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Showing drug card for Clindamycin (DB01190)

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Version 2.5
Creation Date 2005-06-13 13:24:05
Update Date 2009-06-23 18:06:59
Primary Accession Number DB01190
Secondary Accession Number
  • APRD00566
Name Clindamycin
Drug Type
  • Approved
  • Investigational
  • Small Molecule
Description An antibacterial agent that is a semisynthetic analog of lincomycin. [PubChem]
Synonyms
  1. Clindamicina [INN-Spanish]
  2. Clindamycin Hcl
  3. Clindamycin Hydrochloride
  4. Clindamycin Phosphate
  5. Clindamycine [French]
  6. Clindamycine [INN-French]
  7. Clindamycinum [INN-Latin]
  8. clindamycin
Brand Names
  1. Chlolincocin
  2. Cleocin
  3. Cleocin Hcl
  4. Cleocin Pediatric
  5. Cleocin Phosphate
  6. Cleocin T
  7. Cleocin T Gel
  8. Cleocin T Lotion
  9. Cleocin T Topical Solution
  10. Clinda-Derm
  11. Clindagel
  12. Clindesse
  13. Clindets
  14. Clinimycin
  15. Dalacin
  16. Dalacin C
  17. Dalacin C Flavored Granules
  18. Dalacin C Phosphate
  19. Dalacin T Topical Solution
  20. Evoclin
  21. ResiDerm A
  22. Sobelin
  23. Zindaclin
Brand Mixtures Not Available
Chemical IUPAC Name (2S,4R)-N-[2-chloro-1-[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-methylsulfanyloxan-2-yl]propyl]-1-methyl-4-propylpyrrolidine-2-carboxamide
Chemical Formula C18H33ClN2O5S
Chemical Structure Structure
CAS Registry Number 18323-44-9
InChI Identifier InChI=1/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/f/h20H
InChI Key KDLRVYVGXIQJDK-MUUPOQBDDB
KEGG Drug D00277 Link Image
KEGG Compound C06914 Link Image
PubChem Compound 29029 Link Image
PubChem Substance 171415 Link Image
ChEBI ID 3745 Link Image
PharmGKB ID PA449035 Link Image
HET ID CLY Link Image
GenBank ID Not Available
Drug ID Number [DIN] 02258331 Link Image
RxList Link http://www.rxlist.com/cgi/generic2/clindam.htm Link Image
PDRhealth Link Not Available
Wikipedia Link http://en.wikipedia.org/wiki/Clindamycin Link Image
FDA Label
Material Safety Data Sheet (MSDS)
Synthesis Reference Birkenmeyer, U.S. Pat. 3,475,407(1970)
Average Molecular Weight 424.9830
Monoisotopic Molecular Weight 424.1799
State Solid
Melting Point 255 oC
Experimental Water Solubility 30.6 mg/L Source: PhysProp
Predicted Water Solubility 3.10e+00 mg/mL Calculated using ALOGPS
Experimental LogP/Hydrophobicity 1.6 Source: PhysProp
Predicted LogP 1.76 Calculated using ALOGPS
Experimental LogS Not Available
Predicted LogS -2.14 Calculated using ALOGPS
Experimental Caco2 Permeability Not Available
pKa/Isoelectric Point Not Available
Mass Spectrum Not Available
MOL File Show Link Image | Download Link Image
SDF File Show Link Image | Download Link Image
PDB File Show Link Image | Download Link Image
2D Structure
3D Structure
Experimental PDB ID Not Available
Isomeric SMILES CCC[C@@H]1C[C@H](N(C)C1)C(=O)N[C@H]([C@H](C)Cl)[C@H]1O[C@H](SC)[C@H](O)[C@@H](O)[C@H]1O
Canonical SMILES CCCC1CC(N(C)C1)C(=O)NC(C(C)Cl)C1OC(SC)C(O)C(O)C1O
Drug Category
  • Anti-Bacterial Agents
  • Lincomycins
  • Protein Synthesis Inhibitors
ATC Codes
AHFS Codes
  • 08:12.28.20
  • 84:04.04
Indication For the treatment of serious infections caused by susceptible anaerobic bacteria (anaerobes, streptococci, pneumococci, and staphylococci)
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.
Mechanism of Action Systemic/Vaginal-Clindamycin inhibits protein synthesis of bacteria by binding to the 50 S ribosomal subunits of the bacteria. Topical-Clindamycin reduces free fatty acid concentrations on the skin and to suppress the growth of Propionibacterium acnes (Corynebacterium acnes) , an anaerobe found in sebaceous glands and follicles.
Absorption Rapidly absorbed after oral administration. Absorption of an oral dose is virtually complete (90%), and the concomitant administration of food does not appreciably modify the serum concentrations; serum levels have been uniform and predictable from person to person and dose to dose.
Toxicity Orally and parenterally administered clindamycin has been associated with severe colitis (pseudomembranous colitis) which may result in patient death. 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.
Protein Binding 92-94%
Biotransformation Hepatic
Half Life 2.4 hours
Dosage Forms
Form Route
Capsule Oral
Cream Intravaginal
Cream Topical
Liquid Intramuscular
Liquid Intravenous
Powder, for solution Oral
Solution Intravenous
Solution Topical
Patient Information Show Link Image
Contraindications Show Link Image
Interactions Show Link Image
Drug Interactions
Drug Interaction
Aluminium The aluminium salt decreases the absorption of lincosamides
Atracurium The agent increases the effect of muscle relaxant
Attapulgite The aluminium salt decreases the absorption of lincosamides
Cyclosporine Decreases the effect of cyclosporine
Dihydroxyaluminium The aluminium salt decreases the absorption of lincosamides
Doxacurium The agent increases the effect of muscle relaxant
Gallamine Triethiodide The agent increases the effect of muscle relaxant
Kaolin The aluminium salt decreases the absorption of lincosamides
Metocurine The agent increases the effect of muscle relaxant
Mivacurium The agent increases the effect of muscle relaxant
Pancuronium The agent increases the effect of muscle relaxant
Pipecuronium The agent increases the effect of muscle relaxant
Rocuronium The agent increases the effect of muscle relaxant
Succinylcholine The agent increases the effect of muscle relaxant
Tubocurarine The agent increases the effect of muscle relaxant
Vecuronium The agent increases the effect of muscle relaxant
Food Interactions
  • Take with food.
Pathways
Name SMPDB Link KEGG Link
Clindamycin Pathway SMP00249 Link Image
General References
  1. Lamont RF: Can antibiotics prevent preterm birth--the pro and con debate. BJOG. 2005 Mar;112 Suppl 1:67-73. [PubMed Link Image]
  2. 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 Link Image]
  3. 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 Link Image]
  4. Klempner MS, Styrt B: Clindamycin uptake by human neutrophils. J Infect Dis. 1981 Nov;144(5):472-9. [PubMed Link Image]
  5. Drugs.com Link Image
  6. Wikipedia Link Image
  7. RxList Link Image
Organisms Affected
  • Enteric bacteria and other eubacteria
Phase 1 Metabolizing Enzymes
  1. Cytochrome P450 3A4 (CYP3A4)
Targets
  1. 50S ribosomal protein L10
Phase 1 Metabolizing Enzyme 1 [top]
Enzyme 1 Name Cytochrome P450 3A4 (CYP3A4)
Enzyme 1 Gene Name CYP3A4
Enzyme 1 SwissProt ID P08684 Link Image
Enzyme 1 SNPs SNPJam Report Link Image
Enzyme 1 Protein Sequence >sp|P08684|CP3A4_HUMAN Cytochrome P450 3A4 (EC 1.14.13.67) 
ALIPDLAMETWLLLAVSLVLLYLYGTHSHGLFKKLGIPGPTPLPFLGNILSYHKGFCMFD
MECHKKYGKVWGFYDGQQPVLAITDPDMIKTVLVKECYSVFTNRRPFGPVGFMKSAISIA
EDEEWKRLRSLLSPTFTSGKLKEMVPIIAQYGDVLVRNLRREAETGKPVTLKDVFGAYSM
DVITSTSFGVNIDSLNNPQDPFVENTKKLLRFDFLDPFFLSITVFPFLIPILEVLNICVF
PREVTNFLRKSVKRMKESRLEDTQKHRVDFLQLMIDSQNSKETESHKALSDLELVAQSII
FIFAGYETTSSVLSFIMYELATHPDVQQKLQEEIDAVLPNKAPPTYDTVLQMEYLDMVVN
ETLRLFPIAMRLERVCKKDVEINGMFIPKGWVVMIPSYALHRDPKYWTEPEKFLPERFSK
KNKDNIDPYIYTPFGSGPRNCIGMRFALMNMKLALIRVLQNFSFKPCKETQIPLKLSLGG
LLQPEKPVVLKVESRDGTVSGA
Drug Target 1 [top]
Target 1 ID 818
Target 1 Name 50S ribosomal protein L10
Target 1 Synonyms Not Available
Target 1 Gene Name rplJ
Target 1 Protein Sequence >50S ribosomal protein L10 
ALNLQDKQAIVAEVSEVAKGALSAVVADSRGVTVDKMTELRKAGREAGVYMRVVRNTLLR
RAVEGTPFECLKDAFVGPTLIAYSMEHPGAAARLFKEFAKANAKFEVKAAAFEGELIPAS
QIDRLATLPTYEEAIARLMATMKEASAGKLVRTLAAVRDAKEAA
Target 1 Number of Residues 166
Target 1 Molecular Weight 17581
Target 1 Theoretical pI 9.51
Target 1 GO Classification
Function
structural molecule activity
structural constituent of ribosome
Process
metabolism
macromolecule metabolism
macromolecule biosynthesis
protein biosynthesis
physiological process
cellular physiological process
cell organization and biogenesis
organelle organization and biogenesis
ribosome biogenesis and assembly
Component
protein complex
ribonucleoprotein complex
ribosome
cell
intracellular
Target 1 General Function Translation, ribosomal structure and biogenesis
Target 1 Specific Function Protein L10 is also a translational repressor protein. It controls the translation of the rplJL-rpoBC operon by binding to its mRNA
Target 1 Pathways Not Available
Target 1 Reactions Not Available
Target 1 Pfam Domain Function
Target 1 Signals
  • None
Target 1 Transmembrane Regions
  • None
Target 1 Essentiality Essential
Target 1 GenBank ID Protein 24054563 Link Image
Target 1 UniProtKB/Swiss-Prot ID P0A7J6 Link Image
Target 1 UniProtKB/Swiss-Prot Entry Name RL10_SHIFL Link Image
Target 1 PDB ID Not Available
Target 1 Cellular Location Not Available
Target 1 Gene Sequence >498 bp 
ATGGCTTTAAATCTTCAAGACAAACAAGCGATTGTTGCTGAAGTCAGCGAAGTAGCCAAA
GGCGCGCTGTCTGCAGTAGTTGCGGATTCCCGTGGCGTAACTGTAGATAAAATGACTGAA
CTGCGTAAAGCAGGTCGCGAAGCTGGCGTATACATGCGTGTTGTTCGTAACACCCTGCTG
CGCCGTGCTGTTGAAGGTACTCCGTTCGAGTGCCTGAAAGACGCGTTTGTTGGTCCGACC
CTGATTGCATACTCTATGGAACACCCGGGCGCTGCTGCTCGTCTGTTCAAAGAGTTCGCG
AAAGCGAATGCAAAATTTGAGGTCAAAGCCGCTGCCTTTGAAGGTGAGCTGATCCCGGCG
TCTCAGATCGACCGCCTGGCAACTCTGCCGACCTACGAAGAAGCAATTGCACGCCTGATG
GCAACCATGAAAGAAGCTTCGGCTGGCAAACTGGTTCGTACTCTGGCTGCTGTACGCGAT
GCGAAAGAAGCTGCTTAA
Target 1 GenBank Gene ID
Target 1 GeneCard ID Not Available
Target 1 GenAtlas ID Not Available
Target 1 HGNC ID Not Available
Target 1 Chromosome Location Not Available
Target 1 Locus Not Available
Target 1 SNPs SNPJam Report Link Image
Target 1 General References
  1. Jin Q, Yuan Z, Xu J, Wang Y, Shen Y, Lu W, Wang J, Liu H, Yang J, Yang F, Zhang X, Zhang J, Yang G, Wu H, Qu D, Dong J, Sun L, Xue Y, Zhao A, Gao Y, Zhu J, Kan B, Ding K, Chen S, Cheng H, Yao Z, He B, Chen R, Ma D, Qiang B, Wen Y, Hou Y, Yu J: Genome sequence of Shigella flexneri 2a: insights into pathogenicity through comparison with genomes of Escherichia coli K12 and O157. Nucleic Acids Res. 2002 Oct 15;30(20):4432-41. [PubMed Link Image]
  2. Wei J, Goldberg MB, Burland V, Venkatesan MM, Deng W, Fournier G, Mayhew GF, Plunkett G 3rd, Rose DJ, Darling A, Mau B, Perna NT, Payne SM, Runyen-Janecky LJ, Zhou S, Schwartz DC, Blattner FR: Complete genome sequence and comparative genomics of Shigella flexneri serotype 2a strain 2457T. Infect Immun. 2003 May;71(5):2775-86. [PubMed Link Image]
Target 1 Drug References
  1. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed Link Image]
  2. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed Link Image]

This project is supported by Genome Alberta & Genome Canada, a not-for-profit organization that is leading Canada's national genomics strategy with $600 million in funding from the federal government. This project is also supported in part by GenomeQuest, Inc., an enterprise genomic information company serving the life science community.