Clindamycin phosphate

Clindamycin
Clinical data


Pronunciation	/klɪndəˈmaɪsɪn/
Trade names	Cleocin, Dalacin, Clinacin
Synonyms	7-chloro-lincomycin 7-chloro-7-deoxylincomycin
AHFS/Drugs.com	Monograph
MedlinePlus	a682399
License data	US FDA: Clindamycin
Pregnancy category	AU: A US: B (No risk in non-human studies)
Routes of administration	by mouth, topical, IV, intravaginal
ATC code	J01FF01 (WHO) D10AF01 (WHO) G01AA10 (WHO)
Legal status
Legal status	AU: S4 (Prescription only) UK: POM (Prescription only) US: ℞-only
Pharmacokinetic data
Bioavailability	90% (oral) 4–5% (topical)
Protein binding	95%
Metabolism	Hepatic
Biological half-life	2–3 hours
Excretion	Biliary and renal (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^Y
PubChem CID	446598
DrugBank	DB01190^Y
ChemSpider	393915^Y
UNII	3U02EL437C
KEGG	D00277^Y
ChEBI	CHEBI:3745^N
ChEMBL	CHEMBL1753^N
ECHA InfoCard	100.038.357
Chemical and physical data
Formula	C₁₈H₃₃ClN₂O₅S
Molar mass	424.98 g/mol
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^Y Key:KDLRVYVGXIQJDK-AWPVFWJPSA-N^Y
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Clindamycin is an antibiotic useful for the treatment of a number of bacterial infections. This includes middle ear infections, bone or joint infections, pelvic inflammatory disease, strep throat, pneumonia, and endocarditis among others. It can be useful against some cases of methicillin-resistant Staphylococcus aureus (MRSA). It may also be used for acne and in addition to quinine for malaria. It is available by mouth, intravenously, and as a cream to be applied to the skin or in the vagina.

Common side effects include nausea, diarrhea, rash, and pain at the site of injection. It increases the risk of hospital-acquired Clostridium difficile colitis about fourfold. Other antibiotics may be recommended instead due to this reason. 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 1967. It is on the World Health Organization's List of Essential Medicines, the most effective and safe medicines needed in a health system. It is available as a generic medication and is not very expensive. The wholesale cost in the developing world is about 0.06 to 0.12 USD per pill. In the United States it costs about 2.70 USD a dose.

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