Lactulose

HCID 11333CAS 4618-18-2

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

lactuloseD-Lactulose4618-18-2BifiteralCephulacChronulacConstilacLactulosaAcilacCholacConstuloseLactulosum
Weitere Namen anzeigen
Lactulose Concentrateruguotang[UL-13C12]lactulose4-O-hexopyranosylhex-2-ulofuranoseLactulose for peak identification CRS(3S,4R,5R)-1,3,5,6-tetrahydroxy-4-(((2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxyMethyl)tetrahydro-2H-pyran-2-yl)oxy)hexan-2-one
EnuloseGenerlacHeptalacLaxilosePortalacKristaloseLattulosioDTXSID5045833

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

Experimentelle und physikochemische Eigenschaften

DrugsPharmaceuticals -> Listed in ZINC15
Cosmetics · 2 Einträge

Cosmetic ingredients (Lactulose) -> CIR (Cosmetic Ingredient Review)

Skin conditioning; Humectant

LogP-4.3
Solubility · 2 Einträge

Soluble in cold water, hot water. Solubility in water: 76.4% @ 30 deg. C

764.0 mg/mL

Human Drugs · 4 Einträge

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

Melting Point169 °C

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.

Sicherheit und Regulatorisches

GHS-Klassifizierung

GHS Classification · 3 Einträge

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

Regulatory InformationLactulose: Does not have an individual approval but may be used under an appropriate group standard
Hazard Classes and CategoriesNot Classified

Toxikologische Informationen

Adverse Effects · 1 Eintrag

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 · 2 Einträge

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 · 6 Einträge

Drug Induced Liver Injury Rank (DILIrank 2.0)

Lactulose

vNo-DILI-concern

0

No match

DOI:10.1016/j.drudis.2016.02.015

Effects During Pregnancy and Lactation◉ Summary of Use during Lactation

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 · 4 Einträge

A06AD11

A - Alimentary tract and metabolism

QA - Alimentary tract and metabolism

A06AD11

Protein BindingNegligible amounts of lactulose - metabolized or non-metabolized - are absorbed into the body.. Regardless, data regarding the protein binding of lactulose is not readily available or accessible.
Pharmacodynamics · 1 Eintrag

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 · 1 Eintrag

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.

Biological Half-LifeThe data regarding the half-life of lactulose is not readily available or accessible.
Metabolism/Metabolites · 1 Eintrag

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.

Verwendung und Herstellung

UsesCIR ingredient: Lactulose
Use ClassificationCosmetics -> Skin conditioning; Humectant

Anwendungen

VerwendenLactulose is is a synthetic, non-digestible sugar used in the treatment of chronic constipation; laxative.

Anbieter50 Anbieter

国药集团化学试剂有限公司86-21-63210123 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
合肥翰刚医药科技有限公司+8618062405514 · [email protected]
河北创海生物科技有限公司+86-86-13131129325 · [email protected]
上海如吉生物科技发展有限公司+86-21-65211385-8001 36031160 · [email protected]

Ergänzende Hinweise

DefinitionChEBI: A synthetic galactosylfructose disaccharide used in the treatment of constipation and hepatic encephalopathy.

Zugehörige Reaktionen

9

Verknüpfte Notizen

Wird geladen…