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Identification
NameSucralfate
Accession NumberDB00364  (APRD01238)
Typesmall molecule
Groupsapproved
Description

A basic aluminum complex of sulfated sucrose. [PubChem]

Structure
Thumb
Synonyms
SynonymLanguageCode
Hexadeca-μ-hydroxytetracosahydroxy[μ8-[1,3,4,6-tetra-O-sulfo-β-Dfructofuranosyl-α-D-glucopyranoside tetrakis(hydrogen sulfato)8-)]]hexadecaaluminumNot AvailableIUPAC
SucralfatGermanINN
SucralfateNot AvailableBAN, USAN, JAN, DCF, Ph. Eur. 7, USP 34
SucralfatoNot AvailableDCIT
SucralfatumLatinINN
SaltsNot Available
Brand names
NameCompany
AntepsinOrion
CarafateAptalis
SucramalMenarini
SucraxolMedifarma
SulcrateAxcan
UlcogantMerck
Brand mixturesNot Available
CategoriesNot Available
CAS number54182-58-0
WeightAverage: 1448.682
Monoisotopic: 1447.588619666
Chemical FormulaC11H28Al8O51S8
InChI KeyInChIKey=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
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
Mass SpecNot Available
Taxonomy
KingdomOrganic Compounds
SuperclassOrganooxygen Compounds
ClassCarbohydrates and Carbohydrate Conjugates
SubclassDisaccharides
Direct parentMixed Pentose/Hexose Disaccharides
Alternative parentsO-glycosyl Compounds; Oxanes; Tetrahydrofurans; Oxolanes; Organic Sulfuric Acids and Derivatives; Polyamines; Acetals
Substituentsglycosyl compound; o-glycosyl compound; oxane; tetrahydrofuran; sulfuric acid derivative; oxolane; polyamine; ether; acetal
Classification descriptionThis compound belongs to the mixed pentose/hexose disaccharides. These are disaccharides containing both an hexose and a pentose.
Pharmacology
IndicationFor 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.
PharmacodynamicsSucralfate 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 actionAlthough 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.
AbsorptionMinimally absorbed from the gastrointestinal tract (up to 5% of the disaccharide component and less than 0.02% of aluminum).
Volume of distributionNot Available
Protein bindingNot Available
Metabolism
Route of eliminationThe small amounts of the sulfated disaccharide that are absorbed are excreted primarily in the urine.
Half lifeNot known.
ClearanceNot Available
ToxicityAcute 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
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
Property Value Probability
Human Intestinal Absorption - 0.7959
Blood Brain Barrier + 0.8803
Caco-2 permeable - 0.6433
P-glycoprotein substrate Non-substrate 0.8087
P-glycoprotein inhibitor I Non-inhibitor 0.5656
P-glycoprotein inhibitor II Non-inhibitor 0.986
Renal organic cation transporter Non-inhibitor 0.8471
CYP450 2C9 substrate Non-substrate 0.8611
CYP450 2D6 substrate Non-substrate 0.8256
CYP450 3A4 substrate Non-substrate 0.6233
CYP450 1A2 substrate Non-inhibitor 0.772
CYP450 2C9 substrate Non-inhibitor 0.8211
CYP450 2D6 substrate Non-inhibitor 0.8865
CYP450 2C19 substrate Non-inhibitor 0.7869
CYP450 3A4 substrate Non-inhibitor 0.9828
CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.9328
Ames test Non AMES toxic 0.5805
Carcinogenicity Non-carcinogens 0.5356
Biodegradation Not ready biodegradable 0.8432
Rat acute toxicity 2.4219 LD50, mol/kg Not applicable
hERG inhibition (predictor I) Weak inhibitor 0.7937
hERG inhibition (predictor II) Non-inhibitor 0.8793
Pharmacoeconomics
Manufacturers
  • Axcan pharma us inc
  • Nostrum laboratories inc
  • Teva pharmaceuticals usa inc
Packagers
Dosage forms
FormRouteStrength
SuspensionOral
TabletOral
Prices
Unit descriptionCostUnit
Sucralfate 1 gm/10ml Suspension 10ml Cup13.99USDcup
Carafate 1 gm tablet1.45USDtablet
Sucralfate 1 gm tablet0.72USDtablet
Sucralfate powder0.6USDg
Sulcrate 1 g Tablet0.59USDtablet
Apo-Sucralfate 1 g Tablet0.31USDtablet
Novo-Sucralate 1 g Tablet0.31USDtablet
Nu-Sucralfate 1 g Tablet0.31USDtablet
Pms-Sucralfate 1 g Tablet0.31USDtablet
Carafate 1 gm/10ml Suspension0.24USDml
Sulcrate Suspension Plus 200 mg/ml Suspension0.11USDml
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
PatentsNot Available
Properties
Statesolid
Experimental Properties
PropertyValueSource
water solubilityInsoluble in cold waterNot Available
Predicted Properties
PropertyValueSource
water solubility7.14e-01 g/lALOGPS
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 area772.17ChemAxon
rotatable bond count36ChemAxon
refractivity175.09ChemAxon
polarizability105.22ChemAxon
number of rings2ChemAxon
bioavailability0ChemAxon
rule of fiveNoChemAxon
Ghose filterNoChemAxon
Veber's ruleNoChemAxon
MDDR-like ruleNoChemAxon
Spectra
SpectraNot Available
References
Synthesis Reference

Nick V. Lazaridis, Moo K. Park, Yousry Sayed, “Method for preparing high potency sucralfate.” U.S. Patent US4990610, issued March, 1973.

US4990610
General Reference
  1. Rees WD: Mechanisms of gastroduodenal protection by sucralfate. Am J Med. 1991 Aug 8;91(2A):58S-63S. Pubmed
External Links
ResourceLink
KEGG CompoundC07314
PharmGKBPA451524
Drug Product Database2239912
RxListhttp://www.rxlist.com/cgi/generic/sucral.htm
Drugs.comhttp://www.drugs.com/cdi/sucralfate.html
PDRhealthhttp://www.pdrhealth.com/drug_info/rxdrugprofiles/drugs/car1065.shtml
WikipediaSucralfate
ATC CodesA02BX02
AHFS Codes
  • 56:28.32
PDB EntriesNot Available
FDA labelNot Available
MSDSshow(73.6 KB)
Interactions
Drug Interactions
Drug
CalcipotriolVitamin 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.
CholecalciferolVitamin 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.
CiprofloxacinFormation of non-absorbable complexes
ClodronateFormation of non-absorbable complexes
Etidronic acidFormation of non-absorbable complexes
FosphenytoinSucralfate decreases the effect of hydantoin
GatifloxacinFormation of non-absorbable complexes
GemifloxacinFormation of non-absorbable complexes
GrepafloxacinFormation of non-absorbable complexes
IbandronateFormation of non absorbable complexes
ItraconazoleSucralfate may decrease the absorption of itraconazole.
KetoconazoleSucralfate may decrease the absorption of ketoconazole.
LansoprazoleSucralfate decreases the effect of lansoprazole
LevofloxacinFormation of non-absorbable complexes
LevothyroxineSucralfate decreases the effect of levothyroxine
MoxifloxacinFormation of non-absorbable complexes
NorfloxacinFormation of non-absorbable complexes
OfloxacinFormation of non-absorbable complexes
PhenytoinSucralfate decreases the effect of hydantoin
TrovafloxacinSucralfate 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.
WarfarinSucralfate 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.

1. Pepsin

Kind: protein group

Organism: Human

Pharmacological action: yes

Actions: inhibitor

Components

Name UniProt ID Details

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. Fibroblast growth factor 2

Kind: protein

Organism: Human

Pharmacological action: yes

Actions: agonist

Components

Name UniProt ID Details
Fibroblast growth factor 2 P09038 Details

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

Kind: protein

Organism: Human

Pharmacological action: yes

Actions: inducer

Components

Name UniProt ID Details
Pro-epidermal growth factor P01133 Details

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

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: antagonist

Components

Name UniProt ID Details
Fibrinogen alpha chain P02671 Details

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

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: antagonist

Components

Name UniProt ID Details
Fibrinogen beta chain P02675 Details

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

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: antagonist

Components

Name UniProt ID Details
Fibrinogen gamma chain P02679 Details

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

1. Serum albumin

Kind: protein

Organism: Human

Pharmacological action: unknown

Components

Name UniProt ID Details
Serum albumin P02768 Details

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 November 04, 2013 16:36