Clindamycin

Clindamycin
Clinical data
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
License data	US DailyMed: Clindamycin;
Pregnancy; category	AU: A;
Routes of; administration	By mouth, topical, intravenous, intravaginal
Drug class	Lincosamide antibiotic
ATC code	J01FF01 (WHO) D10AF01 (WHO) G01AA10 (WHO) D10AF51 (WHO);
Legal status
Legal status	AU: S4 (Prescription only); CA: ℞-only; UK: POM (Prescription only); US: ℞-only;
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%)
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	18323-44-9 ;
PubChem CID	446598;
DrugBank	DB01190 ;
ChemSpider	393915 ;
UNII	3U02EL437C;
KEGG	D00277 ; as HCl: D02132 ;
ChEBI	CHEBI:3745 ;
ChEMBL	ChEMBL1753 ;
PDB ligand	CLY (PDBe, RCSB PDB);
CompTox Dashboard (EPA)	DTXSID90928608 ;
ECHA InfoCard	100.038.357
Chemical and physical data
Formula	C18H33ClN2O5S
Molar mass	424.98 g·mol−1
3D model (JSmol)	Interactive image;
	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 ; Key:KDLRVYVGXIQJDK-AWPVFWJPSA-N ;
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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. It can also be used to treat acne, and some cases of methicillin-resistant Staphylococcus aureus (MRSA). In combination with quinine, it can be used to treat malaria. 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.

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

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