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targets (2) enzymes (1)
for drugs
Identification
Name Clindamycin
Accession Number DB01190 (APRD00566)
Type small molecule
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.
Structure Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  • Clindamicina [INN-Spanish]
  • clindamycin
  • Clindamycin Hcl
  • Clindamycin Hydrochloride
  • Clindamycin Phosphate
  • Clindamycine [French]
  • Clindamycine [INN-French]
  • Clindamycinum [INN-Latin]
Brand names
  • Chlolincocin
  • Cleocin
  • Cleocin Hcl
  • Cleocin Pediatric
  • Cleocin Phosphate
  • Cleocin T
  • Cleocin T Gel
  • Cleocin T Lotion
  • Cleocin T Topical Solution
  • Clinda-Derm
  • Clindagel
  • Clindesse
  • Clindets
  • Clinimycin
  • Dalacin
  • Dalacin C
  • Dalacin C Flavored Granules
  • Dalacin C Phosphate
  • Dalacin T Topical Solution
  • Evoclin
  • ResiDerm A
  • Sobelin
  • Zindaclin
Brand name mixtures Not Available
Categories
  • Anti-Bacterial Agents
  • Protein Synthesis Inhibitors
  • Lincomycins
CAS number 18323-44-9
Weight Average: 424.983
Monoisotopic: 424.179870573
Chemical Formula C18H33ClN2O5S
InChI Key InChIKey=KDLRVYVGXIQJDK-NOWPCOIGSA-N
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
Plain Text
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
Plain Text
Mass Spec Not Available
Taxonomy
Kingdom Organic
Classes
  • Glycerol and Derivatives
  • Pyrans
Substructures
  • Glycerol and Derivatives
  • Hydroxy Compounds
  • Pyrans
  • Amino Ketones
  • Pyrrolidines
  • Ethers
  • Carboxylic Acids and Derivatives
  • Aliphatic and Aryl Amines
  • Alkyl Halides
  • Alcohols and Polyols
  • Heterocyclic compounds
  • Carboxamides and Derivatives
  • Acetals and Derivatives
Pharmacology
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.
Pharmacodynamics 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 50S ribosomal subunits of the bacteria. Specifically, it binds primarily to the 23s RNA subunit. Topical clindamycin reduces free fatty acid concentrations on the skin and suppresses the growth of Propionibacterium acnes (Corynebacterium acnes) , an anaerobe found in sebaceous glands and follicles.
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.
Volume of distribution Not Available
Protein binding 92-94%
Metabolism

Hepatic
Route of elimination Approximately 10% of the bioactivity is excreted in the urine and 3.6% in the feces; the remainder is excreted as bioinactive metabolites.
Half life 2.4 hours
Clearance Not Available
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
Pathways
Pathway Name SMPDB ID
Smp00249 Clindamycin Pathway SMP00249
Pharmacoeconomics
Manufacturers
  • Pharmacia and upjohn co
  • Aurobindo pharma ltd
  • Corepharma llc
  • Lannett holdings inc
  • Ranbaxy laboratories ltd
  • Teva pharmaceuticals usa inc
  • Watson laboratories inc
  • Zydus pharmaceuticals usa inc
  • Paddock laboratories inc
  • Perrigo uk finco ltd partnership
  • Stiefel laboratories inc
  • Nycomed us inc
  • Kv pharmaceutical co
  • Galderma laboratories lp
  • Altana inc
  • Abraxis pharmaceutical products
  • App pharmaceuticals llc
  • Astrazeneca lp
  • Baxter healthcare corp anesthesia and critical care
  • Bedford laboratories div ben venue laboratories inc
  • Bristol myers squibb pharma co
  • Hospira inc
  • Loch pharmaceuticals inc
  • Marsam pharmaceuticals llc
  • Solopak laboratories inc
  • Teva parenteral medicines inc
  • Abbott laboratories
  • Baxter healthcare corp
  • Actavis mid atlantic llc
  • Boca pharmacal inc
  • Copley pharmaceutical inc
  • E fougera div altana inc
  • Perrigo new york inc
  • Stiefel a gsk co
  • Taro pharmaceutical industries ltd
  • Versapharm inc
  • Wockhardt eu operations (swiss) ag
  • Perrigo co
Packagers
Dosage forms
Form Route Strength
Capsule Oral
Cream Intravaginal
Cream Topical
Liquid Intramuscular
Liquid Intravenous
Powder, for solution Oral
Solution Intravenous
Solution Topical
Prices
Unit description Cost Unit
Clindagel 1% Gel 75ml Bottle 324.48 USD bottle
Evoclin 1% Foam 100 gm Can 306.79 USD can
Clindamycin Phosphate 1% Foam 100 gm Can 286.04 USD can
Evoclin 1% Foam 50 gm Can 207.67 USD can
Clindagel 1% Gel 40ml Bottle 203.42 USD bottle
Clindamycin Phosphate 1% Foam 50 gm Can 186.9 USD can
Clindamycin Phos-Benzoyl Perox 1-5% Gel 50 gm Jar 176.42 USD jar
Cleocin-T 1% Gel 60 gm Tube 112.84 USD tube
Cleocin-T 1% Lotion 60ml Bottle 86.09 USD bottle
Cleocin-T 60 1% Swab Box 82.6 USD box
Cleocin 2% Cream 40 gm Tube 81.56 USD tube
Cleocin 3 100 mg Suppository Box 80.05 USD box
Cleocin 75 mg/5ml Solution 100ml Bottle 78.7 USD bottle
Clindamycin hcl crystals 74.9 USD g
Clindamycin Phosphate 1% Gel 60 gm Tube 71.42 USD tube
Cleocin-T 1% Solution 60ml Bottle 69.29 USD bottle
Cleocin-T 1% Gel 30 gm Tube 62.98 USD tube
Clindamycin Phosphate 2% Cream 40 gm Tube 54.99 USD tube
Clindamycin Phosphate 60 1% Swab Box 47.74 USD box
Clindamycin Phosphate 1% Lotion 60ml Bottle 46.92 USD bottle
Clindesse 2% vaginal cream 39.08 USD g
Clindamycin Phosphate 1% Gel 30 gm Tube 33.41 USD tube
Clindamycin Phosphate 1% Solution 60ml Bottle 24.07 USD bottle
Clindamycin phosphate powdr 21.42 USD g
Clindamycin Phosphate 1% Solution 30ml Bottle 14.99 USD bottle
Cleocin hcl 300 mg capsule 9.11 USD capsule
Clindamycin phos crystals 7.73 USD g
Evoclin 1% foam 4.9 USD g
Clindagel 1% gel 4.89 USD ml
Cleocin 150 mg capsule 4.66 USD capsule
Dalacin C Phosphate 150 mg/ml 4.53 USD ml
Clindamycin hcl 300 mg capsule 3.98 USD capsule
Clindamycin phosphate 1% foam 3.59 USD g
Clindamycin 150 mg/ml 3.48 USD ml
Clindamycin (60 & 120 Ml) 150 mg/ml 3.41 USD ml
Cleocin hcl 150 mg capsule 2.79 USD capsule
Cleocin hcl 75 mg capsule 2.28 USD capsule
Dalacin C 300 mg Capsule 2.12 USD capsule
Cleocin 2% vaginal cream 1.97 USD g
Clindamycin 150 mg/ml addvan 1.97 USD ml
Cleocin phos 150 mg/ml vial 1.91 USD ml
Cleocin t 1% gel 1.81 USD g
Clindamycin ph 300 mg/2 ml vial 1.74 USD ml
Clindamax 2% vaginal cream 1.37 USD g
Clindamycin 2% vaginal cream 1.27 USD g
Clindamycin hcl 150 mg capsule 1.21 USD capsule
Clindets 1% pledgets 1.1 USD each
Dalacin C 150 mg Capsule 1.06 USD capsule
Apo-Clindamycin 300 mg Capsule 1.02 USD capsule
Mylan-Clindamycin 300 mg Capsule 1.02 USD capsule
Novo-Clindamycin 300 mg Capsule 1.02 USD capsule
Clindamycin ph 9 g/60 ml vial 0.93 USD ml
Apo-Clindamycin 150 mg Capsule 0.51 USD capsule
Mylan-Clindamycin 150 mg Capsule 0.51 USD capsule
Novo-Clindamycin 150 mg Capsule 0.51 USD capsule
Clinda-derm 1% solution 0.4 USD ml
Cleocin 900 mg-d5w-galaxy 0.37 USD ml
Cleocin 600 mg-d5w-galaxy 0.3 USD ml
Dalacin C Palmitate 15 mg/ml Solution 0.14 USD ml
Patents
Country Patent Number Approved Expires
United States 7374747 2006-08-09 2026-08-09
United States 5266329 1993-11-30 2010-11-30
Properties
State solid
Melting point 142 [HCl salt]
Experimental Properties
Property Value Source
water solubility 30.6 mg/L PhysProp
logP 1.6 PhysProp
Predicted Properties
Property Value Source
water solubility 3.10e+00 g/l ALOGPS
logP 1.76 ALOGPS
logP 1.04 ChemAxon Molconvert
logS -2.14 ALOGPS
pKa 12.75 ChemAxon Molconvert
hydrogen acceptor count 6 ChemAxon Molconvert
hydrogen donor count 4 ChemAxon Molconvert
polar surface area 102.26 ChemAxon Molconvert
rotatable bond count 7 ChemAxon Molconvert
refractivity 105.72 ChemAxon Molconvert
polarizability 44.49 ChemAxon Molconvert
References
Synthesis Reference Not Available
General Reference
  1. 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
  2. Klempner MS, Styrt B: Clindamycin uptake by human neutrophils. J Infect Dis. 1981 Nov;144(5):472-9. Pubmed
  3. Lamont RF: Can antibiotics prevent preterm birth—the pro and con debate. BJOG. 2005 Mar;112 Suppl 1:67-73. Pubmed
  4. 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
Resource Link
KEGG Drug D00277 Link_out
KEGG Compound C06914 Link_out
PubChem Compound 29029 Link_out
PubChem Substance 46506073 Link_out
ChemSpider 27005 Link_out
ChEBI 3745 Link_out
ChEMBL 3745 Link_out
Therapeutic Targets Database DAP000409 Link_out
PharmGKB PA449035 Link_out
HET CLY Link_out
Drug Product Database 2258331 Link_out
RxList http://www.rxlist.com/cgi/generic2/clindam.htm Link_out
Drugs.com http://www.drugs.com/clindamycin.html Link_out
Wikipedia http://en.wikipedia.org/wiki/Clindamycin Link_out
ATC Codes
  • D10AF01
  • G01AA10
  • J01FF01
AHFS Codes
  • 08:12.28.20
  • 84:04.04
PDB Entries Not Available
FDA label show (151.4 KB)
MSDS show (72.8 KB)
Interactions
Drug Interactions Not Available
Food Interactions
  • Take with food.
Targets

1. 50S ribosomal protein L10

Pharmacological action: yes
Actions: inhibitor

Protein L10 is also a translational repressor protein. It controls the translation of the rplJL-rpoBC operon by binding to its mRNA

Organism class: bacterial
UniProt ID: P0A7J6 Link_out
Gene: rplJ
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed
  2. 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
  3. Schlunzen F, Zarivach R, Harms J, Bashan A, Tocilj A, Albrecht R, Yonath A, Franceschi F: Structural basis for the interaction of antibiotics with the peptidyl transferase centre in eubacteria. Nature. 2001 Oct 25;413(6858):814-21. Pubmed

2. 23S rRNA

Pharmacological action: yes
Actions: inhibitor

In prokaryotes, the 23S rRNA is part of the large subunit (the 50S) that joins with the 30S small subunit to create the functional 70S ribosome. The ribosome is comprised of 3 RNAs: the 23S, the 16S and the 5S ribosomal RNAs. The 23S and the 5S associate with their respective proteins to make up the large subunit of the ribosome, while the 16S RNA associates with its proteins to make up the small subunit.

Gene Sequence: FASTA

References:
  1. Schlunzen F, Zarivach R, Harms J, Bashan A, Tocilj A, Albrecht R, Yonath A, Franceschi F: Structural basis for the interaction of antibiotics with the peptidyl transferase centre in eubacteria. Nature. 2001 Oct 25;413(6858):814-21. Pubmed
Enzymes

1. Cytochrome P450 3A4

Actions: substrate, inhibitor

Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4- hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. The enzyme also hydroxylates etoposide

UniProt ID: P08684 Link_out
Gene: CYP3A4
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. Epub 2009 Nov 24. Pubmed
Comments
Drug created on June 13, 2005 07:24 / Updated on November 19, 2010 18:02

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.