(2S,3R,4S,5R,6R)-2-{[(2R,3S,4S,5R)-4,5-dihydroxy-2,5-bis(hydroxymethyl)oxolan-3-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol

• ChemBase ID: 463
• Molecular Formular: C12H22O11
• Molecular Mass: 342.29648
• Monoisotopic Mass: 342.11621152
• SMILES: O([C@H]1[C@H](O)[C@@](O[C@@H]1CO)(O)CO)[C@@H]1O[C@@H]([C@H](O)[C@H](O)[C@H]1O)CO
• Canonical SMILES: OC[C@H]1O[C@]([C@H]([C@@H]1O[C@@H]1O[C@H](CO)[C@@H]([C@@H]([C@H]1O)O)O)O)(O)CO
• InChI: InChI=1S/C12H22O11/c13-1-4-6(16)7(17)8(18)11(21-4)22-9-5(2-14)23-12(20,3-15)10(9)19/h4-11,13-20H,1-3H2/t4-,5-,6+,7+,8-,9-,10+,11+,12-/m1/s1
• InChIKey: JCQLYHFGKNRPGE-FCVZTGTOSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3R,4S,5R,6R)-2-{[(2R,3S,4S,5R)-4,5-dihydroxy-2,5-bis(hydroxymethyl)oxolan-3-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol
• IUPAC Traditional name: lactulose
• Brand Name: Acilac; Bifiteral; Cephulac; Cholac; Chronulac; Constilac; Constulose; D-Lactulose; Duphalac; Enulose; Evalose; Fructofuranose; Generlac; Heptalac; Isolactose; Kristalose; Lactulosa [INN-Spanish]; Lactulosa [Spanish]; Lactulose [USAN:BAN:INN:JAN]; Lactulose, ~98%; Lactulosum [INN-Latin]; Lactulosum [Latin]; Laevolac; Lattulosio [Italian]; Laxilose; Portalac
• Synonyms: Lactulose

Database IDs

• CAS Number: 4618-18-2
• PubChem SID: 46506757; 160963926
• PubChem CID: 11333

CALCULATED PROPERTIES

JChem

• Acid pKa: 10.279233
• H Acceptors: 11
• H Donor: 8
• LogD (pH = 5.5): -4.528842
• LogD (pH = 7.4): -4.5294075
• Log P: -4.528835
• Molar Refractivity: 68.7741 cm^3
• Polarizability: 28.969793 Å^3
• Polar Surface Area: 189.53 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: false

ALOGPS 2.1

• Log P: -3.26
• LOG S: 0.36
• Solubility (Water): 7.92e+02 g/l

PROPERTIES

Physical Property

• Solubility: 764 mg/mL
• Hydrophobicity(logP): -4.3

DETAILS

DrugBank - DB00581

• Drug Groups: approved
• Description: A synthetic disaccharide used in the treatment of constipation and hepatic encephalopathy. It has also been used in the diagnosis of gastrointestinal disorders. (From Martindale, The Extra Pharmacopoeia, 30th ed, p887)
• Indication: For the treatment of constipation and hepatic encephalopathy.
• Pharmacology: Therapeutically, lactulose has laxative and ammonia-detoxifying actions. In treating constipation lactulose metabolites draw water into the bowel, causing a cathartic effect through osmotic action.
• Toxicity: LD₅₀=18.2 g/kg (oral, rat). Side effects include diarrhea and resultant dehydration.
• Affected Organisms: Humans and other mammals
• Biotransformation: Lactulose is completely metabolized in the colon by enteric bacteria, and no lactulose is excreted in the feces.
• Absorption: Poorly absorbed from the gastrointestinal tract as no human enzyme that is capable of hydrolysis of this disaccharide is present in human gastrointestinal tissue.
• Half Life: 1.7-2 hours
• Elimination: The primary route of elimination is fecal. Urinary excretion has been determined to be 3% or less and is essentially complete within 24 hours.
• External Links: Wikipedia; RxList; PDRhealth; Drugs.com