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Clinical data | |
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Pronunciation | /klɪndəˈmaɪsɪn/ |
Trade names | Cleocin, Clinacin, Dalacin, others |
Other names | 7-chloro-lincomycin 7-chloro-7-deoxylincomycin, DARE-BV1 |
AHFS/Drugs.com | Monograph |
MedlinePlus | a682399 |
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Routes of administration | By mouth, topical, intravenous, intravaginal |
Drug class | Lincosamide antibiotic |
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Pharmacokinetic data | |
Bioavailability | 90% (by mouth) 4–5% (topical) |
Protein binding | 95% |
Metabolism | Liver |
Elimination half-life | 2–3 hour |
Excretion | Bile duct and kidney (around 20%) |
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CompTox Dashboard (EPA) | |
ECHA InfoCard | 100.038.357 |
Chemical and physical data | |
Formula | C18H33ClN2O5S |
Molar mass | 424.98 g·mol−1 |
3D model (JSmol) | |
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Clindamycin is a lincosamide antibiotic medication used for the treatment of a number of bacterial infections, including osteomyelitis (bone) or joint infections, pelvic inflammatory disease, strep throat, pneumonia, acute otitis media (middle ear infections), and endocarditis. [5] It can also be used to treat acne, [5] [6] and some cases of methicillin-resistant Staphylococcus aureus (MRSA). [7] In combination with quinine, it can be used to treat malaria. [5] [6] It is available by mouth, by injection into a vein, and as a cream or a gel to be applied to the skin or in the vagina. [4] [5] [6] [8] [9]
Common side effects include nausea and vomiting, diarrhea, skin rashes, and pain at the site of injection. [5] It increases the risk of hospital-acquired Clostridioides difficile colitis about fourfold and thus is only recommended for use when other antibiotics are not appropriate. [10] [5] It appears to be generally safe in pregnancy. [5] It is of the lincosamide class and works by blocking bacteria from making protein. [5]
Clindamycin was first made in 1966 from lincomycin. [11] [12] It is on the World Health Organization's List of Essential Medicines. [13] It is available as a generic medication. [14] [15] In 2022, it was the 147th most commonly prescribed medication in the United States, with more than 3 million prescriptions. [16] [17]
Clindamycin is used primarily to treat anaerobic infections caused by susceptible anaerobic bacteria, including dental infections, [18] and infections of the respiratory tract, skin, and soft tissue, and peritonitis. [19] In people with hypersensitivity to penicillins, clindamycin may be used to treat infections caused by susceptible aerobic bacteria, as well. It is also used to treat bone and joint infections, particularly those caused by Staphylococcus aureus . [19] [20] Topical application of clindamycin phosphate can be used to treat mild to moderate acne. [21] [22]
For the treatment of acne, in the long term, the combined use of topical clindamycin and benzoyl peroxide was similar to salicylic acid plus benzoyl peroxide. [22] [23] Topical clindamycin plus topical benzoyl peroxide is more effective than topical clindamycin alone. [22] [23]
It is most effective against infections involving the following types of organisms:
Most aerobic Gram-negative bacteria (such as Pseudomonas , Legionella , Haemophilus influenzae and Moraxella ) are resistant to clindamycin, [24] [26] as are the facultative anaerobic Enterobacteriaceae. [27] A notable exception is Capnocytophaga canimorsus , for which clindamycin is a first-line drug of choice. [28]
The following represents MIC susceptibility data for a few medically significant pathogens. [29]
When testing a gram-positive culture for sensitivity to clindamycin, it is common to perform a "D-test" to determine if there is a sub-population of bacteria present with the phenotype known as iMLSB. This phenotype of bacteria are resistant to the macrolide-lincosamide-streptogramin B group of antibiotics, however, the resistance mechanism is only induced by the presence of 14-membered ring macrolides, such as erythromycin. During a D-test, bacteria of the iMLSB phenotype demonstrate in vitro erythromycin-induced in vitro resistance to clindamycin. This is because of the activity of the macrolide-inducible plasmid-encoded erm gene. [30]
To perform a D-test, an agar plate is inoculated with the bacteria in question and two drug-impregnated disks (one with erythromycin, one with clindamycin) are placed 15–20 mm apart on the plate. If the area of inhibition around the clindamycin disk is D-shaped, the test result is positive. Despite the apparent susceptibility to clindamycin in the absence of erythromycin, a positive D-test precludes therapeutic use of clindamycin. This is because the erythromycin-inducible erm gene is prone to mutations causing the inducible activity to switch to constitutive (permanently switched on). [31] This in turn, may lead to the therapeutic failure of clindamycin.
If the area of inhibition around the clindamycin disk is circular, the test result is negative and clindamycin can be used. [31]
Given with chloroquine or quinine, clindamycin is effective and well tolerated in treating Plasmodium falciparum malaria; the latter combination is particularly useful for children, and is the treatment of choice for pregnant women who become infected in areas where resistance to chloroquine is common. [32] [33] Clindamycin should not be used as an antimalarial by itself, although it appears to be very effective as such, because of its slow action. [32] [33] Patient-derived isolates of Plasmodium falciparum from the Peruvian Amazon have been reported to be resistant to clindamycin as evidenced by in vitro drug susceptibility testing. [34]
Clindamycin may be useful in skin and soft tissue infections caused by methicillin-resistant Staphylococcus aureus (MRSA). [7] Many strains of MRSA are still susceptible to clindamycin; however, in the United States spreading from the West Coast eastwards, MRSA is becoming increasingly resistant.[ medical citation needed ]
While it has been used in intraabdominal infections, such use is generally not recommended due to resistance. [5]
Clindamycin is used in cases of suspected toxic shock syndrome, [35] often in combination with a bactericidal agent such as vancomycin. The rationale for this approach is a presumed synergy between vancomycin, which causes the death of the bacteria by breakdown of the cell wall, and clindamycin, which is a powerful inhibitor of toxin synthesis. Both in vitro and in vivo studies have shown clindamycin reduces the production of exotoxins by staphylococci; [36] it may also induce changes in the surface structure of bacteria that make them more sensitive to immune system attack (opsonization and phagocytosis). [37] [38]
Clindamycin has been proven to decrease the risk of premature births in women diagnosed with bacterial vaginosis during early pregnancy to about a third of the risk of untreated women. [39]
The combination of clindamycin and quinine is the standard treatment for severe babesiosis. [40]
Clindamycin may also be used to treat toxoplasmosis, [24] [41] [42] and, in combination with primaquine, is effective in treating mild to moderate Pneumocystis jirovecii pneumonia. [43]
Clindamycin, either applied to skin or taken by mouth, may also be used in hidradenitis suppurativa. [44]
Common adverse drug reactions associated with systemic clindamycin therapy –found in over 1% of people –include: diarrhea, pseudomembranous colitis, nausea, vomiting, abdominal pain or cramps and/or rash. High doses (both intravenous and oral) may cause a metallic taste. Common adverse drug reactions associated with topical formulations –found in over 10% of people –include: dryness, burning, itching, scaliness, or peeling of skin (lotion, solution); erythema (foam, lotion, solution); oiliness (gel, lotion). Additional side effects include contact dermatitis. [45] [46] Common side effects –found in over 10% of people –in vaginal applications include fungal infection.[ medical citation needed ]
Rarely – in less than 0.1% of people – clindamycin therapy has been associated with anaphylaxis, blood dyscrasias, polyarthritis, jaundice, raised liver enzyme levels, renal dysfunction, cardiac arrest, and/or hepatotoxicity. [45]
Pseudomembranous colitis is a potentially lethal condition commonly associated with clindamycin, but which also occurs with other antibiotics. [10] [47] Overgrowth of Clostridioides difficile , which is inherently resistant to clindamycin, results in the production of a toxin that causes a range of adverse effects, from diarrhea to colitis and toxic megacolon. [45] [48]
Use of clindamycin during pregnancy is generally considered safe. [49]
Clindamycin is classified as compatible with breastfeeding by the American Academy of Pediatrics, [50] however, the WHO categorizes it as "avoid if possible". [51] It is classified as L2 probably compatible with breastfeeding according to Medications and Mothers' Milk. [52] A 2009 review found it was likely safe in breastfeeding mothers, but did find one complication (hematochezia) in a breastfed infant which might be attributable to clindamycin. [53] LactMed lists potentially negative gastrointestinal effects in babies whose mothers take it while breastfeeding but did not see that as justification to stop breastfeeding. [54]
Clindamycin may prolong the effects of neuromuscular-blocking drugs, such as succinylcholine and vecuronium. [55] [56] [57] Its similarity to the mechanism of action of macrolides and chloramphenicol means they should not be given simultaneously, as this causes antagonism [26] and possible cross-resistance.[ medical citation needed ]
Clindamycin is a semisynthetic derivative of lincomycin, a natural antibiotic produced by the actinobacterium Streptomyces lincolnensis . It is obtained by 7(S)-chloro-substitution of the 7(R)-hydroxyl group of lincomycin. [59] [60] The synthesis of clindamycin was first announced by BJ Magerlein, RD Birkenmeyer, and F Kagan on the fifth Interscience Conference on Antimicrobial Agents and Chemotherapy (ICAAC) in 1966. [61] It has been on the market since 1968. [46]
Clindamycin is white or yellow powder that is very soluble in water. [62] The topically used clindamycin phosphate is a phosphate-ester prodrug of clindamycin. [58]
Clindamycin has a primarily bacteriostatic effect. At higher concentrations, it may be bactericidal. [62] It is a bacterial protein synthesis inhibitor by inhibiting ribosomal translocation, [63] in a similar way to macrolides. It does so by binding to the rRNA of the bacterial 50S ribosome subunit, overlapping with the binding sites of the oxazolidinone, pleuromutilin, and macrolide antibiotics, among others. [24] [64] The binding is reversible. [65] Clindamycin is more effective than lincomycin. [62]
The X-ray crystal structures of clindamycin bound to ribosomes (or ribosomal subunits) derived from Escherichia coli , [66] Deinococcus radiodurans , [67] and Haloarcura marismortui [68] have been determined; the structure of the closely related antibiotic lincomycin bound to the 50S ribosomal subunit of Staphylococcus aureus has also been reported. [69]
Clindamycin is available as a generic medication and is relatively inexpensive. [14] [70]
Clindamycin preparations that are taken by mouth include capsules (containing clindamycin hydrochloride) and oral suspensions (containing clindamycin palmitate hydrochloride). [32] Oral suspension is not favored for administration of clindamycin to children, due to its extremely foul taste and odor. Clindamycin is formulated in a vaginal cream and as vaginal ovules for treatment of bacterial vaginosis. [39] It is also available for topical administration in gel form, as a lotion, and in a foam delivery system (each containing clindamycin phosphate) and a solution in ethanol (containing clindamycin hydrochloride) and is used primarily as a prescription acne treatment. [71]
Several combination acne treatments containing clindamycin are also marketed, such as single-product formulations of clindamycin with benzoyl peroxide—sold as BenzaClin (Sanofi-Aventis), Duac (a gel form made by Stiefel), and Acanya, among other trade names—and, in the United States, a combination of clindamycin and tretinoin, sold as Ziana. [72] In India, vaginal suppositories containing clindamycin in combination with clotrimazole are manufactured by Olive Health Care and sold as Clinsup-V. In Egypt, vaginal cream containing clindamycin produced by Biopharmgroup sold as Vagiclind indicated for vaginosis.[ citation needed ]
Clindamycin is available as a generic drug, for both systemic (oral and intravenous) and topical use. [32] (The exception is the vaginal suppository, which is not available as a generic in the US [73] ).
The veterinary uses of clindamycin are quite similar to its human indications, and include treatment of osteomyelitis, [74] skin infections, and toxoplasmosis, for which it is the preferred drug in dogs and cats. [75] They can be used both by mouth and topically. [62] A disadvantage is that bacterial resistance can develop fairly quickly. [62] Gastrointestinal upset may also occur. [62] Toxoplasmosis rarely causes symptoms in cats, but can do so in very young or immunocompromised kittens and cats.[ citation needed ]
Acne, also known as acne vulgaris, is a long-term skin condition that occurs when dead skin cells and oil from the skin clog hair follicles. Typical features of the condition include blackheads or whiteheads, pimples, oily skin, and possible scarring. It primarily affects skin with a relatively high number of oil glands, including the face, upper part of the chest, and back. The resulting appearance can lead to lack of confidence, anxiety, reduced self-esteem, and, in extreme cases, depression or thoughts of suicide.
Staphylococcus aureus is a gram-positive spherically shaped bacterium, a member of the Bacillota, and is a usual member of the microbiota of the body, frequently found in the upper respiratory tract and on the skin. It is often positive for catalase and nitrate reduction and is a facultative anaerobe, meaning that it can grow without oxygen. Although S. aureus usually acts as a commensal of the human microbiota, it can also become an opportunistic pathogen, being a common cause of skin infections including abscesses, respiratory infections such as sinusitis, and food poisoning. Pathogenic strains often promote infections by producing virulence factors such as potent protein toxins, and the expression of a cell-surface protein that binds and inactivates antibodies. S. aureus is one of the leading pathogens for deaths associated with antimicrobial resistance and the emergence of antibiotic-resistant strains, such as methicillin-resistant S. aureus (MRSA). The bacterium is a worldwide problem in clinical medicine. Despite much research and development, no vaccine for S. aureus has been approved.
Cutibacterium acnes is the relatively slow-growing, typically aerotolerant anaerobic, gram-positive bacterium (rod) linked to the skin condition of acne; it can also cause chronic blepharitis and endophthalmitis, the latter particularly following intraocular surgery. Its genome has been sequenced and a study has shown several genes can generate enzymes for degrading skin and proteins that may be immunogenic.
Mupirocin, sold under the brand name Bactroban among others, is a topical antibiotic useful against superficial skin infections such as impetigo or folliculitis. It may also be used to get rid of methicillin-resistant S. aureus (MRSA) when present in the nose without symptoms. Due to concerns of developing resistance, use for greater than ten days is not recommended. It is used as a cream or ointment applied to the skin.
Adapalene, sold under the brand name Differin among others, is a third-generation topical retinoid primarily used in the treatment of mild-moderate acne, and is also used off-label to treat keratosis pilaris as well as other skin conditions. Studies have found adapalene is as effective as other retinoids, while causing less irritation. It also has several advantages over other retinoids. The adapalene molecule is more stable compared to tretinoin and tazarotene, which leads to less concern for photodegradation. It is also chemically more stable compared to the other two retinoids, allowing it to be used in combination with benzoyl peroxide. Due to its effects on keratinocyte proliferation and differentiation, adapalene is superior to tretinoin for the treatment of comedonal acne and is often used as a first-line agent. The Swiss company Galderma developed adapalene.
Fusidic acid, sold under the brand name Fucidin among others, is a steroid antibiotic that is often used topically in creams or ointments and eyedrops but may also be given systemically as tablets or injections. As of October 2008, the global problem of advancing antimicrobial resistance has led to a renewed interest in its use.
Staphylococcus epidermidis is a Gram-positive bacterium, and one of over 40 species belonging to the genus Staphylococcus. It is part of the normal human microbiota, typically the skin microbiota, and less commonly the mucosal microbiota and also found in marine sponges. It is a facultative anaerobic bacteria. Although S. epidermidis is not usually pathogenic, patients with compromised immune systems are at risk of developing infection. These infections are generally hospital-acquired. S. epidermidis is a particular concern for people with catheters or other surgical implants because it is known to form biofilms that grow on these devices. Being part of the normal skin microbiota, S. epidermidis is a frequent contaminant of specimens sent to the diagnostic laboratory.
Lincosamides are a class of antibiotics, which include lincomycin, clindamycin, and pirlimycin.
Erythromycin/isotretinoin is a topical gel with two active ingredients: erythromycin 2% w/w and isotretinoin 0.05% w/w with a primary indication for the treatment of moderate acne vulgaris.
Lincomycin is a lincosamide antibiotic that comes from the actinomycete Streptomyces lincolnensis. A related compound, clindamycin, is derived from lincomycin by using thionyl chloride to replace the 7-hydroxy group with a chlorine atom with inversion of chirality. It was released for medical use in September 1964.
Clindamycin/benzoyl peroxide, sold under the brand name Benzaclin among others, is a topical gel used for the treatment of acne. It is a fixed-dose combination of clindamycin, as the phosphate, an antibiotic; and benzoyl peroxide, an antiseptic.
Pitted keratolysis is a bacterial skin infection of the foot. The infection is characterized by craterlike pits on the sole of the feet and toes, particularly weight-bearing areas.
Skin flora, also called skin microbiota, refers to microbiota that reside on the skin, typically human skin.
Nadifloxacin is a topical fluoroquinolone antibiotic for the treatment of acne vulgaris. It is also used to treat bacterial skin infections.
A pimple or zit is a kind of comedo that results from excess sebum and dead skin cells getting trapped in the pores of the skin. In its aggravated state, it may evolve into a pustule or papule. Pimples can be treated by acne medications, antibiotics, and anti-inflammatories prescribed by a physician, or various over the counter remedies purchased at a pharmacy.
Infantile acne is a form of acne that begins in very young children. Typical symptoms include inflammatory and noninflammatory lesions, papules and pustules most commonly present on the face. No cause of infantile acne has been established but it may be caused by increased sebaceous gland secretions due to elevated androgens, genetics and the fetal adrenal gland causing increased sebum production. Infantile acne can resolve by itself by age 1 or 2. However, treatment options include topical benzyl peroxide, topical retinoids and topical antibiotics in most cases.
Kerry L. LaPlante is an American pharmacist, academic and researcher. She is the Dean at the University of Rhode Island College of Pharmacy. She is a Professor of Pharmacy and former department Chair of the Department of Pharmacy Practice at the University of Rhode Island, an adjunct professor of medicine at Brown University, an Infectious Diseases Pharmacotherapy Specialist, and the Director of the Rhode Island Infectious Diseases Fellowship and Research Programs at the Veterans Affairs Medical Center in Providence, Rhode Island.
Tretinoin/benzoyl peroxide, sold under the brand name Twyneo, is a fixed-dose combination medication used for the treatment of acne. It contains tretinoin, a vitamin A derivative, and benzoyl peroxide, an oxidizing agent.
Clindamycin/adapalene/benzoyl peroxide, sold under the brand name Cabtreo, is a fixed-dose combination medication used for the treatment of acne. It contains clindamycin, as the phosphate, a lincosamide antibacterial; adapalene, a synthetic retinoid; and benzoyl peroxide, an oxidizing agent. It is applied to the skin.
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