Clindamycin

Clindamycin
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
IUPAC name
  • methyl 7-chloro-6,7,8-trideoxy-6-{[(4R)-1-methyl-4-propyl-L-prolyl]amino}-1-thio-L-threo-α-D-galacto-octopyranoside
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
PDB ligand
CompTox Dashboard (EPA)
ECHA InfoCard100.038.357
Chemical and physical data
FormulaC18H33ClN2O5S
Molar mass424.98 g·mol−1
3D model (JSmol)
SMILES
  • Cl[C@@H](C)[C@@H](NC(=O)[C@H]1N(C)C[C@H](CCC)C1)[C@H]2O[C@H](SC)[C@H](O)[C@@H](O)[C@H]2O
InChI
  • InChI=1S/C18H33ClN2O5S/c1-5-6-10-7-11(21(3)8-10)17(25)20-12(9(2)19)16-14(23)13(22)15(24)18(26-16)27-4/h9-16,18,22-24H,5-8H2,1-4H3,(H,20,25)/t9-,10+,11-,12+,13-,14+,15+,16+,18+/m0/s1 Y
  • Key:KDLRVYVGXIQJDK-AWPVFWJPSA-N Y
 NY (what is this?)  (verify)

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.[4] It can also be used to treat acne,[4][5] and some cases of methicillin-resistant Staphylococcus aureus (MRSA).[6] In combination with quinine, it can be used to treat malaria.[4][5] 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.[3][4][5][7][8]

Common side effects include nausea and vomiting, diarrhea, skin rashes, and pain at the site of injection.[4] 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.[9][4] It appears to be generally safe in pregnancy.[4] It is of the lincosamide class and works by blocking bacteria from making protein.[4]

Clindamycin was first made in 1966 from lincomycin.[10][11] It is on the World Health Organization's List of Essential Medicines.[12] It is available as a generic medication.[13][14] In 2022, it was the 147th most commonly prescribed medication in the United States, with more than 3 million prescriptions.[15][16]

  1. ^ Use During Pregnancy and Breastfeeding
  2. ^ "Product monograph brand safety updates". Health Canada. 6 June 2024. Retrieved 8 June 2024.
  3. ^ a b "Xaciato- clindamycin phosphate gel". DailyMed. Retrieved 24 December 2021.
  4. ^ a b c d e f g h "Clindamycin (Systemic)". The American Society of Health-System Pharmacists. Archived from the original on 12 August 2021. Retrieved 19 December 2021.
  5. ^ a b c Leyden JJ (2006). Hidradenitis suppurativa. Berlin: Springer. p. 152. ISBN 9783540331018. Archived from the original on 8 September 2017.
  6. ^ Daum RS (July 2007). "Clinical practice. Skin and soft-tissue infections caused by methicillin-resistant Staphylococcus aureus". N. Engl. J. Med. 357 (4): 380–90. doi:10.1056/NEJMcp070747. PMID 17652653.
  7. ^ "Clindamycin phosphate- clindamycin phosphate gel usp, 1% gel". DailyMed. Retrieved 19 December 2021.
  8. ^ "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.
  9. ^ Thomas C, Stevenson M, Riley TV (2003). "Antibiotics and hospital-acquired Clostridium difficile-associated diarrhoea: a systematic review". J Antimicrob Chemother. 51 (6): 1339–50. doi:10.1093/jac/dkg254. PMID 12746372.
  10. ^ Smieja M (January 1998). "Current indications for the use of clindamycin: A critical review". The Canadian Journal of Infectious Diseases. 9 (1): 22–8. doi:10.1155/1998/538090. PMC 3250868. PMID 22346533.
  11. ^ Neonatal Formulary: Drug Use in Pregnancy and the First Year of Life (7 ed.). John Wiley & Sons. 2014. p. 162. ISBN 9781118819517. Archived from the original on 8 September 2017.
  12. ^ World Health Organization (2021). World Health Organization model list of essential medicines: 22nd list (2021). Geneva: World Health Organization. hdl:10665/345533. WHO/MHP/HPS/EML/2021.02.
  13. ^ Hamilton R (2015). Tarascon Pocket Pharmacopoeia 2015 Deluxe Lab-Coat Edition. Jones & Bartlett Learning. p. 108. ISBN 9781284057560.
  14. ^ "Competitive Generic Therapy Approvals". U.S. Food and Drug Administration (FDA). 29 June 2023. Archived from the original on 29 June 2023. Retrieved 29 June 2023.
  15. ^ "The Top 300 of 2022". ClinCalc. Archived from the original on 30 August 2024. Retrieved 30 August 2024.
  16. ^ "Clindamycin Drug Usage Statistics, United States, 2013 - 2022". ClinCalc. Retrieved 30 August 2024.
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