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Details

Stereochemistry ABSOLUTE
Molecular Formula C12H22O11
Molecular Weight 342.2965
Optical Activity UNSPECIFIED
Defined Stereocenters 9 / 9
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of .ALPHA.-LACTULOSE

SMILES

[H][C@@]2(O[C@@H]1[C@@H](CO)O[C@](O)(CO)[C@H]1O)O[C@H](CO)[C@H](O)[C@H](O)[C@H]2O

InChI

InChIKey=JCQLYHFGKNRPGE-FCVZTGTOSA-N
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

HIDE SMILES / InChI
Lactulose is a non-absorbable sugar used in the treatment of constipation and hepatic encephalopathy. It is a disaccharide (double-sugar) formed from one molecule each of the simple sugars (monosaccharides) fructose and galactose. Lactulose is not normally present in raw milk but is a product of heat-processed: the greater the heat, the greater amount of this substance. Lactulose is not absorbed in the small intestine nor broken down by human enzymes, thus stays in the digestive bolus through most of its course, causing retention of water through osmosis leading to softer, easier to pass stool. It has a secondary laxative effect in the colon, where it is fermented by the gut flora, producing metabolites which have osmotic powers and peristalsis-stimulating effects (such as acetate), but also methane associated with flatulence. Lactulose is metabolized in the colon by bacterial flora to short chain fatty acids including lactic acid and acetic acid. These partially dissociate, acidifying the colonic contents (increasing the H+ concentration in the gut).[14] This favors the formation of the nonabsorbable NH+4 from NH3, trapping NH3 in the colon and effectively reducing plasma NH3 concentrations. Lactulose is used in the treatment of chronic constipation in patients of all ages as a long-term treatment. Lactulose is used for chronic idiopathic constipation, i.e. chronic constipation occurring without any identifiable cause. Lactulose may be used to counter the constipating effects of opioids, and in the symptomatic treatment of hemorrhoids as a stool softener.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
CEPHULAC

Approved Use

For the prevention and treatment of portal-systemic encephalopathy, including the stages of hepatic pre-coma and coma. Controlled studies have shown that lactulose solution therapy reduces the blood ammonia levels by 25-50%; this is generally paralleled by an improvement in the patients' mental state and by an improvement in EEG patterns. The clinical response has been observed in about 75% of patients, which is at least as satisfactory as that resulting from neomycin therapy. An increase in patients' protein tolerance is also frequently observed with lactulose therapy. In the treatment of chronic portal-systemic encephalopathy, Lactulose has been given for over 2 years in controlled studies.

Launch Date

1.96559995E11
Primary
CEPHULAC

Approved Use

For the prevention and treatment of portal-systemic encephalopathy, including the stages of hepatic pre-coma and coma. Controlled studies have shown that lactulose solution therapy reduces the blood ammonia levels by 25-50%; this is generally paralleled by an improvement in the patients' mental state and by an improvement in EEG patterns. The clinical response has been observed in about 75% of patients, which is at least as satisfactory as that resulting from neomycin therapy. An increase in patients' protein tolerance is also frequently observed with lactulose therapy. In the treatment of chronic portal-systemic encephalopathy, Lactulose has been given for over 2 years in controlled studies.

Launch Date

1.96559995E11
PubMed

PubMed

TitleDatePubMed
Small bowel permeability in diagnosis of celiac disease and monitoring of compliance of a gluten-free diet (gut permeability in celiac disease).
2001
A systematic review of the diagnostic accuracy of physical examination for the detection of cirrhosis.
2001
[Disturbance of liver functions and dysbiosis in patients with lipid distress syndrome and its treatment with lactulose preparation "Duphalac" (lactulose)].
2001
Dietary lactulose decreases apparent nitrogen absorption and increases apparent calcium and magnesium absorption in healthy dogs.
2001 Apr
Importance of increased intestinal permeability after multiple injuries.
2001 Aug
Intestinal permeability testing using lactulose and rhamnose: a comparison between clinically normal cats and dogs and between dogs of different breeds.
2001 Aug
Lactulose in the prevention of recurrent urinary tract infection.
2001 Dec
Enzymatic reactions for the determination of sugars in food samples using the differential pH technique.
2001 Dec
Acute nutritional and intestinal changes after pelvic radiation.
2001 Dec
Lactose malabsorption and intolerance in the elderly.
2001 Dec
Intestinal function and metabolism in the early adaptive phase after massive small bowel resection in the rat.
2001 Dec
In vivo fucosylation of lacto-N-neotetraose and lacto-N-neohexaose by heterologous expression of Helicobacter pylori alpha-1,3 fucosyltransferase in engineered Escherichia coli.
2001 Jun
Effect of skin pressure by clothing on small bowel transit time.
2001 Nov
Purification and characterization of two lectins from a toxic moray, Gymnothrax javanicus.
2001 Nov
A comparative in vitro evaluation of the fermentation properties of prebiotic oligosaccharides.
2001 Nov
Lactulose-induced pneumatosis intestinalis and pneumoperitoneum.
2001 Nov
Double blind randomised controlled trial of topical glyceryl trinitrate in anal fissure.
2001 Nov
Influence of polymeric enteral nutrition supplemented with different doses of glutamine on gut permeability in critically ill patients.
2001 Nov-Dec
Intestinal permeability is increased in a proportion of spouses of patients with Crohn's disease.
2001 Oct
The fluorescence of advanced Maillard products is a good indicator of lysine damage during the Maillard reaction.
2001 Oct
Lactulose may help prevent urinary tract infections.
2001 Oct 20
Liver response to indomethacin-induced intestinal injury.
2002
Efficacy of lactulose plus 13C-acetate breath test in the diagnosis of gastrointestinal motility disorders.
2002
[The response to combined therapy of hepatic encephalopathy in patients with hepatic cirrhosis].
2002
[Different therapeutic approaches for chronic diffuse liver lesions using ornicetil, lactulose, etimizol and corinfar].
2002
Effect of lacZY-marking of the 2,4-diacetyl-phloroglucinol producing Pseudomonas fluorescens-strain 5-2/4 on its physiological performance and root colonization ability.
2002
Economic impact of low dose polyethylene glycol 3350 plus electrolytes compared with lactulose in the management of idiopathic constipation in the UK.
2002
Sugar intolerance: origin and mechanisms of symptoms?
2002 Apr
Alterations in intestinal permeability following the intensified polydrug-chemotherapy IFADIC (ifosfamide, Adriamycin, dacarbazine).
2002 Apr
Mucosal pathology of the upper gastrointestinal tract associated with intensive chemotherapy in children: vitamin A supplements do not prevent lesions.
2002 Apr-May
Nutritional and metabolic consequences of the early Maillard reaction of heat treated milk in the pig. Significance for man.
2002 Feb
Clinical tests of gastrointestinal permeability that rely on the urinary recovery of enterally administered probes can yield invalid results in critically ill patients.
2002 Feb
Typhoid, hepatitis E, or typhoid and hepatitis E: the cause of fulminant hepatic failure--a diagnostic dilemma.
2002 Feb
Home lactulose enema: prevention of hepatic encephalopathy at home.
2002 Jan
Scintigraphy of the small intestine: a simplified standard for study of transit with reference to normal values.
2002 Jan
Small intestinal bacterial overgrowth, intestinal permeability, and non-alcoholic steatohepatitis.
2002 Jan
[Use of lactusan for the correction of microecological intestinal disturbances in children].
2002 Jan-Feb
Evaluation of hydrogen excretion after lactulose administration as a screening test for causes of irritable bowel syndrome.
2002 Jul
A randomised controlled trial investigating the effects of dopexamine on gastrointestinal function and organ dysfunction in the critically ill.
2002 Jul
Multi-antioxidant supplementation does not prevent an increase in gut permeability after lower torso ischemia and reperfusion in humans.
2002 Jul-Aug
The relationships between intestinal damage and circulating endotoxins in experimental Trypanosoma brucei brucei infections.
2002 Jun
Kinetics of urinary recovery of five sugars after orogastric administration in healthy dogs.
2002 Jun
Production of short-chain fatty acids and gas from various oligosaccharides by gut microbes of carp (Cyprinus carpio L.) in micro-scale batch culture.
2002 Jun
Gut-associated lymphoid T cell suppression enhances bacterial translocation in alcohol and burn injury.
2002 Jun
The glucose breath test: a diagnostic test for small bowel stricture(s) in Crohn's disease.
2002 Mar
[Hepatic encephalopathy after TIPS--retrospective study].
2002 May
Comparison of polyethylene glycol 3350 and lactulose for treatment of chronic constipation in children.
2002 May
L-carnitine administration reverses acute mental status changes in a chronic hemodialysis patient with hepatitis C infection.
2002 May
Oligomerization process of the hemolytic lectin CEL-III purified from a sea cucumber, Cucumaria echinata.
2002 May
A 45-kDa midgut glycoprotein from Anopheles albimanus mosquito mediates the killing of trypanosomes.
2002 Sep
Patents

Sample Use Guides

The usual adult, oral dosage is 2 to 3 tablespoonfuls (30 mL to 45 mL, containing 20 grams to 30 grams of Lactulose) three or four times daily. The dosage may be adjusted every day or two to produce 2 or 3 soft stools daily.
Route of Administration: Oral
In Vitro Use Guide
Unknown
Name Type Language
.ALPHA.-LACTULOSE
Common Name English
.ALPHA.-D-FRUCTOFURANOSE, 4-O-.BETA.-D-GALACTOPYRANOSYL-
Systematic Name English
Code System Code Type Description
CAS
58166-25-9
Created by admin on Fri Dec 15 15:45:26 UTC 2023 , Edited by admin on Fri Dec 15 15:45:26 UTC 2023
PRIMARY
PUBCHEM
11333
Created by admin on Fri Dec 15 15:45:26 UTC 2023 , Edited by admin on Fri Dec 15 15:45:26 UTC 2023
PRIMARY
FDA UNII
9XH2P2N8EP
Created by admin on Fri Dec 15 15:45:26 UTC 2023 , Edited by admin on Fri Dec 15 15:45:26 UTC 2023
PRIMARY