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Record Information
Version3.6
Creation Date2012-09-06 15:16:49 UTC
Update Date2016-02-11 01:28:47 UTC
HMDB IDHMDB14508
Secondary Accession NumbersNone
Metabolite Identification
Common NameSucralfate
DescriptionSucralfate is only found in individuals that have used or taken this drug. It is a basic aluminum complex of sulfated sucrose. [PubChem]Although sucralfate's mechanism is not entirely understood, there are several factors that most likely contribute to its action. Sucralfate, with its strong negative charge, binds to exposed positively-charged proteins at the base of ulcers. In this way, it coats the ulcer and forms a physical barrier that protects the ulcer surface from further injury by acid and pepsin. It directly inhibits pepsin (an enzyme that breaks apart proteins) in the presence of stomach acid and binds bile salts coming from the liver via the bile thus protecting the stomach lining from injury caused by the bile acids. Sucralfate may increase prostaglandin production. Prostaglandins are known to protect the lining of the stomach and may also bind epithelial growth factor and fibroblast growth factor, both of which enhance the growth and repair mechanism of the stomach lining.
Structure
Thumb
SynonymsNot Available
Chemical FormulaC11H28Al8O51S8
Average Molecular Weight1448.682
Monoisotopic Molecular Weight1447.588619666
IUPAC Name[({[(2S,3R,4S,5R,6R)-4,5-bis({[(dihydroxyalumanyl)oxy]sulfonyl}oxy)-6-[({[(dihydroxyalumanyl)oxy]sulfonyl}oxy)methyl]-2-{[(2R,3S,4S,5R)-3,4,5-tris({[(dihydroxyalumanyl)oxy]sulfonyl}oxy)-2-[({[(dihydroxyalumanyl)oxy]sulfonyl}oxy)methyl]oxolan-2-yl]oxy}oxan-3-yl]oxy}sulfonyl)oxy]alumanediol
Traditional Namesucralfate
CAS Registry Number54182-58-0
SMILES
O[Al](O)OS(=O)(=O)OC[C@H]1O[C@@H](O[C@]2(COS(=O)(=O)O[Al](O)O)O[C@H](OS(=O)(=O)O[Al](O)O)[C@@H](OS(=O)(=O)O[Al](O)O)[C@@H]2OS(=O)(=O)O[Al](O)O)[C@H](OS(=O)(=O)O[Al](O)O)[C@@H](OS(=O)(=O)O[Al](O)O)[C@@H]1OS(=O)(=O)O[Al](O)O
InChI Identifier
InChI=1S/C11H20O35S8.8Al.16H2O/c12-47(13,14)36-1-3-4(41-49(18,19)20)5(42-50(21,22)23)6(43-51(24,25)26)9(38-3)39-11(2-37-48(15,16)17)8(45-53(30,31)32)7(44-52(27,28)29)10(40-11)46-54(33,34)35;;;;;;;;;;;;;;;;;;;;;;;;/h3-10H,1-2H2,(H,12,13,14)(H,15,16,17)(H,18,19,20)(H,21,22,23)(H,24,25,26)(H,27,28,29)(H,30,31,32)(H,33,34,35);;;;;;;;;16*1H2/q;8*+3;;;;;;;;;;;;;;;;/p-24/t3-,4-,5+,6-,7+,8+,9+,10-,11-;;;;;;;;;;;;;;;;;;;;;;;;/m1......................../s1
InChI KeyInChIKey=MNQYNQBOVCBZIQ-JQOFMKNESA-A
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as disaccharide sulfates. These are disaccharides carrying one or more sulfate group on a sugar unit.
KingdomOrganic compounds
Super ClassOrganooxygen compounds
ClassCarbohydrates and carbohydrate conjugates
Sub ClassDisaccharides
Direct ParentDisaccharide sulfates
Alternative Parents
Substituents
  • Disaccharide sulfate
  • O-glycosyl compound
  • Glycosyl compound
  • Alkyl sulfate
  • Oxane
  • Oxolane
  • Organic sulfuric acid or derivatives
  • Oxacycle
  • Organic metal salt
  • Organoheterocyclic compound
  • Acetal
  • Hydrocarbon derivative
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
StatusExpected but not Quantified
Origin
  • Drug
Biofunction
  • Anti-Ulcer Agents
Application
  • Pharmaceutical
Cellular locations
  • Extracellular
  • Membrane
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility7.14e-01 g/LNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.71 mg/mLALOGPS
logP0.98ALOGPS
logP-5.6ChemAxon
logS-3.3ALOGPS
pKa (Strongest Acidic)13.53ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count35ChemAxon
Hydrogen Donor Count16ChemAxon
Polar Surface Area772.17 Å2ChemAxon
Rotatable Bond Count36ChemAxon
Refractivity175.09 m3·mol-1ChemAxon
Polarizability105.22 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biofluid Locations
  • Blood
  • Urine
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00364
  • Not Applicable
details
UrineExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00364
  • Not Applicable
details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00364
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID26329506
KEGG Compound IDC07314
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkSucralfate
NuGOwiki LinkHMDB14508
Metagene LinkHMDB14508
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Rees WD: Mechanisms of gastroduodenal protection by sucralfate. Am J Med. 1991 Aug 8;91(2A):58S-63S. [1715673 ]

Enzymes

General function:
Involved in receptor binding
Specific function:
Fibrinogen has a double function:yielding monomers that polymerize into fibrin and acting as a cofactor in platelet aggregation
Gene Name:
FGG
Uniprot ID:
P02679
Molecular weight:
51511.3
References
  1. Terao N, Yoshida N, Nagashima R: Sucralfate, a basic aluminum salt of sucrose sulfate. III. Inhibition of peptic hydrolysis of fibrinogen by sucrose sulfate. Arzneimittelforschung. 1980;30(1):76-8. [6892775 ]
General function:
Involved in growth factor activity
Specific function:
The heparin-binding growth factors are angiogenic agents in vivo and are potent mitogens for a variety of cell types in vitro. There are differences in the tissue distribution and concentration of these 2 growth factors
Gene Name:
FGF2
Uniprot ID:
P09038
Molecular weight:
30769.7
References
  1. Szabo S: The mode of action of sucralfate: the 1 x 1 x 1 mechanism of action. Scand J Gastroenterol Suppl. 1991;185:7-12. [1957124 ]
  2. Tarnawski A, Tanoue K, Santos AM, Sarfeh IJ: Cellular and molecular mechanisms of gastric ulcer healing. Is the quality of mucosal scar affected by treatment? Scand J Gastroenterol Suppl. 1995;210:9-14. [8578218 ]
  3. Szabo S, Kusstatscher S, Sakoulas G, Sandor Z, Vincze A, Jadus M: Growth factors: new 'endogenous drugs' for ulcer healing. Scand J Gastroenterol Suppl. 1995;210:15-8. [8578198 ]
  4. Konturek SJ: Role of growth factors in gastroduodenal protection and healing of peptic ulcers. Gastroenterol Clin North Am. 1990 Mar;19(1):41-65. [1970337 ]
  5. Korman MG, Bolin TD, Szabo S, Hunt RH, Marks IN, Glise H: Sucralfate: the Bangkok review. J Gastroenterol Hepatol. 1994 Jul-Aug;9(4):412-5. [7948825 ]
General function:
Involved in calcium ion binding
Specific function:
EGF stimulates the growth of various epidermal and epithelial tissues in vivo and in vitro and of some fibroblasts in cell culture. Magnesiotropic hormone that stimulates magnesium reabsorption in the renal distal convoluted tubule via engagement of EGFR and activation of the magnesium channel TRPM6
Gene Name:
EGF
Uniprot ID:
P01133
Molecular weight:
133993.1
References
  1. Tarnawski A, Tanoue K, Santos AM, Sarfeh IJ: Cellular and molecular mechanisms of gastric ulcer healing. Is the quality of mucosal scar affected by treatment? Scand J Gastroenterol Suppl. 1995;210:9-14. [8578218 ]
  2. Szabo S: The mode of action of sucralfate: the 1 x 1 x 1 mechanism of action. Scand J Gastroenterol Suppl. 1991;185:7-12. [1957124 ]
  3. Konturek SJ: Role of growth factors in gastroduodenal protection and healing of peptic ulcers. Gastroenterol Clin North Am. 1990 Mar;19(1):41-65. [1970337 ]