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Accession NumberDB01256
TypeSmall Molecule

Retapamulin is a topical antibiotic developed by GlaxoSmithKline. It was approved by the United States Food and Drug Administration in April 2007 for the treatment of bacterial skin infections such as impetigo. It is marketed as an ointment under the name brand Altabax.

SynonymsNot Available
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Altabaxointment10 mg/gtopicalGlaxo Smith Kline Llc2007-05-02Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Altabaxointment10 mg/gtopicalRebel Distributors Corp.2010-01-07Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Altabaxointment10 mg/gtopicalPhysicians Total Care, Inc.2010-01-07Not AvailableUs 0a2ef1ad1c84951dc1392a8bbe1f3cb241c91ed59e44ad8268635315440d978c
Generic Prescription ProductsNot Available
Over the Counter ProductsNot Available
International BrandsNot Available
Brand mixturesNot Available
SaltsNot Available
CAS number224452-66-8
WeightAverage: 517.763
Monoisotopic: 517.322579687
Chemical FormulaC30H47NO4S
(1S,2R,3S,4S,6R,7R,8R,14R)-4-ethenyl-3-hydroxy-2,4,7,14-tetramethyl-9-oxotricyclo[¹,⁸]tetradecan-6-yl 2-{[(1R,5S)-8-methyl-8-azabicyclo[3.2.1]octan-3-yl]sulfanyl}acetate
DescriptionThis compound belongs to the class of organic compounds known as pleuromutilin and derivatives. These are mutilins with a hydroxyacetate derivative attached to the C8 carbon atom of the cyclopenta[8]annulene moiety.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassDiterpenoids
Direct ParentPleuromutilin and derivatives
Alternative Parents
  • Pleuromutilin
  • Tropane alkaloid
  • N-alkylpyrrolidine
  • Piperidine
  • Pyrrolidine
  • Cyclic alcohol
  • Tertiary aliphatic amine
  • Tertiary amine
  • Secondary alcohol
  • Ketone
  • Carboxylic acid ester
  • Azacycle
  • Organoheterocyclic compound
  • Dialkylthioether
  • Sulfenyl compound
  • Thioether
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organosulfur compound
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Amine
  • Alcohol
  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic compounds
External DescriptorsNot Available
IndicationFor use in adults and pediatric patients aged 9 months and older for the topical treatment of impetigo (up to 100 cm2 in total area in adults or 2% total body surface area in pediatric patients aged 9 months or older) due to Staphylococcus aureus (methicillin-susceptible isolates only) or Streptococcus pyogenes.
PharmacodynamicsRetapamulin is a semisynthetic pleuromutilin antibiotic. This drug is usually bacteriostatic in action, but may become bactericidal at highed concentrations (when MBC is 1000 times higher than MIC). Retapamulin acts by selectively inhibiting the initiation of protein synthesis in bacteria at the level of bacterial 50S ribosome.
Mechanism of actionRetapamulin is a bacterial protein synthesis inhibitor belonging to a class of compounds called pleuromutilins. These compounds inhibit the initiation of protein synthesis by binding to a specific site on the 50S subunit of bacterial ribosome (domain V of 23S rRNA). This binding site involves ribosomal protein L3 and is in the region of the ribosomal P site and peptidyl transferase center. By virtue of binding to this site, pleuromutilins inhibit peptidyl transfer, block P-site interactions, and prevent the normal formation of active 50S ribosomal subunits.
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingRetapamulin is approximately 94% bound to human plasma proteins, and the protein binding is independent of concentration.

In vitro studies with human liver microsomes demonstrated that retapamulin is extensively metabolized to numerous metabolites, of which the predominant routes of metabolism were mono-oxygenation and N-demethylation. The major enzyme responsible for metabolism of retapamulin in human liver microsomes was cytochrome P450 3A4 (CYP3A4).

Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityNot Available
Affected organisms
  • Bacteria
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
Predicted ADMET features
Human Intestinal Absorption+0.5359
Blood Brain Barrier+0.8647
Caco-2 permeable+0.5282
P-glycoprotein substrateSubstrate0.6692
P-glycoprotein inhibitor IInhibitor0.881
P-glycoprotein inhibitor IIInhibitor0.7432
Renal organic cation transporterInhibitor0.5618
CYP450 2C9 substrateNon-substrate0.7457
CYP450 2D6 substrateNon-substrate0.7732
CYP450 3A4 substrateSubstrate0.7848
CYP450 1A2 substrateNon-inhibitor0.7993
CYP450 2C9 substrateNon-inhibitor0.7935
CYP450 2D6 substrateNon-inhibitor0.882
CYP450 2C19 substrateNon-inhibitor0.8004
CYP450 3A4 substrateNon-inhibitor0.5938
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.8717
Ames testNon AMES toxic0.7256
BiodegradationNot ready biodegradable1.0
Rat acute toxicity2.7920 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9704
hERG inhibition (predictor II)Non-inhibitor0.7819
ManufacturersNot Available
Dosage forms
Ointmenttopical10 mg/g
Unit descriptionCostUnit
Altabax 1% ointment8.64USD g
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
CountryPatent NumberApprovedExpires (estimated)
United StatesRE391281998-10-272018-10-27
Experimental Properties
logP5Not Available
Predicted Properties
Water Solubility0.000394 mg/mLALOGPS
pKa (Strongest Acidic)14.43ChemAxon
pKa (Strongest Basic)9.69ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area66.84 Å2ChemAxon
Rotatable Bond Count6ChemAxon
Refractivity145.45 m3·mol-1ChemAxon
Polarizability59.49 Å3ChemAxon
Number of Rings5ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Mass Spec (NIST)Not Available
SpectraNot Available
Synthesis Reference

Eli Lancry, Lilach Hedvati, Greta Sterimbaum, Ariel Mittelman, Tali Katav, “Amorphous retapamulin and processes for preparation thereof.” U.S. Patent US20090234125, issued September 17, 2009.

General Reference
  1. CenterWatch Link
  2. Jones RN, Fritsche TR, Sader HS, Ross JE: Activity of retapamulin (SB-275833), a novel pleuromutilin, against selected resistant gram-positive cocci. Antimicrob Agents Chemother. 2006 Jul;50(7):2583-6. Pubmed
  3. Yang LP, Keam SJ: Retapamulin: a review of its use in the management of impetigo and other uncomplicated superficial skin infections. Drugs. 2008;68(6):855-73. Pubmed
  4. Novak R, Shlaes DM: The pleuromutilin antibiotics: a new class for human use. Curr Opin Investig Drugs. 2010 Feb;11(2):182-91. Pubmed
  5. Jacobs MR: Retapamulin: a semisynthetic pleuromutilin compound for topical treatment of skin infections in adults and children. Future Microbiol. 2007 Dec;2:591-600. Pubmed
  6. Parish LC, Parish JL: Retapamulin: a new topical antibiotic for the treatment of uncomplicated skin infections. Drugs Today (Barc). 2008 Feb;44(2):91-102. Pubmed
  7. Retapamulin for impetigo and other infections. Drug Ther Bull. 2008 Oct;46(10):76-9. Pubmed
  8. Nagabushan H: Retapamulin: a novel topical antibiotic. Indian J Dermatol Venereol Leprol. 2010 Jan-Feb;76(1):77-9. Pubmed
  9. Shawar R, Scangarella-Oman N, Dalessandro M, Breton J, Twynholm M, Li G, Garges H: Topical retapamulin in the management of infected traumatic skin lesions. Ther Clin Risk Manag. 2009 Feb;5(1):41-9. Epub 2009 Mar 26. Pubmed
External Links
ATC CodesD06AX13
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSNot Available
Drug InteractionsSearched, but no interactions found.
Food InteractionsNot Available


1. 50S ribosomal protein L3

Kind: protein

Organism: Streptococcus pyogenes serotype M1

Pharmacological action: yes

Actions: inhibitor


Name UniProt ID Details
50S ribosomal protein L3 Q9A1X4 Details


  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. Gentry DR, Rittenhouse SF, McCloskey L, Holmes DJ: Stepwise exposure of Staphylococcus aureus to pleuromutilins is associated with stepwise acquisition of mutations in rplC and minimally affects susceptibility to retapamulin. Antimicrob Agents Chemother. 2007 Jun;51(6):2048-52. Epub 2007 Apr 2. Pubmed
  4. Retapamulin for impetigo and other infections. Drug Ther Bull. 2008 Oct;46(10):76-9. Pubmed
  5. Dubois EA, Cohen AF: Retapamulin. Br J Clin Pharmacol. 2010 Jan;69(1):2-3. Pubmed
  6. Nagabushan H: Retapamulin: a novel topical antibiotic. Indian J Dermatol Venereol Leprol. 2010 Jan-Feb;76(1):77-9. Pubmed
  7. Shawar R, Scangarella-Oman N, Dalessandro M, Breton J, Twynholm M, Li G, Garges H: Topical retapamulin in the management of infected traumatic skin lesions. Ther Clin Risk Manag. 2009 Feb;5(1):41-9. Epub 2009 Mar 26. Pubmed
  8. Gelmetti C: Local antibiotics in dermatology. Dermatol Ther. 2008 May-Jun;21(3):187-95. Pubmed
  9. Champney WS, Rodgers WK: Retapamulin inhibition of translation and 50S ribosomal subunit formation in Staphylococcus aureus cells. Antimicrob Agents Chemother. 2007 Sep;51(9):3385-7. Epub 2007 Jun 11. Pubmed


1. Cytochrome P450 3A4

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: substrate


Name UniProt ID Details
Cytochrome P450 3A4 P08684 Details


  1. GlaxoSmithKline. ALTABAX® (retapamulin) ointment prescribing information. Research Triangle Park, NC; 2010 June.

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Drug created on May 15, 2007 08:24 / Updated on September 16, 2013 17:13