Chemistry:Clindamycin

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Short description: Antibiotic
Clindamycin
Clindamycin.svg
Clindamycin 3D 3jz0.png
Clinical data
Pronunciation/klɪndəˈmaɪsɪn/
Trade namesCleocin, Clinacin, Dalacin, others
Other names7-chloro-lincomycin
7-chloro-7-deoxylincomycin, DARE-BV1
AHFS/Drugs.comMonograph
MedlinePlusa682399
License data
Pregnancy
category
Routes of
administration		By mouth, topical, intravenous, intravaginal
Drug classLincosamide antibiotic
ATC code
Legal status
Legal status
Pharmacokinetic data
Bioavailability90% (by mouth)
4–5% (topical)
Protein binding95%
MetabolismLiver
Elimination half-life2–3 hour
ExcretionBile duct and kidney (around 20%)
Identifiers
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
PDB ligand
Chemical and physical data
FormulaC18H33ClN2O5S
Molar mass424.98 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.[3] It can also be used to treat acne,[3][4] and some cases of methicillin-resistant Staphylococcus aureus (MRSA).[5] In combination with quinine, it can be used to treat malaria.[3][4] 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.[2][3][4][6][7]

Common side effects include nausea and vomiting, diarrhea, rashes, and pain at the site of injection.[3] It increases the risk of hospital-acquired Clostridium difficile colitis about fourfold and thus is only recommended when other antibiotics are not appropriate.[8][3] Alternative antibiotics may be recommended as a result.[3] It appears to be generally safe in pregnancy.[3] It is of the lincosamide class and works by blocking bacteria from making protein.[3]

Clindamycin was first made in 1966 from lincomycin.[9][10] It is on the World Health Organization's List of Essential Medicines.[11] It is available as a generic medication.[12][13] In 2020, it was the 125th most commonly prescribed medication in the United States, with more than 5 million prescriptions.[14][15]

Medical uses

Clindamycin is used primarily to treat anaerobic infections caused by susceptible anaerobic bacteria, including dental infections,[16] and infections of the respiratory tract, skin, and soft tissue, and peritonitis.[17] 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.[17][18] Topical application of clindamycin phosphate can be used to treat mild to moderate acne.[19][20]

Acne

Clindamycin phosphate topical solution

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.[20][21] Topical clindamycin plus topical benzoyl peroxide is more effective than topical clindamycin alone.[20][21]

Susceptible bacteria

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,[22][24] as are the facultative anaerobic Enterobacteriaceae.[25] A notable exception is Capnocytophaga canimorsus, for which clindamycin is a first-line drug of choice.[26]

The following represents MIC susceptibility data for a few medically significant pathogens.[27]

  • Staphylococcus aureus: 0.016 μg/mL – >256 μg/mL
  • Streptococcus pneumoniae: 0.002 μg/mL – >256 μg/mL
  • Streptococcus pyogenes: <0.015 μg/mL – >64 μg/mL

D-test

D-test

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.[28]

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).[29] 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.[29]

Malaria

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.[30][31] Clindamycin should not be used as an antimalarial by itself, although it appears to be very effective as such, because of its slow action.[30][31] 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.[32]

Other

Clindamycin may be useful in skin and soft tissue infections caused by methicillin-resistant Staphylococcus aureus (MRSA).[5] 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.

While it has been used in intraabdominal infections, such use is generally not recommended due to resistance.[3]

Clindamycin is used in cases of suspected toxic shock syndrome,[33] 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;[34] it may also induce changes in the surface structure of bacteria that make them more sensitive to immune system attack (opsonization and phagocytosis).[35][36]

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.[37]

The combination of clindamycin and quinine is the standard treatment for severe babesiosis.[38]

Clindamycin may also be used to treat toxoplasmosis,[22][39][40] and, in combination with primaquine, is effective in treating mild to moderate Pneumocystis jirovecii pneumonia.[41]

Clindamycin, either applied to skin or taken by mouth, may also be used in hidradenitis suppurativa.[42]

Side effects

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.[43][44] Common side effects – found in over 10% of people – in vaginal applications include fungal infection.

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.[43]

Clostridioides difficile

Pseudomembranous colitis is a potentially lethal condition commonly associated with clindamycin, but which also occurs with other antibiotics.[8][45] 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.[43][46]

Pregnancy and breastfeeding

Use of clindamycin during pregnancy is generally considered safe.[47]

Clindamycin is classified as compatible with breastfeeding by the American Academy of Pediatrics,[48] however, the WHO categorizes it as "avoid if possible".[49] It is classified as L2 probably compatible with breastfeeding according to Medications and Mothers' Milk.[50] 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.[51] LactMed lists potentially negative gastrointestinal effects in babies whose mothers take it while breastfeeding but did not see that as justification to stop breastfeeding.[52]

Interactions

Clindamycin may prolong the effects of neuromuscular-blocking drugs, such as succinylcholine and vecuronium.[53][54][55] Its similarity to the mechanism of action of macrolides and chloramphenicol means they should not be given simultaneously, as this causes antagonism[24] and possible cross-resistance.

Chemistry

Clindamycin phosphate[56]

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.[57][58] 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.[59] It has been on the market since 1968.[44]

Clindamycin is white or yellow.[60] It is very soluble in water.[60] The topically used clindamycin phosphate is a phosphate-ester prodrug of clindamycin.[56]

Mechanism of action

Clindamycin mechanism

Clindamycin has a primarily bacteriostatic effect. At higher concentrations, it may be bactericidal.[60] It is a bacterial protein synthesis inhibitor by inhibiting ribosomal translocation,[61] 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.[22][62] The binding is reversible.[63] Clindamycin is more effective than lincomycin.[60]

The X-ray crystal structures of clindamycin bound to ribosomes (or ribosomal subunits) derived from Escherichia coli,[64] Deinococcus radiodurans,[65] and Haloarcura marismortui[66] have been determined; the structure of the closely related antibiotic lincomycin bound to the 50S ribosomal subunit of Staphylococcus aureus has also been reported.[67]

Society and culture

Economics

Clindamycin is available as a generic medication and is relatively inexpensive.[12][68]

Available forms

Clindamycin capsules

Clindamycin preparations that are taken by mouth include capsules (containing clindamycin hydrochloride) and oral suspensions (containing clindamycin palmitate hydrochloride).[30] 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.[37] 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.[69]

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.[70] 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.[30] (The exception is the vaginal suppository, which is not available as a generic in the US[71]).

Veterinary use

The veterinary uses of clindamycin are quite similar to its human indications, and include treatment of osteomyelitis,[72] skin infections, and toxoplasmosis, for which it is the preferred drug in dogs and cats.[73] They can be used both by mouth and topically.[60] A disadvantage is that bacterial resistance can develop fairly quickly.[60] Gastrointestinal upset may also occur.[60] Toxoplasmosis rarely causes symptoms in cats, but can do so in very young or immunocompromised kittens and cats.[citation needed]

References

  1. ↑ Use During Pregnancy and Breastfeeding
  2. ↑ 2.0 2.1 "Xaciato- clindamycin phosphate gel". https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=1f55f371-a27d-4331-815b-d8a90874223a. 
  3. ↑ 3.0 3.1 3.2 3.3 3.4 3.5 3.6 3.7 3.8 3.9 "Clindamycin (Systemic)". The American Society of Health-System Pharmacists. https://www.drugs.com/monograph/clindamycin-systemic.html. 
  4. ↑ 4.0 4.1 4.2 Hidradenitis suppurativa. Berlin: Springer. 2006. p. 152. ISBN 9783540331018. https://books.google.com/books?id=hpKFsXwcKlgC&pg=PA152. 
  5. ↑ 5.0 5.1 "Clinical practice. Skin and soft-tissue infections caused by methicillin-resistant Staphylococcus aureus". N. Engl. J. Med. 357 (4): 380–90. July 2007. doi:10.1056/NEJMcp070747. PMID 17652653. 
  6. ↑ "Clindamycin phosphate- clindamycin phosphate gel usp, 1% gel". https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=ac21d7ad-f94e-4d57-95e3-1648add7ad0b. 
  7. ↑ "Daré Announces FDA Approval of Xaciato (clindamycin phosphate) Vaginal Gel as a Treatment for Bacterial Vaginosis". Daré Bioscience (Press release). 7 December 2021. Retrieved 19 December 2021.
  8. ↑ 8.0 8.1 "Antibiotics and hospital-acquired Clostridium difficile-associated diarrhoea: a systematic review". J Antimicrob Chemother 51 (6): 1339–50. 2003. doi:10.1093/jac/dkg254. PMID 12746372. 
  9. ↑ "Current indications for the use of clindamycin: A critical review". The Canadian Journal of Infectious Diseases 9 (1): 22–8. January 1998. doi:10.1155/1998/538090. PMID 22346533. 
  10. ↑ Neonatal Formulary: Drug Use in Pregnancy and the First Year of Life (7 ed.). John Wiley & Sons. 2014. p. 162. ISBN 9781118819517. https://books.google.com/books?id=EORvBAAAQBAJ&pg=PA162. 
  11. ↑ World Health Organization model list of essential medicines: 22nd list (2021). Geneva: World Health Organization. 2021. WHO/MHP/HPS/EML/2021.02. 
  12. ↑ 12.0 12.1 Tarascon Pocket Pharmacopoeia 2015 Deluxe Lab-Coat Edition. Jones & Bartlett Learning. 2015. p. 108. ISBN 9781284057560. 
  13. ↑ "Competitive Generic Therapy Approvals". 29 June 2023. https://www.fda.gov/drugs/generic-drugs/competitive-generic-therapy-approvals. 
  14. ↑ "The Top 300 of 2020". https://clincalc.com/DrugStats/Top300Drugs.aspx. 
  15. ↑ "Clindamycin - Drug Usage Statistics". https://clincalc.com/DrugStats/Drugs/Clindamycin. 
  16. ↑ "Clindamycin in dentistry: more than just effective prophylaxis for endocarditis?". Oral Surg Oral Med Oral Pathol Oral Radiol Endod 100 (5): 550–8. November 2005. doi:10.1016/j.tripleo.2005.02.086. PMID 16243239. 
  17. ↑ 17.0 17.1 "Cleocin I.V. Indications & Dosage". RxList.com. 2007. http://www.rxlist.com/cgi/generic/clindamyciniv_ids.htm. 
  18. ↑ "Antibiotic treatment of gram-positive bone and joint infections". J Antimicrob Chemother 53 (6): 928–35. 2004. doi:10.1093/jac/dkh191. PMID 15117932. 
  19. ↑ "Diagnosis and treatment of acne". Am Fam Physician 69 (9): 2123–30. May 2004. PMID 15152959. https://www.aafp.org/afp/2004/0501/p2123.html. 
  20. ↑ 20.0 20.1 20.2 "Acne Vulgaris: Diagnosis and Treatment". Am Fam Physician 100 (8): 475–84. October 2019. PMID 31613567. https://www.aafp.org/afp/2019/1015/p475.html. 
  21. ↑ 21.0 21.1 "Meta-analysis comparing efficacy of benzoyl peroxide, clindamycin, benzoyl peroxide with salicylic acid, and combination benzoyl peroxide/clindamycin in acne". J. Am. Acad. Dermatol. 63 (1): 52–62. July 2010. doi:10.1016/j.jaad.2009.07.052. PMID 20488582. 
  22. ↑ 22.0 22.1 22.2 22.3 "Lincosamides, Oxazolidinones, and Streptogramins". Merck Manual of Diagnosis and Therapy. Merck & Co.. May 2020. https://www.merckmanuals.com/professional/infectious-diseases/bacteria-and-antibacterial-drugs/lincosamides,-oxazolidinones,-and-streptogramins. 
  23. ↑ "Anaerobic bloodstream infections in Italy (ITANAEROBY): A 5-year retrospective nationwide survey". Anaerobe 75: 102583. June 2022. doi:10.1016/j.anaerobe.2022.102583. PMID 35568274. 
  24. ↑ 24.0 24.1 "Clindamycin: new look at an old drug". Infectious Diseases in Children. January 2005. http://www.pediatricsupersite.com/view.aspx?rid=35957. 
  25. ↑ "Macrolides and clindamycin". Clinical infectious diseases: a practical approach. Oxford: Oxford University Press. 1999. pp. 291–7. ISBN 978-0-19-508103-9. https://books.google.com/books?id=zvCOpighJggC&pg=PA294.  Retrieved 19 January 2009.through Google Book Search.
  26. ↑ "Antimicrobial treatment of Capnocytophaga infections". Int J Antimicrob Agents 29 (4): 367–73. April 2007. doi:10.1016/j.ijantimicag.2006.10.005. PMID 17250994. 
  27. ↑ "Clindamycin Phosphate Susceptibility and Minimum Inhibitory Concentration (MIC) Data". 2020-06-01. https://www.toku-e.com/content/product-documents/MIC_Clindamycin%20Phosphate.pdf. 
  28. ↑ "Mechanisms of Resistance to Macrolides and Lincosamides: Nature of the Resistance Elements and Their Clinical Implications". Clinical Infectious Diseases 34 (4): 482–92. February 2002. doi:10.1086/324626. PMID 11797175. 
  29. ↑ 29.0 29.1 "Macrolide-inducible resistance to clindamycin and the D-test". The Pediatric Infectious Disease Journal 28 (12): 1115–8. December 2009. doi:10.1097/INF.0b013e3181c35cc5. PMID 19935273. 
  30. ↑ 30.0 30.1 30.2 30.3 "Clindamycin as an antimalarial drug: review of clinical trials". Antimicrobial Agents and Chemotherapy 46 (8): 2315–20. 2002. doi:10.1128/AAC.46.8.2315-2320.2002. ISSN 0066-4804. PMID 12121898. 
  31. ↑ 31.0 31.1 "Treatment of malaria in the United States: a systematic review". JAMA 297 (20): 2264–77. 2007. doi:10.1001/jama.297.20.2264. PMID 17519416. 
  32. ↑ "Genome scanning of Amazonian Plasmodium falciparum shows subtelomeric instability and clindamycin-resistant parasites". Genome Research 20 (11): 1534–44. 2010. doi:10.1101/gr.105163.110. PMID 20829224. 
  33. ↑ "Managing toxic shock syndrome with antibiotics". Expert Opin Pharmacother 5 (8): 1701–10. 2004. doi:10.1517/14656566.5.8.1701. PMID 15264985. 
  34. ↑ "Targeting bacterial virulence: the role of protein synthesis inhibitors in severe infections. Insights from the Society of Infectious Diseases Pharmacists". Pharmacotherapy 23 (5): 638–42. May 2003. doi:10.1592/phco.23.5.638.32191. PMID 12741438. 
  35. ↑ "Regulation of protein A biosynthesis in Staphylococcus aureus by certain antibiotics: its effect on phagocytosis by leukocytes". J Antimicrob Chemother 12 (6): 587–97. 1983. doi:10.1093/jac/12.6.587. PMID 6662837. 
  36. ↑ "Potentiation of opsonization and phagocytosis of Streptococcus pyogenes following growth in the presence of clindamycin". J Clin Invest 67 (5): 1249–56. May 1981. doi:10.1172/JCI110152. PMID 7014632. 
  37. ↑ 37.0 37.1 "Can antibiotics prevent preterm birth—the pro and con debate". BJOG 112 (Suppl 1): 67–73. 2005. doi:10.1111/j.1471-0528.2005.00589.x. PMID 15715599. 
  38. ↑ "Babesiosis". Clin Microbiol Rev 13 (3): 451–69. July 2000. doi:10.1128/CMR.13.3.451-469.2000. PMID 10885987. 
  39. ↑ "Okuläre Toxoplasmose" (in de). Ophthalmologe 104 (7): 603–16. 2007. doi:10.1007/s00347-007-1535-8. PMID 17530262. 
  40. ↑ "Intérêt de la clindamycine dans le traitement de la toxoplasmose oculaire" (in fr). Journal Français d'Ophtalmologie 20 (6): 418–22. 1997. ISSN 0181-5512. PMID 9296037. 
  41. ↑ "Treatment of infection due to Pneumocystis carinii". Antimicrobial Agents and Chemotherapy 42 (6): 1309–14. June 1998. doi:10.1128/AAC.42.6.1309. PMID 9624465. 
  42. ↑ "Hidradenitis Suppurativa: Advances in Diagnosis and Treatment". JAMA 318 (20): 2019–32. November 2017. doi:10.1001/jama.2017.16691. PMID 29183082. 
  43. ↑ 43.0 43.1 43.2 Australian Medicines Handbook. Adelaide: AMH Pty Ltd. 2006. 
  44. ↑ 44.0 44.1 "Clindamycin and taste disorders". British Journal of Clinical Pharmacology 64 (4): 542–5. October 2007. doi:10.1111/j.1365-2125.2007.02908.x. PMID 17635503. 
  45. ↑ "Clostridium difficile associated diarrhoea: diagnosis and treatment". BMJ 331 (7515): 498–501. 2005. doi:10.1136/bmj.331.7515.498. PMID 16141157. 
  46. ↑ "Clostridium difficile colitis". New England Journal of Medicine 330 (4): 257–62. January 1994. doi:10.1056/NEJM199401273300406. PMID 8043060. 
  47. ↑ "Clindamycin as an antimalarial drug: review of clinical trials". Antimicrobial Agents and Chemotherapy 46 (8): 2315–20. August 2002. doi:10.1128/AAC.46.8.2315-2320.2002. PMID 12121898. 
  48. ↑ "Transfer of drugs and other chemicals into human milk". Pediatrics 108 (3): 776–89. September 2001. doi:10.1542/peds.108.3.776. PMID 11533352. 
  49. ↑ Organization, World Health (2002). Breastfeeding and maternal medication : recommendations for drugs in the Eleventh WHO Model List of Essential Drugs. Geneva, Switzerland: World Health Organization. 
  50. ↑ Medications & mothers' milk. Rowe, Hilary E. (Seventeenth ed.). New York, NY: Springer. 2017. ISBN 9780826128584. OCLC 959873270. 
  51. ↑ "Excretion of antimicrobials used to treat methicillin-resistant Staphylococcus aureus infections during lactation: safety in breastfeeding infants". Pharmacotherapy 29 (9): 1103–9. September 2009. doi:10.1592/phco.29.9.1103. PMID 19698015. 
  52. ↑ "Clindamycin". Drugs and Lactation Database (LactMed) (National Library of Medicine (US)). 2006. Bookshelf ID: NBK501208. PMID 30000267. https://www.ncbi.nlm.nih.gov/books/NBK501208/. 
  53. ↑ "Prolongation of a pancuronium-induced neuromuscular blockade by clindamycin". Anesthesiology 41 (4): 407–8. 1974. doi:10.1097/00000542-197410000-00023. PMID 4415332. 
  54. ↑ "Clindamycin-induced neuromuscular blockade". Can J Anaesth 42 (7): 614–7. 1995. doi:10.1007/BF03011880. PMID 7553999. 
  55. ↑ "Prolongation of rapacuronium neuromuscular blockade by clindamycin and magnesium". Anesth Analg 94 (1): 123–4, table of contents. 2002. doi:10.1097/00000539-200201000-00023. PMID 11772813. 
  56. ↑ 56.0 56.1 "Clindamycin Phosphate Topical Solution". https://www.rxlist.com/clindamycin-phosphate-topical-solution-drug.htm. 
  57. ↑ "Lincomycin. XI. Synthesis and structure of clindamycin, a potent antibacterial agent". Journal of Medicinal Chemistry 13 (4): 616–19. July 1970. doi:10.1021/jm00298a007. PMID 4916317. 
  58. ↑ "Microbiological and Pharmacological Behavior of 7-Chlorolincomycin". Appl Microbiol 17 (5): 653–7. 1969. doi:10.1128/AEM.17.5.653-657.1969. PMID 4389137. 
  59. ↑ "Chemical modification of lincomycin". Antimicrobial Agents and Chemotherapy 6: 727–36. 1966. PMID 5985307. 
  60. ↑ 60.0 60.1 60.2 60.3 60.4 60.5 60.6 "Lincomycin, clindamycin and their applications". Applied Microbiology and Biotechnology 64 (4): 455–64. May 2004. doi:10.1007/s00253-003-1545-7. PMID 14762701. 
  61. ↑ Clindamycin University of Michigan. Retrieved 31 July 2009
  62. ↑ "Ribosome-targeting antibiotics and mechanisms of bacterial resistance". Nature Reviews Microbiology 12 (1): 35–48. January 2014. doi:10.1038/nrmicro3155. PMID 24336183. 
  63. ↑ Beauduy CE, Winston LG. Tetracyclines, Macrolides, Clindamycin, Chloramphenicol, Streptogramins, & Oxazolidinones. In: Katzung BG. eds. Basic & Clinical Pharmacology, 14e New York, NY: McGraw-Hill; .
  64. ↑ "Structures of the Escherichia coli ribosome with antibiotics bound near the peptidyl transferase center explain spectra of drug action". Proceedings of the National Academy of Sciences 107 (40): 17152–57. October 2010. doi:10.1073/pnas.1007988107. PMID 20876128. Bibcode: 2010PNAS..10717152D. 
  65. ↑ "Structural basis for the interaction of antibiotics with the peptidyl transferase centre in eubacteria". Nature 413 (6858): 814–21. October 2001. doi:10.1038/35101544. PMID 11677599. Bibcode: 2001Natur.413..814S. 
  66. ↑ "Structures of MLSBK antibiotics bound to mutated large ribosomal subunits provide a structural explanation for resistance". Cell 121 (2): 257–70. April 2005. doi:10.1016/j.cell.2005.02.005. PMID 15851032. 
  67. ↑ "Structural insights of lincosamides targeting the ribosome of Staphylococcus aureus". Nucleic Acids Research 45 (17): 10284–92. September 2017. doi:10.1093/nar/gkx658. PMID 28973455. 
  68. ↑ Infectious Diseases in Critical Care Medicine. CRC Press. 2009. p. 506. ISBN 978-1-4200-9241-7. https://books.google.com/books?id=syasCQAAQBAJ&dq=Cephalexin+inexpensive&pg=PA506. 
  69. ↑ "A randomized, double-blind comparison of a clindamycin phosphate/benzoyl peroxide gel formulation and a matching clindamycin gel with respect to microbiologic activity and clinical efficacy in the topical treatment of acne vulgaris". Clin Ther 24 (7): 1117–33. 2002. doi:10.1016/S0149-2918(02)80023-6. PMID 12182256. 
  70. ↑ "FDA Approvals: Ziana, Kadian, Polyphenon E". 1 December 2006. https://www.medscape.com/viewarticle/548709. 
  71. ↑ "Generic Cleocin Vaginal Availability". https://www.drugs.com/availability/generic-cleocin-vaginal.html. 
  72. ↑ (8 February 2005) "Osteomyelitis" , in Kahn, Cynthia M., Line, Scott, Aiello, Susan E. (ed.): The Merck Veterinary Manual, 9th ed., John Wiley & Sons . ISBN:0-911910-50-6. Retrieved 14 December 2007.
  73. ↑ (8 February 2005) "Toxoplasmosis: Introduction" , in Kahn, Cynthia M., Line, Scott, Aiello, Susan E. (ed.): The Merck Veterinary Manual, 9th ed., John Wiley & Sons . ISBN:0-911910-50-6. Retrieved 14 December 2007.

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