Retapamulin

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Retapamulin
Category Antibiotics
Catalog number BBF-03853
CAS 224452-66-8
Molecular Weight 517.76
Molecular Formula C30H47NO4S
Purity 97%

Ordering Information

Catalog Number Size Price Stock Quantity
BBF-03853 1 g $176 In stock
BBF-03853 2.5 g $386 In stock

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Description

Retapamulin (SB-275833) is a topical antibiotic, which binds to both E. coli and S. aureus ribosomes with similar potencies with Kd of 3 nM.

Specification

Synonyms [(3-exo)-8-Methyl-8-azabicyclo[3.2.1]oct-3-yl]thio]acetic Acid; [(3aS,4R,5S,6S,8R,9R,9aR,10R)-6-ethenyldecahydro-5-hydroxy-4,6,9,10-tetramethyl-1-oxo-3a,9-propano-3aH-cyclopentacycloocten-8-yl Ester; Altabax; Altargo; Mutilin; 14-(exo-8-Methyl-8-azabicyclo[3.2.1]oct-3-ylsulfanyl)acetate; SB-275833; SB275833; SB 275833
Storage Store at -20°C
IUPAC Name [(1S,2R,3S,4S,6R,7R,8R,14R)-4-ethenyl-3-hydroxy-2,4,7,14-tetramethyl-9-oxo-6-tricyclo[5.4.3.01,8]tetradecanyl] 2-[[(1R,5S)-8-methyl-8-azabicyclo[3.2.1]octan-3-yl]sulfanyl]acetate
Canonical SMILES CC1CCC23CCC(=O)C2C1(C(CC(C(C3C)O)(C)C=C)OC(=O)CSC4CC5CCC(C4)N5C)C
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
InChI Key STZYTFJPGGDRJD-FJJJPKKESA-N

Properties

Appearance White Solid
Application For research use only
Boiling Point 623.8°C at 760 mmHg
Melting Point 127-129°C
Density 1.160±0.10 g/cm3 (Predicted)
Solubility Soluble in Chloroform, DMSO, Ethanol, Methanol

Reference Reading

1. Nasal vestibulitis due to targeted therapies in cancer patients
Janelle N. Ruiz & Viswanath Reddy Belum & Christine B. Boers-Doets & Mini Kamboj. Support Care Cancer (2015) 23:2391–2398
As proposed earlier, we found that mild/moderate NV responded to intranasal antibiotics (90 %, mupirocin-based), while severe cases required oral antibiotics. Many patients had no dermatology follow-up (34 %); however, NV cleared in 60 % of episodes without complications/hospitalization, perhaps due to timely treatment. For mild cases, saline humidification, nasal emollients, and use of antibiotic ointments (e.g., mupirocin, retapamulin, bacitracin zinc/polymyxin B, chlorhexidine/neomycin) are advised. With the use of emollients (e.g., petroleum jelly, mineral oils) inappropriate for intranasal use, the rare development of lipoid pneumoniamust be considered. For severe infections, it is appropriate to administer oral antibiotics based on susceptibility patterns. For recurrences, consider decolonization; however, this approach has limited success; indiscriminate use of intranasal mupirocin may lead to development of resistance. Resistance rates range from 3 to 5 % among MRSA isolates in US/Canadian hospitals; and 1.7 % for MSSA in Latin America. Lastly, in chronic/persistent NV, cutaneous neoplasms (e.g., basal or squamous cell carcinoma) should be ruled out.
2. Treatment of Community-Associated Methicillin-Resistant Staphylococcus aureus
KyleJ. Popovich, Bala Hota. Current Infectious Disease Reports 2008, 10: 411- 420
A new agent, retapamulin, was recently FDA approved for the topical treatment of impetigo due to susceptible strains of S. aureus and GAS. Retapamulin is a pleuromutilin, a new antibiotic class that inhibits protein synthesis, and resistance to retapamulin may be less likely to develop due to its unique mechanism of action. In vitro studies have found that retapamulin has activity against MSSA, MRSA, and GAS.

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