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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

Molecular Formula C50H63N9O10
Molecular Weight 950.0895
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 7 / 7
E/Z Centers 0
Optical Activity UNSPECIFIED

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
A comparison of a new oral streptogramin XRP 2868 with quinupristin-dalfopristin against antibiotic-resistant strains of haemophilus influenzae, Staphylococcus aureus, and Streptococcus pneumoniae.
2005 Dec
Pharmacodynamics of a new streptogramin, XRP 2868, in murine thigh and lung infection models.
2006 Jan
Activity of a new oral streptogramin, XRP2868, against gram-positive cocci harboring various mechanisms of resistance to streptogramins.
2006 Jan
Effects of various media on the activity of NXL103 (formerly XRP 2868), a new oral streptogramin, against Haemophilus influenzae.
2006 Nov
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
Substance Class Chemical
Created
by admin
on Sat Dec 16 18:03:04 UTC 2023
Edited
by admin
on Sat Dec 16 18:03:04 UTC 2023
Record UNII
312V80FR4J
Record Status Validated (UNII)
Record Version
  • Download
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 UTC 2023 , Edited by admin on Sat Dec 16 18:03:04 UTC 2023
PRIMARY
FDA UNII
312V80FR4J
Created by admin on Sat Dec 16 18:03:04 UTC 2023 , Edited by admin on Sat Dec 16 18:03:04 UTC 2023
PRIMARY
SMS_ID
300000034358
Created by admin on Sat Dec 16 18:03:04 UTC 2023 , Edited by admin on Sat Dec 16 18:03:04 UTC 2023
PRIMARY
NCI_THESAURUS
C166621
Created by admin on Sat Dec 16 18:03:04 UTC 2023 , Edited by admin on Sat Dec 16 18:03:04 UTC 2023
PRIMARY
WIKIPEDIA
LINOPRISTIN
Created by admin on Sat Dec 16 18:03:04 UTC 2023 , Edited by admin on Sat Dec 16 18:03:04 UTC 2023
PRIMARY
EPA CompTox
DTXSID10186288
Created by admin on Sat Dec 16 18:03:04 UTC 2023 , Edited by admin on Sat Dec 16 18:03:04 UTC 2023
PRIMARY
INN
8973
Created by admin on Sat Dec 16 18:03:04 UTC 2023 , Edited by admin on Sat Dec 16 18:03:04 UTC 2023
PRIMARY
CAS
325965-23-9
Created by admin on Sat Dec 16 18:03:04 UTC 2023 , Edited by admin on Sat Dec 16 18:03:04 UTC 2023
PRIMARY
Related Record Type Details
ACTIVE MOIETY