[({[(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

• ChemBase ID: 248
• Molecular Formular: C11H28Al8O51S8
• Molecular Mass: 1448.681724
• Monoisotopic Mass: 1447.58862356
• 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
• Canonical SMILES: O[Al](OS(=O)(=O)O[C@H]1[C@@H](O[C@@H]([C@H]([C@@H]1OS(=O)(=O)O[Al](O)O)OS(=O)(=O)O[Al](O)O)COS(=O)(=O)O[Al](O)O)O[C@]1(COS(=O)(=O)O[Al](O)O)O[C@@H]([C@H]([C@@H]1OS(=O)(=O)O[Al](O)O)OS(=O)(=O)O[Al](O)O)OS(=O)(=O)O[Al](O)O)O
• 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
• InChIKey: MNQYNQBOVCBZIQ-JQOFMKNESA-A

NAMES AND DATABASE IDS

Names

• 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
• IUPAC Traditional name: ({[(2S,3R,4S,5R,6R)-4,5-di{[(dihydroxyalumanyl)oxysulfonyl]oxy}-6-({[(dihydroxyalumanyl)oxysulfonyl]oxy}methyl)-2-{[(2R,3S,4S,5R)-3,4,5-tri{[(dihydroxyalumanyl)oxysulfonyl]oxy}-2-({[(dihydroxyalumanyl)oxysulfonyl]oxy}methyl)oxolan-2-yl]oxy}oxan-3-yl]oxysulfonyl}oxy)alumanediol
• Brand Name: Antepsin; Apo-sucralfate; Carafate; Sulcrate; Sulcrate Suspension Plus; Ulcar; Ulcerban; Ulcerlmin; Ulcogant; Sucramal; Ulcermin
• Synonyms: sucralfate; Sucralfate

Database IDs

• CAS Number: 54182-58-0
• PubChem SID: 160963711
• PubChem CID: 70789197

CALCULATED PROPERTIES

JChem

• Acid pKa: 13.533897
• H Acceptors: 35
• H Donor: 16
• LogD (pH = 5.5): -5.6049
• LogD (pH = 7.4): -5.6049004
• Log P: -5.6049
• Molar Refractivity: 175.0943 cm^3
• Polarizability: 101.12676 Å^3
• Polar Surface Area: 772.17 Å^2
• Rotatable Bonds: 36
• Lipinski's Rule of Five: false

ALOGPS 2.1

• Log P: 0.98
• LOG S: -3.31
• Solubility (Water): 7.14e-01 g/l

PROPERTIES

Physical Property

• Solubility: Insoluble in cold water

DETAILS

DrugBank - DB00364

• Drug Groups: approved; investigational
• Description: A basic aluminum complex of sulfated sucrose. [PubChem]
• 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.
• Pharmacology: 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.
• 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
• Absorption: Minimally absorbed from the gastrointestinal tract (up to 5% of the disaccharide component and less than 0.02% of aluminum).
• Half Life: Not known.
• Elimination: The small amounts of the sulfated disaccharide that are absorbed are excreted primarily in the urine.
• References: Rees WD: Mechanisms of gastroduodenal protection by sucralfate. Am J Med. 1991 Aug 8;91(2A):58S-63S. [Pubmed]
• External Links: Wikipedia; RxList; PDRhealth; Drugs.com

REFERENCES

• Rees WD: Mechanisms of gastroduodenal protection by sucralfate. Am J Med. 1991 Aug 8;91(2A):58S-63S. Pubmed