Lactulose

Structural formula
General
Non-proprietary name	Lactulose
other names	4- O - β - D -galactopyranosyl- D -fructofuranose LACTULOSE ( INCI )
Molecular formula	C 12 H 22 O 11
Brief description	colorless crystals or solution
External identifiers / databases
CAS number 4618-18-2 EC number 225-027-7 ECHA InfoCard 100,022,752 PubChem 11333 ChemSpider 10856 DrugBank DB00581 Wikidata Q422689
Drug information
ATC code	A06 AD11
Drug class	Laxative
properties
Molar mass	342.30 g · mol -1
Physical state	firmly
Melting point	163-165 ° C
safety instructions
Please note the exemption from the labeling requirement for drugs, medical devices, cosmetics, food and animal feed GHS labeling of hazardous substances no GHS pictograms H and P phrases H: no H-phrases P: no P-phrases
Toxicological data	18.16 g kg −1 ( LD 50 ,  rat ,  oral )
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Lactulose , also called lactulose, is a synthetic disaccharide ( double sugar ), consisting of D- galactose and fructose , which is obtained from lactose (milk sugar) by isomerization (rearrangement) . This de Bruyn-van-Ekenstein rearrangement takes place in an alkaline environment or at high temperature. This is why lactulose is also produced in low concentrations during the heat treatment of milk. The lactulose concentration in milk can be used as an indicator of such treatment. Typical concentrations are 10 mg / kg for pasteurized , 20–30 mg / kg for directly or indirectly heated ESL milk and 100 to 500 mg / kg for ultra-high temperature milk ; Sterilized milk contains 600 to 1400 mg of lactulose per kilogram of milk. Lactulose cannot be detected in raw milk. Lactulose is one of the reducing sugars . Lactulose for use as a laxative or as a prebiotic can be produced enzymatically using immobilized β-galactosidase .

Historical

The representation of lactulose was first described in 1929/1930 by Edna Montgomery and Claude S. Hudson (1881–1952). The Austrian doctor and chemist Friedrich Petuely (1922–1994) discovered the medicinal effects of lactulose. During his work at the University of Graz on the nutrition and intestinal flora of infants, he first observed a positive influence of heated lactose and finally of lactulose on the intestinal flora of infants. In a subsequent study of the effect on adults, he discovered the laxative effect. Petuely also received several patents for a method of making a lactulose-rich nutritional supplement for infants and a lactulose-based laxative.

Properties and use

Lactulose shows mutarotation . In contrast to lactose, it cannot be used by the human body. This explains the use of lactulose as an osmotic laxative . To achieve this effect, adults are recommended to take 5 to 10 grams once or twice a day, and up to 120 g / day for portocaval encephalopathy. The sugar cannot be absorbed into the blood in the intestine. It binds water to itself, thus increasing the intestinal volume and making the stool soft. Another part of the mechanism of action of lactulose is that it is partially broken down or fermented by intestinal bacteria, mainly lactic acid bacteria and bifidobacteria , into low molecular weight fatty acids , hydrogen and methane . This is also known as the bifidogenic or prebiotic effect of lactulose, as the growth of these bacteria can be increased. The acids formed and the increase in bacterial mass in the large intestine stimulate the peristalsis and intensify the laxative effect.

Another indication for lactulose is hepatic encephalopathy (syn. Portocaval encephalopathy) in liver cirrhosis . Lactulose influences the intestinal flora in such a way that lactic acid-producing intestinal bacteria are favored. This suppresses ammonia-forming intestinal bacteria and inhibits their urease , which catalyzes ammonia formation. In addition, at the now lower pH value, ammonia is protonated to ammonium , which is excreted as salt with the stool. In portocaval encephalopathy, lactulose reduces the blood ammonia concentration by around 25–50%, and a therapeutic effect can be expected within hours to a few days.

For comparison: the naturally occurring lactose .

To determine the small intestine transit time and to test for small intestinal colonization, lactulose is administered in a hydrogen breath test .

proof

In addition to enzymatic methods based on the hydrolysis of lactulose , the determination of lactulose can be carried out by chromatographic methods ( gas chromatography and HPLC ) and by fluorescence spectroscopy.

Trade names

Monopreparations

Bifinorm (D), Bifiteral (D), Lactulose-ratiopharm Syrup (D), Laevolac (A), Duphalac (CH), Eugalac (D), Gatinar (CH), Legendal (CH), Rudolac (CH), Tulotract ( D), numerous generics (D)

Combination preparations

Eugalan (D)

Web links

Commons : Lactulose  - Collection of Pictures, Videos and Audio Files

• Entry on lactulose in the Pharmawiki

Individual evidence

1. ↑ Entry on LACTULOSE in the CosIng database of the EU Commission, accessed on March 26, 2020.
2. ↑ ^{a b c d e f} Entry on lactulose. In: Römpp Online . Georg Thieme Verlag, accessed on July 5, 2011.
3. ↑ ^{a b} Data sheet Lactulose, purum, ≥98.0% (HPLC) from Sigma-Aldrich , accessed on February 19, 2013 ( PDF ).
4. ↑ Entry on lactulose in the ChemIDplus database of the United States National Library of Medicine (NLM) .
5. ↑ Walter Strahm and Pius Eberhard: Milk is heated up or filtered ( memento of the original from April 29, 2014 in the Internet Archive ) Info: The archive link was inserted automatically and has not yet been checked. Please check the original and archive link according to the instructions and then remove this notice. . In: Alimenta 12/2009. 
6. ↑ Eberhard Hetzner (Ed.): Handbuch Milch . Hamburg: Behr's Verlag, 1992.
7. ↑ Enzymatic production of lactulose in milk products containing lactose and technical lactose solutions (PDF). ( Memento from February 21, 2014 in the Internet Archive ) Research Group of the Food Industry eV (FEI), Bonn, 2009.
8. ^ Edna M. Montgomery, Claude Silbert Hudson : Relations Between Rotatory Power and Structure in the Sugar Group. XXVII. Synthesis of a New Disaccharide Ketose (Lactulose) From Lactose . In: American Chemical Society ACS (Ed.): Journal of the American Chemical Society . tape 52 , no. 5 , May 1, 1930, pp. 2101-2106 , doi : 10.1021 / ja01368a060 .
9. ↑ ^{a b} Friedrich Petuely: About the bifidus factor lactulose . In: Bifidobacteria and Microflora . tape 5 , no. 1 , 1986, pp. 3-11 , doi : 10.12938 / bifidus1982.5.1_3 ( jst.go.jp ).
10. ↑ Patent AT198428 : Process for the production of a bifidus-active concentrate and a dietary nutritional preparation. Registered June 17, 1952 , published July 10, 1958 , inventor: Friedrich Petuely. ‌
11. ↑ Patent US3272705 : Laxative composition and method of using same. Registered on June 13, 1963 , published September 13, 1966 , inventor: Friedrich Petuely. ‌
12. ↑ Lactulose package insert

This article is about a health issue. It is not used for self-diagnosis and does not replace a diagnosis by a doctor. Please note the information on health issues !