Flopristin

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

Flopristin
Names
IUPAC name
(7R,10R,11R,12Z,17Z,19Z,21S,23R)-23-fluoro-21-hydroxy-11,19-dimethyl-10-propan-2-yl-9,26-dioxa-3,15,28-triazatricyclo[23.2.1.03,7]octacosa-1(27),12,17,19,25(28)-pentaene-2,8,14-trione
Other names
(16R)-16-Desoxy-16-fluoropristinamycin IIB; RPR 132552; RPR 132552A
Identifiers
CAS Number
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.218.104
EC Number
  • 690-752-1
PubChem CID
UNII
InChI
  • InChI=1S/C28H38FN3O6/c1-17(2)26-19(4)9-10-24(34)30-11-5-7-18(3)13-21(33)14-20(29)15-25-31-22(16-37-25)27(35)32-12-6-8-23(32)28(36)38-26/h5,7,9-10,13,16-17,19-21,23,26,33H,6,8,11-12,14-15H2,1-4H3,(H,30,34)/b7-5-,10-9-,18-13-/t19-,20-,21-,23-,26-/m1/s1
    Key: DFSJQGCLWZVMOD-ZITBLJMASA-N
SMILES
  • O[C@H](/C=C(C)/C=C/CNC(/C=C/[C@@H](C)[C@H](OC1=O)C(C)C)=O)C[C@@H](F)CC2=NC(C(N3[C@@H]1CCC3)=O)=CO2
Properties
Chemical formula
 C28H38FN3O6
Molar mass 531.625 g·mol−1
Hazards
GHS labelling:
Pictograms
Signal word
 Warning
Hazard statements
 H302, H312, H317, H332, H341
Precautionary statements
 P201, P202, P261, P264, P270, P271, P272, P280, P281, P301+P312, P302+P352, P304+P312, P304+P340, P308+P313, P312, P321, P322, P330, P333+P313, P363, P405, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Flopristin is one of the components of the experimental drug NXL103.[1]

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.


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