Linopristin

Last updated
Linopristin
Linopristin.svg
Names
Systematic IUPAC name
N-[(6R,9S,10R,13S,15aS,22S,24aS)-22-{[4-(Dimethylamino)phenyl]methyl}-6-ethyl-10,23-dimethyl-18-[(morpholin-4-yl)methyl]-5,8,12,15,21,24-hexaoxo-13-phenyl-1,2,3,5,6,7,8,9,10,13,14,15,15a,16,19,21,22,23,24,24a-icosahydro-12H-pyrido[2,1-f]pyrrolo[2,1-l] [1,4,7,10,13,16]oxapentaazacyclononadecin-9-yl]-3-hydroxypyridine-2-carboxamide
Other names
RPR 202698; RPR 202868
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.218.103 OOjs UI icon edit-ltr-progressive.svg
PubChem CID
UNII
  • 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
    Key: NVGNYGXBILPHOS-VXNAYKIUSA-N
  • O=C([C@H](CC1=CC=C(N(C)C)C=C1)N(C)C([C@H]2N(CCC2)C3=O)=O)N4[C@H](C(N[C@H](C(O[C@H](C)[C@@H](C(N[C@@H]3CC)=O)NC(C5=NC=CC=C5O)=O)=O)C6=CC=CC=C6)=O)CC=C(CN7CCOCC7)C4
Properties
C50H63N9O10
Molar mass 950.107 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Linopristin is an antibiotic of the streptogramin B class. It is one of the components of the antibiotic combination NXL103. [1]

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<span class="mw-page-title-main">Macrolide</span> Class of natural products

The Macrolides are a class of natural products that consist of a large macrocyclic lactone ring to which one or more deoxy sugars, usually cladinose and desosamine, may be attached. The lactone rings are usually 14-, 15-, or 16-membered. Macrolides belong to the polyketide class of natural products. Some macrolides have antibiotic or antifungal activity and are used as pharmaceutical drugs. Rapamycin is also a macrolide and was originally developed as an antifungal, but is now used as an immunosuppressant drug and is being investigated as a potential longevity therapeutic.

<span class="mw-page-title-main">Aminoglycoside</span> Antibacterial drug

Aminoglycoside is a medicinal and bacteriologic category of traditional Gram-negative antibacterial medications that inhibit protein synthesis and contain as a portion of the molecule an amino-modified glycoside (sugar). The term can also refer more generally to any organic molecule that contains amino sugar substructures. Aminoglycoside antibiotics display bactericidal activity against Gram-negative aerobes and some anaerobic bacilli where resistance has not yet arisen but generally not against Gram-positive and anaerobic Gram-negative bacteria.

<span class="mw-page-title-main">Clindamycin</span> Antibiotic

Clindamycin is an antibiotic medication used for the treatment of a number of bacterial infections, including osteomyelitis (bone) or joint infections, pelvic inflammatory disease, strep throat, pneumonia, acute otitis media, and endocarditis. It can also be used to treat acne, and some cases of methicillin-resistant Staphylococcus aureus (MRSA). In combination with quinine, it can be used to treat malaria. It is available by mouth, by injection into a vein, and as a cream or a gel to be applied to the skin or in the vagina.

<span class="mw-page-title-main">Quinupristin/dalfopristin</span> Combination drug

Quinupristin/dalfopristin, or quinupristin-dalfopristin, is a combination of two antibiotics used to treat infections by staphylococci and by vancomycin-resistant Enterococcus faecium.

<span class="mw-page-title-main">Quinupristin</span> Chemical compound

Quinupristin is a streptogramin B antibiotic, used in combination with dalfopristin under the trade name Synercid. It has activity against Gram-positive and atypical bacteria but not Gram-negative bacteria. It inhibits bacterial protein synthesis. The combination of quinupristin and dalfopristin is not active against Enterococcus faecalis and needs to be given in combination with other antibacterials for mixed infections that involve Gram-negative organisms.

<span class="mw-page-title-main">Lincosamides</span> Group of antibiotics

Lincosamides are a class of antibiotics, which include lincomycin, clindamycin, and pirlimycin.

<span class="mw-page-title-main">Pristinamycin</span> Group of chemical compounds

Pristinamycin (INN), also spelled pristinamycine, is an antibiotic used primarily in the treatment of staphylococcal infections, and to a lesser extent streptococcal infections. It is a streptogramin group antibiotic, similar to virginiamycin, derived from the bacterium Streptomyces pristinaespiralis. It is marketed in Europe by Sanofi-Aventis under the trade name Pyostacine.

<span class="mw-page-title-main">Dalfopristin</span> Chemical compound

Dalfopristin is a semi-synthetic streptogramin antibiotic analogue of ostreogyrcin A. The combination quinupristin/dalfopristin was brought to the market by Rhone-Poulenc Rorer Pharmaceuticals in 1999. Synercid is used to treat infections by staphylococci and by vancomycin-resistant Enterococcus faecium.

<span class="mw-page-title-main">Virginiamycin</span> Combination antimicrobial

Virginiamycin is a streptogramin antibiotic similar to pristinamycin and quinupristin/dalfopristin. It is a combination of pristinamycin IIA and virginiamycin S1. Virginiamycin is used in the fuel ethanol industry to prevent microbial contamination. It is also used in agriculture, specifically in livestock, to accelerate the growth of the animals and to prevent and treat infections. Antibiotics also save as much as 30% in feed costs among young swine, although the savings fade as pigs get older, according to a USDA study.

<span class="mw-page-title-main">Aminocoumarin</span> Class of antibiotic chemical compounds

Aminocoumarin is a class of antibiotics that act by an inhibition of the DNA gyrase enzyme involved in the cell division in bacteria. They are derived from Streptomyces species, whose best-known representative – Streptomyces coelicolor – was completely sequenced in 2002. The aminocoumarin antibiotics include:

<span class="mw-page-title-main">Protein synthesis inhibitor</span> Inhibitors of translation

A protein synthesis inhibitor is a compound that stops or slows the growth or proliferation of cells by disrupting the processes that lead directly to the generation of new proteins.

Streptogramin A is a group of antibiotics within the larger family of antibiotics known as streptogramins. They are synthesized by the bacteria Streptomyces virginiae. The streptogramin family of antibiotics consists of two distinct groups: group A antibiotics contain a 23-membered unsaturated ring with lactone and peptide bonds while group B antibiotics are depsipeptides. While structurally different, these two groups of antibiotics act synergistically, providing greater antibiotic activity than the combined activity of the separate components. These antibiotics have until recently been commercially manufactured as feed additives in agriculture, although today there is increased interest in their ability to combat antibiotic-resistant bacteria, particularly vancomycin-resistant bacteria.

Streptogramin B is a subgroup of the streptogramin antibiotics family. These natural products are cyclic hexa- or hepta depsipeptides produced by various members of the genus of bacteria Streptomyces. Many of the members of the streptogramins reported in the literature have the same structure and different names; for example, pristinamycin IA = vernamycin Bα = mikamycin B = osteogrycin B.

<span class="mw-page-title-main">Pristinamycin IA</span> Chemical compound

Pristinamycin IA is an antibiotic cyclic peptide. It is a member of the streptogramin B group of antibiotics and one component of pristinamycin.

<span class="mw-page-title-main">Virginiamycin S1</span> Chemical compound

Virginiamycin S1 is a macrolide antibiotic in the group of antibiotics known as streptogramin B.

Linopristin/flopristin is an experimental drug candidate under development by Novexel. It is an oral streptogramin antibiotic that has potent in vitro activity against certain Gram-positive bacteria including methicillin resistant Staphylococcus aureus (MRSA), as well as the important respiratory pathogens including penicillin-, macrolide- and quinolone-resistant strains. It is a combination of linopristin and flopristin.

<span class="mw-page-title-main">Flopristin</span> Chemical compound

Flopristin is a semi-synthetic antibiotic of the streptogramin A class. It is a fluorinated derivative of pristinamycin IIB.

<span class="mw-page-title-main">Pristinamycin IIB</span> Chemical compound

Pristinamycin IIB is an antibiotic of the streptogramin A class. It was isolated from Streptomyces pristinaespiralis and its chemical structure was first determined in 1966.

<span class="mw-page-title-main">Etamycin</span> Chemical compound

Etamycin, also known as viridogrisein, is a cyclic peptide antibiotic isolate of marine actinomycete. Etamycin was first isolated from a Streptomyces species in 1957 by Lawson and co-workers.

References

  1. Pankuch, Glenn A.; Kelly, Linda M.; Lin, Gengrong; Bryskier, Andre; Couturier, Catherine; Jacobs, Michael R.; Appelbaum, Peter C. (2003). "Activities of a new oral streptogramin, XRP 2868, compared to those of other agents against Streptococcus pneumoniae and Haemophilus species". Antimicrobial Agents and Chemotherapy. 47 (10): 3270–3274. doi:10.1128/AAC.47.10.3270-3274.2003. PMC   201162 . PMID   14506040.