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Identification
Name Sucralfate
Accession Number DB00364 (APRD01238)
Type small molecule
Groups approved
Description

A basic aluminum complex of sulfated sucrose. [PubChem]
Structure Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms Not Available
Salts Not Available
Brand names
Name Company
Antepsin
Apo-sucralfate
Carafate
Sucramal
Sulcrate
Sulcrate Suspension Plus
Ulcar
Ulcerban
Ulcerlmin
Ulcermin
Ulcogant
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Brand mixtures Not Available
Categories
  • Anti-Ulcer Agents
CAS number 54182-58-0
Weight Average: 1448.682
Monoisotopic: 1447.588619666
Chemical Formula C11H28Al8O51S8
InChI Key InChIKey=MNQYNQBOVCBZIQ-JQOFMKNESA-A
InChI
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
Plain Text
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
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
Plain Text
Mass Spec Not Available
Taxonomy
Kingdom Not Available
Classes Not Available
Substructures Not Available
Pharmacology
Indication For the short-term treatment (up to 8 weeks) of active duodenal ulcer, as well as maintenance therapy for duodenal ulcer patients at reduced dosage (1 gram twice a day) after healing of acute ulcers. Also used for the short-term treatment of gastric ulcer.
Pharmacodynamics Sucralfate is a prescription medication used to treat peptic ulcers. The current clinical uses of sucralfate are limited. It is effective for the healing of duodenal ulcers, but it is not frequently used for this since more effective drugs (e.g. proton pump inhibitors) have been developed. Although the mechanism of sucralfate's ability to accelerate healing of duodenal ulcers remains to be fully defined, it is known that it exerts its effect through a local, rather than systemic, action. Chemically, sucralfate is a complex of the disaccharide sugar, sucrose, combined with sulfate and aluminum. In acidic solutions (e.g. gastric acid) it forms a thick paste that has a strong negative charge.
Mechanism of action 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.
Absorption Minimally absorbed from the gastrointestinal tract (up to 5% of the disaccharide component and less than 0.02% of aluminum).
Volume of distribution Not Available
Protein binding Not Available
Metabolism Not Available
Route of elimination The small amounts of the sulfated disaccharide that are absorbed are excreted primarily in the urine.
Half life Not known.
Clearance Not Available
Toxicity Acute oral toxicity (LD50) in mice is >8000 mg/kg. There is limited experience in humans with overdosage of sucralfate. Sucralfate is only minimally absorbed from the gastrointestinal tract and thus risks associated with acute overdosage should be minimal. In rare reports describing sucralfate overdose, most patients remained asymptomatic.
Affected organisms
  • Humans and other mammals
Pathways Not Available
Pharmacoeconomics
Manufacturers
  • Axcan pharma us inc
  • Nostrum laboratories inc
  • Teva pharmaceuticals usa inc
Packagers
Dosage forms
Form Route Strength
Suspension Oral
Tablet Oral
Prices
Unit description Cost Unit
Sucralfate 1 gm/10ml Suspension 10ml Cup 13.99 USD cup
Carafate 1 gm tablet 1.45 USD tablet
Sucralfate 1 gm tablet 0.72 USD tablet
Sucralfate powder 0.6 USD g
Sulcrate 1 g Tablet 0.59 USD tablet
Apo-Sucralfate 1 g Tablet 0.31 USD tablet
Novo-Sucralate 1 g Tablet 0.31 USD tablet
Nu-Sucralfate 1 g Tablet 0.31 USD tablet
Pms-Sucralfate 1 g Tablet 0.31 USD tablet
Carafate 1 gm/10ml Suspension 0.24 USD ml
Sulcrate Suspension Plus 200 mg/ml Suspension 0.11 USD ml
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Patents Not Available
Properties
State solid
Experimental Properties
Property Value Source
water solubility Insoluble in cold water Not Available
Predicted Properties
Property Value Source
water solubility 7.14e-01 g/l ALOGPS
logP 0.98 ALOGPS
logP -5.6 ChemAxon
logS -3.3 ALOGPS
pKa (strongest acidic) 13.53 ChemAxon
pKa (strongest basic) -3 ChemAxon
physiological charge 0 ChemAxon
hydrogen acceptor count 35 ChemAxon
hydrogen donor count 16 ChemAxon
polar surface area 772.17 ChemAxon
rotatable bond count 36 ChemAxon
refractivity 175.09 ChemAxon
polarizability 105.22 ChemAxon
References
Synthesis Reference Not Available
General Reference
  1. Rees WD: Mechanisms of gastroduodenal protection by sucralfate. Am J Med. 1991 Aug 8;91(2A):58S-63S. Pubmed
External Links
Resource Link
KEGG Compound C07314 Link_out
PharmGKB PA451524 Link_out
Drug Product Database 2239912 Link_out
RxList http://www.rxlist.com/cgi/generic/sucral.htm Link_out
Drugs.com http://www.drugs.com/cdi/sucralfate.html Link_out
PDRhealth http://www.pdrhealth.com/drug_info/rxdrugprofiles/drugs/car1065.shtml Link_out
Wikipedia http://en.wikipedia.org/wiki/Sucralfate Link_out
ATC Codes
  • A02BX02
AHFS Codes
  • 56:28.32
PDB Entries Not Available
FDA label Not Available
MSDS show (73.6 KB)
Interactions
Drug Interactions
Drug Interaction
Calcipotriol Vitamin D Analogs may increase the serum concentration of Sucralfate. Specifically, the absorption of aluminum from sucralfate may be increased, leading to an increase in the serum aluminum concentration. Avoid chronic and/or excessive use of aluminum and aluminum-containing products (such as sucralfate) in patients who are also taking vitamin D analogs. Any patients consuming such a combination should be monitored closely for aluminum status and signs/symptoms of aluminum-related toxicities.
Cholecalciferol Vitamin D analogs such as cholecalciferol may increase the serum concentration of sucralfate. Specifically, the absorption of aluminum from sucralfate may be increased, leading to an increase in the serum aluminum concentration. Avoid chronic and/or excessive use of aluminum and aluminum-containing products (such as sucralfate) in patients who are also taking vitamin D analogs. Any patients consuming such a combination should be monitored closely for aluminum status and signs/symptoms of aluminum-related toxicities.
Ciprofloxacin Formation of non-absorbable complexes
Clodronate Formation of non-absorbable complexes
Etidronic acid Formation of non-absorbable complexes
Fosphenytoin Sucralfate decreases the effect of hydantoin
Gatifloxacin Formation of non-absorbable complexes
Gemifloxacin Formation of non-absorbable complexes
Grepafloxacin Formation of non-absorbable complexes
Ibandronate Formation of non absorbable complexes
Itraconazole Sucralfate may decrease the absorption of itraconazole.
Ketoconazole Sucralfate may decrease the absorption of ketoconazole.
Lansoprazole Sucralfate decreases the effect of lansoprazole
Levofloxacin Formation of non-absorbable complexes
Levothyroxine Sucralfate decreases the effect of levothyroxine
Moxifloxacin Formation of non-absorbable complexes
Norfloxacin Formation of non-absorbable complexes
Ofloxacin Formation of non-absorbable complexes
Phenytoin Sucralfate decreases the effect of hydantoin
Trovafloxacin Sucralfate may decrease the absorption of orally administered Trovafloxacin. The Sucralfate formulation contains aluminum ions that may intefere with Trovafloxacin absorption. Administer Trovafloxacin 2 hours before or 6 hours after the Sucralfate dose to minimize the interaction.
Warfarin Sucralfate may reduce the absorption of warfarin. Warfarin should be administered at least 2 hours before or 6 hours after sucralfate administration. Monitor for changes in prothrombin time if sucralfate is initiated, discontinued or dose changed.
Food Interactions
  • Avoid alcohol.
  • Do not take calcium, aluminum, magnesium or Iron supplements within 2 hours of taking this medication.
  • Take on empty stomach: 1 hour before or 2 hours after meals.
  • Take with a full glass of water.
Targets

1. Pepsin A

Pharmacological action: yes
Actions: inhibitor

Shows particularly broad specificity; although bonds involving phenylalanine and leucine are preferred, many others are also cleaved to some extent

Organism class: human
UniProt ID: P00790 Link_out
Gene: PGA3 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Jensen SL, Funch Jensen P: Role of sucralfate in peptic disease. Dig Dis. 1992;10(3):153-61. Pubmed
  2. Hollander D, Tarnawski A: The protective and therapeutic mechanisms of sucralfate. Scand J Gastroenterol Suppl. 1990;173:1-5. Pubmed
  3. Peterson WL: Pathogenesis and therapy of peptic ulcer disease. J Clin Gastroenterol. 1990;12 Suppl 2:S1-6. Pubmed

2. Heparin-binding growth factor 2

Pharmacological action: yes
Actions: agonist

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

Organism class: human
UniProt ID: P09038 Link_out
Gene: FGF2 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Szabo S: The mode of action of sucralfate: the 1 × 1 × 1 mechanism of action. Scand J Gastroenterol Suppl. 1991;185:7-12. Pubmed
  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. Pubmed
  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. Pubmed
  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. Pubmed
  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. Pubmed

3. Pro-epidermal growth factor

Pharmacological action: yes
Actions: inducer

EGF stimulates the growth of various epidermal and epithelial tissues in vivo and in vitro and of some fibroblasts in cell culture

Organism class: human
UniProt ID: P01133 Link_out
Gene: EGF Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

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. Pubmed
  2. Szabo S: The mode of action of sucralfate: the 1 × 1 × 1 mechanism of action. Scand J Gastroenterol Suppl. 1991;185:7-12. Pubmed
  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. Pubmed

4. Fibrinogen alpha chain

Pharmacological action: unknown
Actions: antagonist

Fibrinogen has a double function:yielding monomers that polymerize into fibrin and acting as a cofactor in platelet aggregation

Organism class: human
UniProt ID: P02671 Link_out
Gene: FGA Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

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. Pubmed

5. Fibrinogen beta chain [Contains: Fibrinopeptide B]

Pharmacological action: unknown
Actions: antagonist

Fibrinogen has a double function:yielding monomers that polymerize into fibrin and acting as a cofactor in platelet aggregation

Organism class: human
UniProt ID: P02675 Link_out
Gene: FGB Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

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. Pubmed

6. Fibrinogen gamma chain

Pharmacological action: unknown
Actions: antagonist

Fibrinogen has a double function:yielding monomers that polymerize into fibrin and acting as a cofactor in platelet aggregation

Organism class: human
UniProt ID: P02679 Link_out
Gene: FGG Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

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. Pubmed
Carriers

1. Serum albumin

Serum albumin, the main protein of plasma, has a good binding capacity for water, Ca(2+), Na(+), K(+), fatty acids, hormones, bilirubin and drugs. Its main function is the regulation of the colloidal osmotic pressure of blood

UniProt ID: P02768 Link_out
Gene: ALB Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. Pubmed
  3. 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. Pubmed
Comments
Drug created on June 13, 2005 07:24 / Updated on February 08, 2013 16:19