Fosmidomycin

Title: Fosmidomycin
CAS Registry Number: 66508-53-0
CAS Name: [3-(Formylhydroxyamino)propyl]phosphonic acid
Molecular Formula: C4H10NO5P
Molecular Weight: 183.10
Percent Composition: C 26.24%, H 5.50%, N 7.65%, O 43.69%, P 16.92%
Literature References: Inhibitor of microbial nonmevalonate isoprenoid biosynthesis. Prepn: T. Kamiya et al., US 4206156 (1980 to Fujisawa); K. Hemmi et al., Chem. Pharm. Bull. 29, 646 (1981); eidem, ibid. 30, 111 (1982). Synthesis: E. Ohler, S. Kanzler, Synthesis 1995, 539 (1995). CE determn in serum and urine: S. Bronner et al., J. Chromatogr. B 806, 255 (2004). Mode of action: T. Kuzuyama et al., Tetrahedron Lett. 39, 7913 (1998); H. Jomaa et al., Science 285, 1573 (1999). Pharmacokinetics: T. Murakawa et al., Antimicrob. Agents Chemother. 21, 224 (1982); H.-P. Kuemmerle et al., Int. J. Clin. Pharmacol. Ther. Toxicol. 23, 515, 521 (1985). Clinical evaluation in malaria: M. A. Missinou et al., Lancet 360, 1941 (2002); in combination with clindamycin: S. Borrmann et al., J. Infect. Dis. 189, 901 (2004); idem et al., ibid. 190, 1534 (2004). Interaction with other antimalarial drugs and synergy with clindamycin: J. Wiesner et al., Antimicrob. Agents Chemother. 46, 2889 (2002). Review: idem et al., Parasitol. Res. 90, S71-S76 (2003).
Properties: Colorless crystals from methanol, mp 158-160° (dec) (Ohler); also reported as crystals from water-ethanol, mp 160-166° (dec) (Hemmi). LD50 in mice and rats (mg/kg): >11000 orally; ~8000 s.c. (Wiesner, 2003).
Melting point: mp 158-160° (dec); mp 160-166° (dec) (Hemmi)
Toxicity data: LD50 in mice and rats (mg/kg): >11000 orally; ~8000 s.c. (Wiesner, 2003)
Derivative Type: Monosodium salt
CAS Registry Number: 66508-37-0
Manufacturers' Codes: FR-31564
Molecular Formula: C4H10NNaO5P
Molecular Weight: 206.09
Percent Composition: C 23.31%, H 4.89%, N 6.80%, Na 11.16%, O 38.82%, P 15.03%
Properties: Crystals from methanol-ethanol, mp 189-191° (dec).
Melting point: Crystals from methanol-ethanol, mp 189-191° (dec)
Therap-Cat: Antimalarial.
Keywords: Antimalarial.
Fosphenytoin Fospirate Fospropofol Fosthiazate Fosthietan

Fosmidomycin
Fosmidomycin.svg
Systematic (IUPAC) name
3-[Formyl(hydroxy)amino]propylphosphonic acid
Clinical data
Legal status  ?
Identifiers
CAS number 66508-53-0 N
ATC code None
PubChem CID 572
DrugBank DB02948
ChemSpider 555 YesY
UNII 5829E3D9I9 YesY
ChEBI CHEBI:443725 YesY
ChEMBL CHEMBL203125 YesY
Chemical data
Formula C4H10NO5P 
Mol. mass 183.100 g/mol
 N (what is this?)  (verify)

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]