Clindamycin

Structural formula
General
Non-proprietary name	Clindamycin
other names	Methyl-6-amino-7-chloro-6,7,8-trideoxy- N - [(2 S , 4 R ) -1-methyl-4-propylprolyl] -1-thio-β- L - threo - D - galactooctopyranoside ( IUPAC )
Molecular formula	C 18 H 33 ClN 2 O 5 S
External identifiers / databases
EC number	242-209-1
ECHA InfoCard	100.038.357
PubChem	29029
ChemSpider	27005
DrugBank	DB01190
Wikidata	Q422273
Drug information
ATC code	J01 FF01 ; D10 AF01 ; G01 AA10 ;
Drug class	antibiotic
Mechanism of action	Protein synthesis inhibitors
properties
Molar mass	424.98 g mol −1
Physical state	firmly
Melting point	141–143 ° C (hydrochloride monohydrate)
pK s value	7.6 (hydrochloride monohydrate)
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: 302
	P: no P-phrases
Toxicological data	1832 mg kg −1 ( LD 50 , rat , oral , as phosphate)
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Clindamycin is a drug from the group of lincosamide antibiotics. It is a chlorinated derivative of lincomycin and is produced semi-synthetically .

Clindamycin has a bacteriostatic effect in the usual dose , and in high doses it is also bactericidal, mainly against gram-positive aerobic germs such as streptococci or staphylococci , against anaerobes , especially gram-negative ones and also against chlamydia . In combination with pyrimethamine , it is effective against Toxoplasma gondii .

Mechanism of action

Like macrolides, clindamycin binds to the 50-S subunit of the (prokaryotic) ribosomes to inhibit protein synthesis in bacteria . Because of the identical mechanism of action, there is sometimes cross-resistance.

Clindamycin is approximately 90% absorbed after oral ingestion and 92–94% is bound to plasma proteins. The plasma half-life is 2.4 hours. In addition to the internal organs, it also reaches the pleural fluid , synovia , bone marrow , milk and skin . The antibiotic also penetrates the placenta . It is remodeled in the liver and excreted in the urine and faeces .

application

In medicine, clindamycin is mainly used for abscessing pneumonia , osteomyelitis of the diabetic foot ( malum perforans ), chronic osteomyelitis with Staphylococcus aureus , infections of the oral cavity and acne . The field of application of this lincosamide is largely similar to that of the more compatible macrolides , except for staphylococcal infections, whereas macrolides are largely ineffective. Furthermore, clindamycin is a substitute drug for patients with penicillin allergy.

In veterinary medicine, it is also used for severe skin infections ( pyoderma ), respiratory tract infections or eye infections.

Side effects and contraindications

Clindamycin mainly has gastrointestinal side effects such as vomiting, diarrhea and stomach cramps. Drug-related pseudomembranous colitis (inflammation of the colon) is particularly dangerous . This occurs much more frequently with clindamycin than with other antibiotics, but less often and milder than with the related lincomycin. Clostridium difficile -related and serious adverse effects should always lead to discontinuation of clindamycin. Itching , vaginal catarrh ( vaginal discharge ) and exfoliating blistering skin inflammation are mentioned as rather rare side effects . It is also contraindicated during breastfeeding due to the high level of excretion in breast milk.

In herbivores such as horses , ruminants , rabbits , hamsters , guinea pigs , chinchillas , gerbils and bush rats , the drug can cause fatal colitis due to resistant clostridia , which is why clindamycin can only be used in these animals under strict indications and close monitoring.

Interactions with other substances

Due to physical incompatibility, joint parenteral administration with theophylline , barbiturates , calcium gluconate and phenytoin is excluded. Clindamycin may increase the effects of muscle relaxants due to its neuromuscular blockade ; this can lead to life-threatening incidents during anesthesia.

synthesis

Clindamycin is obtained semi-synthetically from the natural substance lincomycin . For this purpose, the hydroxyl group is chlorinated with triphenylphosphine and carbon tetrachloride .

Trade names

Monopreparations

Basocin (D), Clindasol (D), Clindac (A), Clinda-Saar (D), Clin-Sanorania (D), Dalacin (A, CH), Dentomycin (D), Jutaclin (D), Lanacine (A) , Sobelin (D), Turimycin (D), Zindaclin (D, A), numerous generics (D, A, CH)

Veterinary medicine: aniclindan, Antirobe, Cleorobe, Clinacin, Clinda, Permycin

Combination preparations

Duac (D, CH), Indoxyl (A)

Web links

Entry on clindamycin at Vetpharm, accessed August 11, 2012.

der-arzneimittelbrief.de: Clindamycin

Entry on clindamycin in Flexikon , a Wiki of the DocCheck company

Individual evidence

↑ ^a ^b entry on clindamycin. In: Römpp Online . Georg Thieme Verlag, accessed on October 1, 2014.
↑ ^a ^b ^c data sheet clindamycin 2-phosphate from Sigma-Aldrich , accessed on March 23, 2011 ( PDF ).
↑ Germ spectrum of antibiotics, Medical Laboratories Düsseldorf ( Memento from September 3, 2013 in the Internet Archive ).
↑ Scientific opinion: Use of antibiotics in dental practice. German Society for Dentistry, Oral and Maxillofacial Medicine. 28 February 2012.
↑ J. Bogner: Infections pocket. Verlag Börm Bruckmeier, February 2004, ISBN 3-89862-216-9 .
↑ Jack L. Le Frock, Albert S. Klainer, Stuart Chen, Robert B. Gainer, Mohammed Omar and William Anderson: The Journal of Infectious Diseases , Oxford University Press, Vol. 131, Supplement. May 1975, p. 108.
↑ FDA: Cleocin HCL (clindamycin hydrochloride) capsules. FDA notification dated December 2009.
↑ K. Aktories, U. Förstermann, FB Hofmann, K. Starke (ed.): General and special pharmacology and toxicology. Edition 10, Verlag Urban & Fischer, 2009, ISBN 3-437-42522-6 , p. 830. Limited preview in the Google book search.
↑ Hagers Handbook of Pharmaceutical Practice, p. 996 Springer Berlin 1993 ISBN 3-540-52640-4 .
↑ Red List online, as of October 2009.
^ AM Compendium of Switzerland, as of October 2009.
↑ AGES-PharmMed, as of October 2009.

[RÖMPP_Online-1] try on clindamycin. In: Römpp Online . Georg Thieme Verlag, accessed on October 1, 2014.

[Sigma-2] ta sheet clindamycin 2-phosphate from Sigma-Aldrich , accessed on March 23, 2011 ( PDF ).

[3] Germ spectrum of antibiotics, Medical Laboratories Düsseldorf ( Memento from September 3, 2013 in the Internet Archive ).

[4] Scientific opinion: Use of antibiotics in dental practice. German Society for Dentistry, Oral and Maxillofacial Medicine. 28 February 2012.

[5] J. Bogner: Infections pocket. Verlag Börm Bruckmeier, February 2004, ISBN 3-89862-216-9 .

[6] Jack L. Le Frock, Albert S. Klainer, Stuart Chen, Robert B. Gainer, Mohammed Omar and William Anderson: The Journal of Infectious Diseases , Oxford University Press, Vol. 131, Supplement. May 1975, p. 108.

[7] FDA: Cleocin HCL (clindamycin hydrochloride) capsules. FDA notification dated December 2009.

[8] K. Aktories, U. Förstermann, FB Hofmann, K. Starke (ed.): General and special pharmacology and toxicology. Edition 10, Verlag Urban & Fischer, 2009, ISBN 3-437-42522-6 , p. 830. Limited preview in the Google book search.

[9] Hagers Handbook of Pharmaceutical Practice, p. 996 Springer Berlin 1993 ISBN 3-540-52640-4 .

[10] Red List online, as of October 2009.

[11] AM Compendium of Switzerland, as of October 2009.

[12] AGES-PharmMed, as of October 2009.