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Clindamycin

Catalog No. DB01190 Name DrugBank
CAS Number 18323-44-9 Website http://www.ualberta.ca/
M. F. C18H33ClN2O5S Telephone (780) 492-3111
M. W. 424.98302 Fax (780) 492-1071
Purity Email david.wishart@ualberta.ca
Storage Chembase ID: 1061

SYNONYMS

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
IUPAC Traditional name
7(S)-chloro-7-deoxylincomycin
Brand Name
Cleocin T
Dalacin C Flavored Granules
Evoclin
Dalacin T Topical Solution
Dalacin C Phosphate
Cleocin Hcl
Cleocin T Lotion
Cleocin T Topical Solution
Clinda-Derm
Clindesse
Clinimycin
ResiDerm A
Chlolincocin
Cleocin
Cleocin Pediatric
Cleocin Phosphate
Cleocin T Gel
Clindagel
Clindets
Dalacin
Dalacin C
Sobelin
Zindaclin
Synonyms
Clindamycine [INN-French]
Clindamycin Hcl
Clindamycine [French]
clindamycin
Clindamicina [INN-Spanish]
Clindamycin Hydrochloride
Clindamycin Phosphate
Clindamycinum [INN-Latin]

DATABASE IDS

PubChem SID 46506073
PubChem CID 29029
CAS Number 18323-44-9

PROPERTIES

Hydrophobicity(logP) 1.6
Solubility 30.6 mg/L

DETAILS

Description (English)
Item Information
Drug Groups approved
Description Clindamycin is a semisynthetic lincosamide antibiotic that has largely replaced lincomycin due to an improved side effect profile. Clindamycin inhibits bacterial protein synthesis by binding to bacterial 50S ribosomal subunits. It may be bacteriostatic or bactericidal depending on the organism and drug concentration.
Indication 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.
Pharmacology Clindamycin is an antibiotic, similar to and a derivative of lincomycin. Clindamycin can be used in topical or systemic treatment. It is effective as an anti-anaerobic antibiotic and antiprotozoal.
Toxicity Adverse effects include nausea (may be dose-limiting), diarrhea, pseudomembranous colitis, allergic reactions, hepatoxicity, transient neutropenia and eosinophilia and agranulocytosis. Pseudomembranous colitis occurs in 0.01 - 10% of patients and occurs more commonly than with other antibiotics. Use of the topical formulation of clindamycin results in absorption of the antibiotic from the skin surface. Diarrhea, bloody diarrhea, and colitis (including pseudomembranous colitis) have been reported with the use of topical and systemic clindamycin.
Affected Organisms
Enteric bacteria and other eubacteria
Biotransformation Hepatic
Absorption Rapidly absorbed after oral administration with peak serum concentrations observed after about 45 minutes. Absorption of an oral dose is virtually complete (90%) and the concomitant intake of food does not appreciably modify the serum concentrations; serum levels have been uniform and predictable from person to person and dose to dose. Clindamycin does not penetrate the blood brain barrier.
Half Life 2.4 hours
Protein Binding 92-94%
Elimination Approximately 10% of the bioactivity is excreted in the urine and 3.6% in the feces; the remainder is excreted as bioinactive metabolites.
References
Daum RS: Clinical practice. Skin and soft-tissue infections caused by methicillin-resistant Staphylococcus aureus. N Engl J Med. 2007 Jul 26;357(4):380-90. [Pubmed]
Klempner MS, Styrt B: Clindamycin uptake by human neutrophils. J Infect Dis. 1981 Nov;144(5):472-9. [Pubmed]
Lamont RF: Can antibiotics prevent preterm birth--the pro and con debate. BJOG. 2005 Mar;112 Suppl 1:67-73. [Pubmed]
Plaisance KI, Drusano GL, Forrest A, Townsend RJ, Standiford HC: Pharmacokinetic evaluation of two dosage regimens of clindamycin phosphate. Antimicrob Agents Chemother. 1989 May;33(5):618-20. [Pubmed]
External Links
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REFERENCES

  • Lamont RF: Can antibiotics prevent preterm birth--the pro and con debate. BJOG. 2005 Mar;112 Suppl 1:67-73. Pubmed
  • Plaisance KI, Drusano GL, Forrest A, Townsend RJ, Standiford HC: Pharmacokinetic evaluation of two dosage regimens of clindamycin phosphate. Antimicrob Agents Chemother. 1989 May;33(5):618-20. Pubmed
  • Klempner MS, Styrt B: Clindamycin uptake by human neutrophils. J Infect Dis. 1981 Nov;144(5):472-9. Pubmed
  • Daum RS: Clinical practice. Skin and soft-tissue infections caused by methicillin-resistant Staphylococcus aureus. N Engl J Med. 2007 Jul 26;357(4):380-90. Pubmed