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Identification
NameClindamycin
Accession NumberDB01190  (APRD00566)
TypeSmall Molecule
GroupsApproved
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
Synonyms
SynonymLanguageCode
7-CDLNot AvailableNot Available
7(S)-Chloro-7-deoxylincomycinNot AvailableNot Available
Cleocin (tn)Not AvailableNot Available
ClindamicinaSpanishINN
ClindamycinNot AvailableNot Available
ClindamycineFrenchINN
ClindamycinumLatinINN
Methyl 7-chloro-6,7,8-trideoxy-6-(1-methyl-trans-4-propyl-L-2-pyrrolidinecarboxamido)-1-thio-L-threo-alpha-D-galacto-octopyranosideNot AvailableNot Available
Salts
Name/CAS Structure Properties
Clindamycin Phosphate
24729-96-2
Thumb
  • InChI Key: UFUVLHLTWXBHGZ-KUWMELJBSA-N
  • Monoisotopic Mass: 504.146200983
  • Average Mass: 504.963
DBSALT000778
Brand names
NameCompany
CleocinPfizer
Clinda-DermPaddock
ClindagelNot Available
ClindamaxNot Available
ClindesseNot Available
ClindetsPerrigo
ClinimycinHayat
Dalacin CPfizer
Dalacin T Topical SolutionPfizer
EvoclinStiefel
ZindaclinCrawford
Brand mixtures
Brand NameIngredients
VELTINTretinoin + Clindamycin
Categories
CAS number18323-44-9
WeightAverage: 424.983
Monoisotopic: 424.179870573
Chemical FormulaC18H33ClN2O5S
InChI KeyKDLRVYVGXIQJDK-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
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
Mass SpecNot Available
Taxonomy
KingdomOrganic Compounds
SuperclassOrganic Acids and Derivatives
ClassCarboxylic Acids and Derivatives
SubclassAmino Acids, Peptides, and Analogues
Direct parentAlpha Amino Acid Amides
Alternative parentsPyrrolidinecarboxamides; Oxanes; Dithioacetals; 1,2-Diols; Secondary Carboxylic Acid Amides; Tertiary Amines; Secondary Alcohols; Ethers; Thioethers; Enolates; Carboxylic Acids; Polyamines; Alkyl Chlorides; Organochlorides
Substituentspyrrolidine-2-carboxamide; pyrrolidine carboxylic acid or derivative; oxane; pyrrolidine; thioacetal; tertiary amine; secondary alcohol; 1,2-diol; carboxamide group; secondary carboxylic acid amide; polyol; thioether; ether; enolate; carboxylic acid; polyamine; organonitrogen compound; organochloride; organohalogen; amine; alcohol; alkyl halide; alkyl chloride
Classification descriptionThis compound belongs to the alpha amino acid amides. These are amide derivatives of alpha amino acids.
Pharmacology
IndicationFor 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.
PharmacodynamicsClindamycin 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 actionSystemic/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.
AbsorptionRapidly 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 distributionNot Available
Protein binding92-94%
Metabolism

Hepatic

Route of eliminationApproximately 10% of the bioactivity is excreted in the urine and 3.6% in the feces; the remainder is excreted as bioinactive metabolites.
Half life2.4 hours
ClearanceNot Available
ToxicityAdverse 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
PathwayCategorySMPDB ID
Clindamycin Action PathwayDrug actionSMP00249
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
Property Value Probability
Human Intestinal Absorption + 0.8143
Blood Brain Barrier - 0.9697
Caco-2 permeable - 0.8236
P-glycoprotein substrate Substrate 0.7653
P-glycoprotein inhibitor I Non-inhibitor 0.7311
P-glycoprotein inhibitor II Inhibitor 0.7894
Renal organic cation transporter Non-inhibitor 0.8784
CYP450 2C9 substrate Non-substrate 0.8214
CYP450 2D6 substrate Non-substrate 0.9116
CYP450 3A4 substrate Substrate 0.6762
CYP450 1A2 substrate Non-inhibitor 0.9045
CYP450 2C9 substrate Non-inhibitor 0.9071
CYP450 2D6 substrate Non-inhibitor 0.9231
CYP450 2C19 substrate Non-inhibitor 0.9025
CYP450 3A4 substrate Non-inhibitor 0.8876
CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.9107
Ames test Non AMES toxic 0.6967
Carcinogenicity Non-carcinogens 0.9172
Biodegradation Not ready biodegradable 0.994
Rat acute toxicity 2.3192 LD50, mol/kg Not applicable
hERG inhibition (predictor I) Weak inhibitor 0.9887
hERG inhibition (predictor II) Non-inhibitor 0.59
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
FormRouteStrength
CapsuleOral
CreamIntravaginal
CreamTopical
LiquidIntramuscular
LiquidIntravenous
Powder, for solutionOral
SolutionIntravenous
SolutionTopical
Prices
Unit descriptionCostUnit
Clindagel 1% Gel 75ml Bottle324.48USDbottle
Evoclin 1% Foam 100 gm Can306.79USDcan
Clindamycin Phosphate 1% Foam 100 gm Can286.04USDcan
Evoclin 1% Foam 50 gm Can207.67USDcan
Clindagel 1% Gel 40ml Bottle203.42USDbottle
Clindamycin Phosphate 1% Foam 50 gm Can186.9USDcan
Clindamycin Phos-Benzoyl Perox 1-5% Gel 50 gm Jar176.42USDjar
Cleocin-T 1% Gel 60 gm Tube112.84USDtube
Cleocin-T 1% Lotion 60ml Bottle86.09USDbottle
Cleocin-T 60 1% Swab Box82.6USDbox
Cleocin 2% Cream 40 gm Tube81.56USDtube
Cleocin 3 100 mg Suppository Box80.05USDbox
Cleocin 75 mg/5ml Solution 100ml Bottle78.7USDbottle
Clindamycin hcl crystals74.9USDg
Clindamycin Phosphate 1% Gel 60 gm Tube71.42USDtube
Cleocin-T 1% Solution 60ml Bottle69.29USDbottle
Cleocin-T 1% Gel 30 gm Tube62.98USDtube
Clindamycin Phosphate 2% Cream 40 gm Tube54.99USDtube
Clindamycin Phosphate 60 1% Swab Box47.74USDbox
Clindamycin Phosphate 1% Lotion 60ml Bottle46.92USDbottle
Clindesse 2% vaginal cream39.08USDg
Clindamycin Phosphate 1% Gel 30 gm Tube33.41USDtube
Clindamycin Phosphate 1% Solution 60ml Bottle24.07USDbottle
Clindamycin phosphate powdr21.42USDg
Clindamycin Phosphate 1% Solution 30ml Bottle14.99USDbottle
Cleocin hcl 300 mg capsule9.11USDcapsule
Clindamycin phos crystals7.73USDg
Evoclin 1% foam4.9USDg
Clindagel 1% gel4.89USDml
Cleocin 150 mg capsule4.66USDcapsule
Dalacin C Phosphate 150 mg/ml4.53USDml
Clindamycin hcl 300 mg capsule3.98USDcapsule
Clindamycin phosphate 1% foam3.59USDg
Clindamycin 150 mg/ml3.48USDml
Clindamycin (60 & 120 Ml) 150 mg/ml3.41USDml
Cleocin hcl 150 mg capsule2.79USDcapsule
Cleocin hcl 75 mg capsule2.28USDcapsule
Dalacin C 300 mg Capsule2.12USDcapsule
Cleocin 2% vaginal cream1.97USDg
Clindamycin 150 mg/ml addvan1.97USDml
Cleocin phos 150 mg/ml vial1.91USDml
Cleocin t 1% gel1.81USDg
Clindamycin ph 300 mg/2 ml vial1.74USDml
Clindamax 2% vaginal cream1.37USDg
Clindamycin 2% vaginal cream1.27USDg
Clindamycin hcl 150 mg capsule1.21USDcapsule
Clindets 1% pledgets1.1USDeach
Dalacin C 150 mg Capsule1.06USDcapsule
Apo-Clindamycin 300 mg Capsule1.02USDcapsule
Mylan-Clindamycin 300 mg Capsule1.02USDcapsule
Novo-Clindamycin 300 mg Capsule1.02USDcapsule
Clindamycin ph 9 g/60 ml vial0.93USDml
Apo-Clindamycin 150 mg Capsule0.51USDcapsule
Mylan-Clindamycin 150 mg Capsule0.51USDcapsule
Novo-Clindamycin 150 mg Capsule0.51USDcapsule
Clinda-derm 1% solution0.4USDml
Cleocin 900 mg-d5w-galaxy0.37USDml
Cleocin 600 mg-d5w-galaxy0.3USDml
Dalacin C Palmitate 15 mg/ml Solution0.14USDml
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
CountryPatent NumberApprovedExpires (estimated)
United States73747472006-08-092026-08-09
United States52663291993-11-302010-11-30
Properties
Statesolid
Experimental Properties
PropertyValueSource
melting point142 [HCl salt]Not Available
water solubility30.6 mg/LNot Available
logP2.16HANSCH,C ET AL. (1995)
Predicted Properties
PropertyValueSource
Water Solubility3.1ALOGPS
logP1.76ALOGPS
logP1.04ChemAxon
logS-2.1ALOGPS
pKa (Strongest Acidic)12.16ChemAxon
pKa (Strongest Basic)7.55ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area102.26 Å2ChemAxon
Rotatable Bond Count7ChemAxon
Refractivity105.72 m3·mol-1ChemAxon
Polarizability44.49 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
SpectraNot Available
References
Synthesis Reference

Donald E. Ayer, Carl A. Schlagel, Gordon L. Flynn, “Topical clindamycin preparations.” U.S. Patent US4018918, issued January, 1971.

US4018918
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
ResourceLink
KEGG DrugD00277
KEGG CompoundC06914
PubChem Compound29029
PubChem Substance46506073
ChemSpider27005
ChEBI3745
ChEMBLCHEMBL2303635
Therapeutic Targets DatabaseDAP000409
PharmGKBPA449035
HETCLY
Drug Product Database2258331
RxListhttp://www.rxlist.com/cgi/generic2/clindam.htm
Drugs.comhttp://www.drugs.com/clindamycin.html
WikipediaClindamycin
ATC CodesD10AF01G01AA10J01FF01
AHFS Codes
  • 08:12.28.20
  • 84:04.04
PDB EntriesNot Available
FDA labelshow(151 KB)
MSDSshow(72.8 KB)
Interactions
Drug Interactions
Drug
AluminiumThe aluminium salt decreases the absorption of lincosamides
AtracuriumThe agent increases the effect of muscle relaxant
AttapulgiteThe aluminium salt decreases the absorption of lincosamides
CyclosporineClindamycin may decrease the therapeutic effect of cyclosporine.
DihydroxyaluminiumThe aluminium salt decreases the absorption of lincosamides
Doxacurium chlorideThe agent increases the effect of muscle relaxant
KaolinThe aluminium salt decreases the absorption of lincosamides
MetocurineThe agent increases the effect of muscle relaxant
MivacuriumThe agent increases the effect of muscle relaxant
PancuroniumThe agent increases the effect of muscle relaxant
PipecuroniumThe agent increases the effect of muscle relaxant
RocuroniumThe agent increases the effect of muscle relaxant
SuccinylcholineThe agent increases the effect of muscle relaxant
TubocurarineThe agent increases the effect of muscle relaxant
VecuroniumThe agent increases the effect of muscle relaxant
Food Interactions
  • Take with food.

Targets

1. 50S ribosomal protein L10

Kind: protein

Organism: Shigella flexneri

Pharmacological action: yes

Actions: inhibitor

Components

Name UniProt ID Details
50S ribosomal protein L10 P0A7J6 Details

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

Kind: nucleotide

Organism: Enteric bacteria and other eubacteria

Pharmacological action: yes

Actions: inhibitor

Components

Name UniProt ID Details

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

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: substrate inhibitor

Components

Name UniProt ID Details
Cytochrome P450 3A4 P08684 Details

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
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Drug created on June 13, 2005 07:24 / Updated on September 16, 2013 17:13