Structure via PubChem · Public domain (PubChem)
clindamycin
Sign in to saveAlso known as 7-CDL, methyl 7-chloro-6,7,8-trideoxy-6-(1-methyl-trans-4-propyl-L-2-pyrrolidinecarboxamido)-1-thio-L-threo-alpha-D-galacto-octopyranoside, 7(S)-chloro-7-deoxylincomycin
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.
Chemical data
- Formula
- C18H33ClN2O5S
- Molecular weight
- 425 g/mol
- IUPAC name
- (2S,4R)-N-[(1S,2S)-2-chloro-1-[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-methylsulfanyloxan-2-yl]propyl]-1-methyl-4-propylpyrrolidine-2-carboxamide
- SMILES
- CCC[C@@H]1C[C@H](N(C1)C)C(=O)N[C@@H]([C@@H]2[C@@H]([C@@H]([C@H]([C@H](O2)SC)O)O)O)[C@H](C)Cl
- InChIKey
- KDLRVYVGXIQJDK-AWPVFWJPSA-N
- XLogP
- 2.2
- Polar surface area
- 128 Ų
- H-bond donors
- 4
- H-bond acceptors
- 7
- Formal charge
- 0
via PubChem
Research
15,880 papers- Clindamycin.The Medical clinics of North America · 1987
- Clindamycin.Obstetrics and gynecology clinics of North America · 1992
- Clindamycin.The Medical clinics of North America · 1982
- Is clindamycin dangerous?General dentistry · 2017
- Clindamycin--efficacy and toxicity.The Western journal of medicine · 1975
via PubMed
Wikidata facts
- Mass
- 424.179871
Show 5 more facts
- chemical formula
- C₁₈H₃₃ClN₂O₅S
- Commons category
- Clindamycin
- isomeric SMILES
- CCC[C@@H]1C[C@H](N(C1)C)C(=O)NC([C@@H]2[C@@H]([C@@H]([C@H]([C@H](O2)SC)O)O)O)C(C)Cl
- canonical SMILES
- CCCC1CC(N(C1)C)C(=O)NC(C2C(C(C(C(O2)SC)O)O)O)C(C)Cl
- defined daily dose
- 0.1
via Wikidata · CC0
~16 min read
Article
18 sectionsContents
- Medical uses
- Acne
- Susceptible bacteria
- D-test
- Malaria
- Other
- Side effects
- ''Clostridioides difficile''
- Pregnancy and breastfeeding
- Interactions
- Chemistry
- Mechanism of action
- Society and culture
- Economics
- Available forms
- Veterinary use
- References
- External links
{{Drugbox | Verifiedfields = changed | verifiedrevid = 457629722 | image = Clindamycin skeletal formula labelled.svg | image_class = skin-invert-image | width = 250 | alt = | image2 = Clindamycin 3D 3jz0.png | image_class2 = bg-transparent | width2 = 250 | alt2 = | caption =
| pronounce = | tradename = Cleocin, Clinacin, Dalacin, others | Drugs.com = | MedlinePlus = a682399 | DailyMedID = Clindamycin | pregnancy_AU = A | pregnancy_AU_comment = | pregnancy_category = | routes_of_administration = By mouth, topical, intravenous, intravaginal | class = Lincosamide antibiotic | ATC_prefix = J01 | ATC_suffix = FF01 | ATC_supplemental =