Fosmidomycin

Fosmidomycin

Clinical data
ATC code	none
Identifiers
IUPAC name 3-[Formyl(hydroxy)amino]propylphosphonic acid
CAS Number	66508-53-0 N
PubChem CID	572
DrugBank	DB02948 Y
ChemSpider	555 Y
UNII	5829E3D9I9
ChEBI	CHEBI:443725 Y
ChEMBL	CHEMBL203125 Y
Chemical and physical data
Formula	C4H10NO5P
Molar mass	183.100 g/mol
3D model (JSmol)	Interactive image
SMILES O=P(O)(O)CCCN(O)C=O
InChI InChI=1S/C4H10NO5P/c6-4-5(7)2-1-3-11(8,9)10/h4,7H,1-3H2,(H2,8,9,10) Y Key:GJXWDTUCERCKIX-UHFFFAOYSA-N Y
NY (what is this?)

Fosmidomycin is an antibiotic that was originally isolated from culture broths of bacteria of the genus Streptomyces. 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.

The discovery of the non-mevalonate pathway in malaria parasites has indicated the use of fosmidomycin and other such inhibitors as antimalarial drugs. Indeed, fosmidomycin has been tested in combination treatment with clindamycin for treatment of malaria with favorable results. 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.