Antiinflammatory and Antirheumatic Products, Non-Steroids
• Carbohydrates
• Hexosamines
• Musculo-Skeletal System

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

Aminosaccharides / Oxanes / Secondary alcohols / Hemiacetals / 1,2-aminoalcohols / Polyols / Oxacyclic compounds / Primary alcohols / Organopnictogen compounds / Monoalkylamines / Hydrocarbon derivatives

show 1 more

Substituents

1,2-aminoalcohol / Alcohol / Aliphatic heteromonocyclic compound / Amine / Amino saccharide / Hemiacetal / Hexose monosaccharide / Hydrocarbon derivative / Organic nitrogen compound / Organoheterocyclic compound / Organonitrogen compound / Organopnictogen compound / Oxacycle / Oxane / Polyol / Primary alcohol / Primary aliphatic amine / Primary amine / Secondary alcohol

show 9 more

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

D-glucosamine (CHEBI:47977) / Amino sugars (C00329)

Affected organisms

• Humans and other mammals

Chemical Identifiers

UNII

N08U5BOQ1K

CAS number

3416-24-8

InChI Key

MSWZFWKMSRAUBD-IVMDWMLBSA-N

InChI

InChI=1S/C6H13NO5/c7-3-5(10)4(9)2(1-8)12-6(3)11/h2-6,8-11H,1,7H2/t2-,3-,4-,5-,6?/m1/s1

IUPAC Name

(3R,4R,5S,6R)-3-amino-6-(hydroxymethyl)oxane-2,4,5-triol

SMILES

N[C@H]1C(O)O[C@H](CO)[C@@H](O)[C@@H]1O

References

Synthesis Reference

Yuichi Yamamura, Ichiro Azuma, Shigeru Kobayashi, "Glucosamine peptide derivatives, their production and use." U.S. Patent US4369178, issued July, 1978.

US4369178

General References

1. Towheed TE, Maxwell L, Anastassiades TP, Shea B, Houpt J, Robinson V, Hochberg MC, Wells G: Glucosamine therapy for treating osteoarthritis. Cochrane Database Syst Rev. 2005 Apr 18;(2):CD002946. [Article]
2. Roseman S: Reflections on glycobiology. J Biol Chem. 2001 Nov 9;276(45):41527-42. Epub 2001 Sep 11. [Article]
3. GHOSH S, BLUMENTHAL HJ, DAVIDSON E, ROSEMAN S: Glucosamine metabolism. V. Enzymatic synthesis of glucosamine 6-phosphate. J Biol Chem. 1960 May;235:1265-73. [Article]
4. Buse MG: Hexosamines, insulin resistance, and the complications of diabetes: current status. Am J Physiol Endocrinol Metab. 2006 Jan;290(1):E1-E8. [Article]
5. Laverty S, Sandy JD, Celeste C, Vachon P, Marier JF, Plaas AH: Synovial fluid levels and serum pharmacokinetics in a large animal model following treatment with oral glucosamine at clinically relevant doses. Arthritis Rheum. 2005 Jan;52(1):181-91. [Article]
6. Black C, Clar C, Henderson R, MacEachern C, McNamee P, Quayyum Z, Royle P, Thomas S: The clinical effectiveness of glucosamine and chondroitin supplements in slowing or arresting progression of osteoarthritis of the knee: a systematic review and economic evaluation. Health Technol Assess. 2009 Nov;13(52):1-148. doi: 10.3310/hta13520. [Article]
7. Vasiliadis HS, Tsikopoulos K: Glucosamine and chondroitin for the treatment of osteoarthritis. World J Orthop. 2017 Jan 18;8(1):1-11. doi: 10.5312/wjo.v8.i1.1. eCollection 2017 Jan 18. [Article]
8. Adebowale A, Du J, Liang Z, Leslie JL, Eddington ND: The bioavailability and pharmacokinetics of glucosamine hydrochloride and low molecular weight chondroitin sulfate after single and multiple doses to beagle dogs. Biopharm Drug Dispos. 2002 Sep;23(6):217-25. doi: 10.1002/bdd.315. [Article]
9. Setnikar I, Palumbo R, Canali S, Zanolo G: Pharmacokinetics of glucosamine in man. Arzneimittelforschung. 1993 Oct;43(10):1109-13. [Article]
10. Persiani S, Matthews A, Larger P, Hall M, Rotini R, Trisolino G, Antonioli D, Zaccarelli L, Rovati LC: Glucosamine binding to proteins in plasma and synovial fluid and blood cell/plasma partitioning in mouse and man in vitro. Drug Metabol Drug Interact. 2009;24(2-4):211-27. doi: 10.1515/dmdi.2009.24.2-4.211. [Article]
11. Williams C, Ampat G: Glucosamine Sulfate . [Article]
12. Setnikar I, Rovati LC: Absorption, distribution, metabolism and excretion of glucosamine sulfate. A review. Arzneimittelforschung. 2001 Sep;51(9):699-725. doi: 10.1055/s-0031-1300105. [Article]
13. Persiani S, Roda E, Rovati LC, Locatelli M, Giacovelli G, Roda A: Glucosamine oral bioavailability and plasma pharmacokinetics after increasing doses of crystalline glucosamine sulfate in man. Osteoarthritis Cartilage. 2005 Dec;13(12):1041-9. doi: 10.1016/j.joca.2005.07.009. Epub 2005 Sep 13. [Article]
14. Jerosch J: Effects of Glucosamine and Chondroitin Sulfate on Cartilage Metabolism in OA: Outlook on Other Nutrient Partners Especially Omega-3 Fatty Acids. Int J Rheumatol. 2011;2011:969012. doi: 10.1155/2011/969012. Epub 2011 Aug 2. [Article]
15. Sarrazin S, Bonnaffe D, Lubineau A, Lortat-Jacob H: Heparan sulfate mimicry: a synthetic glycoconjugate that recognizes the heparin binding domain of interferon-gamma inhibits the cytokine activity. J Biol Chem. 2005 Nov 11;280(45):37558-64. Epub 2005 Sep 9. [Article]
16. Chen JT, Liang JB, Chou CL, Chien MW, Shyu RC, Chou PI, Lu DW: Glucosamine sulfate inhibits TNF-alpha and IFN-gamma-induced production of ICAM-1 in human retinal pigment epithelial cells in vitro. Invest Ophthalmol Vis Sci. 2006 Feb;47(2):664-72. [Article]
17. Chen JT, Chen CH, Horng CT, Chien MW, Lu DW, Liang JB, Tai MC, Chang YH, Chen PL, Chen YH: Glucosamine sulfate inhibits proinflammatory cytokine-induced icam-1 production in human conjunctival cells in vitro. J Ocul Pharmacol Ther. 2006 Dec;22(6):402-16. [Article]
18. Chen JT, Chen PL, Chang YH, Chien MW, Chen YH, Lu DW: Glucosamine sulfate inhibits leukocyte adhesion in response to cytokine stimulation of retinal pigment epithelial cells in vitro. Exp Eye Res. 2006 Nov;83(5):1052-62. doi: 10.1016/j.exer.2006.05.010. Epub 2006 Jul 5. [Article]
19. Dahmer S, Schiller RM: Glucosamine. Am Fam Physician. 2008 Aug 15;78(4):471-6. [Article]
20. Fox BA, Stephens MM: Glucosamine hydrochloride for the treatment of osteoarthritis symptoms. Clin Interv Aging. 2007;2(4):599-604. doi: 10.2147/cia.s1632. [Article]
21. National Research Council; Institute of Medicine; Food and Nutrition Board; Board on Life Sciences; Committee on the Framework for Evaluating the Safety of the Dietary Supplements (2005). Dietary Supplements A Framework for Evaluating Safety:. National Academies Press (US). [ISBN:0-309-09110-1]
22. TITCK Product Information: Dona (crystalline glucosamine sulfate) for intramuscular injection [Link]
23. TITCK Product Information: Dona Plus (chondroitin sulfate/glucosamine sulfate) powder for oral use [Link]
24. Zoetisus Safety Data Sheet: Glucosamine sulfate [Link]
25. AAFP (American Family Physician): Glucosamine [Link]
26. NIH MedlinePlus: Glucosamine [Link]
27. DailyMed: Theraflex advance (ibuprofen, glucosamine sulfate, Chondroitin sulfate) oral tablet [Link]
28. National Capital Poison Center: What you need to know about glucosamine [Link]

External Links

Human Metabolome Database

HMDB0001514

KEGG Drug

D04334

KEGG Compound

C00329

PubChem Compound

439213

PubChem Substance

46506420

ChemSpider

388352

RxNav

4845

ChEBI

47977

ChEMBL

CHEMBL493287

Therapeutic Targets Database

DAP001097

PharmGKB

PA164747613

Drugs.com

Drugs.com Drug Page

Wikipedia

Glucosamine

MSDS

Download (73.2 KB)

Clinical Trials

Clinical Trials

Phase	Status	Purpose	Conditions	Count
4	Completed	Basic Science	Osteoarthritis of the Knee	1
4	Completed	Treatment	Back pain	1
4	Completed	Treatment	Back Pain Lower Back	1
4	Completed	Treatment	Diacerein / Glucosamine / Osteoarthritis (OA)	1
4	Completed	Treatment	Oral Lichen Planus	1
4	Completed	Treatment	Osteoarthritis (OA)	1
4	Completed	Treatment	Osteoarthritis of the Knee	3
4	Recruiting	Treatment	Rotator Cuff Tears	1
3	Completed	Treatment	Osteoarthritis (OA)	1
3	Completed	Treatment	Osteoarthritis of the Knee	5

Pharmacoeconomics

Manufacturers

Not Available

Packagers

• 21st Century Healthcare Inc.
• Equaline Vitamins
• Freeda Vitamins
• Janssen-Ortho Inc.
• LeaderPharma
• Mckesson Corp.
• Mericon
• Nexgen Pharma Inc.
• Professional Co.
• Sunmark
• Walgreen Co.
• Zylera Pharmaceuticals LLC

Dosage Forms

Form	Route	Strength
Tablet	Oral
Capsule	Oral
Powder, for solution	Oral	1884 mg
Powder, for solution	Oral
Granule	Oral
Injection, solution, concentrate	Intramuscular
Tablet, coated	Oral	250 MG
Tablet, film coated	Oral	750 MG
Solution	Intramuscular
Capsule	Oral	750 mg
Powder, for suspension	Oral
Solution	Intramuscular	400 mg
Powder, for solution	Oral	1500.14 mg
Capsule, coated	Oral	500 mg
Tablet, coated	Oral
Powder, for solution	Oral	2400 mg
Capsule, liquid filled	Oral
Powder, for solution	Oral	1200 mg
Tablet, effervescent	Oral
Powder, for solution	Oral	30 g
Powder, for solution	Oral	1500 mg
Capsule, coated	Oral	250 mg
Capsule	Oral
Powder, for solution	Oral	49.69 g
Capsule, liquid filled	Oral	250 mg
Capsule, coated	Oral	400 mg
Tablet	Oral	1000 mg
Solution	Oral
Tablet, effervescent	Oral
Powder	Oral
Powder	Oral
Tablet, film coated
Capsule	Oral	628 mg
Tablet	Oral	750 mg
Capsule, coated	Oral
Tablet	Oral
Drug delivery system	Oral	1500.00 mg
Granule	Oral
Tablet, film coated	Oral	392.6 mg
Patch	Topical
Tablet, film coated	Oral
Tablet, effervescent	Oral	1500 MG
Tablet, effervescent	Oral	500 MG
Granule	Oral	1500.000 mg
Drug delivery system	Oral
Injection, solution	Intramuscular
Powder, for solution	Oral
Tablet, film coated	Oral
Tablet, delayed release	Oral
Tablet	Oral	300.000 mg
Capsule
Cream	Topical
Capsule	Oral	450 mg
Tablet, coated	Oral	750 mg
Capsule	Oral	550 mg
Tablet	Oral	250 mg
Tablet	Oral	500 mg
Capsule	Oral	375 mg
Tablet, film coated	Oral	500 mg
Capsule	Oral	250 mg
Capsule	Oral	500 mg
Granule, for solution	Oral	1500 mg/1sachet
Powder	Oral	1500 mg/1sachet
Granule	Oral	1500 mg/1sachet
Tablet, film coated	Oral	1500 mg
Tablet, coated	Oral	500 mg
Powder, for solution	Oral	1500 mg/1sachet

Prices

Unit description	Cost	Unit
Glucosamine hcl (d) powder	1.05USD	g
Cidatrine 500 mg tablet	0.81USD	tablet
Glucosamine 500 mg tablet	0.23USD	tablet
Glucosamine hcl 500 mg tablet	0.21USD	tablet
Sm glucosamine hcl 1500 mg tablet	0.2USD	tablet
Eql glucosamine 1000 mg tablet	0.17USD	tablet
Glucosamine sulf 750 mg cplt	0.16USD	caplet
Glucosamine 500 mg caplet	0.12USD	tablet
Glucosamine relief 1000 mg tablet	0.09USD	tablet
Glucosamine 750 mg caplet	0.08USD	caplet

DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.

Patents

Not Available

Properties

State

Solid

Experimental Properties

Property	Value	Source
melting point (°C)	88 °C	PhysProp

Predicted Properties

Property	Value	Source
Water Solubility	551.0 mg/mL	ALOGPS
logP	-2.7	ALOGPS
logP	-3	Chemaxon
logS	0.49	ALOGPS
pKa (Strongest Acidic)	11.73	Chemaxon
pKa (Strongest Basic)	8.23	Chemaxon
Physiological Charge	1	Chemaxon
Hydrogen Acceptor Count	6	Chemaxon
Hydrogen Donor Count	5	Chemaxon
Polar Surface Area	116.17 Å2	Chemaxon
Rotatable Bond Count	1	Chemaxon
Refractivity	37.58 m3·mol-1	Chemaxon
Polarizability	16.87 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	-	0.8589
Blood Brain Barrier	-	0.9143
Caco-2 permeable	-	0.8221
P-glycoprotein substrate	Non-substrate	0.7833
P-glycoprotein inhibitor I	Non-inhibitor	0.9452
P-glycoprotein inhibitor II	Non-inhibitor	0.976
Renal organic cation transporter	Non-inhibitor	0.9261
CYP450 2C9 substrate	Non-substrate	0.8377
CYP450 2D6 substrate	Non-substrate	0.8469
CYP450 3A4 substrate	Non-substrate	0.7168
CYP450 1A2 substrate	Non-inhibitor	0.9503
CYP450 2C9 inhibitor	Non-inhibitor	0.9347
CYP450 2D6 inhibitor	Non-inhibitor	0.9494
CYP450 2C19 inhibitor	Non-inhibitor	0.9115
CYP450 3A4 inhibitor	Non-inhibitor	0.9777
CYP450 inhibitory promiscuity	Low CYP Inhibitory Promiscuity	0.9769
Ames test	Non AMES toxic	0.7558
Carcinogenicity	Non-carcinogens	0.9716
Biodegradation	Ready biodegradable	0.8286
Rat acute toxicity	1.2287 LD50, mol/kg	Not applicable
hERG inhibition (predictor I)	Weak inhibitor	0.9659
hERG inhibition (predictor II)	Non-inhibitor	0.969

ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)

Not Available

Spectra

Spectrum	Spectrum Type	Splash Key
Predicted GC-MS Spectrum - GC-MS	Predicted GC-MS	Not Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)	Predicted LC-MS/MS	Not Available

Targets

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Details1. Interferon gamma

Kind

Protein

Organism

Humans

Pharmacological action

Unknown

Actions

Inhibitor

Curator comments

Data supported by in vitro studies only. Clinical relevance is unknown.

General Function

Interferon-gamma receptor binding

Specific Function

Produced by lymphocytes activated by specific antigens or mitogens. IFN-gamma, in addition to having antiviral activity, has important immunoregulatory functions. It is a potent activator of macrop...

Gene Name

IFNG

Uniprot ID

P01579

Uniprot Name

Interferon gamma

Molecular Weight

19348.165 Da

References

1. Sarrazin S, Bonnaffe D, Lubineau A, Lortat-Jacob H: Heparan sulfate mimicry: a synthetic glycoconjugate that recognizes the heparin binding domain of interferon-gamma inhibits the cytokine activity. J Biol Chem. 2005 Nov 11;280(45):37558-64. Epub 2005 Sep 9. [Article]
2. Chen JT, Liang JB, Chou CL, Chien MW, Shyu RC, Chou PI, Lu DW: Glucosamine sulfate inhibits TNF-alpha and IFN-gamma-induced production of ICAM-1 in human retinal pigment epithelial cells in vitro. Invest Ophthalmol Vis Sci. 2006 Feb;47(2):664-72. [Article]
3. Lortat-Jacob H: Interferon and heparan sulphate. Biochem Soc Trans. 2006 Jun;34(Pt 3):461-4. [Article]
4. Chen JT, Chen CH, Horng CT, Chien MW, Lu DW, Liang JB, Tai MC, Chang YH, Chen PL, Chen YH: Glucosamine sulfate inhibits proinflammatory cytokine-induced icam-1 production in human conjunctival cells in vitro. J Ocul Pharmacol Ther. 2006 Dec;22(6):402-16. [Article]

Details2. Transcription factor p65

Kind

Protein

Organism

Humans

Pharmacological action

Unknown

Actions

Inhibitor

Curator comments

Data supported by in vitro studies only. Clinical relevance is unknown.

General Function

Ubiquitin protein ligase binding

Specific Function

NF-kappa-B is a pleiotropic transcription factor present in almost all cell types and is the endpoint of a series of signal transduction events that are initiated by a vast array of stimuli related...

Gene Name

RELA

Uniprot ID

Q04206

Uniprot Name

Transcription factor p65

Molecular Weight

60218.53 Da

References

1. Chen JT, Liang JB, Chou CL, Chien MW, Shyu RC, Chou PI, Lu DW: Glucosamine sulfate inhibits TNF-alpha and IFN-gamma-induced production of ICAM-1 in human retinal pigment epithelial cells in vitro. Invest Ophthalmol Vis Sci. 2006 Feb;47(2):664-72. [Article]
2. Chen JT, Chen PL, Chang YH, Chien MW, Chen YH, Lu DW: Glucosamine sulfate inhibits leukocyte adhesion in response to cytokine stimulation of retinal pigment epithelial cells in vitro. Exp Eye Res. 2006 Nov;83(5):1052-62. doi: 10.1016/j.exer.2006.05.010. Epub 2006 Jul 5. [Article]

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Drug created at June 13, 2005 13:24 / Updated at September 28, 2021 21:54