Grundinformationen
- Standard-SMILES
OC[C@H]1O[C@@H](O[C@@H]2[C@@H](CO)O[C@](O)(CO)[C@H]2O)[C@H](O)[C@@H](O)[C@H]1O- InChIKey
JCQLYHFGKNRPGE-FCVZTGTOSA-N- Summenformel
- C12H22O11
- Durchschnittliche Molmasse
- 342,3 g/mol
- Monoisotopische Masse
- 342,11621152
Überblick
Lactulose is a synthetic galactosylfructose disaccharide used in the treatment of constipation and hepatic encephalopathy. It has a role as a laxative and a gastrointestinal drug.
Namen und Bezeichner
- Bevorzugter Name
- Lactulose
- IUPAC
- (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
- Lokaler Name
- Lactulose
- Englischer Name
- Lactulose
- Summenformel
- C12H22O11
- Molmasse
- 342.3
Namen und Synonyme
Weitere Namen anzeigen
Datenbank-Bezeichner
- CAS
4618-18-2、58166-24-8、58166-25-9- PubChem CID
- 11333
- DTXSID
DTXSID5045833- ChEMBL
CHEMBL296306- ChEBI
CHEBI:6359- UNII
- 9XH2P2N8EP
- EC Number
- 225-027-7
- Nikkaji
- J3.412F
Eigenschaften
Berechnete Struktureigenschaften
- XLogP
- -4,3
- Polarare Oberfläche (TPSA)
- 190 Ų
- H-Brücken-Donoren
- 8
- H-Brücken-Akzeptoren
- 11
- Frei drehbare Bindungen
- 5
- Schwere Atome
- 23
- Formalladung
- 0
- Komplexität
- 395
Experimentelle und physikochemische Eigenschaften
Cosmetics
Cosmetic ingredients (Lactulose) -> CIR (Cosmetic Ingredient Review)
Skin conditioning; Humectant
Solubility
Soluble in cold water, hot water. Solubility in water: 76.4% @ 30 deg. C
764.0 mg/mL
Human Drugs
Breast Feeding; Lactation; Milk, Human; Gastrointestinal Agents; Laxatives
FDA approved drugs -> Active ingredient
FDA approved drugs -> Active ingredient
Medicines for other common symptoms in palliative care
Collision Cross Section
164.63 Ų [M+H-H2O]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
180.1 Ų [M+Na]+ [CCS Type: DT; Method: stepped-field]
169.2 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
179 Ų [M+Na]+
Physikochemische Eigenschaften
- Schmelzpunkt
- 169 °C · ~169 °C (dec.)
- Siedepunkt
- 397.76 °C · 397.76°C (rough estimate)
- Dichte
- 1 · 1,32g/cm
- Brechungsindex
- 1 · 1,45-1,47
- storage temp.
- Refrigerator
- Löslichkeit
- Freely soluble in water, sparingly soluble in methanol, practically insoluble in toluene.
- Aggregatzustand
- Powder
- pka
- 11.67 · 11.67±0.20(Predicted)
- Farbe
- White to almost white
- Wasserlöslichkeit
- 76.4 G/100 · 76.4 G/100 ML (30 ºC)
- Merck
- 5346 · 5346
- BRN
- 93773 · 93773
- BCS Class
- 2 · 2
- Kosmetik-Inhaltsstoffe Funktionen
- HUMECTANTSKIN CONDITIONING
- 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
- PFCRQPBOOFTZGQ-VZXVHDRGSA-N
- SMILES
- OC[C@H]1O[C@@H](O[C@@H]2[C@@H](CO)O[C@@](O)(CO)[C@H]2O)[C@H](O)[C@@H](O)[C@H]1O
- LogP
- -2.885 · -2.885 (est)
- CAS Datenbank
- 4618 · 4618-18-2(CAS DataBase Reference)
- EPA chemische Informationen
- 4 · D-Fructose, 4-O-.beta.-D-galactopyranosyl- (4618-18-2)
- CAS Number Unlabeled
- 4618 · 4618-18-2
Sicherheit und Regulatorisches
GHS-Klassifizierung
GHS Classification
This chemical does not meet GHS hazard criteria for 100% (9 of 9) of all reports.
Not Classified
Aggregated GHS information provided per 9 reports by companies from 2 notifications to the ECHA C&L Inventory.
Gefahrenhinweise
Toxikologische Informationen
Adverse Effects
Because lactulose has insignificant absorption by the gut and undergoes rapid excretion by the kidneys, its effects remain localized to the gut microenvironment. Side effects would include increased bowel sounds (borborygmi), increased flatus, and a sensation of bloating. Since lactulose's intended use is to soften the stool quantity and increase the stool amount, its most significant side effect remains diarrhea. The diarrhea is dose-dependent and decreases in severity with a reduction in the dose of lactulose.
Toxicity Summary
Safe in the present practices of use and concentration. Ingredient, concentration, and use information are available in documents discoverable at https://cir-reports.cir-safety.org
Clinically, documentation on lactulose toxicity is lacking. Specific studies using rats inoculated with various concentrations of lactulose syrup ranging from 0.5% to 5% revealed no evidence of toxicity. However, there have been study results indicating the ability of lactulose to induce lithium toxicity in psychiatric patients. This effect is more broadly attributable to lactulose's ability to induce dehydration through its osmotic action, depletion of total body volume, and the resultant poor renal excretion of lithium. Although rare, documented allergic reactions to lactulose have been recorded in patients with milk allergies.
Drug Induced Liver Injury
Drug Induced Liver Injury Rank (DILIrank 2.0)
Lactulose
vNo-DILI-concern
0
No match
DOI:10.1016/j.drudis.2016.02.015
Sicherheitsdaten
- wgk
- 2
- tsca
- TSCA listed
- hs_code
- 29400090
- RTECS-Nr.
- LS6965000
- safety_code
- 24/25
- Speicherklasse
- 11 - Combustible Solids
Chemie und Industrie
Pharmakologische Informationen
ATC Code
A06AD11
A - Alimentary tract and metabolism
QA - Alimentary tract and metabolism
A06AD11
Pharmacodynamics
Lactulose formulations are most commonly administered via the oral route or the rectal route. Consequently, because the substance experiences minimal absorption by the gut it typically remains localized in the gastrointestinal tract environment and ultimately demonstrates almost all of its pharmacologic effects within the gut. In particular, as lactulose elicits its laxative effects in enhancing stool amounts and softening stool, such biochemical and physiologic activities can cause increased bowel sounds (borborygmi), a feeling of bloatedness, belching, frequent flatus, and diarrhea.
Mechanism of Action
Lactulose is a synthetic disaccharide derivative of lactose that consists of one molecule of galactose and one molecule of fructose. Saccharolytic bacteria present in the large intestine subsequently break the substance down into organic acids like lactic acid and small amounts of formic and acetic acids. Such resultant volatile fatty acid metabolites, in combination with hydrogen and methane that is also generated consequently enhance intraluminal gas formation, peristaltic gut motility, and elicit an osmotic effect that facilitates an increase in the water content of stool as well as associated stool softening. All of these actions ultimately assist in facilitating and increasing the frequency of bowel movements in patients experiencing constipation, although it may take 24 to 48 hours after using the medication for this laxative effect to become evident. At the same time, the formation of such acids via the metabolism of lactulose by colonic bacteria also acidifies the contents of the colon, thereby contributing to the treatment of portal-systemic encephalopathy (PSE). As one of the principal features of PSE involves the accumulation of nitrogenous waste products like ammonia in the systemic circulation, a state in which the colonic contents become more acidic than blood allows ammonia in the circulation to diffuse into the colon.. Furthermore, ammonia that diffuses into the acidic colon is ionized to ammonium ions that are incapable of being absorbed back into the blood. These effects, combined with the laxative action of lactulose facilitates the excretion of excess ammonia. And finally, it is also believed that an acidic colonic environment results in the elimination of urease-producing bacteria that contribute to the formation of ammonia while surviving colonic bacteria use up any trapped ammonia in the colon as a source of nitrogen for protein synthesis.
Metabolism/Metabolites
Lactulose is essentially only metabolized in the colon by saccharolytic bacteria that are present there. In particular, the substance is broken down into lactic acid and small amounts of acetic and formic acid. Specific examples of bacteria that normally inhabit the large intestine that are capable of lactulose metabolism include Lactobacilli, Bacteroides, Escherichia coli, and Clostridia.
FDA Pharmacological Classification
9U7D5QH5AE
LACTULOSE
Established Pharmacologic Class [EPC] - Osmotic Laxative
Mechanisms of Action [MoA] - Osmotic Activity
Mechanisms of Action [MoA] - Acidifying Activity
Physiologic Effects [PE] - Stimulation Large Intestine Fluid/Electrolyte Secretion
Absorption, Distribution and Excretion
After administration by the oral route, less than 3% of the given dose of lactulose solution is absorbed by the small intestine. The remaining unabsorbed lactulose reaches the large intestine where it is metabolized - but even then, negligible quantities of unchanged lactulose or its metabolites are absorbed across the colon.
The renal excretion of any lactulose that manages to be absorbed into the circulation has been determined to be 3% or less and is generally complete within 24 hours. Any unabsorbed lactulose is largely excreted with stool.
Negligible amounts of lactulose - metabolized or non-metabolized - are absorbed into the body.. Most lactulose that is administered subsequently remains predominantly around the gastrointestinal tract area.
Negligible amounts of lactulose - metabolized or non-metabolized - are absorbed into the body.. Regardless, data regarding the clearance of lactulose is not readily available or accessible.
Verwendung und Herstellung
Anwendungen
VerwendenLactulose is is a synthetic, non-digestible sugar used in the treatment of chronic constipation; laxative.
Vor- und nachgelagerte Produkte
Vorgelagerte Rohstoffe
Anbieter50 Anbieter
Ergänzende Hinweise
DefinitionChEBI: A synthetic galactosylfructose disaccharide used in the treatment of constipation and hepatic encephalopathy.
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