Details of the Drug

General Information of Drug (ID: DM0N19Y)

Drug Name
Chondroitin sulfate
Synonyms
Chondritinsulfate; Chondritinsulphate; Chondroitin 4 and 6 sulfate; Chondroitin 4-sulfate; Chondroitin 6-sulfate; Chondroitin polysulfate; Chondroitin sulfate; Chondroitin sulfuric acid; Chondroitin sulfuric acids; Chondroitin sulphate; Chondroitin, CHONDROITIN SULFATES; hydrogen sulfate; Chondroitine sulfate; Chondroitinsulfate C; Chondroitinsulfuric acids; Chondron; Chonsurid; Condrosan; Condrosulf; Sodium chondroitin sulfate; Structum; Uropol S; chondroitin sulfate C; 9007-28-7; EINECS 232-696-9; Gepan; UNII-6IC1M3OG5Z
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 3 Molecular Weight (mw) 463.37
Logarithm of the Partition Coefficient (xlogp) -4.8
Rotatable Bond Count (rotbonds) 6
Hydrogen Bond Donor Count (hbonddonor) 8
Hydrogen Bond Acceptor Count (hbondacc) 15
ADMET Property
Bioavailability
The bioavailability of drug is 10-20% [1]
Elimination
After intramuscular administration, about 37% of the administered dose is excreted by urine during the first 24 hours as high- and low-molecular-weight derivatives [1]
Half-life
The concentration or amount of drug in body reduced by one-half in 15 hours [2]
Metabolism
The drug is not metabolised [2]
Vd
The volume of distribution (Vd) of drug is 0.40 L/kg [3]
Chemical Identifiers
Formula
C13H21NO15S
IUPAC Name
(2S,3S,4S,5R,6R)-6-[(2R,3R,4R,5R,6R)-3-acetamido-2,5-dihydroxy-6-sulfooxyoxan-4-yl]oxy-3,4,5-trihydroxyoxane-2-carboxylic acid
Canonical SMILES
CC(=O)NC1C(C(C(OC1O)OS(=O)(=O)O)O)OC2C(C(C(C(O2)C(=O)O)O)O)O
InChI
KXKPYJOVDUMHGS-OSRGNVMNSA-N
InChIKey
1S/C13H21NO15S/c1-2(15)14-3-8(7(19)13(28-11(3)22)29-30(23,24)25)26-12-6(18)4(16)5(17)9(27-12)10(20)21/h3-9,11-13,16-19,22H,1H3,(H,14,15)(H,20,21)(H,23,24,25)/t3-,4+,5+,6-,7-,8-,9+,11-,12-,13-/m1/s1
Cross-matching ID
PubChem CID
24766
CAS Number
9007-28-7
DrugBank ID
DB09301
INTEDE ID
DR0317

Molecular Interaction Atlas of This Drug


Drug-Metabolizing Enzyme (DME)
DME Name DME ID UniProt ID MOA REF
Arylsulfatase B (ARSB) DEHKRDS ARSB_HUMAN Substrate [4]
Iduronate 2-sulfatase (IDS) DEL45C2 IDS_HUMAN Substrate [4]
N-acetyl-beta-glucosaminidase beta (HEXB) DE6AY40 HEXB_HUMAN Substrate [4]
Beta-glucuronidase (GUSB) DEP54UE BGLR_HUMAN Substrate [4]
Alpha-L-iduronidase (IDUA) DELTYX6 IDUA_HUMAN Substrate [4]
Chondroitin 6-sulfotransferase (CHST3) DEQIZP2 CHST3_HUMAN Substrate [5]
Hyaluronoglucosaminidase (nagH) DEV7UZD NAGH_CLOPE Substrate [6], [7]
Hyaluronate lyase (hyaL) DEH31BC D1AWD4_STRM9 Substrate [8], [9]

Drug Off-Target (DOT)
DOT Name DOT ID UniProt ID Interaction REF
Arylsulfatase B (ARSB) OTTYDDNU ARSB_HUMAN Regulation of Drug Effects [10]
C-C motif chemokine 2 (CCL2) OTAD2HEL CCL2_HUMAN Protein Interaction/Cellular Processes [11]
Coagulation factor XII (F12) OTBFD2FU FA12_HUMAN Gene/Protein Processing [12]
Complement C3 (C3) OTCH5GS0 CO3_HUMAN Protein Interaction/Cellular Processes [12]
Complement C5 (C5) OTSL3OIC CO5_HUMAN Protein Interaction/Cellular Processes [12]
Fibroblast growth factor 10 (FGF10) OTDSATGA FGF10_HUMAN Protein Interaction/Cellular Processes [13]
Fibroblast growth factor 2 (FGF2) OT7YUJ9F FGF2_HUMAN Protein Interaction/Cellular Processes [13]
Midkine (MDK) OTF24HKC MK_HUMAN Protein Interaction/Cellular Processes [13]
Plasma kallikrein (KLKB1) OTGSEISX KLKB1_HUMAN Gene/Protein Processing [12]
Pleiotrophin (PTN) OTYC7M2A PTN_HUMAN Protein Interaction/Cellular Processes [13]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

References

1 da Cunha AL, de Oliveira LG, Maia LF, de Oliveira LF, Michelacci YM, de Aguiar JA: Pharmaceutical grade chondroitin sulfate: Structural analysis and identification of contaminants in different commercial preparations. Carbohydr Polym. 2015 Dec 10;134:300-8. doi: 10.1016/j.carbpol.2015.08.006. Epub 2015 Aug 8.
2 Chondroitin sulfate in the treatment of osteoarthritis: from in vitro studies to clinical recommendations. Ther Adv Musculoskelet Dis. 2010 Dec;2(6):335-48. doi: 10.1177/1759720X10383076.
3 Ronca G, Conte A: Metabolic fate of partially depolymerized shark chondroitin sulfate in man. Int J Clin Pharmacol Res. 1993;13 Suppl:27-34.
4 MFN human ref: Chondroitin sulfate degradation.
5 Variants in chondroitin sulfate metabolism genes in thrombotic storm. Thromb Res. 2018 Jan;161:43-51.
6 An extracellular enzyme with hyaluronidase and chondroitinase activities from some oral anaerobic spirochaetes. Microbiology. 1996 Sep;142 ( Pt 9):2567-76.
7 Identification of a Treponema denticola OppA homologue that binds host proteins present in the subgingival environment. Infect Immun. 2000 Apr;68(4):1884-92.
8 A bacterial ABC transporter enables import of mammalian host glycosaminoglycans. Sci Rep. 2017 Apr 21;7(1):1069.
9 A case of Streptobacillus moniliformis infection with cutaneous leukocytoclastic vasculitis. Acta Med Okayama. 2016 Oct;70(5):377-381. Case Reports
10 Decline in arylsulfatase B expression increases EGFR expression by inhibiting the protein-tyrosine phosphatase SHP2 and activating JNK in prostate cells. J Biol Chem. 2018 Jul 13;293(28):11076-11087. doi: 10.1074/jbc.RA117.001244. Epub 2018 May 24.
11 Monocyte chemoattractant protein 1 released from glycosaminoglycans mediates its profibrotic effects in systemic sclerosis via the release of interleukin-4 from T cells. Arthritis Rheum. 2006 Jan;54(1):214-25. doi: 10.1002/art.21497.
12 Contaminated heparin associated with adverse clinical events and activation of the contact system. N Engl J Med. 2008 Jun 5;358(23):2457-67. doi: 10.1056/NEJMoa0803200. Epub 2008 Apr 23.
13 Specific molecular interactions of oversulfated chondroitin sulfate E with various heparin-binding growth factors. Implications as a physiological binding partner in the brain and other tissues. J Biol Chem. 2002 Nov 15;277(46):43707-16. doi: 10.1074/jbc.M207105200. Epub 2002 Sep 6.