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Clindamycin
Identifiers
CAS	18323-44-9
ATC	J01FF01
PubChem	29029
DrugBank	APRD00566
Chemical data
IUPAC name	(2S,4R)-N-((1R)-2-chloro- 1-((3R,4R,5S,6R)-3,4,5-trihydroxy- 6-(methylthio)-tetrahydro-2H-pyran-2-yl)propyl)- 1-methyl-4-propylpyrrolidine-2-carboxamide
Formula	C18H33ClN2O5S
Mol. weight	424.98
Pharmacokinetic data
Bioavailability	90% (oral) 4–5% (topical)
%Protein Bound	{{{protein_bound}}}
Metabolism	hepatic
Half life	1.5–5 hours
Excretion	renal
Therapeutic considerations
Pregnancy	A (Aust) B (U.S.)
Legal status	Schedule 4 (Aust) POM (UK) Prescription only (U.S.)
Dependence Liability	{{{dependency_liability}}}
Routes	oral, topical, IV, intravaginal

Clindamycin (rINN) (IPA: [klɪndəˈmaɪsən]) is a lincosamide antibiotic used in the treatment of infections caused by susceptible microorganisms. Clindamycin is a semisynthetic antibiotic derived from lincomycin by 7(S)-chloro-substitution of the 7(R)-hydroxyl group of the lincomycin. Clindamycin is marketed under various trade names including Dalacin (Pfizer), Cleocin (Pfizer) and Evoclin (Connetics) - in a foam delivery system. Image File history File links Clindamycin. ... CAS registry numbers are unique numerical identifiers for chemical compounds, polymers, biological sequences and alloys. ... The Anatomical Therapeutic Chemical Classification System is used for the classification of drugs. ... A section of the Anatomical Therapeutic Chemical Classification System. ... PubChem is a database of chemical molecules . ... DrugBank is a database available at the University of Alberta that provides information about thousands of products. ... IUPAC nomenclature is a systematic way of naming organic chemical compounds. ... A chemical formula (also called molecular formula) is a concise way of expressing information about the atoms that constitute a particular chemical compound. ... The molecular mass of a substance (less accurately called molecular weight and abbreviated as MW) is the mass of one molecule of that substance, relative to the unified atomic mass unit u (equal to 1/12 the mass of one atom of carbon-12). ... In pharmacology, bioavailability is used to describe the fraction of an administered dose of medication that reaches the systemic circulation, one of the principal pharmacokinetic properties of drugs. ... You may be looking for albumen, or egg white. ... Santorio Santorio (1561-1636) in his steelyard balance, from Ars de statica medecina, first published 1614 Metabolism (from μεταβολισμος (metabolismos)) is the biochemical modification of chemical compounds in living organisms anggjgjhnd cell (b). ... The liver is an organ in vertebrates including humans. ... The elimination half-life of a drug (or any xenobiotic agent) refers to the timecourse necessary for the quantity of the xenobiotic agent in the body (or plasma concentration) to be reduced to half of its original level through various elimination processes. ... Excretion is the biological process by which an organism chemically separates waste products from its body. ... Kidneys viewed from behind with spine removed The kidneys are bean-shaped excretory organs in vertebrates. ... The pregnancy category of a pharmaceutical agent is an assessment of the risk of fetal injury due to the pharmaceutical, if it is used as directed by the mother. ... Motto: none (formerly Advance Australia) Anthem: Advance Australia Fair Royal anthem: God Save the Queen Capital Canberra Largest city Sydney Official language(s) English (de facto)1 Government Const. ... For other uses, see United States (disambiguation) and US (disambiguation). ... The regulation of therapeutic goods, that is drugs and therapeutic devices, varies by jurisdiction. ... Motto: none (formerly Advance Australia) Anthem: Advance Australia Fair Royal anthem: God Save the Queen Capital Canberra Largest city Sydney Official language(s) English (de facto)1 Government Const. ... For other uses, see United States (disambiguation) and US (disambiguation). ... In medicine, a topical medication is applied to body surfaces such as the skin or mucous membranes such as the vagina, nasopharynx, or the eye. ... An intravenous drip in a hospital Intravenous therapy or IV therapy is the administration of liquid substances directly into a vein. ... This article needs cleanup. ... An International Nonproprietary Name (INN) is the official non-proprietary or generic name given to a pharmaceutical substance, as designated by the World Health Organization. ... The International Phonetic Alphabet (IPA) is a system of phonetic notation devised by linguists to accurately and uniquely represent each of the wide variety of sounds (phones or phonemes) used in spoken human language. ... Lincomycin is an antibiotic that comes from the bacteria streptomyces lincolnensis. ... An antibiotic is a drug that kills or slows the growth of bacteria. ... Lincomycin is an antibiotic that comes from the bacteria streptomyces lincolnensis. ... General Name, Symbol, Number chlorine, Cl, 17 Series halogens Group, Period, Block 17 (VIIA), 3, p Density, Hardness 3. ... // Hydroxyl group The term hydroxyl group is used to describe the functional group -OH when it is a substituent in an organic compound. ... A trade name, also known as a trading name or a business name, is the legal name of a business, or the name which a business trades under for commercial purposes. ... Pfizer, Incorporated (NYSE: PFE), is a global pharmaceutical company, with headquarters in New York City. ... Pfizer, Incorporated (NYSE: PFE), is a global pharmaceutical company, with headquarters in New York City. ...

Indications

Clindamycin is used primarily to treat infections caused by susceptible anaerobic bacteria. Such infections might include respiratory infections, septicemia and peritonitis. In patients with hypersensitivity to penicillins, clindamycin may be used to treat susceptible aerobic infections as well. It is also used to treat bone-infections caused by Staphylococcus aureus. Topical application of clindamycin phosphate can be used to treat severe acne. Phyla/Divisions Actinobacteria Aquificae Bacteroidetes/Chlorobi Chlamydiae/Verrucomicrobia Chloroflexi Chrysiogenetes Cyanobacteria Deferribacteres Deinococcus-Thermus Dictyoglomi Fibrobacteres/Acidobacteria Firmicutes Fusobacteria Gemmatimonadetes Nitrospirae Omnibacteria Planctomycetes Proteobacteria Spirochaetes Thermodesulfobacteria Thermomicrobia Thermotogae Bacteria (singular, bacterium) are a major group of living organisms. ... It has been suggested that Gas exchange be merged into this article or section. ... Sepsis (in Greek Σήψις) is a serious medical condition caused by a severe systemic infection leading to a systemic inflammatory response. ... Hypersensitivity is an immune response that damages the bodys own tissues. ... Penicillin nucleus Penicillin refers to a group of β-lactam antibiotics used in the treatment of bacterial infections caused by susceptible, usually Gram-positive, organisms. ... Binomial name Staphylococcus aureus Rosenbach 1884 Staphylococcus aureus (which is occasionally given the nickname golden staph) is a bacterium, frequently living on the skin or in the nose of a healthy person, that can cause illnesses ranging from minor skin infections (such as pimples, boils, and cellulitis) and abscesses, to...

It is most effective against infections involving the following types of organisms: Infection is also the title of an episode of the television series Babylon 5, and the English title of the Japanese film Kansen. ...

• Aerobic gram-positive cocci, including some members of the Staphylococcus and Streptococcus (eg. pneumococcus) genera.
• Anaerobic gram-negative bacilli, including some members of the Bacteroides and Fusobacterium genera.

An aerobic organism or aerobe is an organism that has an oxygen based metabolism. ... Gram-positive bacteria are those that are stained dark blue or violet by gram staining, in contrast to gram-negative bacteria, which are not affected by the stain. ... coccus (plural - cocci) are any spherical or near spherical bacteria. ... Species S. aureus S. caprae S. epidermidis S. haemolyticus S. hominis S. lugdunensis S. saprophyticus S. warneri S. xylosus Staphylococcus (in Greek staphyle means bunch of grapes and coccos means granule) is a genus of gram-positive bacteria. ... Species S. agalactiae S. bovis S. mutans S. pneumoniae S. pyogenes S. salivarius S. sanguinis S. suis Streptococcus viridans group etc. ... Binomial name Streptococcus pneumoniae Streptococcus pneumoniae is a species of Streptococcus that is a major human pathogen. ... In biology, a genus (plural genera) is a taxonomic grouping. ... An anaerobic organism or anaerobe is any organism that does not require oxygen for growth. ... Bacteria that are Gram-negative are not stained dark blue or violet by Gram staining, in contrast to Gram-positive bacteria. ... Orders Bacillales Lactobacillales The term bacilli (singular bacillus) is used to refer to any rod-shaped bacteria. ... A genus of gram-negative, anaerobic, rod-shaped, non-sporeforming bacteria that occur in the respiratory, intestinal, and urogenital tracts of warm-blooded animals and include some pathogenic species. ... Fusobacteria contribute to several diseases, including periodontal diseases, Lemierres syndrome, and tropical skin ulcers. ...

Available forms

Clindamycin preparations for oral administration include capsules (containing clindamycin hydrochloride) and oral suspensions (containing clindamycin palmitate hydrochloride). It is also available for intravenous injection as clindamycin phosphate. Topical preparations contain either clindamycin hydrochloride or clindamycin phosphate.

Mechanism of action

Clindamycin has a bacteriostatic effect. Clindamycin interferes with bacterial protein synthesis, in a similar way as erythromycin and chloramphenicol, by binding to the 50S subunit of the bacterial ribosome. This causes antagonism if administered simultaneously and possible cross-resistance. Biological and artificial methods for creation of proteins differ significantly. ... Erythromycin is a macrolide antibiotic which has an antimicrobial spectrum similar to or slightly wider than that of penicillin, and is often used for people who have an allergy to penicillins - this is not necessarily a good idea , as after all , erythromycin is itself a penicillin derivative. ... Chloramphenicol (or 2,2-dichlor-N-[(aR,bR)-b-hydroxy-a-hydroxymethyl-4-nitrophenethyl]acetamide) is an antibiotic that was derived from the bacterium Streptomyces venezuelae and is now produced synthetically. ... Figure 1: Ribosome structure indicating small subunit (A) and large subunit (B). ...

Pharmacokinetics

Approximately 90% of an oral dose of clindamycin is absorbed from the gastrointestinal tract and it is widely distributed throughout the body, excluding the central nervous system. Adequate therapeutic concentrations can be achieved in bone. There is also active uptake into leucocytes. The gastrointestinal tract or digestive tract, also referred to as the GI tract or the alimentary canal or the gut, is the system of organs within multicellular animals which takes in food, digests it to extract energy and nutrients, and expels the remaining waste. ... A diagram showing the CNS: 1. ... Grays illustration of a human femur, a typically recognized bone. ... White Blood Cells is also the name of a White Stripes album. ...

Clindamycin is extensively metabolised in the liver, with some of its metabolites being active, such as N-dimethyl clindamycin and clindamycin sulfoxide. The elimination half-life is 1.5–5 hours. Both clindamycin and its metabolites are excreted primarily in the urine (Klasco, 2006). The elimination half-life of a drug (or any xenobiotic agent) refers to the timecourse necessary for the quantity of the xenobiotic agent in the body (or plasma concentration) to be reduced to half of its original level through various elimination processes. ...

Adverse effects

Common adverse drug reactions (ADRs) (≥1% of patients) associated with clindamycin therapy include: diarrhoea, pseudomembranous colitis, nausea, vomiting, abdominal pain/cramps, rash, and/or itch. High intravenous doses may cause a metallic taste, and topical application may cause contact dermatitis (Rossi, 2006). An adverse drug reaction (abbreviated ADR) is a term to describe the unwanted, negative consequences sometimes associated with the use of medications. ... Pseudomembranous colitis is a infection of the colon caused by the bacterium Clostridium difficile. ... An intravenous drip in a hospital Intravenous therapy or IV therapy is the administration of liquid substances directly into a vein. ... Dermatitis, also known as eczema, is a skin irritation characterized by red, flaky skin, sometimes with cracks or tiny blisters. ...

Pseudomembranous colitis is a potentially-lethal condition commonly associated with clindamycin and lincomycin therapy, but also occurs with other antibiotics. It may affect up to 2–10% of patients treated with clindamycin. Overgrowth of Clostridium difficile, which is inherently resistant to clindamycin, results in the production of a toxin that causes a range of adverse effects ranging from diarrhoea to colitis and toxic megacolon (Rossi, 2006). Lincomycin is an antibiotic that comes from the bacteria streptomyces lincolnensis. ... Binomial name Clostridium difficile Hall & OToole, 1935 Clostridium difficile ( ) (also referred to as C. diff or C-diff) is a species of bacteria of the genus Clostridium which are Gram-positive, anaerobic, spore-forming rods. ... Colitis is a digestive disease characterized by inflammation of the colon. ... Toxic megacolon is a medical condition characterized by the loss of tone and dilatation in the colon. ...

Rarely (<0.1% of patients), clindamycin therapy has been associated with anaphylaxis, blood dyscrasias, polyarthritis, jaundice, raised liver enzymes and/or hepatotoxicity (Rossi, 2006). In medicine, anaphylaxis is a severe and rapid systemic allergic reaction. ... Dyscrasia (from Greek Dyskrasia, meaning bad mixture), in Ancient Greek medicine, is the imbalance of the four humours, and was believed to be the direct cause of all disease. ... Polyarthritis is any type of arthritis which involves more than one joint. ... Jaundice, also known as icterus (attributive adjective: icteric), is a yellowing of the skin, sclera (the white of the eyes) and mucous membranes caused by increased levels of bilirubin in the human body (or the body of another red blooded animal). ...

References

• Klasco RK, editor. Drugdex system, volume 128. Greenwood Village (CO): Thomson Micromedex; 2006.
• Rossi S, editor. Australian Medicines Handbook 2006. Adelaide: Australian Medicines Handbook; 2006.

The Australian Medicines Handbook or AMH is a medical reference text commonly used in practice by health professionals (particularly general practitioners and pharmacists) in Australia. ...