Responsive image

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

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

Responsive image

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 Responsive image C(=O)N 0.1240
FDBF00007 propane Responsive image C(C)C 0.2412
FDBF00209 1-methylpyrrolidine Responsive image N1(CCCC1)C 0.0076
FDBF02702 (2S,4R)-1,4-dimethylpyrrolidine-2-carboxamide Responsive image N1(C(CC(C1)C)C(=O)N)C 0.0007
FDBF02703 (3R)-1-methyl-3-propyl-pyrrolidine Responsive image N1(CCC(C1)CCC)C 0.0007
FDBF02705 N-[(2R)-2-chloropropyl]formamide Responsive image C(C(Cl)C)NC=O 0.0003
FDBF02706 (2S,4R)-N,1,4-trimethylpyrrolidine-2-carboxamide Responsive image CNC(=O)C1N(CC(C1)C)C 0.0007
FDBF02707 (2S)-N-[(2R)-2-chloropropyl]-1-methyl-pyrrolidine-2-carboxamide Responsive image C(C(Cl)C)NC(=O)C1N(CCC1)C 0.0003
FDBF02709 (2S,4R)-N-[(2R)-2-chloropropyl]-1,4-dimethyl-pyrrolidine-2-carboxamide Responsive image C(C(Cl)C)NC(=O)C1N(CC(C1)C)C 0.0003
FDBF02710 (2S,4R)-N,1-dimethyl-4-propyl-pyrrolidine-2-carboxamide Responsive image CNC(=O)C1N(CC(C1)CCC)C 0.0007
16 , 2