Lincomycin

Structural formula
General
Non-proprietary name	Lincomycin
other names	(2 S , 4 R ) - N - [(1 S ) -2-hydroxy-1 - [(3 R , 4 S , 5 R , 6 R ) -3,4,5-trihydroxy-6-methylsulfanyloxane-2 -yl] propyl] -1-methyl-4-propylpyrrolidine-2-carboxamide
Molecular formula	C 18 H 34 N 2 O 6 S
External identifiers / databases
EC number	205-824-6
ECHA InfoCard	100.005.296
PubChem	3000540
ChemSpider	2272112
DrugBank	DB01627
Wikidata	Q423428
Drug information
ATC code	J01 FF02
Drug class	antibiotic
properties
Molar mass	406.54 g · mol -1
Melting point	145–147 ° C (hydrochloride monohydrate) ; 155–157 ° C (monohydrochloride) ;
safety instructions
	Please note the exemption from the labeling requirement for drugs, medical devices, cosmetics, food and animal feed
GHS labeling of hazardous substances Caution
H and P phrases	H: 315-319-335
	P: 261-305 + 351 + 338
Toxicological data	> 4000 mg kg −1 ( LD 50 , rat , oral , hydrochloride monohydrate)
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Lincomycin (Lincomycin A) is an antibiotically effective drug from the group of lincosamides . Lincomycin is isolated from the bacterium Streptomyces lincolnensis , a genus of the Streptomycetes .

chemistry

Lincomycin A consists of propylproline, a derivative of the amino acid proline , and the amino sugar methylthiolincosaminide, a derivative of the C8 sugar octose , which are linked by an amide bond . Lincomycin hydrochloride monohydrate is used medicinally.

effect

Lincomycin has a similar spectrum of activity as clindamycin , but is less potent. It acts like macrolides by binding to the 50 S subunit of the bacterial ribosomes, which prevents the protein synthesis of the sensitive pathogens. The antibiotic is particularly effective against gram-positive pathogens such as staphylococci and streptococci and is mainly used for infections of the respiratory tract.

After administration, the antibiotic accumulates in macrophages and reaches the sources of infection via these. In the cerebrospinal fluid sufficient concentrations are achieved. It is broken down in the liver and excreted in faeces and urine .

application areas

Lincomycin is indicated for the treatment of infectious diseases caused by lincomycin-sensitive pathogens. Lincomycin is widely used in veterinary medicine, e.g. B. in dogs, cats, pigs, cattle and poultry.

Contraindications and side effects

Oral administration of lincomycin is contraindicated in herbivores (e.g. horses , ruminants , guinea pigs , rabbits and hamsters ) as it can lead to fatal colon inflammation caused by lincomycin-resistant clostridia .

The intramuscular injection can cause painful swelling at the injection site. If the intravenous injection is too rapid , thrombophlebitis, a drop in blood pressure and cardiac arrest can occur. For oral administration, a can gastroenteritis with vomiting and bloody diarrhea occur.

Admission

In veterinary medicine, Lincomycin is offered as a monopreparation (Lincobel ^® , Lincocin ^® , Lincomycin ^® , Lincomysel ^® ) or in combination with other antibiotics (Albiotic ^® , Aviosan ^® , Lincospectin ^® , Lincocin Neo ^® , Pyanosid ^® , Spectolin ^® ). Lincomycin is not approved in human medicine in Germany, but is approved in the USA (Lincocin ^® , Lincorex ^® ) and Canada (Lincocin ^® ).

Web links

Vetpharm entry for lincomycin , accessed November 21, 2011.

Individual evidence

↑ ^a ^b entry on lincomycin. In: Römpp Online . Georg Thieme Verlag, accessed on November 10, 2014.
↑ ^a ^b Datasheet Lincomycin hydrochloride from Sigma-Aldrich , accessed on April 7, 2011 ( PDF ).
↑ Data sheet LINCOMYCIN HYDROCHLORIDE CRS (PDF) at EDQM , accessed on June 21, 2009.
↑ Kleemann, A .; Engel, J .; Kutscher, B .; Reichert, D .: Pharmaceutical Substances - Synthesis, Patens, Applications- , 4th Edition, Thieme Chemistry, Stuttgart 2001, ISBN 3-13-115134-X .
↑ External identifiers of or database links to lincomycin hydrochloride monohydrate : CAS number: 7179-49-9, EC number: 615-424-7, ECHA InfoCard: 100.119.494 , PubChem : 71476 , ChemSpider : 64555 , Wikidata : Q27283566 .

[RÖMPP_Online-1] try on lincomycin. In: Römpp Online . Georg Thieme Verlag, accessed on November 10, 2014.

[Sigma-2] Datasheet Lincomycin hydrochloride from Sigma-Aldrich , accessed on April 7, 2011 ( PDF ).

[Ph._Eur.-3] Data sheet LINCOMYCIN HYDROCHLORIDE CRS (PDF) at EDQM , accessed on June 21, 2009.

[4] Kleemann, A .; Engel, J .; Kutscher, B .; Reichert, D .: Pharmaceutical Substances - Synthesis, Patens, Applications- , 4th Edition, Thieme Chemistry, Stuttgart 2001, ISBN 3-13-115134-X .

[5] External identifiers of or database links to lincomycin hydrochloride monohydrate : CAS number: 7179-49-9, EC number: 615-424-7, ECHA InfoCard: 100.119.494 , PubChem : 71476 , ChemSpider : 64555 , Wikidata : Q27283566 .