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| {{drugbox | | | {{Details0|Clindamycin hydrochloride (injection)}} |
| |image=Clindamycin skeletal.svg
| | {{Details0|Clindamycin hydrochloride (oral)}} |
| |IUPAC_name = (2''S'',4''R'')-''N''-((1''R'')-2-chloro-<br />1-((3''R'',4''R'',5''S'',6''R'')-3,4,5-trihydroxy-<br />6-(methylthio)-tetrahydro-2''H''-pyran-2-yl)propyl)-<br />1-methyl-4-propylpyrrolidine-2-carboxamide
| | {{Details0|Clindamycin hydrochloride (vaginal)}} |
| |CAS_number = 18323-44-9
| | {{Details0|Clindamycin phosphate (gel)}} |
| | ATC_prefix=J01
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| | ATC_suffix=FF01
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| | ATC_supplemental={{ATC|G01|AA10}}
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| | PubChem=29029
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| | DrugBank=APRD00566
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| | C=18 | H=33 | Cl=1 | N=2 | O=5 | S=1
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| |molecular_weight = 424.98 g/mol
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| |bioavailability = 90% (oral)<br />4–5% (topical)
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| |metabolism = [[Liver|Hepatic]]
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| |protein_bound = 90%
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| |elimination_half-life = 2–3 hours
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| |excretion = [[Kidney|Renal]]
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| |pregnancy_US = B
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| |pregnancy_AU = A
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| |legal_status = Schedule 4 ([[Australia|Aust]])<br />POM ([[United Kingdom|UK]])<br />Prescription only ([[U.S.]])
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| |routes_of_administration = Oral, [[topical]], [[intravenous|IV]], [[pessary|intravaginal]]
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| }}
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| {{SI}}
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| __NOTOC__
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| {{See also|Clindamycin hydrochloride|Clindamycin palmitate hydrochloride|Clindamycin phosphate}} | |
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| {{CMG}}
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| ==Overview==
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| '''Clindamycin''' ([[International Nonproprietary Name|rINN]]) ([[International Phonetic Alphabet|IPA]]: {{IPA|[klɪndəˈmaɪsən]}}) is a [[lincomycin|lincosamide]] [[antibiotic]] used in the treatment of [[infection]]s caused by susceptible [[microorganism]]s. 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 name]]s including '''Dalacin''' ([[Pfizer]]), '''Cleocin''' ([[Pfizer]]), and in a foam as '''Evoclin''' (Connetics) and '''Duac'''([[Stiefel]]).
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| ==Indications==
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| Clindamycin is used primarily to treat infections caused by susceptible [[anaerobic organism|anaerobic]] [[bacteria]]. Such infections might include infections of the [[respiratory tract]], [[septicemia]] and [[peritonitis]]. In patients with [[hypersensitivity]] to [[penicillin]]s, clindamycin may be used to treat infections caused by susceptible [[aerobic organism|aerobic]] bacteria as well. It is also used to treat bone infections caused by ''[[Staphylococcus aureus]]''. [[Topical application]] of clindamycin phosphate can be used to treat moderate to severe [[acne]]. | |
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| It is most effective against infections involving the following types of organisms:
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| * Aerobic [[gram-positive]] [[cocci]], including some members of the ''[[Staphylococcus]]'' and ''[[Streptococcus]]'' (eg. [[pneumococcus]]) [[genus|genera]].
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| * Anaerobic [[gram-negative]] [[bacilli]], including some members of the ''[[Bacteroides]]'' and ''[[Fusobacterium]]'' genera.
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| Clindamycin is also used occasionally in cases of suspected [[toxic shock syndrome]] in combination with a [[bactericidal]] agent such as [[vancomycin]]. The rationale for this approach is a presumed synergy between the bactericidal antibiotic, which causes the death of the bacteria by [[lysis|breakdown of the cell membrane]], and clindamycin, which inhibits toxin synthesis.
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| Clindamycin has been proven to decrease the risk of [[preterm birth]]s in women diagnosed with [[bacterial vaginosis]] during early pregnancy to about a third of the risk of untreated women (Lamont, 2005).
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| Recently, clindamycin has been found to be useful in skin and [[soft tissue]] infections caused by [[methicillin-resistant Staphylococcus aureus|methicillin-resistant ''Staphylococcus aureus'']] (Daum, 2007).
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| == Available forms ==
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| Clindamycin preparations for oral administration include capsules (containing clindamycin [[hydrochloride]]) and oral suspensions (containing clindamycin [[palmitate]] hydrochloride). It is also available for [[topical]] administration, in [[gel]] form and in a foam delivery system (both containing clindamycin [[phosphate]]), primarily as a prescription acne treatment.
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| == Adverse effects ==
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| Common [[adverse drug reaction]]s (ADRs) associated with clindamycin therapy—found in over 1% of patients—include: [[diarrhea]], [[pseudomembranous colitis]], [[nausea]], [[vomiting]], [[abdomen|abdominal]] pain or [[cramp]]s, [[rash]], and/or [[itch]]. High [[intravenous]] doses may cause a metallic taste, and topical application may cause [[contact dermatitis]] (Rossi, 2006).
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| [[Pseudomembranous colitis]] is a potentially-[[lethal]] condition commonly associated with clindamycin, but which also occurs with other antibiotics. Overgrowth of ''[[Clostridium difficile]]'', which is inherently [[antibiotic resistance|resistant]] to clindamycin, results in the production of a toxin that causes a range of adverse effects, from diarrhea to [[colitis]] and [[toxic megacolon]] (Rossi, 2006).
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| Rarely—in less than 0.1% of patients—clindamycin therapy has been associated with [[anaphylaxis]], blood [[dyscrasia]]s, [[polyarthritis]], [[jaundice]], [[elevated transaminases|raised liver enzymes]] and/or [[hepatotoxicity]] (Rossi, 2006).
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| == Pharmacology ==
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| === Pharmacokinetics ===
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| 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 [[white blood cell]]s, most importantly [[neutrophil granulocyte|neutrophil]]s. (Klempner and Styrt, 1981)
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| Clindamycin is extensively metabolised in the liver, with some metabolites being active, such as ''N''-dimethyl clindamycin and clindamycin [[sulfoxide]]. The [[elimination half-life]] is 1.5 to 5 hours. Clindamycin is primarily eliminated by hepatic metabolism; after an intravenous dose of clindamycin phosphate, about 4.5% of the dose is excreted in urine as clindamycin and about 0.35% as the phosphate salt (Plaisance, 1989). The metabolites of clindamycin are excreted primarily in the urine (Klasco, 2006).
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| === Mechanism of action ===
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| Clindamycin has a [[bacteriostatic]] effect. It interferes with bacterial [[protein synthesis]], in a similar way to [[erythromycin]] and [[chloramphenicol]], by binding to the [[50S]] subunit of the bacterial [[ribosome]]. This causes antagonism if administered simultaneously and possible cross-resistance.
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| == Veterinary use ==
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| === In cats ===
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| Clindamycin has been used successfully in treating cats that are displaying symptoms of [[toxoplasmosis]]. This disease rarely causes symptoms in cats, but can do so in very young or [[immunocompromised]] kittens and cats. Toxoplasmosis is contagious to humans, and therefore cat owners, particularly pregnant women, should take precautions to prevent the spread of the disease.
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| == References ==
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| *{{cite journal |author=Daum RS |title=Clinical practice. Skin and soft-tissue infections caused by methicillin-resistant Staphylococcus aureus |journal=N Engl J Med |volume=357 |issue=4 |pages=380–90 |year=2007 |pmid=17652653 |doi=10.1056/NEJMcp070747}}
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| * Klasco RK, editor. Drugdex system, volume 128. Greenwood Village (CO): Thomson Micromedex; 2006.
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| * {{cite journal |author=Klempner MS, Styrt B |title=Clindamycin uptake by human neutrophils |journal=J. Infect. Dis. |volume=144 |issue=5 |pages=472–9 |year=1981 |pmid=6171600 |doi=}}
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| * {{cite journal |author=Lamont RF |title=Can antibiotics prevent preterm birth--the pro and con debate |journal=BJOG |volume=112 Suppl 1 |issue= |pages=67–73 |year=2005 |pmid=15715599 |doi=10.1111/j.1471-0528.2005.00589.x}}
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| * {{cite journal |author=Plaisance KI ''et al.'' |title=Pharmacokinetic evaluation of two dosage regimens of clindamycin phosphate |journal=Antimicrob Agents Chemother |volume=33 |issue=5 |pages=618–20 |year=1989 |pmid=2751277 |doi=}} {{PMC|172501}}.
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| * Rossi S, editor. [[Australian Medicines Handbook]] 2006. Adelaide: Australian Medicines Handbook; 2006.
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| {{-}}
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| {{Acne Agents}}
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| {{Gynecological anti-infectives and antiseptics}}
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| {{Macrolides, lincosamides and streptogramins}}
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| [[Category:Lincosamide antibiotics]]
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| [[de:Clindamycin]]
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| [[es:Clindamicina]]
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| [[ja:クリンダマイシン]]
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| [[pl:Klindamycyna]]
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| [[pt:Clindamicina]]
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| [[fi:Klindamysiini]]
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| [[th:คลินดามัยซิน]]
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