U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

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
Structure of LINOPRISTIN

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

HIDE SMILES / InChI
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.

Approval Year

PubMed

PubMed

TitleDatePubMed
NXL-103, a combination of flopristin and linopristin, for the potential treatment of bacterial infections including community-acquired pneumonia and MRSA.
2010 Feb
In vitro pharmacokinetic/pharmacodynamic activity of NXL103 versus clindamycin and linezolid against clinical Staphylococcus aureus and Streptococcus pyogenes isolates.
2011 Oct
Synergy of streptogramin antibiotics occurs independently of their effects on translation.
2014 Sep
Name Type Language
LINOPRISTIN
INN   WHO-DD  
INN  
Official Name English
linopristin [INN]
Common Name English
Linopristin [WHO-DD]
Common Name English
RPR-202868
Code English
NXL-103 COMPONENT RPR-202868
Common Name English
RPR202868
Code English
Code System Code Type Description
PUBCHEM
9919429
Created by admin on Sat Dec 16 18:03:04 GMT 2023 , Edited by admin on Sat Dec 16 18:03:04 GMT 2023
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FDA UNII
312V80FR4J
Created by admin on Sat Dec 16 18:03:04 GMT 2023 , Edited by admin on Sat Dec 16 18:03:04 GMT 2023
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SMS_ID
300000034358
Created by admin on Sat Dec 16 18:03:04 GMT 2023 , Edited by admin on Sat Dec 16 18:03:04 GMT 2023
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NCI_THESAURUS
C166621
Created by admin on Sat Dec 16 18:03:04 GMT 2023 , Edited by admin on Sat Dec 16 18:03:04 GMT 2023
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WIKIPEDIA
LINOPRISTIN
Created by admin on Sat Dec 16 18:03:04 GMT 2023 , Edited by admin on Sat Dec 16 18:03:04 GMT 2023
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EPA CompTox
DTXSID10186288
Created by admin on Sat Dec 16 18:03:04 GMT 2023 , Edited by admin on Sat Dec 16 18:03:04 GMT 2023
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INN
8973
Created by admin on Sat Dec 16 18:03:04 GMT 2023 , Edited by admin on Sat Dec 16 18:03:04 GMT 2023
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CAS
325965-23-9
Created by admin on Sat Dec 16 18:03:04 GMT 2023 , Edited by admin on Sat Dec 16 18:03:04 GMT 2023
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