Details of the Drug

General Information of Drug (ID: DM4ZLFD)

Drug Name
Glucosamine
Synonyms
Chitosamine; GCS; Glucosamina; Glucosaminum; D-glucosamine; Glucosamina [INN-Spanish]; Glucosamine [USAN:INN]; Glucosaminum [INN-Latin]; Viartril-S; Beta-D-Glucosamine; Glucosamine (USAN/INN); Partially N-deacetylated poly-beta-1,6-N-acetyl-D-glucosamine; (2R,3R,4R,5S,6R)-3-amino-6-(hydroxymethyl)oxane-2,4,5-triol; (2S,5R)-3-amino-6-(hydroxymethyl)oxane-2,4,5-triol; (3R,4R,5S,6R)-3-amino-6-(hydroxymethyl)oxane-2,4,5-triol; 2-Amino-2-deoxy-D-glucose; 2-Amino-2-deoxy-beta-D-glucopyranose; 2-amino-2-deoxy-D-glucopyranose; 2-amino-2-deoxyglucose
Indication
Disease Entry ICD 11 Status REF
Osteoarthritis FA00-FA05 Approved [1]
Therapeutic Class
Antiinflammatory Agents
Drug Type
Small molecular drug
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 1 Molecular Weight (mw) 179.17
Logarithm of the Partition Coefficient (xlogp) -2.8
Rotatable Bond Count (rotbonds) 1
Hydrogen Bond Donor Count (hbonddonor) 5
Hydrogen Bond Acceptor Count (hbondacc) 6
ADMET Property
Absorption Cmax
The maximum plasma concentration (Cmax) of drug is 10-16 mcg/L []
Absorption Tmax
The time to maximum plasma concentration (Tmax) is 20 min []
Bioavailability
The bioavailability of drug is 67-11% []
Elimination
Fecal excretion of glucosamine in a pharmacokinetic study was 11.3% within 120 hours after administration, and urinary elimination was found to be 1.19% within the first 8 hours post-administration [2]
Half-life
The concentration or amount of drug in body reduced by one-half in 15 hours [2]
Metabolism
The drug is metabolized via the liver [3]
Vd
The volume of distribution (Vd) of drug is 15.4 L/kg [2]
Chemical Identifiers
Formula
C6H13NO5
IUPAC Name
(3R,4R,5S,6R)-3-amino-6-(hydroxymethyl)oxane-2,4,5-triol
Canonical SMILES
C([C@@H]1[C@H]([C@@H]([C@H](C(O1)O)N)O)O)O
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
InChIKey
MSWZFWKMSRAUBD-IVMDWMLBSA-N
Cross-matching ID
PubChem CID
439213
ChEBI ID
CHEBI:47977
CAS Number
3416-24-8
DrugBank ID
DB01296
TTD ID
D07NSU
VARIDT ID
DR00870
INTEDE ID
DR0781

Molecular Interaction Atlas of This Drug


Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
Interleukin-1 beta (IL1B) TTRYK0X IL1B_HUMAN Inhibitor [4]

Drug-Metabolizing Enzyme (DME)
DME Name DME ID UniProt ID MOA REF
Cytochrome P450 2E1 (CYP2E1) DEVDYN7 CP2E1_HUMAN Substrate [5]
Mephenytoin 4-hydroxylase (CYP2C19) DEGTFWK CP2CJ_HUMAN Substrate [5]

Drug Off-Target (DOT)
DOT Name DOT ID UniProt ID Interaction REF
A disintegrin and metalloproteinase with thrombospondin motifs 1 (ADAMTS1) OTTLJH8W ATS1_HUMAN Gene/Protein Processing [6]
A disintegrin and metalloproteinase with thrombospondin motifs 20 (ADAMTS20) OTU0EKLN ATS20_HUMAN Protein Interaction/Cellular Processes [7]
A disintegrin and metalloproteinase with thrombospondin motifs 5 (ADAMTS5) OT953SV2 ATS5_HUMAN Gene/Protein Processing [6]
A disintegrin and metalloproteinase with thrombospondin motifs 9 (ADAMTS9) OTV3Q0DS ATS9_HUMAN Protein Interaction/Cellular Processes [7]
Acetyl-CoA carboxylase 1 (ACACA) OT5CQPZY ACACA_HUMAN Gene/Protein Processing [8]
Aggrecan core protein (ACAN) OTUOCW8K PGCA_HUMAN Gene/Protein Processing [6]
Alkaline phosphatase, tissue-nonspecific isozyme (ALPL) OTG7J4BP PPBT_HUMAN Gene/Protein Processing [9]
Apolipoprotein A-I (APOA1) OT5THARI APOA1_HUMAN Protein Interaction/Cellular Processes [10]
Apolipoprotein B-100 (APOB) OTH0UOCZ APOB_HUMAN Gene/Protein Processing [11]
Bcl-2-like protein 1 (BCL2L1) OTRC5K9O B2CL1_HUMAN Gene/Protein Processing [12]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

Molecular Expression Atlas of This Drug

The Studied Disease Osteoarthritis
ICD Disease Classification FA00-FA05
Molecule Name Molecule Type Gene Name p-value Fold-Change Z-score
Interleukin-1 beta (IL1B) DTT IL1B 4.74E-01 8.78E-03 0.02
Cytochrome P450 2E1 (CYP2E1) DME CYP2E1 1.87E-04 -1.20E-01 -3.22E-01
Mephenytoin 4-hydroxylase (CYP2C19) DME CYP2C19 2.40E-01 -3.31E-02 -1.97E-01
Molecular Expression Atlas (MEA) Jump to Detail Molecular Expression Atlas of This Drug

References

1 URL: http://www.guidetopharmacology.org Nucleic Acids Res. 2015 Oct 12. pii: gkv1037. The IUPHAR/BPS Guide to PHARMACOLOGY in 2016: towards curated quantitative interactions between 1300 protein targets and 6000 ligands. (Ligand id: 4535).
2 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.
3 Edson KZ, Prasad B, Unadkat JD, Suhara Y, Okano T, Guengerich FP, Rettie AE: Cytochrome P450-dependent catabolism of vitamin K: omega-hydroxylation catalyzed by human CYP4F2 and CYP4F11. Biochemistry. 2013 Nov 19;52(46):8276-85. doi: 10.1021/bi401208m. Epub 2013 Nov 7.
4 Glucosamine inhibits IL-1beta-mediated IL-8 production in prostate cancer cells by MAPK attenuation. J Cell Biochem. 2009 Oct 1;108(2):489-98.
5 Characterization of moclobemide N-oxidation in human liver microsomes. Xenobiotica. 2001 Jul;31(7):387-97.
6 Glucosamine decreases expression of anabolic and catabolic genes in human osteoarthritic cartilage explants. Osteoarthritis Cartilage. 2006 Mar;14(3):250-7. doi: 10.1016/j.joca.2005.10.001. Epub 2005 Nov 18.
7 10mM glucosamine prevents activation of proADAMTS5 (aggrecanase-2) in transfected cells by interference with post-translational modification of furin. Osteoarthritis Cartilage. 2010 Mar;18(3):455-63. doi: 10.1016/j.joca.2009.10.014. Epub 2009 Nov 4.
8 Comparative effects of fructose and glucose on lipogenic gene expression and intermediary metabolism in HepG2 liver cells. PLoS One. 2011;6(11):e26583. doi: 10.1371/journal.pone.0026583. Epub 2011 Nov 11.
9 Glucosamine promotes osteogenic differentiation of dental pulp stem cells through modulating the level of the transforming growth factor-beta type I receptor. J Cell Physiol. 2010 Oct;225(1):140-51.
10 Effect of glucosamine on apolipoprotein AI mRNA stabilization and expression in HepG2 cells. Metabolism. 2004 Jun;53(6):766-71. doi: 10.1016/j.metabol.2003.11.027.
11 Glucosamine-induced endoplasmic reticulum stress promotes ApoB100 degradation: evidence for Grp78-mediated targeting to proteasomal degradation. Arterioscler Thromb Vasc Biol. 2005 Mar;25(3):571-7. doi: 10.1161/01.ATV.0000154142.61859.94. Epub 2004 Dec 23.
12 [Role of Bcl-xL in the cathepsin D-associated apoptosis of K562 cells]. Zhongguo Shi Yan Xue Ye Xue Za Zhi. 2005 Jun;13(3):379-82.