Fosmidomycin

Fosmidomycin
Clinical data
ATC code	none;
Identifiers
	IUPAC name 3-[Formyl(hydroxy)amino]propylphosphonic acid;
CAS Number	66508-53-0 ;
PubChem CID	572;
DrugBank	DB02948 ;
ChemSpider	555 ;
UNII	5829E3D9I9;
ChEBI	CHEBI:443725 ;
ChEMBL	ChEMBL203125 ;
CompTox Dashboard (EPA)	DTXSID70216712 ;
Chemical and physical data
Formula	C4H10NO5P
Molar mass	183.100 g·mol−1
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) ; Key:GJXWDTUCERCKIX-UHFFFAOYSA-N ;
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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]

References