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Identification
- Summary
Retapamulin is a topical antibiotic agent used for the treatment of impetigo caused by methicillin-susceptible Staphylococcus aureus or Streptococcus pyogenes.
- Brand Names
- Altabax
- Generic Name
- Retapamulin
- DrugBank Accession Number
- DB01256
- Background
Retapamulin, marketed by GlaxoSmithKline as the ointment Altabax, is an antibiotic for skin infections like impetigo. It was approved by the FDA in April 2007.
- Type
- Small Molecule
- Groups
- Approved
- Structure
Structure for Retapamulin (DB01256)
- Weight
- Average: 517.763
Monoisotopic: 517.322579687 - Chemical Formula
- C30H47NO4S
- Synonyms
- Retapamulin
- Retapamulina
- External IDs
- SB 275833
- SB-275833
- SB275833
Pharmacology
- Indication
For 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.
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Indication Type Indication Combined Product Details Approval Level Age Group Patient Characteristics Dose Form Treatment of Streptococcal impetigo •••••••••••• Treatment of Stapyhlococcal impetigo •••••••••••• - Contraindications & Blackbox Warnings
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Retapamulin 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 action
Retapamulin 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.
Target Actions Organism A50S ribosomal protein L3 inhibitorStreptococcus pyogenes serotype M1 - Absorption
Not Available
- Volume of distribution
Not Available
- Protein binding
Retapamulin is approximately 94% bound to human plasma proteins, and the protein binding is independent of concentration.
- Metabolism
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 elimination
Not Available
- Half-life
Not Available
- Clearance
Not Available
- Adverse Effects
Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.- Toxicity
Not Available
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs
- Not Available
Interactions
- Drug Interactions
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Drug Interaction Integrate drug-drug
interactions in your softwareAbametapir The serum concentration of Retapamulin can be increased when it is combined with Abametapir. Acalabrutinib The metabolism of Retapamulin can be decreased when combined with Acalabrutinib. Acetaminophen The metabolism of Retapamulin can be decreased when combined with Acetaminophen. Acetazolamide The metabolism of Retapamulin can be decreased when combined with Acetazolamide. Adagrasib The metabolism of Retapamulin can be decreased when combined with Adagrasib. - Food Interactions
- No interactions found.
Products
Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.- International/Other Brands
- Aitabax / Altargo
- Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Altabax Ointment 10 mg/1g Topical Almirall, LLC 2016-05-01 Not applicable US 
Altabax Ointment 10 mg/1g Topical Rebel Distributors 2010-01-07 Not applicable US Altabax Ointment 10 mg/1g Topical Glaxosmithkline Inc 2007-05-02 2017-01-01 US Altabax Ointment 10 mg/1g Topical Physicians Total Care, Inc. 2010-01-07 2010-03-02 US Altargo Ointment 1 % Cutaneous Glaxo Group Limited 2024-07-10 2019-02-25 EU 
Categories
- ATC Codes
- D06AX13 — Retapamulin
- Drug Categories
- Chemical TaxonomyProvided by Classyfire
- Description
- This 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.
- Kingdom
- Organic compounds
- Super Class
- Lipids and lipid-like molecules
- Class
- Prenol lipids
- Sub Class
- Diterpenoids
- Direct Parent
- Pleuromutilin and derivatives
- Alternative Parents
- Tropane alkaloids / Piperidines / N-alkylpyrrolidines / Trialkylamines / Secondary alcohols / Ketones / Carboxylic acid esters / Amino acids and derivatives / Sulfenyl compounds / Monocarboxylic acids and derivatives show 5 more
- Substituents
- Alcohol / Aliphatic heteropolycyclic compound / Amine / Amino acid or derivatives / Azacycle / Carbonyl group / Carboxylic acid derivative / Carboxylic acid ester / Dialkylthioether / Hydrocarbon derivative show 20 more
- Molecular Framework
- Aliphatic heteropolycyclic compounds
- External Descriptors
- Not Available
- Affected organisms
- Bacteria
Chemical Identifiers
- UNII
- 4MG6O8991R
- CAS number
- 224452-66-8
- InChI Key
- STZYTFJPGGDRJD-NHUWBDDWSA-N
- InChI
- InChI=1S/C30H47NO4S/c1-7-28(4)16-24(35-25(33)17-36-22-14-20-8-9-21(15-22)31(20)6)29(5)18(2)10-12-30(19(3)27(28)34)13-11-23(32)26(29)30/h7,18-22,24,26-27,34H,1,8-17H2,2-6H3/t18-,19+,20-,21+,22-,24-,26+,27+,28-,29+,30+/m1/s1
- IUPAC Name
- (1S,2R,3S,4S,6R,7R,8R,14R)-4-ethenyl-3-hydroxy-2,4,7,14-tetramethyl-9-oxotricyclo[5.4.3.0^{1,8}]tetradecan-6-yl 2-{[(1R,3S,5S)-8-methyl-8-azabicyclo[3.2.1]octan-3-yl]sulfanyl}acetate
- SMILES
- [H][C@@]12C(=O)CC[C@]11CC[C@@H](C)[C@@]2(C)[C@@H](C[C@@](C)(C=C)[C@@H](O)[C@@H]1C)OC(=O)CS[C@H]1C[C@@H]2CC[C@H](C1)N2C
References
- 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.
US20090234125- General References
- 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. [Article]
- 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. [Article]
- Novak R, Shlaes DM: The pleuromutilin antibiotics: a new class for human use. Curr Opin Investig Drugs. 2010 Feb;11(2):182-91. [Article]
- Jacobs MR: Retapamulin: a semisynthetic pleuromutilin compound for topical treatment of skin infections in adults and children. Future Microbiol. 2007 Dec;2(6):591-600. [Article]
- 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. doi: 10.1358/dot.2008.44.2.1153446. [Article]
- Authors unspecified: Retapamulin for impetigo and other infections. Drug Ther Bull. 2008 Oct;46(10):76-9. doi: 10.1136/dtb.2008.09.0023. [Article]
- Nagabushan H: Retapamulin: a novel topical antibiotic. Indian J Dermatol Venereol Leprol. 2010 Jan-Feb;76(1):77-9. doi: 10.4103/0378-6323.58693. [Article]
- 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. [Article]
- Link [Link]
- FDA Approved Drug Products: ALTABAX (retapamulin) ointment [Link]
- External Links
- PubChem Compound
- 6918462
- PubChem Substance
- 46509062
- ChemSpider
- 25064484
- 642274
- ChEMBL
- CHEMBL1658
- ZINC
- ZINC000100013500
- Therapeutic Targets Database
- DAP000886
- PharmGKB
- PA164749341
- PDBe Ligand
- G34
- RxList
- RxList Drug Page
- Drugs.com
- Drugs.com Drug Page
- Wikipedia
- Retapamulin
- PDB Entries
- 2ogo / 8ceu
Clinical Trials
- Clinical Trials
Clinical Trial & Rare Diseases Add-on Data Package
Explore 4,000+ rare diseases, orphan drugs & condition pairs, clinical trial why stopped data, & more. Preview package Phase Status Purpose Conditions Count Start Date Why Stopped 100+ additional columns Unlock 175K+ rows when you subscribe.View sample dataNot Available Completed Not Available Bacterial skin infections 2 somestatus stop reason just information to hide Not Available Completed Not Available Impetigo 1 somestatus stop reason just information to hide Not Available Completed Treatment Foot Eczema / Hand Eczema 1 somestatus stop reason just information to hide 4 Completed Prevention Methicillin Resistant Staphylococcus Aureus (MRSA) 1 somestatus stop reason just information to hide 4 Completed Treatment Atopic Dermatitis / Secondary Infection 1 somestatus stop reason just information to hide
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- GlaxoSmithKline Inc.
- Physicians Total Care Inc.
- Rebel Distributors Corp.
- Dosage Forms
Form Route Strength Ointment Topical 10 mg/1g Ointment Cutaneous 1 % Ointment Topical 1 % Ointment Topical 1 g - Prices
Unit description Cost Unit Altabax 1% ointment 8.64USD g DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.- Patents
Patent Number Pediatric Extension Approved Expires (estimated) Region CA2307551 No 2007-01-01 2018-10-27 Canada 
USRE39128 No 2006-06-13 2021-04-12 US USRE43390 No 2012-05-15 2021-04-12 US US7875630 No 2011-01-25 2027-02-14 US US8207191 No 2012-06-26 2024-08-30 US
Properties
- State
- Solid
- Experimental Properties
Property Value Source logP 5 Not Available - Predicted Properties
Property Value Source Water Solubility 0.000394 mg/mL ALOGPS logP 4.63 ALOGPS logP 4.37 Chemaxon logS -6.1 ALOGPS pKa (Strongest Acidic) 14.43 Chemaxon pKa (Strongest Basic) 9.69 Chemaxon Physiological Charge 1 Chemaxon Hydrogen Acceptor Count 4 Chemaxon Hydrogen Donor Count 1 Chemaxon Polar Surface Area 66.84 Å2 Chemaxon Rotatable Bond Count 6 Chemaxon Refractivity 145.45 m3·mol-1 Chemaxon Polarizability 59.82 Å3 Chemaxon Number of Rings 5 Chemaxon Bioavailability 1 Chemaxon Rule of Five No Chemaxon Ghose Filter No Chemaxon Veber's Rule No Chemaxon MDDR-like Rule Yes Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.5359 Blood Brain Barrier + 0.8647 Caco-2 permeable + 0.5282 P-glycoprotein substrate Substrate 0.6692 P-glycoprotein inhibitor I Inhibitor 0.881 P-glycoprotein inhibitor II Inhibitor 0.7432 Renal organic cation transporter Inhibitor 0.5618 CYP450 2C9 substrate Non-substrate 0.7457 CYP450 2D6 substrate Non-substrate 0.7732 CYP450 3A4 substrate Substrate 0.7848 CYP450 1A2 substrate Non-inhibitor 0.7993 CYP450 2C9 inhibitor Non-inhibitor 0.7935 CYP450 2D6 inhibitor Non-inhibitor 0.882 CYP450 2C19 inhibitor Non-inhibitor 0.8004 CYP450 3A4 inhibitor Non-inhibitor 0.5938 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.8717 Ames test Non AMES toxic 0.7256 Carcinogenicity Non-carcinogens 0.9557 Biodegradation Not ready biodegradable 1.0 Rat acute toxicity 2.7920 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9704 hERG inhibition (predictor II) Non-inhibitor 0.7819
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 217.14232 predictedDeepCCS 1.0 (2019) [M+H]+ 218.97572 predictedDeepCCS 1.0 (2019) [M+Na]+ 225.07246 predictedDeepCCS 1.0 (2019)
Targets
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- Kind
- Protein
- Organism
- Streptococcus pyogenes serotype M1
- Pharmacological action
- Yes
- Actions
- Inhibitor
- General Function
- One of the primary rRNA binding proteins, it binds directly near the 3'-end of the 23S rRNA, where it nucleates assembly of the 50S subunit.
- Specific Function
- rRNA binding
- Gene Name
- rplC
- Uniprot ID
- Q9A1X4
- Uniprot Name
- 50S ribosomal protein L3
- Molecular Weight
- 22438.035 Da
References
- Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
- 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. [Article]
- 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. [Article]
- Authors unspecified: Retapamulin for impetigo and other infections. Drug Ther Bull. 2008 Oct;46(10):76-9. doi: 10.1136/dtb.2008.09.0023. [Article]
- Dubois EA, Cohen AF: Retapamulin. Br J Clin Pharmacol. 2010 Jan;69(1):2-3. doi: 10.1111/j.1365-2125.2009.03505.x. [Article]
- Nagabushan H: Retapamulin: a novel topical antibiotic. Indian J Dermatol Venereol Leprol. 2010 Jan-Feb;76(1):77-9. doi: 10.4103/0378-6323.58693. [Article]
- 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. [Article]
- Gelmetti C: Local antibiotics in dermatology. Dermatol Ther. 2008 May-Jun;21(3):187-95. doi: 10.1111/j.1529-8019.2008.00190.x. [Article]
- 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. [Article]
Enzymes
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- A cytochrome P450 monooxygenase involved in the metabolism of sterols, steroid hormones, retinoids and fatty acids (PubMed:10681376, PubMed:11093772, PubMed:11555828, PubMed:12865317, PubMed:14559847, PubMed:15373842, PubMed:15764715, PubMed:19965576, PubMed:20702771, PubMed:21490593, PubMed:21576599). Mechanistically, uses molecular oxygen inserting one oxygen atom into a substrate, and reducing the second into a water molecule, with two electrons provided by NADPH via cytochrome P450 reductase (NADPH--hemoprotein reductase). Catalyzes the hydroxylation of carbon-hydrogen bonds (PubMed:12865317, PubMed:14559847, PubMed:15373842, PubMed:15764715, PubMed:21490593, PubMed:21576599, PubMed:2732228). Exhibits high catalytic activity for the formation of hydroxyestrogens from estrone (E1) and 17beta-estradiol (E2), namely 2-hydroxy E1 and E2, as well as D-ring hydroxylated E1 and E2 at the C-16 position (PubMed:11555828, PubMed:12865317, PubMed:14559847). Plays a role in the metabolism of androgens, particularly in oxidative deactivation of testosterone (PubMed:15373842, PubMed:15764715, PubMed:22773874, PubMed:2732228). Metabolizes testosterone to less biologically active 2beta- and 6beta-hydroxytestosterones (PubMed:15373842, PubMed:15764715, PubMed:2732228). Contributes to the formation of hydroxycholesterols (oxysterols), particularly A-ring hydroxylated cholesterol at the C-4beta position, and side chain hydroxylated cholesterol at the C-25 position, likely contributing to cholesterol degradation and bile acid biosynthesis (PubMed:21576599). Catalyzes bisallylic hydroxylation of polyunsaturated fatty acids (PUFA) (PubMed:9435160). Catalyzes the epoxidation of double bonds of PUFA with a preference for the last double bond (PubMed:19965576). Metabolizes endocannabinoid arachidonoylethanolamide (anandamide) to 8,9-, 11,12-, and 14,15-epoxyeicosatrienoic acid ethanolamides (EpETrE-EAs), potentially modulating endocannabinoid system signaling (PubMed:20702771). Plays a role in the metabolism of retinoids. Displays high catalytic activity for oxidation of all-trans-retinol to all-trans-retinal, a rate-limiting step for the biosynthesis of all-trans-retinoic acid (atRA) (PubMed:10681376). Further metabolizes atRA toward 4-hydroxyretinoate and may play a role in hepatic atRA clearance (PubMed:11093772). Responsible for oxidative metabolism of xenobiotics. Acts as a 2-exo-monooxygenase for plant lipid 1,8-cineole (eucalyptol) (PubMed:11159812). Metabolizes the majority of the administered drugs. Catalyzes sulfoxidation of the anthelmintics albendazole and fenbendazole (PubMed:10759686). Hydroxylates antimalarial drug quinine (PubMed:8968357). Acts as a 1,4-cineole 2-exo-monooxygenase (PubMed:11695850). Also involved in vitamin D catabolism and calcium homeostasis. Catalyzes the inactivation of the active hormone calcitriol (1-alpha,25-dihydroxyvitamin D(3)) (PubMed:29461981)
- Specific Function
- 1,8-cineole 2-exo-monooxygenase activity
- Gene Name
- CYP3A4
- Uniprot ID
- P08684
- Uniprot Name
- Cytochrome P450 3A4
- Molecular Weight
- 57342.67 Da
Drug created at May 15, 2007 14:24 / Updated at October 07, 2024 13:58