(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,5S)-8-methyl-8-azabicyclo[3.2.1]octan-3-yl]sulfanyl}acetate

• ChemBase ID: 1125
• Molecular Formular: C30H47NO4S
• Molecular Mass: 517.76348
• Monoisotopic Mass: 517.32257999
• SMILES: S(C1C[C@@H]2N([C@H](C1)CC2)C)CC(=O)O[C@H]1[C@]2([C@H]3[C@@]([C@H]([C@H](O)[C@](C1)(C)C=C)C)(CC[C@H]2C)CCC3=O)C
• Canonical SMILES: C=C[C@]1(C)C[C@@H](OC(=O)CSC2C[C@@H]3CC[C@H](C2)N3C)[C@]2(C)[C@H](C)CC[C@]3([C@H]([C@@H]1O)C)[C@H]2C(=O)CC3
• 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
• InChIKey: STZYTFJPGGDRJD-FJJJPKKESA-N

NAMES AND DATABASE IDS

Names

• 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,5S)-8-methyl-8-azabicyclo[3.2.1]octan-3-yl]sulfanyl}acetate; (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,5S)-8-methyl-8-azabicyclo[3.2.1]octan-3-yl]sulfanyl}acetate
• IUPAC Traditional name: @retapamulin; retapamulin
• Brand Name: Altabax (Glaxo)
• Synonyms: SB 275833; Retapamulin

Database IDs

• CAS Number: 224452-66-8
• MDL Number: MFCD11045316
• PubChem SID: 160964588
• PubChem CID: 6918462

CALCULATED PROPERTIES

JChem

• Acid pKa: 14.425539
• H Acceptors: 4
• H Donor: 1
• LogD (pH = 5.5): 0.9535479
• LogD (pH = 7.4): 2.1104655
• Log P: 4.3734345
• Molar Refractivity: 145.4515 cm^3
• Polarizability: 58.145725 Å^3
• Polar Surface Area: 66.84 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: false

ALOGPS 2.1

• Log P: 4.63
• LOG S: -6.12
• Solubility (Water): 3.94e-04 g/l

PROPERTIES

Physical Property

• Hydrophobicity(logP): 5

Product Information

• Purity: 95+%

DETAILS

DrugBank - DB01256

• Drug Groups: approved
• Description: 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.
• Indication: For use in adults and pediatric patients aged 9 months and older for the topical treatment of impetigo (up to 100 cm^2 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.
• Pharmacology: 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.
• Affected Organisms: Bacteria
• Biotransformation: 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).
• Protein Binding: Retapamulin is approximately 94% bound to human plasma proteins, and the protein binding is independent of concentration.
• References: CenterWatch [Link] ; 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] ; 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] ; Novak R, Shlaes DM: The pleuromutilin antibiotics: a new class for human use. Curr Opin Investig Drugs. 2010 Feb;11(2):182-91. [Pubmed] ; 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] ; 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] ; Retapamulin for impetigo and other infections. Drug Ther Bull. 2008 Oct;46(10):76-9. [Pubmed] ; Nagabushan H: Retapamulin: a novel topical antibiotic. Indian J Dermatol Venereol Leprol. 2010 Jan-Feb;76(1):77-9. [Pubmed] ; 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: Wikipedia; RxList; Drugs.com

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. Pubmed
• 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
• Novak R, Shlaes DM: The pleuromutilin antibiotics: a new class for human use. Curr Opin Investig Drugs. 2010 Feb;11(2):182-91. Pubmed
• 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
• 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
• Nagabushan H: Retapamulin: a novel topical antibiotic. Indian J Dermatol Venereol Leprol. 2010 Jan-Feb;76(1):77-9. Pubmed
• 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
• CenterWatch Link
• Retapamulin for impetigo and other infections. Drug Ther Bull. 2008 Oct;46(10):76-9. Pubmed