Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C50H63N9O10 |
Molecular Weight | 950.0895 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 7 / 7 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
[H][C@@]12CCCN1C(=O)[C@@H](CC)NC(=O)[C@@H](NC(=O)C3=NC=CC=C3O)[C@@H](C)OC(=O)[C@@H](NC(=O)[C@]4([H])CC=C(CN5CCOCC5)CN4C(=O)[C@H](CC6=CC=C(C=C6)N(C)C)N(C)C2=O)C7=CC=CC=C7
InChI
InChIKey=NVGNYGXBILPHOS-VXNAYKIUSA-N
InChI=1S/C50H63N9O10/c1-6-36-47(64)58-23-11-14-38(58)48(65)56(5)39(28-32-16-19-35(20-17-32)55(3)4)49(66)59-30-33(29-57-24-26-68-27-25-57)18-21-37(59)44(61)54-42(34-12-8-7-9-13-34)50(67)69-31(2)41(45(62)52-36)53-46(63)43-40(60)15-10-22-51-43/h7-10,12-13,15-20,22,31,36-39,41-42,60H,6,11,14,21,23-30H2,1-5H3,(H,52,62)(H,53,63)(H,54,61)/t31-,36-,37+,38+,39+,41+,42+/m1/s1
Linopristin is a chemically modified form of quinupristin. It is an antibiotic of the streptogramin B class. It is one of the components of the antibiotic combination NXL103 (XRP 2868). NXL-103 is a combination of streptogramin A:streptogramin B components, initially developed in a 70:30 dose ratio. In multiple in vitro studies, NXL-103 demonstrated potent activity against different types of bacteria, such as Staphylococcus aureus (including MRSA), Streptococcus pneumoniae, Streptococcus pyogenes, Enterococcus faecium, Enterococcus faecalis, Haemophilus influenzae and Haemophilus parainfluenzae. In phase I clinical trials, NXL-103 achieved bactericidal levels in plasma and was generally well tolerated, with side effects primarily on the gastrointestinal system. The first phase II trial conducted to evaluate the efficacy of NXL-103 against community-acquired pneumonia revealed that the compound was comparable with amoxicillin. NXL-103 has promise to become an important agent in the treatment of community-acquired pneumonia and complex skin and soft tissue infections, pending further development.
Originator
Approval Year
PubMed
Title | Date | PubMed |
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NXL-103, a combination of flopristin and linopristin, for the potential treatment of bacterial infections including community-acquired pneumonia and MRSA. | 2010 Feb |
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In vitro pharmacokinetic/pharmacodynamic activity of NXL103 versus clindamycin and linezolid against clinical Staphylococcus aureus and Streptococcus pyogenes isolates. | 2011 Oct |
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Synergy of streptogramin antibiotics occurs independently of their effects on translation. | 2014 Sep |
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9919429
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312V80FR4J
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300000034358
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C166621
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LINOPRISTIN
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DTXSID10186288
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8973
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325965-23-9
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ACTIVE MOIETY