
IUPAC name
(2S,4R)-N-{2-chloro-1-[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(methylsulfanyl)oxan-2-yl]propyl}-1-methyl-4-propylpyrrolidine-2-carboxamide
SMILES
CCC[C@@H]1C[C@H](N(C)C1)C(=O)NC(C(C)Cl)[C@H]1O[C@H](SC)[C@H](O)[C@@H](O)[C@H]1O
Compound class
Anti-Bacterial Agents; Protein Synthesis Inhibitors; Anti-Acne Preparations; Antibiotics; Genito Urinary System and Sex Hormones; Antibacterials for Systemic Use; Antiinfectives for Systemic Use; Dermatologicals; Gynecological Antiinfectives and Antiseptics; Anti-Acne Preparations for Topical Use; Antiinfectives for Treatment of Acne; Macrolides, Lincosamides and Streptogramins; Lincosamides; CYP3A4 Inhibitors;
Therapeutic area
For the treatment of serious infections caused by susceptible anaerobic bacteria, including Bacteroides spp., Peptostreptococcus, anaerobic streptococci, Clostridium spp., and microaerophilic streptococci. May be useful in polymicrobic infections such as intra-abdominal or pelvic infections, osteomyelitis, diabetic foot ulcers, aspiration pneumonia and dental infections. May also be used to treat MSSA and respiratory infections caused by S. pneumoniae and S. pyogenes in patients who are intolerant to other indicated antibiotics or who are infected with resistant organism. May be used vaginally to treat vaginosis caused by Gardnerella vaginosa. Clindamycin reduces the toxin producing effects of S. aureus and S. pyogenes and as such, may be particularly useful for treating necrotizing fasciitis. May be used topically to treat acne.
Common name
Clindamycin
IUPAC name
(2S,4R)-N-{2-chloro-1-[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(methylsulfanyl)oxan-2-yl]propyl}-1-methyl-4-propylpyrrolidine-2-carboxamide
SMILES
CCC[C@@H]1C[C@H](N(C)C1)C(=O)NC(C(C)Cl)[C@H]1O[C@H](SC)[C@H](O)[C@@H](O)[C@H]1O
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-/m1/s1
FORMULA
C18H33ClN2O5S

Common name
Clindamycin
IUPAC name
(2S,4R)-N-{2-chloro-1-[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(methylsulfanyl)oxan-2-yl]propyl}-1-methyl-4-propylpyrrolidine-2-carboxamide
Molecular weight
424.983
clogP
0.645
clogS
-1.198
HBond Acceptor
6
HBond Donor
4
Total Polar Surface Area
127.56
Number of Rings
2
Rotatable Bond
7
Drug ID | Common name | Structure CAS | SMILE | Frequency |
---|---|---|---|---|
FDBF00003 | formamide |
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C(=O)N | 0.1240 |
FDBF00007 | propane |
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C(C)C | 0.2412 |
FDBF00209 | 1-methylpyrrolidine |
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N1(CCCC1)C | 0.0076 |
FDBF02702 | (2S,4R)-1,4-dimethylpyrrolidine-2-carboxamide |
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N1(C(CC(C1)C)C(=O)N)C | 0.0007 |
FDBF02703 | (3R)-1-methyl-3-propyl-pyrrolidine |
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N1(CCC(C1)CCC)C | 0.0007 |
FDBF02705 | N-[(2R)-2-chloropropyl]formamide |
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C(C(Cl)C)NC=O | 0.0003 |
FDBF02706 | (2S,4R)-N,1,4-trimethylpyrrolidine-2-carboxamide |
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CNC(=O)C1N(CC(C1)C)C | 0.0007 |
FDBF02707 | (2S)-N-[(2R)-2-chloropropyl]-1-methyl-pyrrolidine-2-carboxamide |
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C(C(Cl)C)NC(=O)C1N(CCC1)C | 0.0003 |
FDBF02709 | (2S,4R)-N-[(2R)-2-chloropropyl]-1,4-dimethyl-pyrrolidine-2-carboxamide |
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C(C(Cl)C)NC(=O)C1N(CC(C1)C)C | 0.0003 |
FDBF02710 | (2S,4R)-N,1-dimethyl-4-propyl-pyrrolidine-2-carboxamide |
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CNC(=O)C1N(CC(C1)CCC)C | 0.0007 |