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药品详细

Retapamulin(Retapamulin)

化学结构式图
中文名
Retapamulin
英文名
Retapamulin
分子式
C30H47NO4S
化学名
(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
分子量
Average: 517.763
Monoisotopic: 517.322579687
CAS号
224452-66-8
ATC分类
药物类型
small molecule
阶段
approved
商品名
同义名
基本介绍

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.

生产厂家
  • Glaxo group ltd dba glaxosmithkline
封装厂家
参考
Synthesis Reference Not Available
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
剂型
规格
化合物类型
Type small molecule
Classes Not Available
Substructures Not Available
适应症
药理
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.
Pharmacodynamics 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.
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
Toxicity Not Available
Affected organisms
  • Bacteria
Pathways Not Available
理化性质
Properties
State solid
Experimental Properties
Property Value Source
logP 5 Not Available
Predicted Properties
Property Value Source
water solubility 3.94e-04 g/l 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 ChemAxon
rotatable bond count 6 ChemAxon
refractivity 145.45 ChemAxon
polarizability 59.49 ChemAxon
药物相互作用
食物相互作用
Not Available

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