Fosmidomycin

Chemical compound From Wikipedia, the free encyclopedia

Fosmidomycin is an antibiotic that was originally isolated from culture broths of bacteria of the genus Streptomyces.[1] It specifically inhibits DXP reductoisomerase, a key enzyme in the non-mevalonate pathway of isoprenoid biosynthesis. It is a structural analogue of 2-C-methyl-D-erythrose 4-phosphate. It inhibits the E. coli enzyme with a KI value of 38 nM (4), MTB at 80 nM, and the Francisella enzyme at 99 nM.[2] Several mutations in the E. coli DXP reductoisomerase were found to confer resistance to fosmidomycin.[3][4]

ATC code
  • none
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Fosmidomycin
Structural formula of fosmidomycin
Ball-and-stick model of the fosmidomycin molecule
Clinical data
ATC code
  • none
Identifiers
  • 3-[Formyl(hydroxy)amino]propylphosphonic acid
CAS Number
PubChem CID
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UNII
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ChEMBL
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Chemical and physical data
FormulaC4H10NO5P
Molar mass183.100 g·mol−1
3D model (JSmol)
  • O=P(O)(O)CCCN(O)C=O
  • InChI=1S/C4H10NO5P/c6-4-5(7)2-1-3-11(8,9)10/h4,7H,1-3H2,(H2,8,9,10) checkY
  • Key:GJXWDTUCERCKIX-UHFFFAOYSA-N checkY
 ☒NcheckY (what is this?)  (verify)
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Use in malaria

The discovery of the non-mevalonate pathway in malaria parasites has indicated the use of fosmidomycin and other such inhibitors as antimalarial drugs.[5] Indeed, fosmidomycin has been tested in combination treatment with clindamycin for treatment of malaria with favorable results.[6][7][8] It has been shown that an increase in copy number of the target enzyme (DXP reductoisomerase) correlates with in vitro fosmidomycin resistance in the lethal malaria parasite, Plasmodium falciparum.[9]

References

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