Cas no 66508-53-0 (Fosmidomycin)

Fosmidomycin is a naturally occurring phosphonic acid antibiotic, originally isolated from Streptomyces lavendulae. It acts as a potent and selective inhibitor of the 1-deoxy-D-xylulose-5-phosphate reductoisomerase (DXR) enzyme, a key target in the non-mevalonate pathway of isoprenoid biosynthesis. This mechanism makes it particularly effective against Gram-negative bacteria, including Escherichia coli and Pseudomonas aeruginosa, as well as the malaria parasite Plasmodium falciparum. Fosmidomycin exhibits high specificity for DXR, minimizing off-target effects, and has been studied for its potential in antimalarial and antibacterial applications. Its unique mode of action and well-characterized biochemical pathway inhibition make it a valuable tool for research in microbial metabolism and drug development.
Fosmidomycin structure
Fosmidomycin structure
Product Name:Fosmidomycin
CAS No:66508-53-0
MF:C4H10NO5P
MW:183.099662303925
CID:858217
PubChem ID:572
Update Time:2025-05-20

Fosmidomycin Chemical and Physical Properties

Names and Identifiers

    • Fosmidomycin
    • Fosmidomycin [INN]
    • (3-(N-Hydroxyformamido)propyl)phosphonic acid
    • Fosmidomycina
    • Fosmidomycina [INN-Spanish]
    • Fosmidomycine
    • Fosmidomycine [INN-French]
    • Fosmidomycinum
    • Fosmidomycinum [INN-Latin]
    • UNII-5829E3D9I9
    • (3-(Formylhydroxyamino)propyl)phosphonic acid, monosodium salt
    • {3-[formyl(hydroxy)amino]propyl}phosphonic acid
    • Fosmidomycin sodium salt hydrate
    • 3-(N-formyl-N-hydroxyamino)propylphosphonic acid
    • 3-(N-formyl-N-hydroxyamino)-propylphosphonic acid
    • AC1L19JA
    • CHEBI:443725
    • 3-(formyl-hydroxyamino)propylphosphonic acid
    • FOM
    • SCHEMBL301404
    • FR-31564
    • CHEMBL203125
    • DTXSID70216712
    • FR 31564
    • Q905038
    • [3-(N-hydroxyformamido)propyl]phosphonic acid
    • 66508-37-0
    • AKOS006272014
    • DB02948
    • [3-(Formyl-hydroxy-amino)-propyl]-phosphonic acid
    • GJXWDTUCERCKIX-UHFFFAOYSA-N
    • NCGC00264107-01
    • 66508-53-0
    • FOSMIDOMYCIN [MI]
    • NS00070647
    • FOSMIDOMYCIN [MART.]
    • (3-(Formylhydroxyamino)propyl)phosphonic acid sodium salt
    • 3-(N-hydroxyformamido)propylphosphonic acid
    • 3-(Formyl-hydroxy-amino)propylphosphonic acid
    • GTPL9739
    • 5829E3D9I9
    • 3-[FORMYL(HYDROXY)AMINO]PROPYLPHOSPHONIC ACID
    • BDBM50153713
    • (3-(N-Hydroxyformamido)propyl)phosphonic acid sodium salt
    • NCGC00264107-02
    • HY-134914
    • CS-0166689
    • DB-249641
    • Inchi: 1S/C4H10NO5P/c6-4-5(7)2-1-3-11(8,9)10/h4,7H,1-3H2,(H2,8,9,10)
    • InChI Key: GJXWDTUCERCKIX-UHFFFAOYSA-N
    • SMILES: P(CCCN(C=O)O)(=O)(O)O

Computed Properties

  • Exact Mass: 183.0297
  • Monoisotopic Mass: 183.02965942g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 3
  • Hydrogen Bond Acceptor Count: 5
  • Heavy Atom Count: 11
  • Rotatable Bond Count: 4
  • Complexity: 166
  • Covalently-Bonded Unit Count: 1
  • Defined Atom Stereocenter Count: 0
  • Undefined Atom Stereocenter Count : 0
  • Defined Bond Stereocenter Count: 0
  • Undefined Bond Stereocenter Count: 0
  • XLogP3: -2.2
  • Topological Polar Surface Area: 98.1?2

Experimental Properties

  • Melting Point: 158-160° (dec); mp 160-166° (dec) (Hemmi)
  • Solubility: H2O: soluble20mg/mL, clear
  • PSA: 98.07

Fosmidomycin Security Information

  • Toxicity:LD50 in mice and rats (mg/kg): >11000 orally; ~8000 s.c. (Wiesner, 2003)

Fosmidomycin Pricemore >>

Related Categories No. Product Name Cas No. Purity Specification Price update time Inquiry
Biosynth
RCA50853-5 mg
Fosmidomycin sodium hydrate
66508-53-0
5mg
$306.10 2023-01-02
Biosynth
RCA50853-10 mg
Fosmidomycin sodium hydrate
66508-53-0
10mg
$489.70 2023-01-02
Biosynth
RCA50853-25 mg
Fosmidomycin sodium hydrate
66508-53-0
25mg
$918.25 2023-01-02
Biosynth
RCA50853-50 mg
Fosmidomycin sodium hydrate
66508-53-0
50mg
$1,469.50 2023-01-02
Biosynth
RCA50853-100 mg
Fosmidomycin sodium hydrate
66508-53-0
100MG
$2,351.00 2023-01-02

Additional information on Fosmidomycin

Fosmidomycin (CAS No: 66508-53-0) - A Comprehensive Overview in Modern Chemical Biology and Medicinal Chemistry

Fosmidomycin, chemically designated as (2S,3S,4R,5R)-4-(4-hydroxyphenyl)-2,3-dihydroxy-5-methyl-oxo-1-azabicyclo[3.1.0]hexane-3-carboxylic acid, is a naturally occurring compound with significant implications in the fields of chemical biology and medicinal chemistry. Its unique structural framework and biological activities have positioned it as a cornerstone in the development of novel therapeutic agents, particularly against bacterial infections resistant to conventional antibiotics.

The molecular structure of Fosmidomycin (CAS No: 66508-53-0) features a complex bicyclic system with multiple stereocenters, making it a challenging yet fascinating subject of study. This intricate architecture contributes to its potent inhibitory effects on bacterial enzymes, specifically targeting the phosphoglycerate dehydrogenase (PGDH) enzyme. PGDH is a crucial enzyme in the bacterial glycolysis pathway, responsible for converting 1,3-bisphosphoglycerate into 3-phosphoglycerate. By inhibiting this enzyme, Fosmidomycin effectively disrupts bacterial energy metabolism, leading to growth inhibition and cell death.

Recent advancements in synthetic chemistry have enabled the efficient production and modification of Fosmidomycin, opening new avenues for drug development. Researchers have explored various derivatives of this compound to enhance its pharmacological properties, including improved solubility, bioavailability, and reduced toxicity. These modifications have not only expanded the therapeutic potential of Fosmidomycin but also provided valuable insights into its mechanism of action.

The pharmacological profile of Fosmidomycin has been extensively studied in both preclinical and clinical settings. Notably, its broad-spectrum activity against Gram-positive and Gram-negative bacteria has made it a promising candidate for treating multidrug-resistant infections. Clinical trials have demonstrated its efficacy in treating urinary tract infections and other bacterial infections caused by pathogens such as *E. coli* and *K. pneumoniae*. The compound's ability to overcome antibiotic resistance mechanisms has garnered significant attention from the medical community.

In addition to its antimicrobial properties, Fosmidomycin has shown potential in other therapeutic areas. Studies have explored its role in inhibiting viral replication and preventing the formation of biofilms, which are resistant to conventional antibiotics. These findings highlight the multifaceted applications of Fosmidomycin in addressing various infectious diseases.

The synthesis of Fosmidomycin (CAS No: 66508-53-0) involves a multi-step process that requires precise control over reaction conditions and stereochemistry. Advances in biocatalysis and enzymatic engineering have facilitated the production of this compound through microbial fermentation processes. These biotechnological approaches have not only improved the yield and purity of Fosmidomycin but also reduced the environmental impact associated with traditional synthetic methods.

The development of novel derivatives of Fosmidomycin has been driven by a deeper understanding of its interaction with target enzymes and receptors. Computational modeling and structure-based drug design techniques have played a pivotal role in identifying key structural features that contribute to its biological activity. These insights have guided the design of analogs with enhanced potency and selectivity.

The future prospects for Fosmidomycin are promising, with ongoing research focusing on expanding its therapeutic applications and improving its pharmacokinetic properties. Collaborative efforts between academic institutions, pharmaceutical companies, and regulatory agencies are essential to translate these findings into clinical practice. The continued exploration of this compound holds great potential for addressing emerging infectious diseases and improving global health outcomes.

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